Methyl 11-[2-[(3Z)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-3-oxopropyl]-16-methyl-17-oxa-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8,11,18-heptaene-19-carboxylate

Details

• Internal ID: 05d1a990-c431-4724-8420-c81c49c948e4
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: methyl 11-[2-[(3E)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-3-oxopropyl]-16-methyl-17-oxa-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8,11,18-heptaene-19-carboxylate
• SMILES (Canonical): CC=C1CN2CCC3=C(C2CC1C(CC4=C[N+]5=C(CC6C(C5)C(OC=C6C(=O)OC)C)C7=C4C8=CC=CC=C8N7)C(=O)OC)NC9=CC=CC=C39
• SMILES (Isomeric): C/C=C\1/CN2CCC3=C(C2CC1C(CC4=C[N+]5=C(CC6C(C5)C(OC=C6C(=O)OC)C)C7=C4C8=CC=CC=C8N7)C(=O)OC)NC9=CC=CC=C39
• InChI: InChI=1S/C42H44N4O5/c1-5-24-19-45-15-14-27-26-10-6-8-12-34(26)43-39(27)36(45)17-29(24)31(41(47)49-3)16-25-20-46-21-32-23(2)51-22-33(42(48)50-4)30(32)18-37(46)40-38(25)28-11-7-9-13-35(28)44-40/h5-13,20,22-23,29-32,36,43H,14-19,21H2,1-4H3/p+1/b24-5-
• InChI Key: QWAUBSSAJRGKPX-ZRJGMHBZSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₅N₄O₅+
• Molecular Weight: 685.80 g/mol
• Exact Mass: 685.33899555 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 6.25
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 36519-42-3
• methyl 11-[2-[(3E)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-3-oxopropyl]-16-methyl-17-oxa-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8,11,18-heptaene-19-carboxylate
• Methyl 11-[2-[(3Z)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-methoxy-3-oxopropyl]-16-methyl-17-oxa-3-aza-13-azoniapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8,11,18-heptaene-19-carboxylate
• NSC72123
• SCHEMBL5578932
• NSC-72123
• AKOS040763095
• Oxayohimbanium,4,5,6,16,17-hexadehydro-6-[(16S,19E)-19,20-didehydro-16-(methoxycarbonyl)corynan-17-yl]-16-(methoxycarbonyl)-19-methyl-, (19.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6819	68.19%
Caco-2	-	0.8042	80.42%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6668	66.68%
OATP2B1 inhibitior	+	0.5836	58.36%
OATP1B1 inhibitior	+	0.8125	81.25%
OATP1B3 inhibitior	+	0.8895	88.95%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9966	99.66%
P-glycoprotein inhibitior	+	0.9100	91.00%
P-glycoprotein substrate	+	0.8045	80.45%
CYP3A4 substrate	+	0.7506	75.06%
CYP2C9 substrate	-	0.8106	81.06%
CYP2D6 substrate	-	0.7974	79.74%
CYP3A4 inhibition	-	0.5664	56.64%
CYP2C9 inhibition	-	0.5227	52.27%
CYP2C19 inhibition	-	0.8210	82.10%
CYP2D6 inhibition	-	0.5805	58.05%
CYP1A2 inhibition	+	0.6797	67.97%
CYP2C8 inhibition	+	0.8499	84.99%
CYP inhibitory promiscuity	-	0.6480	64.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6035	60.35%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9380	93.80%
Skin irritation	-	0.7779	77.79%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7997	79.97%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8750	87.50%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5171	51.71%
Acute Oral Toxicity (c)	III	0.6744	67.44%
Estrogen receptor binding	+	0.8771	87.71%
Androgen receptor binding	+	0.7769	77.69%
Thyroid receptor binding	+	0.6341	63.41%
Glucocorticoid receptor binding	+	0.8374	83.74%
Aromatase binding	+	0.5742	57.42%
PPAR gamma	+	0.7523	75.23%
Honey bee toxicity	-	0.6726	67.26%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9786	97.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.99%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.30%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.96%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.72%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.41%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.01%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.60%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.62%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.92%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.70%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.51%	95.83%
CHEMBL5028	O14672	ADAM10	87.65%	97.50%
CHEMBL2535	P11166	Glucose transporter	86.74%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	86.37%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.81%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.15%	89.00%
CHEMBL4208	P20618	Proteasome component C5	83.24%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.91%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	80.42%	91.19%

Plants that contains it

• Catharanthus roseus
• Rauvolfia serpentina
• Rauvolfia vomitoria

Cross-Links

• PubChem: 24188124
• NPASS: NPC7453