Vinblastine

Details

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Internal ID 11bc7e0e-e71a-4a4e-b40d-eedd40400665
Taxonomy Alkaloids and derivatives > Vinca alkaloids
IUPAC Name 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
SMILES (Canonical) CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
SMILES (Isomeric) CC[C@@]1(C[C@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
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
InChI Key JXLYSJRDGCGARV-CFWMRBGOSA-N
Popularity 27,139 references in papers

Physical and Chemical Properties

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Molecular Formula C46H58N4O9
Molecular Weight 811.00 g/mol
Exact Mass 810.42037944 g/mol
Topological Polar Surface Area (TPSA) 154.00 Ų
XlogP 3.70
Atomic LogP (AlogP) 3.99
H-Bond Acceptor 12
H-Bond Donor 3
Rotatable Bonds 7

Synonyms

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Vinblastin
Vincaleucoblastin
865-21-4
Vincaleucoblastine
Vincaleukoblastine
Vinblastina
Vincoblastine
Rozevin
Nincaluicolflastine
Vinblastinum
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Vinblastine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9418 94.18%
Caco-2 - 0.6792 67.92%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Mitochondria 0.6612 66.12%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8450 84.50%
OATP1B3 inhibitior + 0.8977 89.77%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 1.0000 100.00%
P-glycoprotein inhibitior + 0.8200 82.00%
P-glycoprotein substrate + 0.9455 94.55%
CYP3A4 substrate + 0.7980 79.80%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7622 76.22%
CYP3A4 inhibition - 0.8149 81.49%
CYP2C9 inhibition - 0.9093 90.93%
CYP2C19 inhibition - 0.9025 90.25%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9198 91.98%
CYP2C8 inhibition - 0.7423 74.23%
CYP inhibitory promiscuity - 0.8681 86.81%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5437 54.37%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9388 93.88%
Skin irritation - 0.7957 79.57%
Skin corrosion - 0.9433 94.33%
Ames mutagenesis - 0.9600 96.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6890 68.90%
Micronuclear + 0.7500 75.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8832 88.32%
Respiratory toxicity + 0.9556 95.56%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity - 0.6151 61.51%
Acute Oral Toxicity (c) III 0.6578 65.78%
Estrogen receptor binding + 0.8825 88.25%
Androgen receptor binding + 0.8697 86.97%
Thyroid receptor binding + 0.8462 84.62%
Glucocorticoid receptor binding + 0.8971 89.71%
Aromatase binding - 0.5908 59.08%
PPAR gamma + 0.8708 87.08%
Honey bee toxicity - 0.7281 72.81%
Biodegradation - 0.9750 97.50%
Crustacea aquatic toxicity + 0.5553 55.53%
Fish aquatic toxicity + 0.9584 95.84%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL340 P08684 Cytochrome P450 3A4 26000 nM
IC50
PMID: 18980381
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 316.2 nM
Potency
via Super-PRED
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 30000 nM
IC50
PMID: 17132069
CHEMBL4302 P08183 P-glycoprotein 1 29000 nM
2000 nM
10471.29 nM
19900 nM
34000 nM
17700 nM
10000 nM
29500 nM
IC50
IC50
IC50
IC50
IC50
IC50
IC50
IC50
PMID: 11374943
PMID: 19555122
PMID: 20483615
PMID: 23316950
PMID: 24063582
PMID: 25129171
PMID: 25856683
via CMAUP
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 20.7 nM
Potency
via Super-PRED
CHEMBL1697668 Q9Y6L6 Solute carrier organic anion transporter family member 1B1 46800 nM
IC50
via CMAUP
CHEMBL1743121 Q9NPD5 Solute carrier organic anion transporter family member 1B3 43500 nM
IC50
via CMAUP
CHEMBL1293256 P40225 Thrombopoietin 398.1 nM
Potency
via Super-PRED
CHEMBL1835 P24557 Thromboxane-A synthase 1870 nM
IC50
via CMAUP
CHEMBL1963 P16473 Thyroid stimulating hormone receptor 39.8 nM
Potency
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.83% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 99.21% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.81% 91.11%
CHEMBL5747 Q92793 CREB-binding protein 95.94% 95.12%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.71% 95.56%
CHEMBL2535 P11166 Glucose transporter 95.24% 98.75%
CHEMBL1914 P06276 Butyrylcholinesterase 94.97% 95.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.29% 86.33%
CHEMBL4302 P08183 P-glycoprotein 1 92.24% 92.98%
CHEMBL217 P14416 Dopamine D2 receptor 91.87% 95.62%
CHEMBL2581 P07339 Cathepsin D 90.91% 98.95%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 90.51% 91.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.01% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.26% 94.00%
CHEMBL5028 O14672 ADAM10 87.92% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.44% 97.09%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 86.73% 97.50%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 86.15% 90.95%
CHEMBL205 P00918 Carbonic anhydrase II 85.75% 98.44%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.71% 92.62%
CHEMBL2413 P32246 C-C chemokine receptor type 1 84.67% 89.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.55% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.47% 97.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.39% 82.69%
CHEMBL4073 P09237 Matrix metalloproteinase 7 80.17% 97.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.10% 99.23%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Catharanthus roseus

Cross-Links

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PubChem 13342
NPASS NPC195788
ChEMBL CHEMBL159
LOTUS LTS0102356
wikiData Q105136630