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Showing NP-Card for Acetylsalisylic acid (NP0331793)

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Record Information
Version1.0
Created at2023-09-06 20:02:04 UTC
Updated at2024-04-19 09:51:49 UTC
NP-MRD IDNP0331793
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetylsalisylic acid
DescriptionAspirin, also known as acetylsalicylate or ASA, belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid. Aspirin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, aspirin is involved in acetaminophen action pathway. Outside of the human body, Aspirin has been detected, but not quantified in, herbs and spices. This could make aspirin a potential biomarker for the consumption of these foods. Aspirin is a potentially toxic compound. It was first documented in 1991 (PMID: 1650428). It was isolated from meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839 (PMID: 11203441) (PMID: 11402787) (PMID: 11597554) (PMID: 11733186) (PMID: 12852484) (PMID: 14753751).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0331793 (Acetylsalisylic acid)

945
  Mrv1652305271900032D          

 13 13  0  0  0  0            999 V2000
    3.0791   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
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3D MOL for NP0331793 (Acetylsalisylic acid)

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3D SDF for NP0331793 (Acetylsalisylic acid)
945
  Mrv1652305271900032D          

 13 13  0  0  0  0            999 V2000
    3.0791   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)

> <INCHI_KEY>
BSYNRYMUTXBXSQ-UHFFFAOYSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.104469525543394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)benzoic acid

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.238089698333333

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4147992082888385

> <JCHEM_PKA_STRONGEST_BASIC>
-7.144798751338897

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
44.4466

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aspirin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0331793 (Acetylsalisylic acid)
Download
PDB for NP0331793 (Acetylsalisylic acid)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 945                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748  -0.092   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748   2.218   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081   2.218   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -2.402   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -2.402   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -3.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.092   0.000  0.00  0.00           C+0
CONECT    1    5   12                                                       
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5    8   11                                                  
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    2    3    6                                                  
CONECT   12    1    4   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0331793 (Acetylsalisylic acid)
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SMILES for NP0331793 (Acetylsalisylic acid)
CC(=O)OC1=CC=CC=C1C(O)=O
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INCHI for NP0331793 (Acetylsalisylic acid)
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKegg
AspalonKegg
DurlazaKegg
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
Chemical FormulaC9H8O4
Average Mass180.1574 Da
Monoisotopic Mass180.04226 Da
IUPAC Name2-(acetyloxy)benzoic acid
Traditional Nameaspirin
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChI KeyBSYNRYMUTXBXSQ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-06View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentAcylsalicylic acids  
Alternative Parents
Substituents
  • Acylsalicylic acid
    • 

  • Phenol ester
    • 

  • Benzoic acid
    • 

  • Phenoxy compound
    • 

  • Benzoyl
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP1.43ALOGPS
logP1.24ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.45 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001879  
DrugBank IDDB00945  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000894  
KNApSAcK IDNot Available
Chemspider ID2157  
KEGG Compound IDC01405  
BioCyc IDCPD-524  
BiGG ID45400  
Wikipedia LinkAspirin  
METLIN IDNot Available
PubChem Compound2244  
PDB IDNot Available
ChEBI ID15365  
Good Scents IDNot Available
References
General References
  1. Varga JM, Kalchschmid G, Klein GF, Fritsch P: Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody. Mol Immunol. 1991 Jun;28(6):641-54. doi: 10.1016/0161-5890(91)90133-5. [PubMed:1650428  ] 
  2. Epelde F, Garca-Castrillo Riesgo L, Loma-Osorio A, Verdier J, Recuerda Martnez E: [The use of acetylsalicylic acid in patients with ischemic cardiomyopathy cared for in Spanish emergency services (results of the EVICURE Study). Evaluacion del Manejo de la cardiopatia isquemica en los Servicios de Urgencias Hospitalarios of the Sociedad Espanola de Medicina de Urgencias y Emergencias (SEMES)]. Med Clin (Barc). 2000 Oct 14;115(12):455-7. doi: 10.1016/s0025-7753(00)71590-9. [PubMed:11203441  ] 
  3. Sexton RC Jr: Aspirin in cardiovascular disease. Tenn Med. 2001 Jun;94(6):208-10. [PubMed:11402787  ] 
  4. Schroder A, Levin RM, Kogan BA, Longhurst PA: Aspirin treatment improves bladder function after outlet obstruction in rabbits. Urology. 2001 Oct;58(4):608-13. doi: 10.1016/s0090-4295(01)01291-2. [PubMed:11597554  ] 
  5. Bazzi MD, Rabbani N, Duhaiman AS: Inhibition of camel lens zeta-crystallin by aspirin and aspirin-like analgesics. Int J Biochem Cell Biol. 2002 Jan;34(1):70-7. doi: 10.1016/s1357-2725(01)00099-1. [PubMed:11733186  ] 
  6. Streck RD, Kumpf SW, Ozolins TR, Stedman DB: Rat embryos express transcripts for cyclooxygenase-1 and carbonic anhydrase-4, but not for cyclooxygenase-2, during organogenesis. Birth Defects Res B Dev Reprod Toxicol. 2003 Feb;68(1):57-69. doi:  10.1002/bdrb.10006. [PubMed:12852484  ] 
  7. Kutuk O, Basaga H: Aspirin prevents apoptosis and NF-kappaB activation induced by H2O2 in hela cells. Free Radic Res. 2003 Dec;37(12):1267-76. doi: 10.1080/10715760310001616005. [PubMed:14753751  ] 
  8. Witte KK, Clark AL: The effect of aspirin on the ventilatory response to exercise in chronic heart failure. Eur J Heart Fail. 2004 Oct;6(6):745-8. doi: 10.1016/j.ejheart.2003.11.008. [PubMed:15542410  ] 
  9. Huang ZW, Luo Y, Wu Z, Tao Z, Jones RO, Zhao HB: Paradoxical enhancement of active cochlear mechanics in long-term administration of salicylate. J Neurophysiol. 2005 Apr;93(4):2053-61. doi: 10.1152/jn.00959.2004. Epub 2004 Dec  8. [PubMed:15590729  ] 
  10. Watson HG, Chee YL: Aspirin and other antiplatelet drugs in the prevention of venous thromboembolism. Blood Rev. 2008 Mar;22(2):107-16. doi: 10.1016/j.blre.2007.11.001. Epub 2008 Jan  15. [PubMed:18226435  ]