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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:33 UTC

Update Date

2019-07-23 06:10:14 UTC

HMDB ID

HMDB0032066

Secondary Accession Numbers

HMDB32066

Metabolite Identification

Common Name

Carbanilide

Description

Carbanilide, also known as diphenylurea or diphenylcarbamide, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Carbanilide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Carbanilide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

BSU
  Mrv0541 02241213282D          

 16 17  0  0  0  0            999 V2000
   -0.9845   -0.2601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    0.9774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701   -1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701   -2.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -2.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    2.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    2.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3 11  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  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
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032066

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(NC1=CC=CC=C1)NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)

> <INCHI_KEY>
GWEHVDNNLFDJLR-UHFFFAOYSA-N

> <FORMULA>
C13H12N2O

> <MOLECULAR_WEIGHT>
212.2472

> <EXACT_MASS>
212.094963016

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.914953291481243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-diphenylurea

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.1186551609999995

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.354146234688113

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.534015595804641

> <JCHEM_PKA_STRONGEST_BASIC>
-4.539614945606808

> <JCHEM_POLAR_SURFACE_AREA>
41.129999999999995

> <JCHEM_REFRACTIVITY>
66.05280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-diphenylurea

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: BSU                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.838  -0.486   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.504   0.284   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.504   1.824   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0       0.830  -0.486   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.838  -2.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.504  -2.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.504  -4.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.838  -5.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.171  -4.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.171  -2.796   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.830   2.594   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.830   4.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.163   4.904   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.497   4.134   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.497   2.594   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.163   1.824   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2   11                                                       
CONECT    4    2                                                            
CONECT    5    1    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    3   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0032066
HETATM    1  O1  UNL     1      -0.012   1.034   0.144  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.040  -0.204   0.119  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.175  -0.916   0.136  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.491  -0.400   0.180  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.835   0.919   0.214  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.158   1.367   0.256  1.00  0.00           C  
HETATM    7  C5  UNL     1      -5.186   0.472   0.266  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.883  -0.869   0.233  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.576  -1.294   0.191  1.00  0.00           C  
HETATM   10  N2  UNL     1       1.265  -0.866   0.075  1.00  0.00           N  
HETATM   11  C8  UNL     1       2.533  -0.278   0.049  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.676  -1.084   0.196  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.929  -0.593   0.172  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.119   0.755  -0.005  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.051   1.586  -0.153  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.767   1.042  -0.123  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.036  -1.984   0.112  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.090   1.687   0.209  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.398   2.417   0.282  1.00  0.00           H  
HETATM   20  H4  UNL     1      -6.212   0.800   0.299  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.724  -1.550   0.242  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.346  -2.339   0.166  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.210  -1.934   0.058  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.523  -2.135   0.334  1.00  0.00           H  
HETATM   25  H9  UNL     1       5.792  -1.236   0.287  1.00  0.00           H  
HETATM   26  H10 UNL     1       6.107   1.195  -0.032  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.164   2.666  -0.296  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.947   1.745  -0.254  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   17
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   22
CONECT   10   11   23
CONECT   11   12   12   16
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Diphenylcarbamide	ChEBI
Diphenylcarbamide	ChEBI
Diphenylurea	ChEBI
N,N'-diphenylurea	ChEBI
N-Phenyl-n'-phenylurea	ChEBI
S-Diphenylurea	ChEBI
Sym-diphenylurea	ChEBI
1, 3-Diphenylurea	HMDB
1,3-Diphenyl-urea	HMDB
1,3-Diphenylurea	HMDB
Acardite	HMDB
Acardite I	HMDB
BSU	HMDB
Centralite	HMDB
Karbanilid	HMDB
N,N'-difenylmocovina	HMDB
N,N'-diphenyl-urea	HMDB
N,N-Diphenylurea	HMDB
Urea-based compound, 7	HMDB
Zeonet u	HMDB
Carbanilide	ChEBI

Chemical Formula

C₁₃H₁₂N₂O

Average Molecular Weight

212.2472

Monoisotopic Molecular Weight

212.094963016

IUPAC Name

1,3-diphenylurea

Traditional Name

1,3-diphenylurea

CAS Registry Number

102-07-8

SMILES

O=C(NC1=CC=CC=C1)NC1=CC=CC=C1

InChI Identifier

InChI=1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)

InChI Key

GWEHVDNNLFDJLR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Isourea
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ureas (CHEBI:41320 )

Ontology

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	239 - 240 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 mg/mL	Not Available
LogP	3.00	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.091 g/L	ALOGPS
logP	10^(3.1) g/L	ALOGPS
logP	10^(3.12) g/L	ChemAxon
logS	10^(-3.4) g/L	ALOGPS
pKa (Strongest Acidic)	11.53	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.05 m³·mol⁻¹	ChemAxon
Polarizability	21.91 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.571	31661259
DarkChem	[M-H]-	146.382	31661259
DeepCCS	[M+H]+	147.578	30932474
DeepCCS	[M-H]-	145.205	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbanilide	O=C(NC1=CC=CC=C1)NC1=CC=CC=C1	2743.6	Standard polar	33892256
Carbanilide	O=C(NC1=CC=CC=C1)NC1=CC=CC=C1	1937.4	Standard non polar	33892256
Carbanilide	O=C(NC1=CC=CC=C1)NC1=CC=CC=C1	2248.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carbanilide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)NC1=CC=CC=C1)C1=CC=CC=C1	2061.6	Semi standard non polar	33892256
Carbanilide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)NC1=CC=CC=C1)C1=CC=CC=C1	1944.2	Standard non polar	33892256
Carbanilide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N(C1=CC=CC=C1)[Si](C)(C)C)C1=CC=CC=C1	1976.6	Semi standard non polar	33892256
Carbanilide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N(C1=CC=CC=C1)[Si](C)(C)C)C1=CC=CC=C1	2011.7	Standard non polar	33892256
Carbanilide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=CC=C1)C1=CC=CC=C1	2285.2	Semi standard non polar	33892256
Carbanilide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=CC=C1)C1=CC=CC=C1	2137.6	Standard non polar	33892256
Carbanilide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2416.9	Semi standard non polar	33892256
Carbanilide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2397.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-0006-9000000000-8c505da083f3fc7e2911	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-0006-9000000000-a0fa514c3fc79d9ab070	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-01ox-9040000000-aeb7951e27e369a7e434	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-0006-9000000000-8c505da083f3fc7e2911	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-0006-9000000000-a0fa514c3fc79d9ab070	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carbanilide EI-B (Non-derivatized)	splash10-01ox-9040000000-aeb7951e27e369a7e434	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbanilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9210000000-2605b48ba77a432353bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbanilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 10V, Positive-QTOF	splash10-03dl-5090000000-1ef75040ddfa6013214a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 20V, Positive-QTOF	splash10-0006-9120000000-190a734b7430c2d2c375	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 40V, Positive-QTOF	splash10-00kf-9000000000-69adf544c6c3abf49350	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 10V, Negative-QTOF	splash10-03dl-5390000000-f837ba53508dd5155aaa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 20V, Negative-QTOF	splash10-0006-9330000000-1b96b1755a64ffd89bd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 40V, Negative-QTOF	splash10-0006-9000000000-5c20f4f5f3f10f0af0aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 10V, Positive-QTOF	splash10-03di-3090000000-b610f838b298ab440649	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 20V, Positive-QTOF	splash10-0006-9100000000-3373cd655cfc7e9f4828	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 40V, Positive-QTOF	splash10-0006-9100000000-fa0e18d8e885676a1d2d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 10V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 20V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbanilide 40V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07496

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008775

KNApSAcK ID

C00054091

Chemspider ID

7314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,3-Diphenylurea

METLIN ID

Not Available

PubChem Compound

7595

PDB ID

BSU

ChEBI ID

41320

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1227171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Carbanilide (HMDB0032066)

MOL for HMDB0032066 (Carbanilide)

3D MOL for HMDB0032066 (Carbanilide)

3D SDF for HMDB0032066 (Carbanilide)

3D-SDF for HMDB0032066 (Carbanilide)

PDB for HMDB0032066 (Carbanilide)

3D PDB for HMDB0032066 (Carbanilide)

SMILES for HMDB0032066 (Carbanilide)

INCHI for HMDB0032066 (Carbanilide)

Structure for HMDB0032066 (Carbanilide)

3D Structure for HMDB0032066 (Carbanilide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra