Vincristine

Details

• Internal ID: 99cdcf9f-ce95-4d98-ac79-262690491ec8
• Taxonomy: Alkaloids and derivatives > Vinca alkaloids
• IUPAC Name: 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
• SMILES (Canonical): CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(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=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
• 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
• InChI Key: OGWKCGZFUXNPDA-XQKSVPLYSA-N
• Popularity: 54,951 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₆N₄O₁₀
• Molecular Weight: 825.00 g/mol
• Exact Mass: 824.39964400 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.52
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• 22-Oxovincaleukoblastine
• Vinkristin
• Leurocristine
• Vincrystine
• 57-22-7
• Oncovine
• Vincristina [DCIT]
• Onco TCS
• leucristine
• vincristin
• Vincristina
• Vincristinum
• Vincristinum [INN-Latin]
• Tecnocris
• Vincrstine
• Oncotcs
• rel-Vincristine
• Vincristine [INN:BAN]
• Tecnocris (TN)
• Marqibo
• Vincasar
• Vincristine (INN)
• Vincasar (1:1 sulfate salt)
• Liposomal Vincristine
• CCRIS 5763
• Vincaleukoblastine, 22-oxo-
• oncovin (brand name)
• DTXSID1032278
• CHEBI:28445
• HSDB 3199
• NCI-C04864
• NSC-67574
• C46H56N4O10
• EINECS 200-318-1
• 22-oxo-vincaleukoblastine
• Onkocristin
• Citomid
• Farmistin
• Oncovin (1:1 sulfate salt)
• Vincrex (1:1 sulfate salt)
• DTXCID9012278
• LCR
• Kyocristine
• Vincrisul
• VIN
• NCGC00163700-01
• Oncovin (TN)
• VCR
• vincristin-
• UNII-5J49Q6B70F
• CAS-57-22-7
• 22-Oxovincaleukoblastin
• 1217704-92-1
• Leurocristine;NSC-67574;22-Oxovincaleukoblastine
• D09QVV
• Vincristine (Leurocristine)
• SCHEMBL3709
• CHEMBL90555
• GTPL6785
• L01CA02
• OGWKCGZFUXNPDA-XQKSVPLYSA-N
• HMS2090E19
• Lilly37231 (1:1 sulfate salt)
• Tox21_112067
• BDBM50139772
• LS-228
• Lilly 37231 (1:1 sulfate salt)
• Tox21_112067_1
• NCGC00163700-02
• NCGC00163700-04
• NCGC00263543-01
• NCI60_026703
• SRI-10749-04
• SRI-10749-05
• C07204
• D08679
• Q408977
• Vincaleukoblastine, 22-oxo-22-Oxovincaleukoblastine
• 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
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9433	94.33%
Caco-2	-	0.7058	70.58%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6669	66.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8393	83.93%
OATP1B3 inhibitior	+	0.9059	90.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8211	82.11%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7841	78.41%
CYP3A4 inhibition	-	0.7491	74.91%
CYP2C9 inhibition	-	0.9072	90.72%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9203	92.03%
CYP2C8 inhibition	-	0.5569	55.69%
CYP inhibitory promiscuity	-	0.8574	85.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5637	56.37%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9366	93.66%
Skin irritation	-	0.7959	79.59%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6777	67.77%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8925	89.25%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.5877	58.77%
Acute Oral Toxicity (c)	III	0.6492	64.92%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8477	84.77%
Thyroid receptor binding	+	0.8184	81.84%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	-	0.5606	56.06%
PPAR gamma	+	0.8548	85.48%
Honey bee toxicity	-	0.7155	71.55%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5453	54.53%
Fish aquatic toxicity	+	0.9605	96.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	316.2 nM	Potency	via Super-PRED
CHEMBL5514	P42858	Huntingtin	17.8 nM; 17.8 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	1.1 nM; 1.1 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	926.8 nM	Potency	via Super-PRED
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	44000 nM	IC50	PMID: 22541068
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	36780 nM; 11000 nM	IC50; IC50	PMID: 25618019; PMID: 22541068

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.76%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.50%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.40%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.17%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.06%	95.56%
CHEMBL2535	P11166	Glucose transporter	95.38%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	95.18%	92.98%
CHEMBL5747	Q92793	CREB-binding protein	93.58%	95.12%
CHEMBL1914	P06276	Butyrylcholinesterase	92.85%	95.00%
CHEMBL205	P00918	Carbonic anhydrase II	90.86%	98.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.77%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.44%	89.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	89.62%	91.79%
CHEMBL5028	O14672	ADAM10	89.59%	97.50%
CHEMBL2581	P07339	Cathepsin D	89.55%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.97%	97.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	87.90%	95.69%
CHEMBL2885	P07451	Carbonic anhydrase III	87.88%	87.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.69%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.29%	92.62%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.19%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.00%	94.08%
CHEMBL217	P14416	Dopamine D2 receptor	82.39%	95.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.65%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.64%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.75%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.66%	100.00%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 5978
• NPASS: NPC260909
• ChEMBL: CHEMBL90555
• LOTUS: LTS0189111
• wikiData: Q408977