NP-MRD: Showing NP-Card for (+)-trichostatic acid (NP0251450)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 14:39:03 UTC

Updated at

2022-09-07 14:39:03 UTC

NP-MRD ID

NP0251450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-trichostatic acid

Description

(R)-trichostatic acid, also known as (R)-trichostatate, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (+)-trichostatic acid was first documented in 1990 (PMID: 2211374). Based on a literature review very few articles have been published on (R)-trichostatic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    3.0803   -1.0012    1.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.1188    0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137    0.4139    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.2881    1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629    0.0388    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4128    0.9889    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2107   -0.6524    1.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968    0.8554    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0688    0.6377    0.3985 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4709    1.9845    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714    0.3105   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0078    0.2293   -1.9706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496    0.0885   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7760    0.1131    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602   -0.0916    0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -0.3249   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2197   -0.5309   -0.9040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9163   -0.7739   -2.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9624   -0.4990    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0834   -0.3511   -2.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -0.1445   -2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -1.8834    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -1.4121    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3410   -0.6919    2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0837    1.2173   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5692   -1.1236    1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4921   -1.5850    1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    1.6666   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -0.0755    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    1.9608    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4306    2.2388    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    2.8030    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    0.2794    1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7320   -0.0721    1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    0.0502   -2.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0128   -0.7164   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407   -1.7121   -2.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8653    0.5491    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4712   -1.1525    1.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0173   -0.7485    0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.5340   -3.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069   -0.1800   -3.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  7  1  0
  5  6  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 20  1  0
 20 21  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 21 13  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
  9 29  1  1
  8 28  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 14 33  1  0
 15 34  1  0
 20 41  1  0
 21 42  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv1652309072216392D          

 21 21  0  0  1  0            999 V2000
    1.4289    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    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   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
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   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
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    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
    0.0000    0.8250    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](\C=C(/C)\C=C\C(O)=O)C(=O)C1=CC=C(C=C1)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-12(5-10-16(19)20)11-13(2)17(21)14-6-8-15(9-7-14)18(3)4/h5-11,13H,1-4H3,(H,19,20)/b10-5+,12-11+/t13-/m1/s1

> <INCHI_KEY>
VKEITMNFEJHFCX-QEQCGCAPSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.359

> <EXACT_MASS>
287.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.576323096336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienoic acid

> <JCHEM_LOGP>
2.9848093070194914

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.24023042878197

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5428775251263405

> <JCHEM_PKA_STRONGEST_BASIC>
3.2965158370292147

> <JCHEM_POLAR_SURFACE_AREA>
57.61000000000001

> <JCHEM_REFRACTIVITY>
86.65209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+)-trichostatic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   6.160   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   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
(+)-Trichostatic acid	ChEBI
(+)-Trichostatsaeure	ChEBI
(+)-Trichostatate	Generator
(R)-Trichostatate	Generator

Chemical Formula

C₁₇H₂₁NO₃

Average Mass

287.3590 Da

Monoisotopic Mass

287.15214 Da

IUPAC Name

(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienoic acid

Traditional Name

(+)-trichostatic acid

CAS Registry Number

Not Available

SMILES

C[C@H](\C=C(/C)\C=C\C(O)=O)C(=O)C1=CC=C(C=C1)N(C)C

InChI Identifier

InChI=1S/C17H21NO3/c1-12(5-10-16(19)20)11-13(2)17(21)14-6-8-15(9-7-14)18(3)4/h5-11,13H,1-4H3,(H,19,20)/b10-5+,12-11+/t13-/m1/s1

InChI Key

VKEITMNFEJHFCX-QEQCGCAPSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenylpropane
Benzoyl
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Medium-chain fatty acid
Dialkylarylamine
Aryl alkyl ketone
Amino fatty acid
Branched fatty acid
Methyl-branched fatty acid
Monocyclic benzene moiety
Unsaturated fatty acid
Fatty acyl
Fatty acid
Benzenoid
Amino acid
Tertiary amine
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trichostatic acid (CHEBI:39158 )

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	2.98	ChemAxon
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.65 m³·mol⁻¹	ChemAxon
Polarizability	32.58 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9555572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11380658

PDB ID

Not Available

ChEBI ID

39158

Good Scents ID

Not Available

References

General References

Yoshida M, Hoshikawa Y, Koseki K, Mori K, Beppu T: Structural specificity for biological activity of trichostatin A, a specific inhibitor of mammalian cell cycle with potent differentiation-inducing activity in Friend leukemia cells. J Antibiot (Tokyo). 1990 Sep;43(9):1101-6. doi: 10.7164/antibiotics.43.1101. [PubMed:2211374 ]
LOTUS database [Link]

Showing NP-Card for (+)-trichostatic acid (NP0251450)

MOL for NP0251450 ((+)-trichostatic acid)

3D MOL for NP0251450 ((+)-trichostatic acid)

3D SDF for NP0251450 ((+)-trichostatic acid)

3D-SDF for NP0251450 ((+)-trichostatic acid)

PDB for NP0251450 ((+)-trichostatic acid)

3D PDB for NP0251450 ((+)-trichostatic acid)

SMILES for NP0251450 ((+)-trichostatic acid)

INCHI for NP0251450 ((+)-trichostatic acid)

Structure for NP0251450 ((+)-trichostatic acid)

3D Structure for NP0251450 ((+)-trichostatic acid)