15-hydroxy-9alpha,13alpha-epidioxyabiet-8(14)-en-18-oic acid - Compound Card

15-hydroxy-9alpha,13alpha-epidioxyabiet-8(14)-en-18-oic acid

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15-hydroxy-9alpha,13alpha-epidioxyabiet-8(14)-en-18-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles OC(=O)[C@]1(C)CCC[C@]2(C1CCC1=C[C@@]3(CC[C@]21OO3)C(O)(C)C)C
InChI InChI=1S/C20H30O5/c1-16(2,23)19-10-11-20(25-24-19)13(12-19)6-7-14-17(3,15(21)22)8-5-9-18(14,20)4/h12,14,23H,5-11H2,1-4H3,(H,21,22)/t14?,17-,18+,19+,20-/m1/s1
InChIKey FPDDUPUDFYVZHW-PSTOSHBPSA-N
Formula C20H30O5
HBA 4
HBD 2
MW 350.46
Rotatable Bonds 2
TPSA 75.99
LogP 3.61
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 350.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Juniperus species Cupressaceae Plantae 13100

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2004). Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry,2004,65,2507-2515. [View] [PubMed]
Pubchem: 162987389
Nmrshiftdb2: 80005129

No compound-protein relationship available.

Structure

SMILES: C1CC(OO2)C=C(C123)CCC4C3CCCC4

Level: 0

Mol. Weight: 350.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.58
Plasma Protein Binding
56.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.87
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.17
Rat (Acute)
2.45
Rat (Chronic Oral)
1.94
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
385.54
Hydration Free Energy
-6.5
Log(D) at pH=7.4
0.46
Log(P)
2.95
Log S
-4.19
Log(Vapor Pressure)
-7.54
Melting Point
202.27
pKa Acid
4.07
pKa Basic
7.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8665
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8665
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7726
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7726
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7587
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7587
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7396
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7396
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7353
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7353
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7180
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7180
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7179
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7179
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7099
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7099
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7074
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7074
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7022
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7022

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