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Vincamine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COC(=O)[C@@]1(O)C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3 |
|---|---|
| InChI | InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1 |
| InChIKey | RXPRRQLKFXBCSJ-GIVPXCGWSA-N |
| Formula | C21H26N2O3 |
| HBA | 5 |
| HBD | 1 |
| MW | 354.45 |
| Rotatable Bonds | 2 |
| TPSA | 54.7 |
| LogP | 2.95 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 354.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Catharanthus roseus | Apocynaceae | Plantae | 4058 |
Showing of synonyms
Vincamine
1617-90-9
Pervincamine
Devincan
Arteriovinca
Angiopac
Minorine
Vincamidol
(+)-Vincamine
Oxygeron
Vincafor
Vincagil
Vincamin
Monorin
Novicet
Methyl vincaminate
Anasclerol
Vincafolina
Vincapront
Vincasaunier
Vinkametrin
Decincan
Devinkan
Equipur
Tripervan
Vincadar
Vincamina
Vincimax
Perval
Pervone
Ocu-vinc
Vincamina [DCIT]
Vincaminum
Vraap
Cetal retard
Vincaminum [INN-Latin]
Vincamine [INN:BAN:DCF]
Vincachron
Vincapan
Minorin
Vinodrel retard
Vinca-Ecobi
Vinca-Minor
HSDB 7150
Alkaloid obtained from Vinca minor
Anasclerol (base)
UNII-996XVD0JHT
EINECS 216-576-3
996XVD0JHT
NSC 91998
Vincamine (INN)
Cetal retard (TN)
CHEBI:9985
DTXSID9040134
14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
VINCAMINE [INN]
VINCAMINE [MI]
VINCAMINE [HSDB]
NSC-91998
VINCAMINE [MART.]
VINCAMINE [WHO-DD]
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
DTXCID7020134
VINCAMINE [EP MONOGRAPH]
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.)
Cerebroxine
Vincaminum (INN-Latin)
VINCAMINE (MART.)
Methyl 14beta-hydroxy-14,15-dihydro-3alpha,16alpha-eburnamenine-14alpha-carboxylate
Vinvasaunier
Sostenil
Vincafarm
Vincalen
Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Cis-Vincamine
VINCAMINE (EP MONOGRAPH)
(+)-cis-Vincamine
(3.ALPHA.,14.BETA.,16.ALPHA.)-14,15-DIHYDRO-14-HYDROXYEBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER
Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3.alpha.,14.beta.,16.alpha.)-
Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.0^(2,7).0^(8,18).0^(15,19))nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl vincaminic acid
C04AX07
(3.alpha.,14.beta.,16.alpha.)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
(3alpha, 14beta, 16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
(3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
(3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-1H-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5) naphthyridine-12-carboxylic acid methyl ester
216-576-3
1h-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5)naphthyridine, eburnamenine-14-carboxylic acid deriv.
1h-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenine-14-carboxylic acid deriv.
Rxprrqlkfxbcsj-dqvlvphssa-n
Rxprrqlkfxbcsj-givpxcgwsa-n
Rxprrqlkfxbcsj-mnlritnhsa-n
MFCD00078054
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methylester, (3a,14b,16a)-
Vincamine base
NCGC00094824-01
Prestwick_495
CAS-1617-90-9
Vincamine, 98%
Vincamine (Standard)
Prestwick0_000271
Prestwick1_000271
Prestwick2_000271
Prestwick3_000271
BSPBio_000142
GTPL349
MLS002154249
SCHEMBL147179
SPBio_002361
BPBio1_000158
CHEMBL1165342
BCBcMAP01_000080
HY-B1021R
HMS1568H04
HMS2095H04
HMS2268C20
HMS3712H04
BCP05837
HY-B1021
Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
Tox21_111342
Tox21_301968
S3891
AKOS015896471
Tox21_111342_1
CCG-208544
CS-4536
DB13374
FV65205
KS-5179
SMP1_000314
Vincamine, analytical reference material
NCGC00184983-01
NCGC00184983-03
NCGC00255542-01
AC-22625
SMR000112509
NS00006858
C09251
D08677
Q416225
BRD-K40902647-001-03-7
Methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-,methyl ester, (3alpha,14beta,16alpha)-
Methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0?,?.0?,??.0??,??]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl(15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Methyl(41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
- Hanafy M, Matter M, et al. (2016). Production of indole alkaloids in hairy root cultures of Catharanthus roseus L. and their antimicrobial activity. South African Journal of Botany, 2016, 105, 9-18. [View]
Pubchem:
15376
Cas:
1617-90-9
Gnps:
CCMSLIB00006569525
Zinc:
ZINC000001069082
Kegg Ligand:
C09251
Chebi:
9985
Nmrshiftdb2:
60027672
Metabolights:
MTBLC9985
Chembl:
CHEMBL1165342
Comptox:
DTXSID9040134
Drugbank:
DB13374
CPRiL:
31443
SMILES: c1cccc2n(c3c4c12)CCC5C3N(CC4)CCC5
Level: 0
Mol. Weight: 354.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.790
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.940
- Plasma Protein Binding
- 57.25
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.890
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.290
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.160
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.510
- 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
- -6.560
- Rat (Acute)
- 2.630
- Rat (Chronic Oral)
- 1.730
- Fathead Minnow
- 3.960
- 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
- 428.560
- Hydration Free Energy
- -5.560
- Log(D) at pH=7.4
- 2.670
- Log(P)
- 2.82
- Log S
- -2.79
- Log(Vapor Pressure)
- -8.52
- Melting Point
- 220.75
- pKa Acid
- 8.16
- pKa Basic
- 6.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8731 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8095 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7987 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7915 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7913 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7844 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7469 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7350 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7327 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7286 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7133 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7088 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7024 |
| Ribonuclease 4 | P15468 | RNAS4_PIG | Sus scrofa | 2 | 0.7005 |