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7alpha,15-dihydroxydehydroabietic acid
- Family: Plantae - Pinaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Abietane Diterpene
| Canonical Smiles | OC(=O)[C@]1(C)CCC[C@]2([C@H]1C[C@@H](O)c1c2ccc(c1)C(O)(C)C)C |
|---|---|
| InChI | InChI=1S/C20H28O4/c1-18(2,24)12-6-7-14-13(10-12)15(21)11-16-19(14,3)8-5-9-20(16,4)17(22)23/h6-7,10,15-16,21,24H,5,8-9,11H2,1-4H3,(H,22,23)/t15-,16-,19-,20-/m1/s1 |
| InChIKey | ALGYTGOYQATWBA-XNFNUYLZSA-N |
| Formula | C20H28O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 332.44 |
| Rotatable Bonds | 2 |
| TPSA | 77.76 |
| LogP | 3.5 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 332.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cedrus atlantica | Pinaceae | Plantae | 123597 |
| 2 | Abies numidica | Pinaceae | Plantae | 88725 |
Showing of synonyms
7alpha,15-dihydroxydehydroabietic acid
155205-64-4
7|A,15-Dihydroxydehydroabietic acid
(1R,4aS,9R,10aR)-9-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-9-hydroxy-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-, (1R,4aS,9R,10aR)-
CHEMBL452778
HY-N7830
AKOS040761254
CS-0138250
- Maya B, Abedini A, et al. (2017). A new δ-tocotrienolic acid derivative and other constituents from the cones of Cedrus atlantica and their in vitro antimicrobial activity. Phytochemistry Letters, 2017, 20, 252-258. [View]
- 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]
No compound-protein relationship available.
SMILES: c1cccc(c12)CCC3C2CCCC3
Level: 0
Mol. Weight: 332.44 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.97
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.96
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -4.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.97
- Plasma Protein Binding
- 96.35
- 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
- 7.81
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.36
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.01
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.43
- Micronucleos
- Toxic
- 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
- -0.21
- Rat (Acute)
- 2.59
- Rat (Chronic Oral)
- 2.56
- Fathead Minnow
- 4.05
- 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
- 379.49
- Hydration Free Energy
- -6.99
- Log(D) at pH=7.4
- 0.24
- Log(P)
- 2.34
- Log S
- -3.51
- Log(Vapor Pressure)
- -8.58
- Melting Point
- 188.96
- pKa Acid
- 4.96
- pKa Basic
- 5.65
| 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 | 0.8716 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8363 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 4 | 0.8331 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8205 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 4 | 0.7689 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 3 | 0.7396 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7214 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7188 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7186 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7124 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 3 | 0.7009 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7009 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7002 |