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Vinblastine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1 |
|---|---|
| InChI | InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1 |
| InChIKey | JXLYSJRDGCGARV-CFWMRBGOSA-N |
| Formula | C46H58N4O9 |
| HBA | 12 |
| HBD | 3 |
| MW | 810.99 |
| Rotatable Bonds | 7 |
| TPSA | 154.1 |
| LogP | 3.99 |
| Number Rings | 9 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 59 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 810.42 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Catharanthus roseus | Apocynaceae | Plantae | 4058 |
Showing of synonyms
Vinblastine
865-21-4
Vinblastin
Vincaleucoblastin
Vinblastina
Vincaleukoblastine
Vincoblastine
Rozevin
Nincaluicolflastine
Vinblastinum
VR-8
Vinblastinum [INN-Latin]
CCRIS 9002
HSDB 3263
NCI-C04842
UNII-5V9KLZ54CY
EINECS 212-734-0
5V9KLZ54CY
NSC 47842
NDC 0002-1452-01
NSC-47842
(2ALPHA,2'BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
DTXSID8021430
(3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino(8,1-cd)carbazole-5-carboxylate
1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aalpha,4beta,5beta,5abeta,9(3R*,5S*,7R*,9S*),10bR*,13aalpha))-
Vinblastinum (INN-Latin)
VLB
DTXCID801430
L01CA01
212-734-0
(3ar-(3aalpha,4beta,5beta,5abeta,9(3r*,5s*,7r*,9s*),10br*,13aalpha))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2h-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1h-indolizino (8,1-cd)carbazole-5-carboxylate
Vbl
Vincaleucoblastine
Velban
CHEMBL159
Methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Vinblastina [DCIT]
Vinblastine [INN:BAN]
VINBLASTINE [INN]
Cid_5388983
[3H]-Vinblastine
1z2b
VINBLASTINE [MI]
VINBLASTINE [HSDB]
VINBLASTINE [VANDF]
SCHEMBL3628
BIDD:PXR0201
BSPBio_001228
VINBLASTINE [WHO-DD]
GTPL6851
132142-72-4
MSK15295
BDBM50012278
NSC816570
AKOS015965500
CS-1336
DB00570
NSC-816570
NCGC00022585-04
NCGC00022585-05
NCGC00485975-02
AC-24191
AS-15821
BP-43221
HY-17418
VinblastineVincaleukoblastine
EN300-19874057
VINDESINE SULFATE IMPURITY B [EP IMPURITY]
VINCRISTINE SULFATE IMPURITY H [EP IMPURITY]
BRD-K01188359-001-02-0
BRD-K01188359-001-03-8
BRD-K01188359-065-02-5
BRD-K01188359-065-23-1
(2alpha,2'beta,3alpha,5beta,19beta)-vincaleukoblastine
(2ALPHA,2''''BETA,3BETA,4ALPHA,5BETA)-VINCALEUKOBLASTINE
(3AR-(3AALPHA,4BETA,5BETA,5ABETA,9(3R*,5S*,7R*,9S*),10BR*,13AALPHA))-METHYL 4-(ACETYLOXY)-3A-ETHYL-9-(5-ETHYL-1,4,5,6,7,8,9,10-OCTAHYDRO-5-HYDROXY-9- (METHOXYCARBONYL)-2H-3,7-METHANOAZACYCLOUNDECINO(5,4-B)INDOL-9-YL)- 3A,4,5,5A,6,11,12,13A-OCTAHYDRO-5-HYDROXY-8-METHOXY-6-METHYL-1H-INDOLIZINO (8,1-CD)CARBAZOLE-5-CARBOXYLATE
Methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate
Methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-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:
13342
Cas:
865-21-4
Gnps:
CCMSLIB00000208785
Zinc:
ZINC000085432544
Nmrshiftdb2:
60029538
Chembl:
CHEMBL159
Comptox:
DTXSID8021430
Drugbank:
DB00570
Pdb Ligand:
VLB
Bindingdb:
50012278
CPRiL:
459
SMILES: C1CN(C2)CCCC2CC(c(c1c34)[nH]c3cccc4)c(c5)ccc(c5C678)NC7CCC9C6N(CC8)CC=C9
Level: 1
Mol. Weight: 810.99 g/mol
SMILES: c1cccc2[nH]c(c3c12)CCC4CCCN(C4)CC3
Level: 0
Mol. Weight: 810.99 g/mol
SMILES: c1cccc(c1C234)NC3CCC5C2N(CC4)CC=C5
Level: 0
Mol. Weight: 810.99 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 392.650
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 52076.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.550
- Plasma Protein Binding
- 70.89
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 5.330
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -1213.560
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.110
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.000
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -94515872.820
- Rat (Acute)
- 2.970
- Rat (Chronic Oral)
- 2.470
- Fathead Minnow
- 119310.230
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 10626233.700
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 4.030
- Log(P)
- 3.87
- Log S
- -4.58
- Log(Vapor Pressure)
- -349819.68
- Melting Point
- 224.8
- pKa Acid
- -2486.06
- pKa Basic
- 9.27
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8516 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7644 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7406 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7305 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 4 | 0.7240 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7160 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7154 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7111 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7109 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7058 |