Methyl-12-oxo-8alpha,15-dihydroxyabiet-13-en-19-oate - Compound Card

Methyl-12-oxo-8alpha,15-dihydroxyabiet-13-en-19-oate

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Methyl-12-oxo-8alpha,15-dihydroxyabiet-13-en-19-oate

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@@]1(C)CCC[C@]2(C1CC[C@]1([C@@H]2CC(=O)C(=C1)C(O)(C)C)O)C
InChI InChI=1S/C21H32O5/c1-18(2,24)13-12-21(25)10-7-15-19(3,16(21)11-14(13)22)8-6-9-20(15,4)17(23)26-5/h12,15-16,24-25H,6-11H2,1-5H3/t15?,16-,19+,20+,21+/m1/s1
InChIKey KGNBAPXGJMTHCJ-SOSHZCIPSA-N
Formula C21H32O5
HBA 5
HBD 2
MW 364.48
Rotatable Bonds 2
TPSA 83.83
LogP 2.78
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 364.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Juniperus phoenicea Cupressaceae Plantae 61308

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: 11222281
Nmrshiftdb2: 60071533

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)CC(C12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 364.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.39
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
62.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.170
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.140
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
-3.580
Rat (Acute)
3.250
Rat (Chronic Oral)
1.820
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
399.170
Hydration Free Energy
-7.020
Log(D) at pH=7.4
2.590
Log(P)
2.73
Log S
-3.16
Log(Vapor Pressure)
-6.49
Melting Point
173.05
pKa Acid
8.71
pKa Basic
4.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9099
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9099
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7421
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7421
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7319
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7319
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7303
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7303
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7055
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7055

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