NP-MRD: Showing NP-Card for phenazocine (NP0221935)

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Record Information

Version

1.0

Created at

2022-09-05 23:38:08 UTC

Updated at

2022-09-05 23:38:08 UTC

NP-MRD ID

NP0221935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phenazocine

Description

Phenazocine, also known as narphen or phenbenzorphan, belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions. phenazocine is found in Papaver somniferum. It was first documented in 2015 (PMID: 25972091). Based on a literature review a small amount of articles have been published on Phenazocine (PMID: 31557052) (PMID: 27721146).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201382D          

 24 27  0  0  0  0            999 V2000
    2.2581    0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717    0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    0.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    1.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    1.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    2.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.1662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741    0.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8142    1.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279    2.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390    2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC3=CC=C(O)C=C3C1(C)CCN2CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3

> <INCHI_KEY>
ZQHYKVKNPWDQSL-UHFFFAOYSA-N

> <FORMULA>
C22H27NO

> <MOLECULAR_WEIGHT>
321.464

> <EXACT_MASS>
321.209264493

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.92336877900553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

> <JCHEM_LOGP>
4.076500210849055

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.964461745785233

> <JCHEM_PKA_STRONGEST_BASIC>
10.85511501826945

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
100.04870000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.215   1.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.747   1.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.635  -0.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.171  -0.587   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.179   0.577   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.565  -0.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.840   0.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.729   2.304   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.004   3.168   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.344   2.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.069   2.113   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.905   3.121   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.390   4.582   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.369   3.011   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.361   1.846   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.471   0.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.906  -0.380   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.192   0.468   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.101   2.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.387   2.853   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.296   4.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.919   5.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.633   4.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.724   2.695   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
Hydrobromide, phenazocine	HMDB
Narphen	HMDB
Phenazocine hydrobromide	HMDB
Phenbenzorphan	HMDB
Phenethylazocine	HMDB

Chemical Formula

C₂₂H₂₇NO

Average Mass

321.4640 Da

Monoisotopic Mass

321.20926 Da

IUPAC Name

1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

Traditional Name

1,13-dimethyl-10-(2-phenylethyl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

CAS Registry Number

Not Available

SMILES

CC1C2CC3=CC=C(O)C=C3C1(C)CCN2CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3

InChI Key

ZQHYKVKNPWDQSL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Papaver somniferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

6,7-benzomorphans

Sub Class

2,6-dimethyl-3-benzazocines

Direct Parent

2,6-dimethyl-3-benzazocines

Alternative Parents

Substituents

2,6-dimethyl-3-benzazocine
4-hydroxy-6,7-benzomorphan
Benzazocine
Tetralin
Phenethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.08	ChemAxon
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	10.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.05 m³·mol⁻¹	ChemAxon
Polarizability	37.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0256398

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14031

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenazocine

METLIN ID

Not Available

PubChem Compound

14707

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]
Prezzavento O, Arena E, Sanchez-Fernandez C, Turnaturi R, Parenti C, Marrazzo A, Catalano R, Amata E, Pasquinucci L, Cobos EJ: (+)-and (-)-Phenazocine enantiomers: Evaluation of their dual opioid agonist/sigma1 antagonist properties and antinociceptive effects. Eur J Med Chem. 2017 Jan 5;125:603-610. doi: 10.1016/j.ejmech.2016.09.077. Epub 2016 Sep 26. [PubMed:27721146 ]
Brown R, Howard R, Candy B, Sampson EL: Opioids for agitation in dementia. Cochrane Database Syst Rev. 2015 May 14;(5):CD009705. doi: 10.1002/14651858.CD009705.pub2. [PubMed:25972091 ]
LOTUS database [Link]

Showing NP-Card for phenazocine (NP0221935)

MOL for NP0221935 (phenazocine)

3D MOL for NP0221935 (phenazocine)

3D SDF for NP0221935 (phenazocine)

3D-SDF for NP0221935 (phenazocine)

PDB for NP0221935 (phenazocine)

3D PDB for NP0221935 (phenazocine)

SMILES for NP0221935 (phenazocine)

INCHI for NP0221935 (phenazocine)

Structure for NP0221935 (phenazocine)

3D Structure for NP0221935 (phenazocine)