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Ancistrobreviquinone A
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1cc(O)c2c(c1c1ccc(c3c1C=C(C)C(=O)C3=O)OC)C[C@H](N[C@@H]2C)C |
|---|---|
| InChI | InChI=1S/C24H25NO5/c1-11-8-15-14(6-7-18(29-4)22(15)24(28)23(11)27)21-16-9-12(2)25-13(3)20(16)17(26)10-19(21)30-5/h6-8,10,12-13,25-26H,9H2,1-5H3/t12-,13-/m1/s1 |
| InChIKey | GOTBRJYMVPPJIQ-CHWSQXEVSA-N |
| Formula | C24H25NO5 |
| HBA | 6 |
| HBD | 2 |
| MW | 407.47 |
| Rotatable Bonds | 3 |
| TPSA | 84.86 |
| LogP | 3.84 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 407.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus abbreviatus | Ancistrocladaceae | Plantae | 122295 |
Showing of synonyms
Ancistrobreviquinone A
- Fayez S, Cacciatore A, et al. (2021). Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against heLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus. Bioorganic & Medicinal Chemistry,2021, 30,115950. [View]
No compound-protein relationship available.
SMILES: C1=CC(=O)C(=O)c(c12)cccc2-c3cccc(c34)CNCC4
Level: 1
Mol. Weight: 407.47 g/mol
SMILES: c1cccc(c12)C=CC(=O)C2=O
Level: 0
Mol. Weight: 407.47 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 407.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.810
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.980
- Plasma Protein Binding
- 75.95
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.960
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.690
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.280
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.830
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -28.220
- Rat (Acute)
- 2.580
- Rat (Chronic Oral)
- 2.140
- Fathead Minnow
- 4.960
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 472.880
- Hydration Free Energy
- -5.660
- Log(D) at pH=7.4
- 3.120
- Log(P)
- 2.99
- Log S
- -4.17
- Log(Vapor Pressure)
- -8.98
- Melting Point
- 203.97
- pKa Acid
- 7.01
- pKa Basic
- 6.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9436 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9287 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9179 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8608 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7967 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7803 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7737 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7553 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7527 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7413 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7360 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7238 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7213 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7094 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7072 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7045 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7034 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7027 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7006 |