methyl (1S,15S,16R,20S,21R)-21-hydroxy-16-methyl-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: 9db5d541-b7bb-4a4c-bbd6-f7e568bd2313
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,15S,16R,20S,21R)-21-hydroxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• InChI: InChI=1S/C21H24N2O4/c1-11-14-9-23-8-7-13-12-5-3-4-6-16(12)22-18(13)19(23)20(24)17(14)15(10-27-11)21(25)26-2/h3-6,10-11,14,17,19-20,22,24H,7-9H2,1-2H3/t11-,14+,17+,19+,20-/m1/s1
• InChI Key: HBPNZWWAQVKYPJ-MDLURYLBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄N₂O₄
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.17360725 g/mol
• Topological Polar Surface Area (TPSA): 74.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9026	90.26%
Caco-2	+	0.8458	84.58%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4186	41.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7893	78.93%
P-glycoprotein inhibitior	+	0.5779	57.79%
P-glycoprotein substrate	+	0.6547	65.47%
CYP3A4 substrate	+	0.7187	71.87%
CYP2C9 substrate	-	0.6076	60.76%
CYP2D6 substrate	-	0.6571	65.71%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.7135	71.35%
CYP2C19 inhibition	-	0.8732	87.32%
CYP2D6 inhibition	-	0.6020	60.20%
CYP1A2 inhibition	-	0.5242	52.42%
CYP2C8 inhibition	+	0.5615	56.15%
CYP inhibitory promiscuity	-	0.6479	64.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6342	63.42%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9868	98.68%
Skin irritation	-	0.7562	75.62%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8778	87.78%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8586	85.86%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5779	57.79%
Estrogen receptor binding	-	0.5941	59.41%
Androgen receptor binding	+	0.6522	65.22%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	-	0.5236	52.36%
Aromatase binding	-	0.7170	71.70%
PPAR gamma	-	0.6721	67.21%
Honey bee toxicity	-	0.8308	83.08%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8097	80.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.53%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.16%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.14%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.02%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.83%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL1914	P06276	Butyrylcholinesterase	87.53%	95.00%
CHEMBL5028	O14672	ADAM10	87.36%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.85%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.42%	85.14%
CHEMBL2535	P11166	Glucose transporter	83.15%	98.75%
CHEMBL1951	P21397	Monoamine oxidase A	83.03%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.25%	95.89%

Plants that contains it

• Uncaria attenuata

Cross-Links

• PubChem: 21586699
• LOTUS: LTS0153619
• wikiData: Q105025429