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7-oxo-15-hydroxydehydroabietic acid
- Family: Plantae - Pinaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpene
| Canonical Smiles | OC(=O)[C@]1(C)CCC[C@]2([C@H]1CC(=O)c1c2ccc(c1)C(C)C)C |
|---|---|
| InChI | InChI=1S/C20H26O3/c1-12(2)13-6-7-15-14(10-13)16(21)11-17-19(15,3)8-5-9-20(17,4)18(22)23/h6-7,10,12,17H,5,8-9,11H2,1-4H3,(H,22,23)/t17-,19-,20-/m1/s1 |
| InChIKey | MSWJSDLNPCSSNW-MISYRCLQSA-N |
| Formula | C20H26O3 |
| HBA | 2 |
| HBD | 1 |
| MW | 314.43 |
| Rotatable Bonds | 2 |
| TPSA | 54.37 |
| LogP | 4.55 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 314.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cedrus atlantica | Pinaceae | Plantae | 123597 |
| 2 | Desmodium uncinatum | Leguminosae/Fabaceae | Plantae | 225101 |
| 3 | Araucaria bidwillii | Araucariaceae | Plantae | 56993 |
Showing of synonyms
7-oxo-15-hydroxydehydroabietic acid
7-OXODEHYDROABIETIC ACID
18684-55-4
7-Ketodehydroabietic acid
I8PNL8FLID
BRN 3216723
7-ketodehydro-abietic acid
13-Isopropyl-7-oxopodocarpa-8,11,13-trien-15-oic acid
Podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-
4-10-00-02942 (Beilstein Handbook Reference)
(1R,4AS,10AR)-1,4A-DIMETHYL-9-OXO-7-(PROPAN-2-YL)-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE-1-CARBOXYLIC ACID
15654-55-4
898-391-3
(1R,4aS,10aR)-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-9-oxo-, (1R,4aS,10aR)-
UNII-I8PNL8FLID
7-oxocallitrisic acid
CHEMBL597919
SCHEMBL3212768
DTXSID5075074
MSK162040
AKOS027324385
FS-8481
DA-60583
PD207163
HY-133620
CS-0128446
H26716
EN300-6733727
Q27280582
7-Oxodehydroabietic acidPodocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-7-oxo-
- 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]
- Guchu SM, Yenesew A, et al. (2007). C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum.. Phytochemistry,2007,68(5),646-651. [View] [PubMed]
- Ebada S, Talaat A, et al. (2017). Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. Tetrahedron, 2017, 73(21), 3048-3055. [View]
Pubchem:
29212
Cas:
18684-55-4
Zinc:
ZINC000005447545
Nmrshiftdb2:
60032537
Chembl:
CHEMBL597919
Comptox:
DTXSID5075074
CPRiL:
449488
SMILES: c1cccc(c12)C3C(CC2=O)CCCC3
Level: 0
Mol. Weight: 314.43 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.48
- Plasma Protein Binding
- 99.36
- 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
- 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
- 5.84
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.8
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.02
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.63
- 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
- 1.42
- Rat (Acute)
- 2.15
- Rat (Chronic Oral)
- 2.3
- Fathead Minnow
- 4.0
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 368.12
- Hydration Free Energy
- -7.97
- Log(D) at pH=7.4
- 1.47
- Log(P)
- 4.56
- Log S
- -4.59
- Log(Vapor Pressure)
- -7.77
- Melting Point
- 170.25
- pKa Acid
- 5.02
- pKa Basic
- 5.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8123 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8123 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8004 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8004 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7422 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7422 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7146 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7146 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7134 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7134 |