(-)-Buprenorphine hydrochloride

Details

• Internal ID: 7189b33f-aff7-460e-b97b-cd60de07c29b
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azoniahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol chloride
• InChI: InChI=1S/C29H41NO4.ClH/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;1H/t20-,21-,24-,26+,27-,28+,29-;/m1./s1
• InChI Key: UAIXRPCCYXNJMQ-RZIPZOSSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂ClNO₄
• Molecular Weight: 504.10 g/mol
• Exact Mass: 503.2802365 g/mol
• Topological Polar Surface Area (TPSA): 63.40 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• (-)-buprenorphine hydrochloride
• (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol hydrochloride
• (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-3-hydroxy-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-17-ium chloride
• 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol hydrochloride
• 2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8922	89.22%
Caco-2	+	0.5387	53.87%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Lysosomes	0.7233	72.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8644	86.44%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7668	76.68%
P-glycoprotein inhibitior	-	0.5787	57.87%
P-glycoprotein substrate	+	0.8161	81.61%
CYP3A4 substrate	+	0.7017	70.17%
CYP2C9 substrate	-	0.6330	63.30%
CYP2D6 substrate	-	0.6811	68.11%
CYP3A4 inhibition	-	0.7862	78.62%
CYP2C9 inhibition	-	0.8461	84.61%
CYP2C19 inhibition	-	0.7287	72.87%
CYP2D6 inhibition	-	0.6859	68.59%
CYP1A2 inhibition	-	0.8736	87.36%
CYP2C8 inhibition	+	0.6942	69.42%
CYP inhibitory promiscuity	-	0.9352	93.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.5643	56.43%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7964	79.64%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5808	58.08%
skin sensitisation	-	0.8295	82.95%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7374	73.74%
Acute Oral Toxicity (c)	III	0.5219	52.19%
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	-	0.7403	74.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.4053	40.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	0.9 nM	IC50	PMID: 11585443
CHEMBL237	P41145	Kappa opioid receptor	1.2 nM	IC50	PMID: 11585443
CHEMBL233	P35372	Mu opioid receptor	1.7 nM	IC50	PMID: 11585443

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.62%	91.11%
CHEMBL233	P35372	Mu opioid receptor	97.96%	97.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.96%	96.09%
CHEMBL237	P41145	Kappa opioid receptor	97.57%	98.10%
CHEMBL236	P41143	Delta opioid receptor	96.92%	99.35%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.98%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.66%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	91.21%	91.03%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.03%	91.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.66%	95.89%
CHEMBL1902	P62942	FK506-binding protein 1A	88.89%	97.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.38%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.91%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.14%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.96%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.39%	93.99%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.83%	96.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.59%	94.00%
CHEMBL1914	P06276	Butyrylcholinesterase	82.16%	95.00%
CHEMBL2581	P07339	Cathepsin D	81.78%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.16%	93.04%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.85%	95.71%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.72%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.65%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.34%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	80.31%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.22%	92.62%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 45265653
• NPASS: NPC302449
• ChEMBL: CHEMBL1200401