Showing NP-Card for Citric acid (NP0000152)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:40:18 UTC
NP-MRD IDNP0000152
Secondary Accession NumbersNone
Natural Product Identification
Common NameCitric acid
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000152 (Citric acid)

  Mrv1652309032023522D          

 13 12  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 11  1  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  8  1  0  0  0  0
  8  9  1  0  0  0  0
 12 10  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000152 (Citric acid)

HMDB0000094
     RDKit          3D
Citric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    2.1927    1.4096    0.7597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175    0.5612   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    0.2555   -0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -0.1051   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    0.3623    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    0.0714    1.7032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.3008    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -1.7640    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6602   -2.3881   -0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283   -2.4749    0.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    1.8246    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010    2.5412    1.2760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8286    2.4268   -0.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -0.6834   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6030    0.0676   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853   -1.1840   -0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -0.6342    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3876    0.1042    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.0295   -0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -3.2326    0.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176    3.1721   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

3D SDF for NP0000152 (Citric acid)

  Mrv1652309032023522D          

 13 12  0  0  0  0            999 V2000
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 11  1  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  8  1  0  0  0  0
  8  9  1  0  0  0  0
 12 10  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(O)(CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

> <INCHI_KEY>
KRKNYBCHXYNGOX-UHFFFAOYSA-N

> <FORMULA>
C6H8O7

> <MOLECULAR_WEIGHT>
192.1235

> <EXACT_MASS>
192.02700261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.53525731872116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxypropane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-1.3226874519999998

> <ALOGPS_LOGS>
-0.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.674836176324

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0479515131680732

> <JCHEM_PKA_STRONGEST_BASIC>
-4.185693450231931

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
35.6239

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000152 (Citric acid)

HMDB0000094
     RDKit          3D
Citric acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    2.1927    1.4096    0.7597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175    0.5612   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    0.2555   -0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -0.1051   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2769    0.3623    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    0.0714    1.7032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.3008    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -1.7640    0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6602   -2.3881   -0.0097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283   -2.4749    0.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    1.8246    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010    2.5412    1.2760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8286    2.4268   -0.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -0.6834   -0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6030    0.0676   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853   -1.1840   -0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7242   -0.6342    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3876    0.1042    0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.0295   -0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -3.2326    0.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176    3.1721   -0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

PDB for NP0000152 (Citric acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   11    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8                                                            
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   12                                                       
CONECT   11    4   12                                                       
CONECT   12   10   11    1   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for NP0000152 (Citric acid)

COMPND    HMDB0000094
HETATM    1  O1  UNL     1       2.193   1.410   0.760  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.117   0.561  -0.155  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.269   0.256  -0.847  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.849  -0.105  -0.502  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.277   0.362   0.357  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.032   0.071   1.703  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.582  -0.301   0.086  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.609  -1.764   0.279  1.00  0.00           C  
HETATM    9  O4  UNL     1      -2.660  -2.388  -0.010  1.00  0.00           O  
HETATM   10  O5  UNL     1      -0.528  -2.475   0.764  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.502   1.825   0.254  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.401   2.541   1.276  1.00  0.00           O  
HETATM   13  O7  UNL     1      -0.829   2.427  -0.969  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.630  -0.683  -0.762  1.00  0.00           H  
HETATM   15  H2  UNL     1       0.603   0.068  -1.577  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.985  -1.184  -0.382  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.724  -0.634   1.709  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.388   0.104   0.769  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.977  -0.030  -0.940  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.132  -3.233   0.198  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.518   3.172  -0.996  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    7   11
CONECT    6   17
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   13
CONECT   13   21
END
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SMILES for NP0000152 (Citric acid)

OC(=O)CC(O)(CC(O)=O)C(O)=O
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INCHI for NP0000152 (Citric acid)

InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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View in JSmol
Synonyms
Chemical FormulaC6H8O7
Average Mass192.1235 Da
Monoisotopic Mass192.02700 Da
IUPAC Name2-hydroxypropane-1,2,3-tricarboxylic acid
Traditional Namecitric acid
CAS Registry Number77-92-9
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-19View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, 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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-21View Spectrum
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility592 mg/mLNot Available
LogP-1.64Avdeef, A., Box, K. J., Comer, J. E. A., Hibbert, C., & Tam, K. Y. (1998). pH-Metric logP 10. Determination of liposomal membrane-water partition coefficients of lonizable drugs. Pharmaceutical research, 15(2), 209-215.
Predicted Properties
PropertyValueSource
Water Solubility106 g/LALOGPS
logP-1.3ALOGPS
logP-1.3ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.62 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000094
DrugBank IDDB04272
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030735
KNApSAcK IDC00007619
Chemspider ID305
KEGG Compound IDC00158
BioCyc IDCIT
BiGG ID34080
Wikipedia LinkCitric_Acid
METLIN ID124
PubChem Compound311
PDB IDNot Available
ChEBI ID30769
Good Scents IDrw1000441
References
General References