NP-MRD: Showing NP-Card for (R)-3-Hydroxydodecanoic acid (NP0334781)

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Record Information

Version

2.0

Created at

2024-09-10 19:56:05 UTC

Updated at

2024-09-10 19:56:05 UTC

NP-MRD ID

NP0334781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-3-Hydroxydodecanoic acid

Description

(R)-3-Hydroxydodecanoic acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (R)-3-Hydroxydodecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxydodecanoic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, (R)-3-hydroxydodecanoic acid participates in a number of enzymatic reactions. In particular, (R)-3-hydroxydodecanoic acid can be biosynthesized from 3-oxododecanoic acid; which is catalyzed by the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-hydroxydodecanoic acid can be converted into trans-dodec-2-enoic acid through the action of the enzyme fatty acid synthase. Dyhydrase domain. In humans, (R)-3-hydroxydodecanoic acid is involved in fatty acid biosynthesis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241201182D          

 16 15  0  0  1  0            999 V2000
    9.2913   -6.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0057   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7202   -6.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4347   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1491   -6.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8636   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5781   -6.3422    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2926   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0071   -6.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7215   -6.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0071   -5.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5768   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8623   -6.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1478   -6.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9209   -5.6151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1649   -5.5653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 15  1  1  0  0  0
  7 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(CCCCCCCCC)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m1/s1

> <INCHI_KEY>
MUCMKTPAZLSKTL-LLVKDONJSA-N

> <FORMULA>
C12H24O3

> <MOLECULAR_WEIGHT>
216.3172

> <EXACT_MASS>
216.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.587142030134192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-hydroxydodecanoic acid

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.2474970506666665

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
60.1951

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-3-hydroxydodecanoic 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      17.344 -11.839   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.677 -12.609   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.011 -11.839   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.345 -12.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.678 -11.839   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.012 -12.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.346 -11.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.680 -12.609   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.013 -11.839   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      29.347 -12.609   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      28.013 -10.299   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      16.010 -12.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.676 -11.839   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.343 -12.609   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      24.119 -10.482   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      26.441 -10.389   0.000  0.00  0.00           H+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15   16                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
(R)-3-Hydroxydodecanoate	Generator
(3R)-3-Hydroxydodecanoic acid	ChEBI
(3R)-3-Hydroxylauric acid	ChEBI
(R)-3-OH Dodecanoic acid	ChEBI
(R)-3-OH Lauric acid	ChEBI
(R)-beta-Hydroxydodecanoic acid	ChEBI
(R)-beta-Hydroxylauric acid	ChEBI
(R)-beta-OH Dodecanoic acid	ChEBI
(R)-beta-OH Lauric acid	ChEBI
D-(-)-3-Hydroxydodecanoic acid	ChEBI
D-3-Hydroxydodecanoic acid	ChEBI
(3R)-3-Hydroxydodecanoate	Generator
(3R)-3-Hydroxylaate	Generator
(3R)-3-Hydroxylaic acid	Generator
(R)-3-OH Dodecanoate	Generator
(R)-3-OH Laate	Generator
(R)-3-OH Laic acid	Generator
(R)-b-Hydroxydodecanoate	Generator
(R)-b-Hydroxydodecanoic acid	Generator
(R)-beta-Hydroxydodecanoate	Generator
(R)-β-hydroxydodecanoate	Generator
(R)-β-hydroxydodecanoic acid	Generator
(R)-b-Hydroxylaate	Generator
(R)-b-Hydroxylaic acid	Generator
(R)-beta-Hydroxylaate	Generator
(R)-beta-Hydroxylaic acid	Generator
(R)-β-hydroxylaate	Generator
(R)-β-hydroxylaic acid	Generator
(R)-b-OH Dodecanoate	Generator
(R)-b-OH Dodecanoic acid	Generator
(R)-beta-OH Dodecanoate	Generator
(R)-β-OH dodecanoate	Generator
(R)-β-OH dodecanoic acid	Generator
(R)-b-OH Laate	Generator
(R)-b-OH Laic acid	Generator
(R)-beta-OH Laate	Generator
(R)-beta-OH Laic acid	Generator
(R)-β-OH laate	Generator
(R)-β-OH laic acid	Generator
D-(-)-3-Hydroxydodecanoate	Generator
D-3-Hydroxydodecanoate	Generator

Chemical Formula

C₁₂H₂₄O₃

Average Mass

216.3172 Da

Monoisotopic Mass

216.17254 Da

IUPAC Name

(3R)-3-hydroxydodecanoic acid

Traditional Name

(R)-3-hydroxydodecanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CCCCCCCCC)CC(O)=O

InChI Identifier

InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m1/s1

InChI Key

MUCMKTPAZLSKTL-LLVKDONJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(3R)-3-hydroxy fatty acid (CHEBI:43197 )
3-hydroxylauric acid (CHEBI:43197 )
Hydroxy fatty acids (LMFA01050251 )

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	3.63	ALOGPS
logP	3.25	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	60.2 m³·mol⁻¹	ChemAxon
Polarizability	26.59 Å³	ChemAxon
Number of Rings	0	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

HMDB0010728

DrugBank ID

DB07930

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027875

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (R)-3-Hydroxydodecanoic acid (NP0334781)

MOL for NP0334781 ((R)-3-Hydroxydodecanoic acid)

3D MOL for NP0334781 ((R)-3-Hydroxydodecanoic acid)

3D SDF for NP0334781 ((R)-3-Hydroxydodecanoic acid)

3D-SDF for NP0334781 ((R)-3-Hydroxydodecanoic acid)

PDB for NP0334781 ((R)-3-Hydroxydodecanoic acid)

3D PDB for NP0334781 ((R)-3-Hydroxydodecanoic acid)

SMILES for NP0334781 ((R)-3-Hydroxydodecanoic acid)

INCHI for NP0334781 ((R)-3-Hydroxydodecanoic acid)

Structure for NP0334781 ((R)-3-Hydroxydodecanoic acid)

3D Structure for NP0334781 ((R)-3-Hydroxydodecanoic acid)