NP-MRD: Showing NP-Card for buprenorphine (NP0158889)

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Record Information

Version

2.0

Created at

2022-09-02 16:33:12 UTC

Updated at

2022-09-02 16:33:12 UTC

NP-MRD ID

NP0158889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

buprenorphine

Description

Buprenorphine, also known as buprenorfina or temgesic, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. Buprenorphine is a very strong basic compound (based on its pKa). In humans, buprenorphine is involved in buprenorphine action pathway. buprenorphine is found in Apis cerana. buprenorphine was first documented in 1995 (PMID: 7714228). Buprenorphine is a potentially toxic compound (PMID: 11303059) (PMID: 15966752) (PMID: 10649968) (PMID: 16650985).

Structure

MOL 3D MOL SDF PDB SMILES InChI

644073
  Mrv0541 02231215062D          

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M  END

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M  END

644073
  Mrv0541 02231215062D          

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  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  6  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 20  1  0  0  0  0
 18 23  1  0  0  0  0
 18 25  1  1  0  0  0
 20 26  1  0  0  0  0
 21 27  2  0  0  0  0
 22 24  1  0  0  0  0
 23 32  1  0  0  0  0
 23 33  1  0  0  0  0
 23 34  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  1  0  0  0  0
 26 31  2  0  0  0  0
 27 31  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1CC1CC1)=C(O)C=C4

> <INCHI_IDENTIFIER>
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-IHFGGWKQSA-N

> <FORMULA>
C29H41NO4

> <MOLECULAR_WEIGHT>
467.6401

> <EXACT_MASS>
467.303558805

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
53.11389565315854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.5498807580676903

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.298024374194792

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.503441933795022

> <JCHEM_PKA_STRONGEST_BASIC>
12.535459044638307

> <JCHEM_POLAR_SURFACE_AREA>
62.160000000000004

> <JCHEM_REFRACTIVITY>
131.7623

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
buprenorphine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 644073                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.041  -4.202   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.936  -4.522   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.504  -0.211   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.181  -4.522   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.598   2.194   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.598  -0.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.828  -1.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.138  -3.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.598  -3.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.909  -1.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.138  -0.473   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.828   0.861   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.711  -1.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.129  -2.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.059  -0.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.288  -1.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.288   0.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.504  -1.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.041   2.471   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.518  -0.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.518  -3.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.045   2.868   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.100  -1.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.185   4.457   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.504  -3.402   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.978  -0.473   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.978  -3.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.512   5.904   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.101   5.764   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.138  -5.904   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.208  -1.807   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.695  -1.807   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.100  -3.402   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.100  -0.211   0.000  0.00  0.00           C+0
CONECT    1    9   21                                                       
CONECT    2    8   30                                                       
CONECT    3   18                                                            
CONECT    4   27                                                            
CONECT    5   12   19   22                                                  
CONECT    6    7   11   12   13                                             
CONECT    7    6    9   15   16                                             
CONECT    8    2    9   10   14                                             
CONECT    9    1    7    8                                                  
CONECT   10    8   11   18                                                  
CONECT   11    6   10                                                       
CONECT   12    5    6   17                                                  
CONECT   13    6   14                                                       
CONECT   14    8   13                                                       
CONECT   15    7   19                                                       
CONECT   16    7   20   21                                                  
CONECT   17   12   20                                                       
CONECT   18    3   10   23   25                                             
CONECT   19    5   15                                                       
CONECT   20   16   17   26                                                  
CONECT   21    1   16   27                                                  
CONECT   22    5   24                                                       
CONECT   23   18   32   33   34                                             
CONECT   24   22   28   29                                                  
CONECT   25   18                                                            
CONECT   26   20   31                                                       
CONECT   27    4   21   31                                                  
CONECT   28   24   29                                                       
CONECT   29   24   28                                                       
CONECT   30    2                                                            
CONECT   31   26   27                                                       
CONECT   32   23                                                            
CONECT   33   23                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Value	Source
(-)-Buprenorphine	ChEBI
17-Cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	ChEBI
2-(N-Cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol	ChEBI
2-[3-Cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-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	ChEBI
21-Cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	ChEBI
Buprenorfina	ChEBI
Buprenorphinum	ChEBI
Temgesic	Kegg
17-Cyclopropylmethyl-4,5a-epoxy-7a-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	Generator
17-Cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	Generator
2-(N-Cyclopropylmethyl-4,5a-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6a-yl)-3,3-dimethyl-2-butanol	Generator
2-(N-Cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol	Generator
21-Cyclopropyl-7a-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	Generator
21-Cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	Generator
Buprenophine	HMDB
Essex brand OF buprenorphine hydrochloride	HMDB
Key brand OF buprenorphine hydrochloride	HMDB
Reckitt benckiser brand OF buprenorphine hydrochloride	HMDB
Buprex	HMDB
Temgésic	HMDB
Buprenorphine hydrochloride	HMDB
Grünenthal brand OF buprenorphine	HMDB
Reckitt and colman brand 2 OF buprenorphine hydrochloride	HMDB
Buprenex	HMDB
Reckitt and colman brand 1 OF buprenorphine hydrochloride	HMDB
Schering plough brand OF buprenorphine hydrochloride	HMDB
Buprenorphine grünenthal brand	HMDB
Prefin	HMDB
RX-6029-m	HMDB
Schering-plough brand OF buprenorphine hydrochloride	HMDB
Grünenthal brand OF buprenorphine hydrochloride	HMDB
Hydrochloride, buprenorphine	HMDB
RX 6029 m	HMDB
Reckitt brand OF buprenorphine hydrochloride	HMDB
Subutex	HMDB

Chemical Formula

C₂₉H₄₁NO₄

Average Mass

467.6401 Da

Monoisotopic Mass

467.30356 Da

IUPAC Name

(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

Traditional Name

buprenorphine

CAS Registry Number

Not Available

SMILES

CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1CC1CC1)=C(O)C=C4

InChI Identifier

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-IHFGGWKQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Azaspirodecane
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:3216 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.53	ALOGPS
logP	3.55	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	12.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.76 m³·mol⁻¹	ChemAxon
Polarizability	53.11 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015057

DrugBank ID

DB00921

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

559124

KEGG Compound ID

C08007

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Buprenorphine

METLIN ID

Not Available

PubChem Compound

644073

PDB ID

Not Available

ChEBI ID

3216

Good Scents ID

Not Available

References

General References

Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. doi: 10.1097/00004714-199502000-00008. [PubMed:7714228 ]
Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. [PubMed:11303059 ]
Elkader A, Sproule B: Buprenorphine: clinical pharmacokinetics in the treatment of opioid dependence. Clin Pharmacokinet. 2005;44(7):661-80. doi: 10.2165/00003088-200544070-00001. [PubMed:15966752 ]
Husbands SM, Lewis JW: Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogues of buprenorphine. J Med Chem. 2000 Jan 27;43(2):139-41. doi: 10.1021/jm991165p. [PubMed:10649968 ]
Park HS, Lee HY, Kim YH, Park JK, Zvartau EE, Lee H: A highly selective kappa-opioid receptor agonist with low addictive potential and dependence liability. Bioorg Med Chem Lett. 2006 Jul 1;16(13):3609-13. doi: 10.1016/j.bmcl.2006.02.017. Epub 2006 May 2. [PubMed:16650985 ]
LOTUS database [Link]

Showing NP-Card for buprenorphine (NP0158889)

MOL for NP0158889 (buprenorphine)

3D MOL for NP0158889 (buprenorphine)

3D SDF for NP0158889 (buprenorphine)

3D-SDF for NP0158889 (buprenorphine)

PDB for NP0158889 (buprenorphine)

3D PDB for NP0158889 (buprenorphine)

SMILES for NP0158889 (buprenorphine)

INCHI for NP0158889 (buprenorphine)

Structure for NP0158889 (buprenorphine)

3D Structure for NP0158889 (buprenorphine)