15-hydroxydehydroabietic acid - Compound Card

15-hydroxydehydroabietic acid

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15-hydroxydehydroabietic acid

Structure
Zoomed Structure
  • Family: Plantae - Pinaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Abietane Diterpene
Canonical Smiles OC(=O)[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(O)(C)C)C
InChI InChI=1S/C20H28O3/c1-18(2,23)14-7-8-15-13(12-14)6-9-16-19(15,3)10-5-11-20(16,4)17(21)22/h7-8,12,16,23H,5-6,9-11H2,1-4H3,(H,21,22)/t16-,19-,20-/m1/s1
InChIKey ILQLITDRYFHAGM-NSISKUIASA-N
Formula C20H28O3
HBA 2
HBD 2
MW 316.44
Rotatable Bonds 2
TPSA 57.53
LogP 4.01
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 316.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Abies numidica Pinaceae Plantae 88725

Showing of synonyms

  • Belhadj Mostefa M, Abedini A, et al. (2017). Abietane diterpenes from the cones of Abies numidica de Lannoy ex Carrière (Pinaceae) and in vitro evaluation of their antimicrobial properties. Natural product research, 2017, 31(5), 568-571. [View] [PubMed]
Pubchem: 14487943
Nmrshiftdb2: 60032544
Bindingdb: 50465338

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCC3C2CCCC3

Level: 0

Mol. Weight: 316.44 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.53
Plasma Protein Binding
98.95
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
6.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.33
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.23
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.69
Rat (Acute)
2.54
Rat (Chronic Oral)
2.38
Fathead Minnow
3.97
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
356.28
Hydration Free Energy
-5.98
Log(D) at pH=7.4
1.14
Log(P)
3.08
Log S
-4.34
Log(Vapor Pressure)
-7.8
Melting Point
173.65
pKa Acid
5.83
pKa Basic
5.42
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 0.8417
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.8223
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.8151
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7741
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7407
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7377
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7333
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7260
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7162
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7136

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