Methyl-12-oxo-8alpha-hydroxyabiet-13-en-19-oate - Compound Card

Methyl-12-oxo-8alpha-hydroxyabiet-13-en-19-oate

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Methyl-12-oxo-8alpha-hydroxyabiet-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(C)C)O)C
InChI InChI=1S/C21H32O4/c1-13(2)14-12-21(24)10-7-16-19(3,17(21)11-15(14)22)8-6-9-20(16,4)18(23)25-5/h12-13,16-17,24H,6-11H2,1-5H3/t16?,17-,19+,20+,21+/m1/s1
InChIKey HDHZYDQBOSLOST-UQRZPSQFSA-N
Formula C21H32O4
HBA 4
HBD 1
MW 348.48
Rotatable Bonds 2
TPSA 63.6
LogP 3.67
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 348.23
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: 11382475
Nmrshiftdb2: 60071537

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 348.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
67.93
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.190
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.190
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
-2.390
Rat (Acute)
2.530
Rat (Chronic Oral)
1.920
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
390.850
Hydration Free Energy
-5.160
Log(D) at pH=7.4
3.480
Log(P)
4.11
Log S
-3.98
Log(Vapor Pressure)
-6.0
Melting Point
144.32
pKa Acid
9.25
pKa Basic
4.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8531
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8531
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7590
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7590
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7314
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7314
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7255
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7255
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7221
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7221
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7121
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7121

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