methyl (2S,13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-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]-18-ethyl-2-(2-oxopropyl)-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

Details

• Internal ID: b0ec76f2-237a-4621-917a-dce194742383
• Taxonomy: Alkaloids and derivatives > Vinca alkaloids
• IUPAC Name: methyl (2S,13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-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]-18-ethyl-2-(2-oxopropyl)-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate
• SMILES (Canonical): CCC12CN3CC(C1O2)CC(C4=C(CC3CC(=O)C)C5=CC=CC=C5N4)(C6=C(C=C7C(=C6)C89CCN1C8C(C=CC1)(C(C(C9N7C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
• SMILES (Isomeric): CC[C@]12CN3C[C@H]([C@H]1O2)C[C@@](C4=C(C[C@H]3CC(=O)C)C5=CC=CC=C5N4)(C6=C(C=C7C(=C6)[C@]89CCN1[C@H]8[C@@](C=CC1)([C@H]([C@@]([C@@H]9N7C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
• InChI: InChI=1S/C49H60N4O10/c1-9-45-16-13-18-52-19-17-47(40(45)52)33-22-34(37(59-6)23-36(33)51(5)41(47)49(58,44(57)61-8)42(45)62-28(4)55)48(43(56)60-7)24-29-25-53(26-46(10-2)39(29)63-46)30(20-27(3)54)21-32-31-14-11-12-15-35(31)50-38(32)48/h11-16,22-23,29-30,39-42,50,58H,9-10,17-21,24-26H2,1-8H3/t29-,30-,39-,40+,41-,42-,45-,46+,47-,48+,49+/m1/s1
• InChI Key: YZYJEFXKAHSJBC-JANXLJFASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₆₀N₄O₁₀
• Molecular Weight: 865.00 g/mol
• Exact Mass: 864.43094412 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.36
• H-Bond Acceptor: 13
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8775	87.75%
Caco-2	-	0.7617	76.17%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4619	46.19%
OATP2B1 inhibitior	-	0.7709	77.09%
OATP1B1 inhibitior	+	0.8347	83.47%
OATP1B3 inhibitior	+	0.9050	90.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8068	80.68%
P-glycoprotein substrate	+	0.9233	92.33%
CYP3A4 substrate	+	0.7710	77.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7922	79.22%
CYP3A4 inhibition	-	0.6099	60.99%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.8031	80.31%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8820	88.20%
CYP2C8 inhibition	-	0.5708	57.08%
CYP inhibitory promiscuity	-	0.7732	77.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5396	53.96%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9271	92.71%
Skin irritation	-	0.7878	78.78%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7218	72.18%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.6801	68.01%
skin sensitisation	-	0.8675	86.75%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.4643	46.43%
Acute Oral Toxicity (c)	III	0.5988	59.88%
Estrogen receptor binding	+	0.8440	84.40%
Androgen receptor binding	+	0.8101	81.01%
Thyroid receptor binding	+	0.7563	75.63%
Glucocorticoid receptor binding	+	0.8372	83.72%
Aromatase binding	+	0.5324	53.24%
PPAR gamma	+	0.8340	83.40%
Honey bee toxicity	-	0.6702	67.02%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5753	57.53%
Fish aquatic toxicity	+	0.9860	98.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.79%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.77%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.48%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.32%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.35%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.47%	94.00%
CHEMBL2535	P11166	Glucose transporter	92.44%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.30%	92.62%
CHEMBL5747	Q92793	CREB-binding protein	91.77%	95.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.87%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.70%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.57%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	87.62%	95.62%
CHEMBL255	P29275	Adenosine A2b receptor	87.10%	98.59%
CHEMBL4073	P09237	Matrix metalloproteinase 7	86.91%	97.56%
CHEMBL5028	O14672	ADAM10	85.70%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.46%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.89%	99.23%
CHEMBL4302	P08183	P-glycoprotein 1	84.74%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.69%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.35%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.06%	89.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.06%	96.47%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.53%	90.95%
CHEMBL205	P00918	Carbonic anhydrase II	80.99%	98.44%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.88%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.73%	95.17%
CHEMBL4208	P20618	Proteasome component C5	80.12%	90.00%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 14190180
• LOTUS: LTS0156577
• wikiData: Q105369596