NP-MRD: Showing NP-Card for 2-Hydroxycampholonic acid (NP0045573)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:05 UTC

Updated at

2022-03-17 19:32:05 UTC

NP-MRD ID

NP0045573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxycampholonic acid

Description

2-Hydroxycampholonic acid belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. 2-Hydroxycampholonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212142D          

 14 14  0  0  0  0            999 V2000
   -3.0054   -0.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6728   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4179   -1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533   -0.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1079   -2.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0054   -2.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9028   -2.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2147   -1.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4574   -0.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136    0.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159    0.6227    0.0000 O   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
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  2 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>
NP0045573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(CC(O)=O)CC(=O)C1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O4/c1-9(2)6(5-8(12)13)4-7(11)10(9,3)14/h6,14H,4-5H2,1-3H3,(H,12,13)

> <INCHI_KEY>
OBFKTGKIOIHLFK-UHFFFAOYSA-N

> <FORMULA>
C10H16O4

> <MOLECULAR_WEIGHT>
200.2316

> <EXACT_MASS>
200.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.31173340064433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl)acetic acid

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
0.7596452376666669

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.877852437350935

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.442326120739339

> <JCHEM_PKA_STRONGEST_BASIC>
-3.727674050965459

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
49.5366

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.610  -0.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.856  -1.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.380  -3.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.840  -3.315   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.364  -1.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.899  -1.374   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.935  -4.561   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.610  -4.648   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.285  -4.561   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.867  -2.916   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.320  -1.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.641   0.132   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -10.105   0.608   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.496   1.162   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9   10                                             
CONECT    4    3    5    7    8                                             
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3                                                            
CONECT   10    3                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxycampholonate	Generator

Chemical Formula

C₁₀H₁₆O₄

Average Mass

200.2316 Da

Monoisotopic Mass

200.10486 Da

IUPAC Name

2-(3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl)acetic acid

Traditional Name

(3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl)acetic acid

CAS Registry Number

141717-34-2

SMILES

CC1(C)C(CC(O)=O)CC(=O)C1(C)O

InChI Identifier

InChI=1S/C10H16O4/c1-9(2)6(5-8(12)13)4-7(11)10(9,3)14/h6,14H,4-5H2,1-3H3,(H,12,13)

InChI Key

OBFKTGKIOIHLFK-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Salvia officinalis	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

11-noriridane monoterpenoid
Monocyclic monoterpenoid
Acyloin
Cyclopentanol
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	0.6	ALOGPS
logP	0.76	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.54 m³·mol⁻¹	ChemAxon
Polarizability	20.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB001459

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

85643153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxycampholonic acid (NP0045573)

MOL for NP0045573 (2-Hydroxycampholonic acid)

3D MOL for NP0045573 (2-Hydroxycampholonic acid)

3D SDF for NP0045573 (2-Hydroxycampholonic acid)

3D-SDF for NP0045573 (2-Hydroxycampholonic acid)

PDB for NP0045573 (2-Hydroxycampholonic acid)

3D PDB for NP0045573 (2-Hydroxycampholonic acid)

SMILES for NP0045573 (2-Hydroxycampholonic acid)

INCHI for NP0045573 (2-Hydroxycampholonic acid)

Structure for NP0045573 (2-Hydroxycampholonic acid)

3D Structure for NP0045573 (2-Hydroxycampholonic acid)