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Beilschmiedic acid A
- Family: Plantae - Lauraceae
- Kingdom: Plantae
-
Class: Polycyclic
- Subclass: Endiandric Acid Derivative
| Canonical Smiles | CCCCCCCC[C@@H]1[C@H]2C=C[C@@H]3[C@@H]4[C@H]2[C@H]1C[C@H]4[C@@H](O)C=C3C(=O)O |
|---|---|
| InChI | InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-13-14-9-10-15-17(22(24)25)12-19(23)18-11-16(13)20(14)21(15)18/h9-10,12-16,18-21,23H,2-8,11H2,1H3,(H,24,25)/t13-,14-,15+,16+,18+,19+,20-,21+/m1/s1 |
| InChIKey | SBFRUSBMDXTFNO-KIBIGZOQSA-N |
| Formula | C22H32O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 344.5 |
| Rotatable Bonds | 8 |
| TPSA | 57.53 |
| LogP | 4.42 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.77 |
| Exact Mass | 344.24 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Beilschmiedia anacardioides | Lauraceae | Plantae | 88849 |
| 2 | Beilschmiedia louisii | Lauraceae | Plantae | 88849 |
Showing of synonyms
Beilschmiedic acid A
Beilschmiedate a
(1S,2S,3R,6R,9R,10R,11S,12S)-9-hydroxy-2-octyltetracyclo(8.2.1.03,12.06,11)trideca-4,7-diene-7-carboxylic acid
(1S,2S,3R,6R,9R,10R,11S,12S)-9-hydroxy-2-octyltetracyclo[8.2.1.03,12.06,11]trideca-4,7-diene-7-carboxylic acid
1162678-17-2
CHEMBL2071413
- Chouna JR, Nkeng-Efouet PA, et al. (2009). Antibacterial endiandric acid derivatives from Beilschmiedia anacardioides.. Phytochemistry,2009, 70(5), 684-688. [View] [PubMed]
- Waleguele CC, Mba'ning BM, et al. (2020). Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae). Molecules. 2020, 25(12), 2862. [View] [PubMed]
Pubchem:
42646683
Cas:
1162678-17-2
Zinc:
ZINC000084671593
Nmrshiftdb2:
70054966
Chembl:
CHEMBL2071413
No compound-protein relationship available.
SMILES: C12C3CC1C=CC4C2C(C3)CC=C4
Level: 0
Mol. Weight: 344.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.02
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.56
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.62
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.16
- Plasma Protein Binding
- 82.75
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -1.15
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.08
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.04
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 3.71
- 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
- -1.23
- Rat (Acute)
- 2.6
- Rat (Chronic Oral)
- 2.73
- Fathead Minnow
- 3.96
- 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
- 421.43
- Hydration Free Energy
- -4.28
- Log(D) at pH=7.4
- 2.88
- Log(P)
- 6.04
- Log S
- -4.74
- Log(Vapor Pressure)
- -8.2
- Melting Point
- 138.92
- pKa Acid
- 4.21
- pKa Basic
- 6.38
| 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 | 0.9211 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8799 |
| Vitamin D3 receptor | P13053 | VDR_RAT | Rattus norvegicus | 3 | 0.8616 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8538 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.8463 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8084 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8074 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8023 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7979 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7904 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.7794 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7768 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7740 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7731 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7701 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7682 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7673 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7659 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7597 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7574 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7562 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7531 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7520 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7462 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7457 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7439 |
| Hemolymph juvenile hormone binding protein | Q9U556 | Q9U556_BOMMO | Bombyx mori | 3 | 0.7400 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7357 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7344 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7214 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7202 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7199 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7172 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7138 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7120 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7097 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7076 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7006 |