NP-MRD: Showing NP-Card for 3-hydroxy-3-(methoxycarbonyl)pentanedioic acid (NP0146643)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 02:04:47 UTC

Updated at

2022-09-02 02:04:47 UTC

NP-MRD ID

NP0146643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3-(methoxycarbonyl)pentanedioic acid

Description

3-Hydroxy-3-(methoxycarbonyl)pentanedioic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 3-hydroxy-3-(methoxycarbonyl)pentanedioic acid is found in Citrus trifoliata. 3-Hydroxy-3-(methoxycarbonyl)pentanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508272D          

 14 13  0  0  0  0            999 V2000
    1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146643

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O7/c1-14-6(12)7(13,2-4(8)9)3-5(10)11/h13H,2-3H2,1H3,(H,8,9)(H,10,11)

> <INCHI_KEY>
HCVBQXINVUFVCE-UHFFFAOYSA-N

> <FORMULA>
C7H10O7

> <MOLECULAR_WEIGHT>
206.15

> <EXACT_MASS>
206.042652662

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.577504250680924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3-(methoxycarbonyl)pentanedioic acid

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-1.1767933959999999

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.08683110808842

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.370463352935788

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1893660152262635

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
40.393

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-(methoxycarbonyl)pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.516  -5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.516  -3.644   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.850  -2.874   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.184  -3.644   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.390  -1.334   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.850   0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   0.976   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.184   2.516   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.517   0.206   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-3-(methoxycarbonyl)pentanedioate	Generator
2-Hydroxy-1,2,3-propanetricarboxylate 2-methyl ester	Generator
2-HPTCA-me CPD	MeSH

Chemical Formula

C₇H₁₀O₇

Average Mass

206.1500 Da

Monoisotopic Mass

206.04265 Da

IUPAC Name

3-hydroxy-3-(methoxycarbonyl)pentanedioic acid

Traditional Name

3-hydroxy-3-(methoxycarbonyl)pentanedioic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)(CC(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C7H10O7/c1-14-6(12)7(13,2-4(8)9)3-5(10)11/h13H,2-3H2,1H3,(H,8,9)(H,10,11)

InChI Key

HCVBQXINVUFVCE-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

Species Name	Source	Reference
Citrus trifoliata	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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
logP	-1.3	ALOGPS
logP	-1.2	ChemAxon
logS	0.01	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.39 m³·mol⁻¹	ChemAxon
Polarizability	17.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12566215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-3-(methoxycarbonyl)pentanedioic acid (NP0146643)

MOL for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

3D MOL for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

3D SDF for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

3D-SDF for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

PDB for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

3D PDB for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

SMILES for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

INCHI for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

Structure for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)

3D Structure for NP0146643 (3-hydroxy-3-(methoxycarbonyl)pentanedioic acid)