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]-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

Details

• Internal ID: f8990897-5aa7-4176-9288-3992b4d78d20
• 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]-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+/m1/s1
• InChI Key: JXLYSJRDGCGARV-XQKSVPLYSA-N
• Popularity: 12,956 references in papers

Physical and Chemical Properties

• 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

• 865-21-4
• Vincaleukoblastine
• CHEBI:27375
• Vinblastina (TN)
• DTXSID8021430
• C46H58N4O9
• C46-H58-N4-O9
• (+)-vinblastine
• VLB
• NCGC00181127-01
• SCHEMBL6146
• CHEMBL22969
• Vinblastine (Vincaleucoblastine)
• SCHEMBL17813675
• BDBM227643
• HMS2090K05
• 132142-72-4
• 72401-36-6
• AKOS015969678
• NCGC00181127-02
• NCGC00263548-07
• NCI60_004200
• LS-187263
• C07201
• D08675
• EN300-130971
• AB01273959-01
• AB01273959-02
• Q282629
• Q-100868
• 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(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 (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]-10-hydroxy-5-methoxy-8-methyl-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 acetoxy-ethyl-(ethyl-hydroxy-methoxycarbonyl-[?]yl)-hydroxy-methoxy-methyl-[?]carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	316.2 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	20.7 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	398.1 nM	Potency	via Super-PRED
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

• Catharanthus roseus
• Diospyros lotus

Cross-Links

• PubChem: 241903
• NPASS: NPC237901
• ChEMBL: CHEMBL22969
• LOTUS: LTS0102738
• wikiData: Q282629