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Vasicinone
- Family: Plantae - Acanthaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinazoline Alkaloid
| Canonical Smiles | O[C@H]1CCn2c1nc1ccccc1c2=O |
|---|---|
| InChI | InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1 |
| InChIKey | SDIVYZXRQHWCKF-VIFPVBQESA-N |
| Formula | C11H10N2O2 |
| HBA | 4 |
| HBD | 1 |
| MW | 202.21 |
| Rotatable Bonds | 0 |
| TPSA | 55.12 |
| LogP | 0.83 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 202.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Adhatoda vasica | Acanthaceae | Plantae | 141317 |
Showing of synonyms
Vasicinone
486-64-6
L-Vasicinone
(-)-Vasicinone
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
UNII-G6T5819NXM
G6T5819NXM
Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3-hydroxy-, (R)-
PYRROLO(2,1-.BETA.)QUINAZOLIN-9(1H)-ONE, 2,3-DIHYDRO-3-HYDROXY-, (3S)-
(3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo(2,1-b)quinazolin-9-one
VASICINONE (CONSTITUENT OF MALABAR NUT TREE, LEAF)
PYRROLO(2,1-BETA)QUINAZOLIN-9(1H)-ONE, 2,3-DIHYDRO-3-HYDROXY-, (3S)-
CHEBI:9936
(3R)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
C10744
(S)-3-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
AC1L9DON
Vasicinone (Standard)
3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
Vasicinone, analytical standard
CHEMBL3120244
HY-N1100R
DTXSID80964090
HY-N1100
MSK191187
ZINC00265484
AKOS030485960
DA-58962
MS-23092
XV164987
CS-0016388
E80802
Q15427947
(3S)-3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one
(3S)-2,3-dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one
- Ali S.K, Hamed A.R, et al. (2016). Kinetics and molecular docking of vasicine from Adhatoda vasica: Anacetylcholinesterase inhibitor for Alzheimer's disease. South African Journal of Botany, 2016, 104, 118–124. [View]
Pubchem:
442935
Cas:
486-64-6
Gnps:
CCMSLIB00006390124
Zinc:
ZINC000100064968
Kegg Ligand:
C10744
Chebi:
9936
Nmrshiftdb2:
60021267
Chembl:
CHEMBL3120244
CPRiL:
93287
SMILES: C1CCn(c12)c(=O)c3c(n2)cccc3
Level: 0
Mol. Weight: 202.21 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.66
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.07
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.58
- Plasma Protein Binding
- 52.12
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- Non-Inhibitor
- CYP 2D6 Substrate
- 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
- Safe
- Bioconcentration Factor
- 0.77
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.52
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.77
- 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
- 1.0
- Rat (Acute)
- 2.39
- Rat (Chronic Oral)
- 1.48
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 362.99
- Hydration Free Energy
- -11.39
- Log(D) at pH=7.4
- 0.53
- Log(P)
- 0.68
- Log S
- -1.93
- Log(Vapor Pressure)
- -7.14
- Melting Point
- 197.82
- pKa Acid
- 11.02
- pKa Basic
- 5.04
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 3 | 0.9439 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.9370 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9342 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 4 | 0.9162 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.9058 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8876 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8836 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8760 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8712 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8655 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.8649 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8645 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8639 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8575 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8536 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8535 |
| Thiosulfate reductase | Q72LA4 | Q72LA4_THET2 | Thermus thermophilus | 3 | 0.8462 |
| D(3) dopamine receptor | P35462 | DRD3_HUMAN | Homo sapiens | 3 | 0.8431 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8359 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8350 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8316 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8244 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.8185 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.8170 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8129 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.8063 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7998 |
| Dihydroorotate dehydrogenase (quinone), mitochondrial | Q08210 | PYRD_PLAF7 | Plasmodium falciparum | 3 | 0.7993 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7983 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7968 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7964 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7940 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7940 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7931 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7919 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7876 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7875 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7841 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7839 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7829 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 4 | 0.7818 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7793 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7793 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7776 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7772 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7749 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7728 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7691 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7683 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7679 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 2 | 0.7659 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7654 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7631 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7611 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7607 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7603 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7602 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7546 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7514 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7505 |
| Probable esterase KAI2 | Q9SZU7 | KAI2_ARATH | Arabidopsis thaliana | 3 | 0.7493 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7492 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7479 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7431 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7403 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7388 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7378 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7359 |
| Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 2 | 0.7345 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7334 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7334 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7329 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7304 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7280 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7270 |
| Glutathione S-transferase A1 | P08263 | GSTA1_HUMAN | Homo sapiens | 2 | 0.7261 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7249 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7245 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7233 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7228 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 2 | 0.7190 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7177 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7174 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7171 |
| Eugenol synthase 1 | Q15GI4 | EGS1_OCIBA | Ocimum basilicum | 3 | 0.7168 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7164 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7157 |
| NADPH-dependent 7-cyano-7-deazaguanine reductase | Q9KTK0 | QUEF_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7153 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7145 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7145 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7131 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.7128 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7124 |
| Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 2 | 0.7124 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7123 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7115 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7078 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 2 | 0.7042 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7041 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7032 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7031 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7015 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7006 |