methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,16S,17R)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazapentacyclo[13.3.1.04,12.04,16.05,10]nonadeca-5,7,9,11-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: 177152ca-f12f-4bcf-aeaa-171468b20643
• Taxonomy: Alkaloids and derivatives > Vinca alkaloids
• IUPAC Name: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,16S,17R)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazapentacyclo[13.3.1.04,12.04,16.05,10]nonadeca-5,7,9,11-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(CN2CCC34C1C(C2)CC(C3=NC5=CC=CC=C45)(C6=C(C=C7C(=C6)C89CCN1C8C(C=CC1)(C(C(C9N7C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
• SMILES (Isomeric): CC[C@@]1(CN2CCC34[C@@H]1C(C2)C[C@@](C3=NC5=CC=CC=C45)(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)O
• InChI: InChI=1S/C46H56N4O9/c1-8-41-15-12-18-50-20-17-44(36(41)50)29-21-30(33(56-5)22-32(29)48(4)37(44)46(55,40(53)58-7)38(41)59-26(3)51)45(39(52)57-6)23-27-24-49-19-16-43(34(27)42(54,9-2)25-49)28-13-10-11-14-31(28)47-35(43)45/h10-15,21-22,27,34,36-38,54-55H,8-9,16-20,23-25H2,1-7H3/t27?,34-,36+,37-,38-,41-,42+,43?,44-,45+,46+/m1/s1
• InChI Key: AYFGUFZGUHLVPW-VAWQDHDZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₅₆N₄O₉
• Molecular Weight: 809.00 g/mol
• Exact Mass: 808.40472938 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 13
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7980	79.80%
Caco-2	-	0.7363	73.63%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6668	66.68%
OATP2B1 inhibitior	-	0.8006	80.06%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9183	91.83%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9963	99.63%
P-glycoprotein inhibitior	+	0.8111	81.11%
P-glycoprotein substrate	+	0.9090	90.90%
CYP3A4 substrate	+	0.7657	76.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7716	77.16%
CYP3A4 inhibition	-	0.5933	59.33%
CYP2C9 inhibition	-	0.8902	89.02%
CYP2C19 inhibition	-	0.8514	85.14%
CYP2D6 inhibition	-	0.8199	81.99%
CYP1A2 inhibition	-	0.9238	92.38%
CYP2C8 inhibition	+	0.5429	54.29%
CYP inhibitory promiscuity	-	0.9306	93.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5649	56.49%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9324	93.24%
Skin irritation	-	0.7822	78.22%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6933	69.33%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.5551	55.51%
skin sensitisation	-	0.8552	85.52%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5815	58.15%
Acute Oral Toxicity (c)	III	0.6022	60.22%
Estrogen receptor binding	+	0.8593	85.93%
Androgen receptor binding	+	0.8020	80.20%
Thyroid receptor binding	+	0.7972	79.72%
Glucocorticoid receptor binding	+	0.8598	85.98%
Aromatase binding	-	0.5524	55.24%
PPAR gamma	+	0.8436	84.36%
Honey bee toxicity	-	0.7036	70.36%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6653	66.53%
Fish aquatic toxicity	+	0.9750	97.50%

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	99.85%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.76%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.95%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.73%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.40%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.44%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.90%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.92%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.89%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.99%	98.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.72%	93.65%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.00%	95.50%
CHEMBL4208	P20618	Proteasome component C5	85.21%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.19%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	83.78%	83.82%
CHEMBL5028	O14672	ADAM10	83.50%	97.50%
CHEMBL2535	P11166	Glucose transporter	83.36%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	82.81%	95.12%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.48%	82.69%
CHEMBL205	P00918	Carbonic anhydrase II	82.32%	98.44%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.08%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.58%	95.89%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 5315219
• NPASS: NPC86782