Page last updated: 2024-12-11

sarcophine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

sarcophine: toxic cembranolide phosphofructokinase inhibitor isolated from coral Sarcophyton glaucum; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Sarcophyton	genus	[no description available]	Orchidaceae	A plant family of the order Asparagales. All members of the orchid family have the same bilaterally symmetrical flower structure, with three sepals, but the flowers vary greatly in color and shape.[MeSH]

Cross-References

ID Source	ID
PubMed CID	6436805
CHEMBL ID	518855
MeSH ID	M0063613

Synonyms (13)

Synonym
55038-27-2
sarcophine
sarcophin
nsc 250434
sarcophin a
oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1ah)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl-, (1as-(1ar,4e,10ar,11e,14ar*))-
oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1ah)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl- (van)
CHEMBL518855
nsc814255
DTXSID001318397
HY-124550
CS-0086898
nsc-814255

Research Excerpts

Overview

Sarcophine is a bioactive cembranoid diterpene isolated from the Red Sea soft coral Sarcophyton glaucum.

Excerpt	Reference	Relevance
"Sarcophine is a related cembranoid isolated from the Red Sea soft coral Sarcophyton glaucum."	( Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine. Avery, MA; Desai, P; El Sayed, KA; Sawant, SS; Sylvester, PW; Youssef, DT, 2004)	1.26
"Sarcophine (1) is a bioactive cembranoid diterpene isolated from the Red Sea soft coral Sarcophyton glaucum. "	( Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors. El Sayed, KA; Hassan, HM; Hifnawy, MS; Mohammed, R; Sallam, AA; Youssef, DT, 2011)	2.07

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay ID	Title	Year	Journal	Article
AID612364	Antiproliferative activity against human PC3 cells at 5 to 50 uM after 24 hrs by MTT assay	2011	Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16	Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.
AID356945	Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID356941	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen induction at 10 molar ratio relative to TPA	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID356943	Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID356940	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen induction at 100 molar ratio relative to TPA	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID356944	Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID333736	Antiproliferative activity against mouse +SA cells assessed as decrease in cell growth at 100 to 1000 uM after 4 days by MTT assay	2004	Journal of natural products, Dec, Volume: 67, Issue:12	Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine.
AID612362	Antiproliferative activity against human MDA-MB-231 cells at 5 to 50 uM after 24 hrs by MTT assay	2011	Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16	Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.
AID422544	Reduction in human pancreatic recombinant 1B PLA2 activity expressed in Escherichia coli assessed as hydrolysis of 1,2-dimyristoyl-sn-3-glycerophosphocholine vesicles at 0.007 mol fraction relative to cholate	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID356939	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen induction at 500 molar ratio relative to TPA	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID356942	Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID592675	Cytotoxicity against human HCT116 cells by MTT assay	2011	Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8	Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
AID422543	Reduction in human pancreatic recombinant 1B PLA2 activity expressed in Escherichia coli assessed as hydrolysis of 1,2-dimyristoyl-sn-3-glycerophosphocholine vesicles at 0.03 mol fraction relative to cholate	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID592676	Cytotoxicity against human MCF7 cells by MTT assay	2011	Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8	Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
AID333735	Antiproliferative activity against mouse +SA cells assessed as decrease in cell growth at 0 to 10 uM after 4 days by MTT assay	2004	Journal of natural products, Dec, Volume: 67, Issue:12	Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine.
AID592673	Cytotoxicity against human HL60 cells by MTT assay	2011	Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8	Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
AID422555	Antagonist activity at human FXR transfected in human HuH7 cells co-transfected with human BSEP promoter reporter plasmid at 10 uM after 30 hrs by dual-luciferase reporter assay relative to chenodeoxycholate	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID377683	Inhibition of mouse B16B15b cell migration after 16 hrs by wound-healing assay	2006	Journal of natural products, Jul, Volume: 69, Issue:7	Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine.
AID422554	Agonist activity at human FXR transfected in human HuH7 cells co-transfected with human BSEP promoter reporter plasmid at 10 uM after 30 hrs by dual-luciferase reporter assay relative to control	2009	Journal of natural products, Jan, Volume: 72, Issue:1	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.
AID356938	Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen induction at 1000 molar ratio relative to TPA	2002	Journal of natural products, Dec, Volume: 65, Issue:12	Semisynthesis of new sarcophine derivatives with chemopreventive activity.
AID592674	Cytotoxicity against human A549 cells by MTT assay	2011	Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8	Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (5.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	10 (50.00)	29.6817
2010's	8 (40.00)	24.3611
2020's	1 (5.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.88

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	18.88 (24.57)
Research Supply Index	3.04 (2.92)
Research Growth Index	4.29 (4.65)
Search Engine Demand Index	15.26 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (18.88)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	20 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.15	1	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	2.06	1	dihydroxyanthraquinone	analgesic; antineoplastic agent
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.03	1	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.05	1	amino sulfonic acid; bile acid taurine conjugate	human metabolite
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	4.29	18	butan-4-olide	metabolite; neurotoxin
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	2.05	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
cembrane cembrane: diterpene with Ca-antagonistic action on rabbit aorta from soft coral of genus Sarcophyton; structure given in first source. cembrane : A 14-membered macrocyclic diterpene carrying an isopropyl group at C-1 and three symmetrically disposed methyl groups at C-4, -8 and -12.	2.02	1	diterpene
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.03	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.21	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	2.05	1	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	2.05	1	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	2.05	1	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.25	1	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
epothilone a Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).	2.21	1	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
4-hydroxyphenylmethylene hydantoin 4-hydroxyphenylmethylene hydantoin: isoalted from the Red Sea sponge Hemimycale arabica; structure in first source	2.06	1
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	2.05	1	bile acid taurine conjugate	human metabolite
cembrene a cembrene A: RN refers to (R-(E,E,E))-isomer; isolated from paracloacal glands of the Chinese alligator (Alligator sinensis); structure given in first source. (R)-cembrene A : A fourteen-membered macrocyclic diterpene consisting of 1,5,9-trimethyl-12-(prop-1-en-2-yl)cyclotetradecane having three endocyclic double bonds located at positions 1, 5 and 9.	2.05	1	cycloalkatriene; diterpene; macrocycle	animal metabolite; bacterial metabolite; coral metabolite
sarcophytol a sarcophytol A: structure given in first source; isolated from a soft coral Sarcophyton glaucum	2.71	3	cembrane diterpenoid
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	7.03	1	chalcogen; nonmetal atom	macronutrient
pregna-4,17-diene-3,16-dione, (17z)-isomer [no description available]	2.05	1
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	2.05	1	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
ngr peptide [no description available]	2.1	1

Condition	Relationship Strength	Studies
Malignant Melanoma [description not available]	2.03	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.03	1
Breast Cancer [description not available]	7.48	2
Cancer of Prostate [description not available]	2.06	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.48	2
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.06	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Absence Seizure [description not available]	2.25	1
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	2.25	1
B16 Melanoma [description not available]	2.49	2
Adenocarcinoma, Basal Cell [description not available]	2.1	1
Hepatocellular Carcinoma [description not available]	2.1	1
Cancer of Liver [description not available]	2.1	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.1	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.1	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.1	1
Angiogenesis, Pathologic [description not available]	2.1	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.05	1
Carcinoma, Epidermoid [description not available]	2.05	1
Cancer, Radiation-Induced [description not available]	2.05	1
Cancer of Skin [description not available]	2.74	3
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.05	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.74	3
Animal Mammary Carcinoma [description not available]	2.03	1
Papilloma, Squamous Cell [description not available]	2.03	1
Papilloma A circumscribed benign epithelial tumor projecting from the surrounding surface; more precisely, a benign epithelial neoplasm consisting of villous or arborescent outgrowths of fibrovascular stroma covered by neoplastic cells. (Stedman, 25th ed)	2.03	1

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