Np mrd loader

Showing NP-Card for 3-Hydroxyadipic acid 3,6-lactone (NP0136247)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-05-12 15:09:35 UTC
Updated at2022-05-12 15:09:35 UTC
NP-MRD IDNP0136247
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyadipic acid 3,6-lactone
Description3-Hydroxyadipic acid 3,6-lactone, also known as 3-ha-3,6-la or (5-oxotetrahydrofuran-2-yl)acetic acid, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. It was first documented in 1989 (PMID: 2739576). 3-Hydroxyadipic acid 3,6-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)


  Mrv1652304062013032D          

 12 12  0  0  0  0            999 V2000
   -3.0594    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403   -0.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5009   -1.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7434   -0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -1.0903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    1.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    0.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185    0.8336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  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
M  END
Download

3D MOL for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.6971   -1.8115    0.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9433   -0.5839    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156   -0.0252    1.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264    0.2495   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.5449   -0.6092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9260   -0.6621   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9473   -0.4947    0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656    0.9435    0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727    1.7330    1.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    1.2073    0.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    0.8057    1.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979   -0.2228   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513    1.2331   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2832    1.2014   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -1.6077   -0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238   -0.6766   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -1.1220    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -0.7121    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  6
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
M  END
Download

3D SDF for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)


  Mrv1652304062013032D          

 12 12  0  0  0  0            999 V2000
   -3.0594    0.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8296   -0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896   -1.0677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403   -0.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5009   -1.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7434   -0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -1.0903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298    0.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    1.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330    0.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185    0.8336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  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
M  END
> <DATABASE_ID>
NP0136247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)CC1([H])CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O4/c7-5(8)3-4-1-2-6(9)10-4/h4H,1-3H2,(H,7,8)

> <INCHI_KEY>
BWEICTHJUIJQPH-UHFFFAOYSA-N

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.1253

> <EXACT_MASS>
144.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.138353684485134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(5-oxooxolan-2-yl)acetic acid

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.0756855796666666

> <ALOGPS_LOGS>
0.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.942735669163634

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043676685152817

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
30.7623

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-oxooxolan-2-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)

Download
PDB for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)
HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -5.711   0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.149  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.068  -1.594   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.581  -1.993   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.742  -0.701   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.402  -2.364   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.254  -0.303   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0      -3.972  -2.035   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -2.856   1.185   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.945   2.274   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.368   0.786   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -0.035   1.556   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    7    8                                             
CONECT    6    3                                                            
CONECT    7    5    9                                                       
CONECT    8    5                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)
Download
SMILES for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)
[H]OC(=O)CC1([H])CCC(=O)O1
Download
INCHI for NP0136247 (3-Hydroxyadipic acid 3,6-lactone)
InChI=1S/C6H8O4/c7-5(8)3-4-1-2-6(9)10-4/h4H,1-3H2,(H,7,8)
Download
View in JSmol
Synonyms
ValueSource
3-Hydroxyadipate 3,6-lactoneGenerator
(5-Oxotetrahydrofuran-2-yl)acetic acidHMDB
2-Furanacetic acidHMDB
3-HA-3,6-laHMDB
2-(5-Oxooxolan-2-yl)acetateGenerator
3-Hydroxyadipic acid 3,6-lactoneMeSH
Chemical FormulaC6H8O4
Average Mass144.1253 Da
Monoisotopic Mass144.04226 Da
IUPAC Name2-(5-oxooxolan-2-yl)acetic acid
Traditional Name(5-oxooxolan-2-yl)acetic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)CC1([H])CCC(=O)O1
InChI Identifier
InChI=1S/C6H8O4/c7-5(8)3-4-1-2-6(9)10-4/h4H,1-3H2,(H,7,8)
InChI KeyBWEICTHJUIJQPH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.11ALOGPS
logP-0.076ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.76 m³·mol⁻¹ChemAxon
Polarizability13.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029171  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID168429  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194109  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tserng KY, Jin SJ, Hoppel CL, Kerr DS, Genuth SM: Urinary 3-hydroxyadipic acid 3,6-lactone: structural identification and effect of fasting in adults and children. Metabolism. 1989 Jul;38(7):655-61. doi: 10.1016/0026-0495(89)90103-0. [PubMed:2739576  ]