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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:57:43 UTC

Update Date

2019-07-23 07:15:01 UTC

HMDB ID

HMDB0060758

Secondary Accession Numbers

HMDB60758

Metabolite Identification

Common Name

4-Anilino-4-oxobutanoic acid

Description

4-Anilino-4-oxobutanoic acid is a metabolite of vorinostat. Vorinostat or suberoylanilide hydroxamic acid (SAHA) is a member of a larger class of compounds that inhibit histone deacetylases (HDAC). Histone deacetylase inhibitors (HDI) have a broad spectrum of epigenetic activities. Vorinostat is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL) when the disease persists, gets worse, or comes back during or after treatment with other medicines. (Wikipedia)

Structure

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

  Mrv0541 07041311572D          

 14 14  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  4  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060758

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC(O)=NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c12-9(6-7-10(13)14)11-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

> <INCHI_KEY>
KTFGFGGLCMGYTP-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.711161699883213

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(phenyl-C-hydroxycarbonimidoyl)propanoic acid

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.7632756006666668

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.154001900396878

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.082568799566876

> <JCHEM_PKA_STRONGEST_BASIC>
1.440079015797459

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
52.5694

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(phenyl-C-hydroxycarbonimidoyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    4    5   11                                                  
CONECT    9    6   11   12                                                  
CONECT   10    7   13   14                                                  
CONECT   11    8    9                                                       
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Anilino-4-oxobutanoate	Generator
N-Phenyl-succinamic acid	HMDB
N-Phenyl-succinamate	HMDB
Succinanilate	HMDB

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

3-(phenyl-C-hydroxycarbonimidoyl)propanoic acid

Traditional Name

3-(phenyl-C-hydroxycarbonimidoyl)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC(O)=NC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H11NO3/c12-9(6-7-10(13)14)11-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

InChI Key

KTFGFGGLCMGYTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
N-arylamide
Fatty amide
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060758)

Organ

Kidney (HMDB: HMDB0060758)
Liver (HMDB: HMDB0060758)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060758)

Cellular substructure

Cytoplasm (HMDB: HMDB0060758)

Source

Endogenous

Endogenous (HMDB: HMDB0060758)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.76	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	1.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.57 m³·mol⁻¹	ChemAxon
Polarizability	19.71 Å³	ChemAxon
Number of Rings	1	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]+	144.522	31661259
DarkChem	[M-H]-	138.802	31661259
DeepCCS	[M+H]+	138.728	30932474
DeepCCS	[M-H]-	136.163	30932474
DeepCCS	[M-2H]-	171.872	30932474
DeepCCS	[M+Na]+	147.066	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.3	32859911
AllCCS	[M+NH4]+	145.9	32859911
AllCCS	[M+Na]+	147.0	32859911
AllCCS	[M-H]-	142.7	32859911
AllCCS	[M+Na-2H]-	143.4	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Anilino-4-oxobutanoic acid	OC(=O)CCC(O)=NC1=CC=CC=C1	3202.8	Standard polar	33892256
4-Anilino-4-oxobutanoic acid	OC(=O)CCC(O)=NC1=CC=CC=C1	1866.1	Standard non polar	33892256
4-Anilino-4-oxobutanoic acid	OC(=O)CCC(O)=NC1=CC=CC=C1	1866.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Anilino-4-oxobutanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(O)=NC1=CC=CC=C1	1832.4	Semi standard non polar	33892256
4-Anilino-4-oxobutanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(CCC(=O)O)=NC1=CC=CC=C1	1829.7	Semi standard non polar	33892256
4-Anilino-4-oxobutanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(=NC1=CC=CC=C1)O[Si](C)(C)C	1805.4	Semi standard non polar	33892256
4-Anilino-4-oxobutanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(O)=NC1=CC=CC=C1	2056.6	Semi standard non polar	33892256
4-Anilino-4-oxobutanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CCC(=O)O)=NC1=CC=CC=C1	2087.3	Semi standard non polar	33892256
4-Anilino-4-oxobutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(=NC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2240.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Anilino-4-oxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-dc60561b43fde73da654	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Anilino-4-oxobutanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9281000000-389b5541408e7188a27f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Anilino-4-oxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Anilino-4-oxobutanoic acid 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 - 4-Anilino-4-oxobutanoic acid 10V, Positive-QTOF	splash10-004l-0900000000-0c24d8141e0787031e02	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 20V, Positive-QTOF	splash10-057m-4900000000-5f8fa50ff89d19c06120	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 40V, Positive-QTOF	splash10-056r-9100000000-7e3c14dfb0575d78d0e6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 10V, Negative-QTOF	splash10-0006-0900000000-d7633988c66a13e03313	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 20V, Negative-QTOF	splash10-006x-3900000000-a528a90540c9eb07e317	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 40V, Negative-QTOF	splash10-0006-9100000000-5b78160315113b6830fb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 10V, Positive-QTOF	splash10-002f-0900000000-d53e2a594f17ddf76821	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 20V, Positive-QTOF	splash10-0563-4900000000-da726e70667cda502a83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 40V, Positive-QTOF	splash10-00mo-9100000000-5b8753c5c5154bcfba16	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 10V, Negative-QTOF	splash10-0006-9400000000-b70cf9c786853686021c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 20V, Negative-QTOF	splash10-05mo-9300000000-0fc3cf7e5f025a34f105	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Anilino-4-oxobutanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-9dc43c5825c21ffa1f98	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7598

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-Anilino-4-oxobutanoic acid (HMDB0060758)

MOL for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

3D MOL for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

3D SDF for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

3D-SDF for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

PDB for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

3D PDB for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

SMILES for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

INCHI for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

Structure for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

3D Structure for HMDB0060758 (4-Anilino-4-oxobutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra