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Catharanthamine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 6a5722c6-4da0-4b59-9d1a-f4c17448b902
Taxonomy Alkaloids and derivatives > Vinca alkaloids
IUPAC Name methyl 4-(11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl)-1-ethyl-2-oxa-6,16-diazapentacyclo[14.3.1.03,18.05,13.07,12]icosa-5(13),7,9,11-tetraene-4-carboxylate
SMILES (Canonical) CCC12CC3CN(C1)CCC4=C(C(C3O2)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41
SMILES (Isomeric) CCC12CC3CN(C1)CCC4=C(C(C3O2)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC1=CC=CC=C41
InChI InChI=1S/C46H56N4O9/c1-8-42-23-27-24-49(25-42)19-15-29-28-13-10-11-14-32(28)47-35(29)45(36(27)59-42,40(52)56-6)31-21-30-33(22-34(31)55-5)48(4)38-44(30)17-20-50-18-12-16-43(9-2,37(44)50)39(58-26(3)51)46(38,54)41(53)57-7/h10-14,16,21-22,27,36-39,47,54H,8-9,15,17-20,23-25H2,1-7H3
InChI Key KMWVJRBQGMUMID-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C46H56N4O9
Molecular Weight 809.00 g/mol
Exact Mass 808.40472938 g/mol
Topological Polar Surface Area (TPSA) 143.00 Ų
XlogP 3.70
Atomic LogP (AlogP) 4.01
H-Bond Acceptor 12
H-Bond Donor 2
Rotatable Bonds 7

Synonyms

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78779-58-5
methyl 4-(11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl)-1-ethyl-2-oxa-6,16-diazapentacyclo[14.3.1.03,18.05,13.07,12]icosa-5(13),7,9,11-tetraene-4-carboxylate
NSC 304422
Vincaleukoblastine, 4'-deoxy-1',4'-epoxy-, (1'beta)-

2D Structure

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2D Structure of Catharanthamine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8658 86.58%
Caco-2 - 0.7497 74.97%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5199 51.99%
OATP2B1 inhibitior - 0.8838 88.38%
OATP1B1 inhibitior + 0.8373 83.73%
OATP1B3 inhibitior + 0.8976 89.76%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 1.0000 100.00%
P-glycoprotein inhibitior + 0.8367 83.67%
P-glycoprotein substrate + 0.9189 91.89%
CYP3A4 substrate + 0.7757 77.57%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7757 77.57%
CYP3A4 inhibition - 0.6970 69.70%
CYP2C9 inhibition - 0.8347 83.47%
CYP2C19 inhibition - 0.8453 84.53%
CYP2D6 inhibition - 0.9154 91.54%
CYP1A2 inhibition - 0.9243 92.43%
CYP2C8 inhibition + 0.4631 46.31%
CYP inhibitory promiscuity - 0.7654 76.54%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5543 55.43%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.9329 93.29%
Skin irritation - 0.7991 79.91%
Skin corrosion - 0.9427 94.27%
Ames mutagenesis - 0.9000 90.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7119 71.19%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.6551 65.51%
skin sensitisation - 0.8769 87.69%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.7350 73.50%
Acute Oral Toxicity (c) III 0.6421 64.21%
Estrogen receptor binding + 0.8557 85.57%
Androgen receptor binding + 0.8131 81.31%
Thyroid receptor binding + 0.7603 76.03%
Glucocorticoid receptor binding + 0.8614 86.14%
Aromatase binding + 0.5289 52.89%
PPAR gamma + 0.8249 82.49%
Honey bee toxicity - 0.7087 70.87%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity + 0.5700 57.00%
Fish aquatic toxicity + 0.9750 97.50%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.84% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.81% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 99.54% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.84% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.13% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.92% 95.56%
CHEMBL5747 Q92793 CREB-binding protein 94.60% 95.12%
CHEMBL2535 P11166 Glucose transporter 93.01% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.36% 86.33%
CHEMBL2581 P07339 Cathepsin D 91.27% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.12% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.89% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.61% 97.09%
CHEMBL5028 O14672 ADAM10 89.17% 97.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.93% 92.62%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 87.91% 90.95%
CHEMBL205 P00918 Carbonic anhydrase II 86.57% 98.44%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 85.71% 95.17%
CHEMBL255 P29275 Adenosine A2b receptor 84.96% 98.59%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.90% 97.14%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 83.73% 97.50%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.89% 89.50%

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 156951
LOTUS LTS0198640
wikiData Q105143240