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(+)-vasicine
- Family: Plantae - Acanthaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinazoline Alkaloid
| Canonical Smiles | O[C@H]1CCN2C1=Nc1ccccc1C2 |
|---|---|
| InChI | InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1 |
| InChIKey | YIICVSCAKJMMDJ-JTQLQIEISA-N |
| Formula | C11H12N2O |
| HBA | 3 |
| HBD | 1 |
| MW | 188.23 |
| Rotatable Bonds | 0 |
| TPSA | 35.83 |
| LogP | 1.3 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.36 |
| Exact Mass | 188.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galega lindblomi | Leguminosae/Fabaceae | Plantae | — |
| 2 | Galega battiscombei | Leguminosae/Fabaceae | Plantae | — |
| 3 | Adhatoda vasica | Acanthaceae | Plantae | 141317 |
Showing of synonyms
(+)-vasicine
Vasicine
6159-55-3
Vasicin
(-)-Peganine
(-)-Vasicine
Vasicin [German]
Peganin
L-Peganine
L-Vasacine
(-)-Linarine
(3S)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol
EINECS 228-180-8
6C2ZBI733P
L-VASICINE
VASICINE [MI]
(R)-1,2,3,9-Tetrahydropyrrolo(2,1-b)quinazolin-3-ol
DTXSID601024261
Pyrrolo[2,1-b]quinazolin-3-ol, 1,2,3,9-tetrahydro-, (3S)-
(3S)-1,2,3,9-tetrahydropyrrolo(2,1-b)quinazolin-3-ol
PYRROLO(2,1-B)QUINAZOLIN-3-OL, 1,2,3,9-TETRAHYDRO-, (3S)-
Peganine hydrochloride dihydrate
DTXCID901508515
VASICINE (CONSTITUENT OF MALABAR NUT TREE, LEAF)
228-180-8
Peganine
CHEMBL2163791
UNII-6C2ZBI733P
Vasicine, analytical standard
SCHEMBL2610722
YIICVSCAKJMMDJ-JTQLQIEISA-N
HY-N1103
BDBM50396012
MSK181320
S5850
AKOS032948347
FS-8877
AC-35070
DA-58961
FV137949
CS-0016391
Q27264469
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
(3S)-1H,2H,3H,9H-PYRROLO[2,1-B]QUINAZOLIN-3-OL
Vasicine(-)-Peganine
- 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]
- Susag L, Mathenge S, et al. (2003). The alkaloids of two species of Afrogalega.. Biochemical systematics and ecology,2003,31(6),645-647. [View] [PubMed]
Pubchem:
667496
Cas:
6159-55-3
Zinc:
ZINC000100051847
Nmrshiftdb2:
60021272
Chembl:
CHEMBL2163791
Bindingdb:
50396012
CPRiL:
74236
SMILES: C1CCN(C1=2)Cc3c(N2)cccc3
Level: 0
Mol. Weight: 188.23 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.33
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.21
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.46
- Plasma Protein Binding
- 35.87
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.44
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.21
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.17
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.15
- 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
- 1.87
- Rat (Acute)
- 2.8
- Rat (Chronic Oral)
- 1.69
- Fathead Minnow
- 3.58
- 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
- 321.87
- Hydration Free Energy
- -8.82
- Log(D) at pH=7.4
- 0.73
- Log(P)
- 0.73
- Log S
- -1.44
- Log(Vapor Pressure)
- -4.5
- Melting Point
- 190.71
- pKa Acid
- 10.3
- pKa Basic
- 9.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Matrix metalloproteinase-20 | O60882 | MMP20_HUMAN | Homo sapiens | 3 | 0.9144 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.8840 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8757 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8437 |
| Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 2 | 0.7869 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 2 | 0.7828 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7797 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7777 |
| Hexokinase-4 | P35557 | HXK4_HUMAN | Homo sapiens | 3 | 0.7713 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7677 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7599 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7571 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7567 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7505 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7456 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 2 | 0.7450 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 3 | 0.7415 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 2 | 0.7409 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7384 |
| Vitamin D3 receptor A | Q9PTN2 | VDRA_DANRE | Danio rerio | 3 | 0.7352 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7318 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7278 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7273 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7268 |
| GMP reductase | Q81JJ9 | GUAC_BACAN | Bacillus anthracis | 2 | 0.7249 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 2 | 0.7216 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7208 |
| Cyclic nucleotide-gated potassium channel mll3241 | Q98GN8 | CNGK1_RHILO | Mesorhizobium japonicum) | 2 | 0.7167 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7153 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 2 | 0.7128 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7117 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7113 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 2 | 0.7107 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7100 |
| Vitamin D3 receptor A | Q9PTN2 | VDRA_DANRE | Danio rerio | 3 | 0.7082 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7036 |