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Vincristine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC |
|---|---|
| InChI | InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1 |
| InChIKey | OGWKCGZFUXNPDA-XQKSVPLYSA-N |
| Formula | C46H56N4O10 |
| HBA | 12 |
| HBD | 3 |
| MW | 824.97 |
| Rotatable Bonds | 8 |
| TPSA | 171.17 |
| LogP | 3.52 |
| Number Rings | 9 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 824.4 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Catharanthus roseus | Apocynaceae | Plantae | 4058 |
Showing of synonyms
Vincristine
22-Oxovincaleukoblastine
Leurocristine
Vinkristin
Vincrystine
Vincristina
Leucristine
Vincristin
Vincristinum [INN-Latin]
Tecnocris
Oncovine
Oncotcs
Vincristinum
Oncovin (brand name)
DTXSID1032278
CHEBI:28445
NSC-67574
22-oxo-vincaleukoblastine
Farmistin
DTXCID9012278
CCRIS 5763
HSDB 3199
NCI-C04864
EINECS 200-318-1
Vincristinum (INN-Latin)
UNII-5J49Q6B70F
LCR
VCR
22-Oxovincaleukoblastin
L01CA02
200-318-1
57-22-7
Vincristina [DCIT]
Rel-Vincristine
Vincristine (INN)
VIN
NCGC00163700-01
Vincrstine
(+)-Vincristine
CAS-57-22-7
Tecnocris (TN)
1217704-92-1
Methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,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]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Vincasar (1:1 sulfate salt)
Oncovin (1:1 sulfate salt)
Vincrex (1:1 sulfate salt)
Vincristine (Leurocristine)
SCHEMBL3709
CHEMBL90555
GTPL6785
HMS2090E19
Tox21_112067
BDBM50139772
Lilly 37231 (1:1 sulfate salt)
Tox21_112067_1
FV73877
NCGC00163700-02
NCGC00163700-04
NCGC00163700-12
NCGC00263543-01
NCI60_026703
SRI-10749-04
SRI-10749-05
NS00009299
C07204
D08679
Q408977
BRD-K49229349-065-01-6
BRD-K49229349-065-02-4
Vincaleukoblastine, 22-oxo- 22-Oxovincaleukoblastine
Methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-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:
5978
Cas:
57-22-7
Gnps:
CCMSLIB00000078066
Zinc:
ZINC000085432549
Kegg Ligand:
C07204
Chebi:
28445
Nmrshiftdb2:
60072790
Metabolights:
MTBLC28445
Chembl:
CHEMBL90555
Comptox:
DTXSID1032278
Bindingdb:
50139772
CPRiL:
166
SMILES: C1CN(C2)CCCC2CC(c(c1c34)[nH]c3cccc4)c(c5)ccc(c5C678)NC7CCC9C6N(CC8)CC=C9
Level: 1
Mol. Weight: 824.97 g/mol
SMILES: c1cccc2[nH]c(c3c12)CCC4CCCN(C4)CC3
Level: 0
Mol. Weight: 824.97 g/mol
SMILES: c1cccc(c1C234)NC3CCC5C2N(CC4)CC=C5
Level: 0
Mol. Weight: 824.97 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.94
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 667.88
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 88047.51
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.5
- Plasma Protein Binding
- 70.92
- 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
- 2.75
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -2050.89
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.94
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.0
- 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
- -159802124.78
- Rat (Acute)
- 3.0
- Rat (Chronic Oral)
- 2.52
- Fathead Minnow
- 201720.34
- 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
- 17968763.73
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.61
- Log(P)
- 3.87
- Log S
- -4.33
- Log(Vapor Pressure)
- -591608.94
- Melting Point
- 248.52
- pKa Acid
- -4245.62
- pKa Basic
- -2.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.8877 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7969 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 4 | 0.7866 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7712 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7641 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 4 | 0.7587 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7427 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7307 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7255 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7202 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7090 |