NP-MRD: Showing NP-Card for [2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid (NP0203633)

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Record Information

Version

1.0

Created at

2022-09-04 23:08:15 UTC

Updated at

2022-09-04 23:08:15 UTC

NP-MRD ID

NP0203633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

Description

Phenatic acid B, also known as phenatate b, 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. It was first documented in 2005 (PMID: 15981411). Based on a literature review a significant number of articles have been published on Phenatic acid B (PMID: 36070501) (PMID: 36070500) (PMID: 36070964) (PMID: 19863073).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.8735    2.6958   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4755    1.2809    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048    0.4846    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -0.8219    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -1.7128    1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -1.3146    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996   -2.6378    0.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217   -0.5324   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -1.0912   -0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -2.2998   -0.6317 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479   -0.3391   -1.6604 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3125   -1.1823   -2.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -0.3315   -2.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661   -0.5444   -3.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371    0.9737   -1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1011    0.5418   -0.7205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7485   -0.3413    0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885    0.3887    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    1.1020    0.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3836    0.3253    2.6411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999    0.7757   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776    3.1715    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8216    2.7762   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    3.3062   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2307    0.8451    1.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7299   -1.2223    2.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1335   -2.6163    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554   -2.1460    2.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908   -3.2239    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446    0.3107   -2.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399    1.4107   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    1.6120   -2.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429    1.3754   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020   -1.1191   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9433   -0.9133    0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -0.4192    3.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000    1.4333   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8 21  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
 21  2  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
 21 37  1  0
 11 30  1  6
 15 31  1  0
 15 32  1  0
 16 33  1  1
 17 34  1  0
 17 35  1  0
 20 36  1  0
M  END


  Mrv1652309052201082D          

 21 22  0  0  0  0            999 V2000
    3.5724    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.4661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109    2.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408    1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914    3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0783    2.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7064    2.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498    1.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(C)=C(O)C(=C1)C(=O)C1OC(=O)CC1CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-7-3-8(2)13(19)10(4-7)14(20)15-9(5-11(16)17)6-12(18)21-15/h3-4,9,15,19H,5-6H2,1-2H3,(H,16,17)

> <INCHI_KEY>
XMMWCOYSUBFDCF-UHFFFAOYSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.844253719472853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

> <JCHEM_LOGP>
2.4563071339999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.737004501396813

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.879823181441921

> <JCHEM_PKA_STRONGEST_BASIC>
-5.153265097922966

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
72.7564

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  12.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  11.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  10.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   8.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   8.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   6.470   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   8.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   8.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   8.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001   6.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.247   5.565   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.771   4.100   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.676   2.854   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.231   4.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.755   5.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.291   6.041   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.146   5.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.319   5.486   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.466   3.504   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  10.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    8    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Phenatate b	Generator

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2870 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC(C)=C(O)C(=C1)C(=O)C1OC(=O)CC1CC(O)=O

InChI Identifier

InChI=1S/C15H16O6/c1-7-3-8(2)13(19)10(4-7)14(20)15-9(5-11(16)17)6-12(18)21-15/h3-4,9,15,19H,5-6H2,1-2H3,(H,16,17)

InChI Key

XMMWCOYSUBFDCF-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

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
Xylenol
Benzoyl
M-xylene
Xylene
O-cresol
P-cresol
Aryl alkyl ketone
Phenol
Alpha-acyloxy ketone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Benzenoid
Oxolane
Vinylogous acid
Lactone
Carboxylic acid ester
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

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

9646699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11471869

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Thalidomide. 2012. [PubMed:36070501 ]
Authors unspecified: Lenalidomide. 2012. [PubMed:36070500 ]
Uehara M, Wada-Hiraike O, Koga K, Yamamoto N, Hirano M, Harada M, Hirota Y, Osuga Y: Prediction of the final menstrual period in women taking Dienogest using estradiol and follicle-stimulating hormone values: a case-control study. Endocr J. 2022 Sep 7. doi: 10.1507/endocrj.EJ22-0158. [PubMed:36070964 ]
Fernandes RA, Chowdhury AK: Total syntheses of all stereoisomers of phenatic acid B. J Org Chem. 2009 Nov 20;74(22):8826-9. doi: 10.1021/jo901927w. [PubMed:19863073 ]
Fukuda T, Matsumoto A, Takahashi Y, Tomoda H, Omura S: Phenatic acids A and B, new potentiators of antifungal miconazole activity produced by Streptomyces sp. K03-0132. J Antibiot (Tokyo). 2005 Apr;58(4):252-9. doi: 10.1038/ja.2005.29. [PubMed:15981411 ]
LOTUS database [Link]

Showing NP-Card for [2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid (NP0203633)

MOL for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

3D MOL for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

3D SDF for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

3D-SDF for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

PDB for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

3D PDB for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

SMILES for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

INCHI for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

Structure for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)

3D Structure for NP0203633 ([2-(2-hydroxy-3,5-dimethylbenzoyl)-5-oxooxolan-3-yl]acetic acid)