isocupressic acid

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

Description

isocupressic acid: a labdane that induces premature LABOR [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	6438138
CHEMBL ID	511193
SCHEMBL ID	13532265
MeSH ID	M0287138

Synonyms (24)

Synonym
isocupressic acid
isocupressicacid
CHEMBL511193
(1s,4ar,5s,8ar)-5-[(e)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2h-naphthalene-1-carboxylic acid
1-naphthalenecarboxylic acid, decahydro-5-((3e)-5-hydroxy-3-methyl-3-pentenyl)-1,4a-dimethyl-6-methylene-, (1s,4ar,5s,8ar)-
15-hydroxylabda-8(17),13-dien-19-oic acid
1909-91-7
6dv5el78he ,
unii-6dv5el78he
1-naphthalenecarboxylic acid, decahydro-5-(5-hydroxy-3-methyl-3-pentenyl)-1,4a-dimethyl-6-methylene-, (1s-(1alpha,4aalpha,5alpha(e),8abeta))-
SCHEMBL13532265
AKOS032948527
Q15426267
labda-8(20),13-dien-19-oic acid, 15-hydroxy-, (e)- (8ci); (1s,4ar,5s,8ar)-decahydro-5-[(3e)-5-hydroxy-3-methyl-3-penten-1-yl]-1,4a-dimethyl-6-methylene-1-naphthalenecarboxylic acid
HY-N3493
CS-0024374
(1s,4ar,5s,8ar)-decahydro-5-[(3e)-5-hydroxy-3-methyl-3-penten-1-yl]-1,4a-dimethyl-6-methylene-1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid, decahydro-5-(5-hydroxy-3-methyl-3-pentenyl)-1,4a-dimethyl-6-methylene-, (1s-(1.alpha.,4a.alpha.,5.alpha.(e),8a.beta.))-
(+)-isocupressic acid
labda-8(20),13-dien-19-oic acid, 15-hydroxy-, (e)-
isocupressic acid, (+)-
1-naphthalenecarboxylic acid, decahydro-5-[(3e)-5-hydroxy-3-methyl-3-penten-1-yl]-1,4a-dimethyl-6-methylene-, (1s,4ar,5s,8ar)-
DTXSID901045341
FS-10528

Research Excerpts

Dosage Studied

Excerpt	Relevance	Reference
" One assay was used to follow the absorption and elimination profile of isocupressic acid metabolites in both cow serum and urine after oral dosage of a cow with common juniper."	( Development of enzyme-linked immunosorbent assays for isocupressic acid and serum metabolites of isocupressic acid. Gardner, DR; Garrosian, M; Lee, ST; Panter, KE; Schoch, TK; Serrequi, AN; Stegelmeier, BL, 2003)	0.8
" When pine needles are dosed orally to cattle, no ICA is detected in their serum, whereas AGA is readily detected."	( A comparison of the metabolism of the abortifacient compounds from Ponderosa pine needles in conditioned versus naive cattle. Gardner, DR; Hall, JO; Panter, KE; Pfister, JA; Welch, KD; Zieglar, J, 2012)	0.38

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

Bioassays (18)

Assay ID	Title	Year	Journal	Article
AID750854	Cytotoxicity against human SMMC7721 cells after 48 hrs by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Diterpenoids from the twigs and leaves of Fokienia hodginsii.
AID1657513	Anti-inflammatory activity against human neutrophils assessed as inhibition of fMLF/CB-induced superoxide anion generation at 10 uM preincubated for 5 mins followed by fMLF addition after priming with CB for 3 mins and measured after 10 mins by spectropho	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID1657512	Anti-inflammatory activity against human neutrophils assessed as inhibition of fMLF/CB-induced superoxide anion generation preincubated for 5 mins followed by fMLF addition after priming with CB for 3 mins and measured after 10 mins by spectrophotometric	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID401216	Induction of membrane modification in erythrocytes assessed as formation of discocyte shape change at 12.5 ug/mL after 48 hrs by phase contrast light microscopy	2004	Journal of natural products, Apr, Volume: 67, Issue:4	Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
AID401212	Induction of membrane modification in erythrocytes assessed as formation of discocyte shape change at 25 ug/mL after 48 hrs by phase contrast light microscopy	2004	Journal of natural products, Apr, Volume: 67, Issue:4	Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
AID1657515	Anti-inflammatory activity against human neutrophils assessed as inhibition in fMLF/CB-induced elastase release at 10 uM preincubated for 5 mins followed by fMLF addition after priming with CB for 3 mins and measured after 10 mins by spectrophotometric an	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID750851	Cytotoxicity against human SW480 cells after 48 hrs by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Diterpenoids from the twigs and leaves of Fokienia hodginsii.
AID750853	Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Diterpenoids from the twigs and leaves of Fokienia hodginsii.
AID750855	Cytotoxicity against human HL60 cells after 48 hrs by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Diterpenoids from the twigs and leaves of Fokienia hodginsii.
AID404064	Cytotoxicity against mouse 26-L5 cells after 24 hrs by MTT assay	1998	Journal of natural products, Jul, Volume: 61, Issue:7	Chemical constituents of Brazilian propolis and their cytotoxic activities.
AID401198	Induction of membrane modification in erythrocytes assessed as formation of stomatocyte type 2 shape change at 100 ug/mL after 48 hrs by phase contrast light microscopy	2004	Journal of natural products, Apr, Volume: 67, Issue:4	Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
AID750852	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	2013	Journal of natural products, Jun-28, Volume: 76, Issue:6	Diterpenoids from the twigs and leaves of Fokienia hodginsii.
AID1657510	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell viability by MTT assay	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID400961	Antiplasmodial activity against Plasmodium falciparum 3D7 by [3H]phenylalanine uptake	2004	Journal of natural products, Apr, Volume: 67, Issue:4	Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
AID1657509	Antiproliferative activity against human HepG2 cells assessed as inhibition of cell viability by MTT assay	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID401206	Induction of membrane modification in erythrocytes assessed as formation of discocyte shape change at 50 ug/mL after 48 hrs by phase contrast light microscopy	2004	Journal of natural products, Apr, Volume: 67, Issue:4	Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells.
AID1657511	Antiproliferative activity against human A549 cells assessed as inhibition of cell viability by MTT assay	2020	Bioorganic & medicinal chemistry letters, 05-15, Volume: 30, Issue:10
AID404063	Cytotoxicity against human HT1080 cells after 24 hrs by MTT assay	1998	Journal of natural products, Jul, Volume: 61, Issue:7	Chemical constituents of Brazilian propolis and their cytotoxic activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	6 (26.09)	18.2507
2000's	5 (21.74)	29.6817
2010's	10 (43.48)	24.3611
2020's	2 (8.70)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.93

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	24.93 (24.57)
Research Supply Index	3.18 (2.92)
Research Growth Index	4.78 (4.65)
Search Engine Demand Index	26.67 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (24.93)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (8.70%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	21 (91.30%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.02	1	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	4.36	3	abietane diterpenoid; monocarboxylic acid	plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.81	3	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
phenalen-1-one phenalen-1-one: fossil fuel combustion product	2.08	1
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	2.01	1	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
arctigenin arctigenin: precursor to catechols; in many plants	2.25	1	lignan
cedrol cedrol: a cyclic terpenoid from cedarwood oil; 8-epicedrol is an epimer	3.16	1	cedrane sesquiterpenoid; tertiary alcohol
ambrox ambrox: structure in first source	3.16	1	naphthofuran
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.63	2	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
pinusolide pinusolide: RN given for (1S-(1alpha,4aalpha,5a,8abeta))-isomer; structure in first source	2.02	1	diterpene lactone	metabolite
sclareol sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.	3.16	1	labdane diterpenoid	antifungal agent; antimicrobial agent; apoptosis inducer; fragrance; plant metabolite
sandaracopimaric acid sandaracopimaric acid: a terpenoid from Sagittaria sanittifolia L.. sandaracopimaric acid : A pimarane diterpenoid that is (1S,4aS,4bS,7R,10aS)-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene carrying a carboxy group at position 1 and a vinyl group at position 7. It is a natural product found in several plant species.	2.48	2	monocarboxylic acid; pimarane diterpenoid; tricyclic diterpenoid	plant metabolite
anthricin anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source. deoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group.	3.05	4	furonaphthodioxole; gamma-lactone; lignan; methoxybenzenes	antineoplastic agent; apoptosis inducer; plant metabolite
ferruginol ferruginol: structure in first source. ferruginol : An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.	2.08	1	abietane diterpenoid; carbotricyclic compound; meroterpenoid; phenols	antibacterial agent; antineoplastic agent; plant metabolite; protective agent
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.21	1
doxorubicin hydrochloride [no description available]	1.99	1	anthracycline
communic acid communic acid: structure in first source	2.81	3
hc 030031 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide: a TRPA1 channel blocker	2.08	1
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	1.99	1	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
kaempferide kaempferide: structure in first source. kaempferide : A monomethoxyflavone that is the 4'-O-methyl derivative of kaempferol.	1.99	1	7-hydroxyflavonol; monomethoxyflavone; trihydroxyflavone	antihypertensive agent; metabolite
sclareolide sclareolide: has antineoplastic activity; synthesized by oxidation of sclareol; a minor constituent of Arnica angustifolia and Sideritis nutans; structure in first source	3.16	1
ermanin ermanin: from Tanacetum microphyllum; structure given in first source. 3,4'-dimethylkaempferol : A dimethoxyflavone that is kaempferol in which the hydroxy groups at position 3 and 4' have been replaced by methoxy groups. It is a component of bee glue and isolated from several plant species including Tanacetum microphyllum.	1.99	1	dihydroxyflavone; dimethoxyflavone	anti-inflammatory agent; antimycobacterial drug; antineoplastic agent; apoptosis inducer; plant metabolite
artepillin c artepillin C: RN refers to (E)-isomer	1.99	1
labdane labdane: from Croton joufra; structure in first source	2.15	1	diterpene; terpenoid fundamental parent
stemodin stemodin: structure given in first source; isolated from Stemodia maritima; a major stemodane diterpene; RN given for (2alpha,5alpha,9beta,13alpha,17beta)-isomer	3.16	1
stemodinone stemodinone: RN given for (4aS-(4aalpha,6abeta,8alpha,9alpha,11aalpha,11bbeta))-isomer; structure in first source	3.16	1
agathic acid agathic acid: labdane; RN given for (1S-(1alpha,4aalpha,5alpha(E),8abeta))-isomer; metabolite of isocupressic acid; structure in first source	3.14	5
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	3.1	1

Condition	Relationship Strength	Studies
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.44	8
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	2.21	1
Breast Cancer [description not available]	2.11	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.11	1
Abortion, Veterinary Premature expulsion of the FETUS in animals.	3.12	5
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	2.11	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.01	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.91	1
Bovine Diseases [description not available]	2.01	1

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