subamolide a profile

subamolide A: cytotoxic constituent of the stems of Cinnamomum subavenium; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	16104909
CHEMBL ID	218924
SCHEMBL ID	12319740
MeSH ID	M0507354

Synonym
subamolide a
CHEMBL218924
SCHEMBL12319740
bdbm50559078
(3z,4r,5r)-4-hydroxy-5-methoxy-5-methyl-3-tetradecylideneoxolan-2-one

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Tyrosinase	Homo sapiens (human)	IC50 (µMol)	1.0000	0.0230	4.4593	10.0000	AID1717710
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
melanin biosynthetic process from tyrosine	Tyrosinase	Homo sapiens (human)
eye pigment biosynthetic process	Tyrosinase	Homo sapiens (human)
visual perception	Tyrosinase	Homo sapiens (human)
cell population proliferation	Tyrosinase	Homo sapiens (human)
response to UV	Tyrosinase	Homo sapiens (human)
response to blue light	Tyrosinase	Homo sapiens (human)
response to vitamin D	Tyrosinase	Homo sapiens (human)
melanin biosynthetic process	Tyrosinase	Homo sapiens (human)
thymus development	Tyrosinase	Homo sapiens (human)
response to cAMP	Tyrosinase	Homo sapiens (human)
pigmentation	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
tyrosinase activity	Tyrosinase	Homo sapiens (human)
copper ion binding	Tyrosinase	Homo sapiens (human)
protein binding	Tyrosinase	Homo sapiens (human)
identical protein binding	Tyrosinase	Homo sapiens (human)
protein homodimerization activity	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Tyrosinase	Homo sapiens (human)
lysosome	Tyrosinase	Homo sapiens (human)
Golgi-associated vesicle	Tyrosinase	Homo sapiens (human)
melanosome membrane	Tyrosinase	Homo sapiens (human)
melanosome	Tyrosinase	Homo sapiens (human)
intracellular membrane-bounded organelle	Tyrosinase	Homo sapiens (human)
perinuclear region of cytoplasm	Tyrosinase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay ID	Title	Year	Journal	Article
AID275111	Cell cycle arrest in SW480 cells by accumulation at S phase at 75 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275116	Cell cycle arrest in SW480 cells by accumulation at G2/M phase at 100 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275108	Cell cycle arrest in SW480 cells by accumulation at G1 phase at 100 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275103	DNA damage assessed as accumulation in subG1 level of cell cycle arrest in SW480 cells at 75 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275110	Cell cycle arrest in SW480 cells by accumulation at S phase at 50 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275104	DNA damage assessed as accumulation in subG1 level of cell cycle arrest in SW480 cells at 100 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID1717710	Inhibition of tyrosinase in human neonatal foreskin epidermal melanocyte cells using L-tyrosine and L-DOPA as substrate preincubated for 2 days followed by cell lysis and subsequent substrate addition and measured after 3 hr by spectrophotometric method	2020	Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22	Advances in the Design of Genuine Human Tyrosinase Inhibitors for Targeting Melanogenesis and Related Pigmentations.
AID275112	Cell cycle arrest in SW480 cells by accumulation at S phase at 100 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID1611941	Inhibition of tyrosinase in zebrafish assessed as reduction in pigmentation level at 10 uM	2018	Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17	Inhibitors of Melanogenesis: An Updated Review.
AID275101	DNA damage assessed as accumulation in subG1 level of cell cycle arrest in SW480 cells at 25 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275106	Cell cycle arrest in SW480 cells by accumulation at G1 phase at 50 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275107	Cell cycle arrest in SW480 cells by accumulation at G1 phase at 75 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275109	Cell cycle arrest in SW480 cells by accumulation at S phase at 25 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275102	DNA damage assessed as accumulation in subG1 level of cell cycle arrest in SW480 cells at 50 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275105	Cell cycle arrest in SW480 cells by accumulation at G1 phase at 25 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID1611956	Inhibition of tyrosinase in human epidemal melanocytes assessed as reduction in melanin formation at 1 uM	2018	Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17	Inhibitors of Melanogenesis: An Updated Review.
AID275113	Cell cycle arrest in SW480 cells by accumulation at G2/M phase at 25 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID275114	Cell cycle arrest in SW480 cells by accumulation at G2/M phase at 50 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
AID1611940	Inhibition of human tyrosinase at 1 uM using L-tyrosine as substrate after 30 mins by ELISA relative to control	2018	Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17	Inhibitors of Melanogenesis: An Updated Review.
AID275115	Cell cycle arrest in SW480 cells by accumulation at G2/M phase at 75 uM after 24 hrs by propidium iodide staining	2007	Journal of natural products, Jan, Volume: 70, Issue:1	Cytotoxic constituents of the stems of Cinnamomum subavenium.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (20.00)	29.6817
2010's	3 (60.00)	24.3611
2020's	1 (20.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (40.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	3 (60.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	3.35	1	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
hydroquinone [no description available]	4.22	2	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hexylresorcinol [no description available]	3.35	1	resorcinols
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	3.27	1	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
kojic acid [no description available]	4.22	2	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
pd 169316 2-(4-nitrophenyl)-4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-imidazole: p38 MAP kinase inhibitor	3.27	1	imidazoles
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	3.35	1	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	3.27	1	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
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.	2.74	3	butan-4-olide	metabolite; neurotoxin
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.35	1	phenols	allergen
gamma-thujaplicin 2-hydroxy-5-isopropyl- 2,4,6-cycloheptatrienone: a metal chelating agent	3.27	1	cyclic ketone
3-hydroxy-1-benzopyran-2-one 3-hydroxycoumarin: Photoprotective from sea urchin gametes and embryonic cells; structure in first source. hydroxycoumarin : Any coumarin carrying at least one hydroxy substituent.	3.35	1	hydroxycoumarin
deoxycytidine [no description available]	2.06	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.06	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
1-hydroxy-2(1h)-pyridinone 1-hydroxy-2(1H)-pyridinone: structure in first source	4.22	2
alpha-thujaplicin alpha-thujaplicin: structure in first source	3.27	1
salicylideneaniline salicylideneaniline: structure in first source	3.27	1
sb 203580 [no description available]	3.27	1	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
moracin m moracin M: has been isolated from Morus alba L.; structure in first source	3.27	1	benzofurans
4-n-butylresorcinol 4-n-butylresorcinol: structure in first source	4.22	2	resorcinols
mimosine L-mimosine : An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.	3.35	1	4-pyridones; amino acid zwitterion; non-proteinogenic L-alpha-amino acid	EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	4.22	2	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	4.22	2	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
6-hydroxyindole 6-hydroxyindole: structure in first source	3.35	1
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	4.22	2	4-coumaric acid	food component; mouse metabolite; plant metabolite
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	3.35	1	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	3.35	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
luteolin [no description available]	3.35	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
hispidol hispidol : A hydroxyaurone that is aurone substituted by hydroxy groups at positions 6 and 4' respectively.	3.27	1	hydroxyaurone	plant metabolite
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	3.35	1	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	4.22	2	stilbenoid
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	4.22	2	4-coumaric acid methyl ester
mulberroside a mulberroside A: structure in first source	3.27	1	glycoside; stilbenoid
morachalcone a morachalcone A: tyrosinase inhibitor from the wood of Artocarpus heterophyllus; structure in first source	3.27	1	chalcones
ginsenoside rb1 [no description available]	3.27	1	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
2,4,2',4'-Tetrahydroxychalcone [no description available]	3.27	1	chalcones
4-(1-phenylethyl)resorcinol 4-(1-phenylethyl)resorcinol: a depigmenting agent for treatment of solar lentigines; structure in first source	3.35	1
3-hydroxyphloretin 3-hydroxyphloretin: compound from Formosan apple that reduces tyrosinase activity in human epidermal melanocytes; structure in first source	3.35	1	chalcones
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.06	1
feruloyldopamine feruloyldopamine: a dopamine metabolite isolated from tomatoes after infection by Pseudomonas syringae; structure in first source	3.35	1

Condition	Relationship Strength	Studies
Malignant Melanoma [description not available]	3.17	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)	3.17	1
Carcinoma, Anaplastic [description not available]	2.06	1
Cancer of the Urinary Tract [description not available]	2.06	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	7.06	1

subamolide a

Description

Cross-References

Synonyms (5)

Protein Targets (1)

Inhibition Measurements

Biological Processes (11)

Molecular Functions (5)

Ceullar Components (7)

Bioassays (20)

Research

Studies (5)

Market Indicators

Research Demand Index: 13.28

Study Types

subamolide a

Description

Cross-References

Synonyms (5)

Protein Targets (1)

Inhibition Measurements

Biological Processes (11)

Molecular Functions (5)

Ceullar Components (7)

Bioassays (20)

Research

Studies (5)

Market Indicators

Research Demand Index: 13.28

Study Types

Related Drugs (40)

Related Conditions (5)