Np mrd loader

Showing NP-Card for 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid (NP0309220)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-09-11 03:39:58 UTC
Updated at2022-09-11 03:39:58 UTC
NP-MRD IDNP0309220
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid
Description2-Acetylsalicylic acid belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid is found in Glycyrrhiza glabra and Pogostemon cablin. It was first documented in 2015 (PMID: 25997576). Based on a literature review a significant number of articles have been published on 2-acetylsalicylic acid (PMID: 33975019) (PMID: 33571616) (PMID: 33352771) (PMID: 30478499).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)


  Mrv1652309112205402D          

 13 13  0  0  0  0            999 V2000
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    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
    0.1842    1.8695    0.0000 O   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
    0.0000    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
   -0.7145    1.2375    0.0000 C   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    0.8250    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    2.8616    0.1305    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033   -0.6610    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -1.7414   -0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199   -0.1003    0.3247 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5002    1.1729    0.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548   -0.9775    1.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084   -1.4654    0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -1.2231   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117   -0.4450   -1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    0.1719   -0.9839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4513    1.6434   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244    2.1625   -2.1774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100    2.3856   -0.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7519   -0.5008    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5862    0.6073    1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    0.9439   -0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3070    1.0914    1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0070   -1.1988    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -2.1104    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.6455   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -0.2042   -2.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3760   -0.2420   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170    2.2059   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 10  4  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  6
 13 23  1  0
M  END
Download

3D SDF for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)


  Mrv1652309112205402D          

 13 13  0  0  0  0            999 V2000
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    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
    0.1842    1.8695    0.0000 O   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
    0.0000    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
   -0.7145    1.2375    0.0000 C   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    0.8250    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1(O)C=CC=CC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-6(10)9(13)5-3-2-4-7(9)8(11)12/h2-5,7,13H,1H3,(H,11,12)

> <INCHI_KEY>
GNYWBJRDQHPSJL-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.175

> <EXACT_MASS>
182.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.092595622185307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

> <JCHEM_LOGP>
0.12716556299999968

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.413044038507692

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0725684607176715

> <JCHEM_PKA_STRONGEST_BASIC>
-4.050560436697649

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
47.11610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)

Download
PDB for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.797   4.937   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+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   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   10                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)
Download
SMILES for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)
CC(=O)C1(O)C=CC=CC1C(O)=O
Download
INCHI for NP0309220 (6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid)
InChI=1S/C9H10O4/c1-6(10)9(13)5-3-2-4-7(9)8(11)12/h2-5,7,13H,1H3,(H,11,12)
Download
View in JSmol
Synonyms
ValueSource
2-AcetylsalicylateGenerator
Chemical FormulaC9H10O4
Average Mass182.1750 Da
Monoisotopic Mass182.05791 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC(=O)C1(O)C=CC=CC1C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c1-6(10)9(13)5-3-2-4-7(9)8(11)12/h2-5,7,13H,1H3,(H,11,12)
InChI KeyGNYWBJRDQHPSJL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycyrrhiza glabraLOTUS Database
Pogostemon cablinLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassGamma-keto acids and derivatives  
Direct ParentGamma-keto acids and derivatives  
Alternative Parents
Substituents
  • Gamma-keto acid
    • 

  • Tertiary alcohol
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15999663  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAspirin  
METLIN IDNot Available
PubChem Compound17841705  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Salgado MTSF, Lopes AC, Fernandes E Silva E, Cardoso JQ, Vidal RS, Cavalcante-Silva LHA, Carvalho DCM, Machado KDS, Rodrigues-Mascarenhas S, Rumjanek VM, Votto APS: Relation between ABCB1 overexpression and COX2 and ALOX5 genes in human erythroleukemia cell lines. Prostaglandins Other Lipid Mediat. 2021 Aug;155:106553. doi:  10.1016/j.prostaglandins.2021.106553. Epub 2021 May 8. [PubMed:33975019  ] 
  2. Sesaazi CD, Peter EL, Mtewa AG: The anti-nociceptive effects of ethanol extract of aerial parts of Schkuhria pinnata in mice. J Ethnopharmacol. 2021 May 10;271:113913. doi: 10.1016/j.jep.2021.113913. Epub  2021 Feb 9. [PubMed:33571616  ] 
  3. Castro-Barquero S, Ribo-Coll M, Lassale C, Tresserra-Rimbau A, Castaner O, Pinto X, Martinez-Gonzalez MA, Sorli JV, Salas-Salvado J, Lapetra J, Gomez-Gracia E, Alonso-Gomez AM, Fiol M, Serra-Majem L, Sacanella E, Basterra-Gortari FJ, Portoles O, Babio N, Cofan M, Ros E, Estruch R, Hernaez A: Mediterranean Diet Decreases the Initiation of Use of Vitamin K Epoxide Reductase Inhibitors and Their Associated Cardiovascular Risk: A Randomized Controlled Trial. Nutrients. 2020 Dec 19;12(12):3895. doi: 10.3390/nu12123895. [PubMed:33352771  ] 
  4. Meskawi M, Hueber PA, Valdivieso R, Karakiewicz PI, Pradere B, Misrai V, Chughtai B, Zorn KC: Complications and functional outcomes of high-risk patient with cardiovascular disease on antithrombotic medication treated with the 532-nm-laser photo-vaporization Greenlight XPS-180 W for benign prostate hyperplasia. World J Urol. 2019 Aug;37(8):1671-1678. doi: 10.1007/s00345-018-2560-8. Epub 2018  Nov 26. [PubMed:30478499  ] 
  5. Gkaniatsou EI, Banti CN, Kourkoumelis N, Skoulika S, Manoli M, Tasiopoulos AJ, Hadjikakou SK: Novel mixed metal Ag(I)-Sb(III)-metallotherapeutics of the NSAIDs, aspirin and salicylic acid: Enhancement of their solubility and bioactivity by using the surfactant CTAB. J Inorg Biochem. 2015 Sep;150:108-19. doi: 10.1016/j.jinorgbio.2015.04.014. Epub  2015 May 1. [PubMed:25997576  ] 
  6. LOTUS database [Link]