methyl (1S,14R,15S,16S,20S)-14-(hydroxymethyl)-16-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Details

• Internal ID: 85126760-7146-4c8f-8b99-5dbc93c64668
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,14R,15S,16S,20S)-14-(hydroxymethyl)-16-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC3C4=C(CCN3C2CO)C5=CC=CC=C5N4)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@H]3C4=C(CCN3[C@H]2CO)C5=CC=CC=C5N4)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C27H34N2O10/c1-36-25(35)15-11-37-26(39-27-24(34)23(33)22(32)19(10-31)38-27)20-14(15)8-17-21-13(6-7-29(17)18(20)9-30)12-4-2-3-5-16(12)28-21/h2-5,11,14,17-20,22-24,26-28,30-34H,6-10H2,1H3/t14-,17+,18+,19-,20+,22-,23+,24-,26+,27+/m1/s1
• InChI Key: FCECVXQMCZMWDG-DCMQMPOPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄N₂O₁₀
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.22134529 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.71
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6675	66.75%
Caco-2	-	0.8190	81.90%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5930	59.30%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.7398	73.98%
OATP1B3 inhibitior	+	0.9298	92.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8632	86.32%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5748	57.48%
CYP3A4 substrate	+	0.7342	73.42%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.7975	79.75%
CYP3A4 inhibition	-	0.9764	97.64%
CYP2C9 inhibition	-	0.7934	79.34%
CYP2C19 inhibition	-	0.8934	89.34%
CYP2D6 inhibition	-	0.8197	81.97%
CYP1A2 inhibition	-	0.6547	65.47%
CYP2C8 inhibition	+	0.6679	66.79%
CYP inhibitory promiscuity	-	0.6783	67.83%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5853	58.53%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9681	96.81%
Skin irritation	-	0.7638	76.38%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7535	75.35%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5879	58.79%
Acute Oral Toxicity (c)	III	0.6162	61.62%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6759	67.59%
Thyroid receptor binding	-	0.5392	53.92%
Glucocorticoid receptor binding	-	0.4925	49.25%
Aromatase binding	-	0.5222	52.22%
PPAR gamma	+	0.6694	66.94%
Honey bee toxicity	-	0.8248	82.48%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.3631	36.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.25%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.46%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.28%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	92.46%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.80%	94.45%
CHEMBL5028	O14672	ADAM10	89.64%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.00%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.03%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.48%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.64%	86.92%
CHEMBL4208	P20618	Proteasome component C5	85.60%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.89%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	80.59%	91.49%

Plants that contains it

• Neolamarckia cadamba

Cross-Links

• PubChem: 154804625
• LOTUS: LTS0276425
• wikiData: Q104993094