NP-MRD: Showing NP-Card for Diazepam (NP0047053)

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Record Information

Version

2.0

Created at

2022-03-17 20:33:50 UTC

Updated at

2022-03-17 20:33:50 UTC

NP-MRD ID

NP0047053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diazepam

Description

Diazepam, also known as valium or diastat, belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Diazepam is a moderately basic compound (based on its pKa). Outside of the human body, Diazepam has been detected, but not quantified in, common wheats and potato. This could make diazepam a potential biomarker for the consumption of these foods. Diazepam is a potentially toxic compound. Diazepam is found in Glycine max, Homo sapiens and Mentha spicata. Diazepam was first documented in 1979 (PMID: 458601). A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5 (PMID: 2450203) (PMID: 3089825) (PMID: 7911332) (PMID: 11995921).

Structure

MOL SDF PDB SMILES InChI

829
  Mrv0541 02231215022D          

 20 22  0  0  0  0            999 V2000
    2.8172   -2.3592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    2.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3080    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3811   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7694   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9781   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5374   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1824   -0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0594   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  9  2  0  0  0  0
  3  6  1  0  0  0  0
  3  9  1  0  0  0  0
  3 13  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
 10 16  2  0  0  0  0
 10 17  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

> <INCHI_KEY>
AAOVKJBEBIDNHE-UHFFFAOYSA-N

> <FORMULA>
C16H13ClN2O

> <MOLECULAR_WEIGHT>
284.74

> <EXACT_MASS>
284.071640755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.386528122049114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.0760865673333337

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.921450447162867

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
79.81190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diazepam

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 829                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.259  -4.404   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.873   4.404   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.581   1.812   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.042   1.812   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.311  -0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.699   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   3.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   3.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.903  -0.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.456  -1.955   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.585  -0.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   2.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.138  -2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.692  -2.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.336  -0.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.673  -2.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.540  -1.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.877  -3.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.311  -2.569   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    9                                                            
CONECT    3    6    9   13                                                  
CONECT    4    7    8                                                       
CONECT    5    6    7   11                                                  
CONECT    6    3    5   12                                                  
CONECT    7    4    5   10                                                  
CONECT    8    4    9                                                       
CONECT    9    2    3    8                                                  
CONECT   10    7   16   17                                                  
CONECT   11    5   14                                                       
CONECT   12    6   15                                                       
CONECT   13    3                                                            
CONECT   14    1   11   15                                                  
CONECT   15   12   14                                                       
CONECT   16   10   18                                                       
CONECT   17   10   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
Methyl diazepinone	ChEBI
Valium	ChEBI
Diastat	Kegg
Methyldiazepinone	HMDB
Apaurin	HMDB
Faustan	HMDB
Relanium	HMDB
Seduxen	HMDB
Diazemuls	HMDB
Sibazon	HMDB
Stesolid	HMDB

Chemical Formula

C₁₆H₁₃ClN₂O

Average Mass

284.7400 Da

Monoisotopic Mass

284.07164 Da

IUPAC Name

7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

diazepam

CAS Registry Number

439-14-5

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

InChI Key

AAOVKJBEBIDNHE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycine max	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Mentha spicata	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Carboxylic acid derivative
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:49575 )
1,4-benzodiazepinone (CHEBI:49575 )

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	2.63	ALOGPS
logP	3.08	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	2.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.81 m³·mol⁻¹	ChemAxon
Polarizability	29.39 Å³	ChemAxon
Number of Rings	3	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

HMDB0014967

DrugBank ID

DB00829

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007103

KNApSAcK ID

Not Available

Chemspider ID

2908

KEGG Compound ID

C06948

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diazepam

METLIN ID

Not Available

PubChem Compound

3016

PDB ID

DZP

ChEBI ID

49575

Good Scents ID

Not Available

References

General References

Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. doi: 10.1002/jps.2600680715. [PubMed:458601 ]
McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. [PubMed:2450203 ]
Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. doi: 10.1016/0014-2999(86)90236-0. [PubMed:3089825 ]
Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. doi: 10.1111/j.1753-6405.1993.tb00167.x. [PubMed:7911332 ]
Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. doi: 10.1248/bpb.25.441. [PubMed:11995921 ]

Showing NP-Card for Diazepam (NP0047053)

MOL for NP0047053 (Diazepam)

3D MOL for NP0047053 (Diazepam)

3D SDF for NP0047053 (Diazepam)

3D-SDF for NP0047053 (Diazepam)

PDB for NP0047053 (Diazepam)

3D PDB for NP0047053 (Diazepam)

SMILES for NP0047053 (Diazepam)

INCHI for NP0047053 (Diazepam)

Structure for NP0047053 (Diazepam)

3D Structure for NP0047053 (Diazepam)