Methyl-15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate - Compound Card

Methyl-15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate

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Methyl-15-hydroxy-8alpha,12alpha-epidioxiabiet-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@]13[C@@H]2C[C@H](OO1)C(=C3)C(O)(C)C)C
InChI InChI=1S/C21H32O5/c1-18(2,23)13-12-21-10-7-15-19(3,16(21)11-14(13)25-26-21)8-6-9-20(15,4)17(22)24-5/h12,14-16,23H,6-11H2,1-5H3/t14-,15?,16+,19-,20-,21-/m0/s1
InChIKey IOWHRFKVRZOMCP-SKTKMLTQSA-N
Formula C21H32O5
HBA 5
HBD 1
MW 364.48
Rotatable Bonds 2
TPSA 64.99
LogP 3.55
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.86
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: 162975263
Nmrshiftdb2: 60071536

No compound-protein relationship available.

Structure

SMILES: C1=CC(OO2)CC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 364.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
53.17
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
11.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.990
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
-4.340
Rat (Acute)
2.330
Rat (Chronic Oral)
1.700
Fathead Minnow
3.920
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
393.450
Hydration Free Energy
-4.810
Log(D) at pH=7.4
3.150
Log(P)
3.59
Log S
-4.55
Log(Vapor Pressure)
-6.32
Melting Point
150.43
pKa Acid
9.79
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8543
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8543
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8207
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8207
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8181
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8181
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8138
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8138
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8127
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8127
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7910
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7910
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7822
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7822
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7715
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7715
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7703
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7703
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7699
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7699
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7644
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7644
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7625
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7600
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7600
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7579
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7579
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7476
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7476
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7447
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7447
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7410
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7410
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7387
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7387
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7343
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7343
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7309
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7301
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7301
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7300
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7300
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7142
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7142
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7135
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7135
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7114
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7114
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7081
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7081
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7048
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7048
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7023
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7023
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7008
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7008

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