methyl (1R,14R,15R,18S,19R,20S)-14-[(2S,3R,12bS)-2-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-hydroxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-9-yl]-8,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

Details

• Internal ID: e395de9d-9cc7-4fd1-9919-87f2f7115785
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1R,14R,15R,18S,19R,20S)-14-[(2S,3R,12bS)-2-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-hydroxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-9-yl]-8,18-dihydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=C(C=C4)C5C6CCC(C(C6CC7N5CCC8=C7NC9=C8C(=CC=C9)O)C(=O)OC)O)O
• SMILES (Isomeric): CC[C@H]1CN2CCC3=C([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=C(C=C4)[C@H]5[C@@H]6CC[C@@H]([C@@H]([C@H]6C[C@H]7N5CCC8=C7NC9=C8C(=CC=C9)O)C(=O)OC)O)O
• InChI: InChI=1S/C43H52N4O8/c1-5-21-19-46-15-13-24-36-30(45-38(24)31(46)17-26(21)28(20-53-2)42(51)54-3)11-9-25(41(36)50)40-22-10-12-34(49)37(43(52)55-4)27(22)18-32-39-23(14-16-47(32)40)35-29(44-39)7-6-8-33(35)48/h6-9,11,20-22,26-27,31-32,34,37,40,44-45,48-50H,5,10,12-19H2,1-4H3/b28-20+/t21-,22+,26-,27-,31-,32+,34-,37+,40+/m0/s1
• InChI Key: KJJIVLXZRLRBDB-QPXBKICLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₂N₄O₈
• Molecular Weight: 752.90 g/mol
• Exact Mass: 752.37851463 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.93
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9653	96.53%
Caco-2	-	0.8461	84.61%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7374	73.74%
OATP2B1 inhibitior	-	0.5664	56.64%
OATP1B1 inhibitior	+	0.8523	85.23%
OATP1B3 inhibitior	+	0.8731	87.31%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8811	88.11%
BSEP inhibitior	+	0.9640	96.40%
P-glycoprotein inhibitior	+	0.7875	78.75%
P-glycoprotein substrate	+	0.8639	86.39%
CYP3A4 substrate	+	0.7510	75.10%
CYP2C9 substrate	+	0.5681	56.81%
CYP2D6 substrate	-	0.7616	76.16%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.8294	82.94%
CYP2C19 inhibition	-	0.8869	88.69%
CYP2D6 inhibition	-	0.8652	86.52%
CYP1A2 inhibition	-	0.7995	79.95%
CYP2C8 inhibition	+	0.7830	78.30%
CYP inhibitory promiscuity	-	0.7702	77.02%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5689	56.89%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9205	92.05%
Skin irritation	-	0.7766	77.66%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7595	75.95%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6403	64.03%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.8283	82.83%
Androgen receptor binding	+	0.7927	79.27%
Thyroid receptor binding	+	0.5454	54.54%
Glucocorticoid receptor binding	+	0.7223	72.23%
Aromatase binding	+	0.6345	63.45%
PPAR gamma	+	0.7204	72.04%
Honey bee toxicity	-	0.7264	72.64%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9523	95.23%

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	99.49%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.48%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.93%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.67%	97.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.66%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.70%	95.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	88.79%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.26%	93.03%
CHEMBL2535	P11166	Glucose transporter	88.05%	98.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.75%	91.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.61%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.47%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.42%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL238	Q01959	Dopamine transporter	85.83%	95.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.66%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL228	P31645	Serotonin transporter	84.19%	95.51%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.94%	89.62%
CHEMBL5028	O14672	ADAM10	83.87%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.59%	99.17%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	83.33%	83.14%
CHEMBL301	P24941	Cyclin-dependent kinase 2	82.76%	91.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.80%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.79%	90.71%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	81.42%	81.88%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.47%	93.99%
CHEMBL217	P14416	Dopamine D2 receptor	80.15%	95.62%

Plants that contains it

• Uncaria callophylla

Cross-Links

• PubChem: 101615678
• LOTUS: LTS0005017
• wikiData: Q104401737