NP-MRD: Showing NP-Card for diclazepam (NP0184746)

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Record Information

Version

1.0

Created at

2022-09-03 23:56:56 UTC

Updated at

2022-09-03 23:56:57 UTC

NP-MRD ID

NP0184746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

diclazepam

Description

2-Chlorodiazepam 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. diclazepam is found in Solanum tuberosum. It was first documented in 2014 (PMID: 24604775). Based on a literature review a significant number of articles have been published on 2-Chlorodiazepam (PMID: 36057450) (PMID: 36057449) (PMID: 36057448) (PMID: 36057447).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.7029   -0.7709    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594   -0.9585    0.2368 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338   -2.2496   -0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -3.1981    0.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -2.5660   -0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -1.8723   -0.4571 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852   -0.6080   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8536   -0.1704    0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    1.0499    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057    1.3678    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172    0.4398    0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.8173    0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -1.1094    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.7230   -0.3676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511    0.4023   -0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    1.5801   -0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826    2.6451   -1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1154    4.1485   -1.7721 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1299    2.4878   -0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720    1.3185   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8156    0.2730   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5748   -0.7251    0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8708   -1.6507    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6818    0.1040    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -3.6427   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0551   -2.1636   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    1.8335    0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732    2.3554    1.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5466    0.6850    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785   -1.5521    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.5903   -1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7931    3.3455   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    1.1509   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 21  1  0
 21 20  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15  7  1  0
  7  6  2  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  3  2  1  0
 13  8  1  0
 15 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 33  1  0
 19 32  1  0
 16 31  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
M  END


  Mrv1652309042201572D          

 21 23  0  0  0  0            999 V2000
    3.4479    1.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.6577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502    1.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -2.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691   -3.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808   -3.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -3.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -1.6824    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0941    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.1434    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=CC=C(Cl)C=C2C(=NCC1=O)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H12Cl2N2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

> <INCHI_KEY>
VPAYQWRBBOGGPY-UHFFFAOYSA-N

> <FORMULA>
C16H12Cl2N2O

> <MOLECULAR_WEIGHT>
319.19

> <EXACT_MASS>
318.0326684

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
31.353382420577127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.6801312436666676

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.1335135657445092

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
84.61670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-5-(2-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.436   2.729   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.779   1.228   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.280   0.885   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.240   2.089   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.948  -0.502   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       8.280  -1.890   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.779  -2.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.436  -3.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.565  -4.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.222  -6.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.751  -6.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.622  -5.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.965  -4.188   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       3.836  -3.140   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.241  -2.042   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       1.574  -2.042   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.241   1.038   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    7   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15    2                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂Cl₂N₂O

Average Mass

319.1900 Da

Monoisotopic Mass

318.03267 Da

IUPAC Name

7-chloro-5-(2-chlorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

7-chloro-5-(2-chlorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one

CAS Registry Number

Not Available

SMILES

CN1C2=CC=C(Cl)C=C2C(=NCC1=O)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H12Cl2N2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3

InChI Key

VPAYQWRBBOGGPY-UHFFFAOYSA-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
Solanum tuberosum	LOTUS Database	35616633

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
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
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	3.68	ChemAxon
pKa (Strongest Basic)	2.13	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	84.62 m³·mol⁻¹	ChemAxon
Polarizability	31.35 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

HMDB0251203

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorodiazepam

METLIN ID

Not Available

PubChem Compound

76168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Moosmann B, Bisel P, Auwarter V: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. Drug Test Anal. 2014 Jul-Aug;6(7-8):757-63. doi: 10.1002/dta.1628. Epub 2014 Mar 6. [PubMed:24604775 ]
LOTUS database [Link]

Showing NP-Card for diclazepam (NP0184746)

MOL for NP0184746 (diclazepam)

3D MOL for NP0184746 (diclazepam)

3D SDF for NP0184746 (diclazepam)

3D-SDF for NP0184746 (diclazepam)

PDB for NP0184746 (diclazepam)

3D PDB for NP0184746 (diclazepam)

SMILES for NP0184746 (diclazepam)

INCHI for NP0184746 (diclazepam)

Structure for NP0184746 (diclazepam)

3D Structure for NP0184746 (diclazepam)