methyl (1R,9R,10S,11R)-11-acetyloxy-12-ethyl-4-[(13S,17R)-17-ethyl-16,17-dihydroxy-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: 8babda4e-83d1-46e2-9beb-da4cdefc44f2
• Taxonomy: Alkaloids and derivatives > Vinca alkaloids
• IUPAC Name: methyl (1R,9R,10S,11R)-11-acetyloxy-12-ethyl-4-[(13S,17R)-17-ethyl-16,17-dihydroxy-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(CN2CCC3=C(C(CC(C2)C1O)(C4=C(C=C5C(=C4)C67CCN8C6C(C=CC8)(C(C(C7N5C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC9=CC=CC=C39)O
• SMILES (Isomeric): CC[C@]1(CN2CCC3=C([C@](CC(C2)C1O)(C4=C(C=C5C(=C4)[C@]67CCN8C6C(C=CC8)([C@H]([C@@]([C@@H]7N5C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)NC9=CC=CC=C39)O
• InChI: InChI=1S/C46H58N4O10/c1-8-42-16-12-18-50-20-17-44(37(42)50)30-21-31(34(57-5)22-33(30)48(4)38(44)46(56,41(54)59-7)39(42)60-26(3)51)45(40(53)58-6)23-27-24-49(25-43(55,9-2)36(27)52)19-15-29-28-13-10-11-14-32(28)47-35(29)45/h10-14,16,21-22,27,36-39,47,52,55-56H,8-9,15,17-20,23-25H2,1-7H3/t27?,36?,37?,38-,39-,42?,43-,44-,45+,46+/m1/s1
• InChI Key: IFGMHVGAHYXLIZ-AOAJRAFESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₈N₄O₁₀
• Molecular Weight: 827.00 g/mol
• Exact Mass: 826.41529406 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8879	88.79%
Caco-2	-	0.7302	73.02%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.6723	67.23%
OATP2B1 inhibitior	-	0.9054	90.54%
OATP1B1 inhibitior	+	0.8415	84.15%
OATP1B3 inhibitior	+	0.9043	90.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9974	99.74%
P-glycoprotein inhibitior	+	0.8026	80.26%
P-glycoprotein substrate	+	0.9384	93.84%
CYP3A4 substrate	+	0.7871	78.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7771	77.71%
CYP3A4 inhibition	-	0.8580	85.80%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.9095	90.95%
CYP2D6 inhibition	-	0.9057	90.57%
CYP1A2 inhibition	-	0.8919	89.19%
CYP2C8 inhibition	-	0.7324	73.24%
CYP inhibitory promiscuity	-	0.9360	93.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5400	54.00%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9347	93.47%
Skin irritation	-	0.7875	78.75%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6841	68.41%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.6926	69.26%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6589	65.89%
Acute Oral Toxicity (c)	III	0.6593	65.93%
Estrogen receptor binding	+	0.8600	86.00%
Androgen receptor binding	+	0.8313	83.13%
Thyroid receptor binding	+	0.8014	80.14%
Glucocorticoid receptor binding	+	0.8714	87.14%
Aromatase binding	-	0.5677	56.77%
PPAR gamma	+	0.8541	85.41%
Honey bee toxicity	-	0.7033	70.33%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6253	62.53%
Fish aquatic toxicity	+	0.9625	96.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.79%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.48%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.38%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL5747	Q92793	CREB-binding protein	95.92%	95.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.49%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.20%	98.95%
CHEMBL2535	P11166	Glucose transporter	92.07%	98.75%
CHEMBL217	P14416	Dopamine D2 receptor	91.45%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.19%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.06%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.97%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.56%	92.62%
CHEMBL4302	P08183	P-glycoprotein 1	88.06%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.78%	95.89%
CHEMBL205	P00918	Carbonic anhydrase II	87.24%	98.44%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.97%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.25%	97.09%
CHEMBL5028	O14672	ADAM10	85.20%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.62%	97.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.59%	95.17%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.57%	90.95%
CHEMBL1914	P06276	Butyrylcholinesterase	82.90%	95.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.70%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.53%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.02%	95.89%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 5315217
• NPASS: NPC157671