Buprenorphine(+)

Details

• Internal ID: 59f44046-5dbd-46e2-b50d-2ca41988337d
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (1S,2S,6R,14R,15S,16R)-5-(cyclopropylmethyl)-16-[(2R)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
• SMILES (Canonical): CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
• SMILES (Isomeric): C[C@@]([C@H]1C[C@@]23CC[C@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O
• InChI: InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26-,27-,28+,29+/m1/s1
• InChI Key: RMRJXGBAOAMLHD-AGMYMXDYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₁NO₄
• Molecular Weight: 467.60 g/mol
• Exact Mass: 467.30355879 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.41
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• Npc32169
• CHEMBL560511
• Buprenorphine(+)
• Buprenorphine(-)
• CHEMBL452845
• SCHEMBL13787498
• BDBM50028147
• 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(15S)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanol(Buprenorphine)
• Buprenorphine2-(3-cyclopropylmethyl-11-hydroxy-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl)-3,3-dimethyl-2-butanol(

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9153	91.53%
Caco-2	+	0.5387	53.87%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.4709	47.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7668	76.68%
P-glycoprotein inhibitior	-	0.5787	57.87%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6928	69.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6173	61.73%
CYP3A4 inhibition	-	0.8322	83.22%
CYP2C9 inhibition	-	0.8692	86.92%
CYP2C19 inhibition	-	0.7801	78.01%
CYP2D6 inhibition	-	0.6721	67.21%
CYP1A2 inhibition	-	0.9153	91.53%
CYP2C8 inhibition	+	0.5508	55.08%
CYP inhibitory promiscuity	-	0.9212	92.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5940	59.40%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8654	86.54%
Skin corrosion	-	0.9629	96.29%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.5752	57.52%
skin sensitisation	-	0.8550	85.50%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7827	78.27%
Acute Oral Toxicity (c)	III	0.5506	55.06%
Estrogen receptor binding	+	0.8588	85.88%
Androgen receptor binding	+	0.7023	70.23%
Thyroid receptor binding	+	0.6833	68.33%
Glucocorticoid receptor binding	+	0.7558	75.58%
Aromatase binding	+	0.7712	77.12%
PPAR gamma	+	0.5932	59.32%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.6827	68.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	1.15 nM	Ki	via Super-PRED
CHEMBL237	P41145	Kappa opioid receptor	0.04 nM; 0.04 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	0.09 nM	Ki	via Super-PRED
CHEMBL2014	P41146	Nociceptin receptor	77 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.79%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.41%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.82%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.49%	97.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.00%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.72%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.13%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.56%	93.04%
CHEMBL2581	P07339	Cathepsin D	89.30%	98.95%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	86.52%	96.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.03%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.97%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.65%	97.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.33%	91.03%
CHEMBL1951	P21397	Monoamine oxidase A	84.01%	91.49%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.97%	93.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.90%	93.40%
CHEMBL234	P35462	Dopamine D3 receptor	81.00%	90.48%
CHEMBL238	Q01959	Dopamine transporter	80.89%	95.88%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.52%	85.14%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 9811785
• NPASS: NPC32169