NP-MRD: Showing NP-Card for xi-7-Hydroxyhexadecanedioic acid (NP0048899)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:56 UTC

Updated at

2022-03-17 21:03:56 UTC

NP-MRD ID

NP0048899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xi-7-Hydroxyhexadecanedioic acid

Description

Xi-7-Hydroxyhexadecanedioic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Xi-7-Hydroxyhexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, xi-7-Hydroxyhexadecanedioic acid has been detected, but not quantified in, fruits and garden tomato. This could make XI-7-hydroxyhexadecanedioic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310022D          

 21 20  0  0  0  0            999 V2000
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2336    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CCCCCCCCC(O)=O)CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O5/c17-14(11-7-5-9-13-16(20)21)10-6-3-1-2-4-8-12-15(18)19/h14,17H,1-13H2,(H,18,19)(H,20,21)

> <INCHI_KEY>
BNKCVLYEVLBHCL-UHFFFAOYSA-N

> <FORMULA>
C16H30O5

> <MOLECULAR_WEIGHT>
302.4064

> <EXACT_MASS>
302.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.10887863018708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxyhexadecanedioic acid

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.5496224856666667

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.147853319970726

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.511879324021734

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2748235333075648

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
80.41849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxyhexadecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.841  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      26.839   7.796   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.503   9.336   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      14.836  11.646   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      36.175  10.106   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      34.842   7.796   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3   10                                                       
CONECT    7    5   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   14                                                       
CONECT   12    8   15                                                       
CONECT   13    9   16                                                       
CONECT   14   10   11   17                                                  
CONECT   15   12   18   19                                                  
CONECT   16   13   20   21                                                  
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
XI-7-hydroxyhexadecanedioate	Generator
10-Hydroxy-hexadecan-1,16-dioate	Generator

Chemical Formula

C₁₆H₃₀O₅

Average Mass

302.4064 Da

Monoisotopic Mass

302.20932 Da

IUPAC Name

7-hydroxyhexadecanedioic acid

Traditional Name

7-hydroxyhexadecanedioic acid

CAS Registry Number

Not Available

SMILES

OC(CCCCCCCCC(O)=O)CCCCCC(O)=O

InChI Identifier

InChI=1S/C16H30O5/c17-14(11-7-5-9-13-16(20)21)10-6-3-1-2-4-8-12-15(18)19/h14,17H,1-13H2,(H,18,19)(H,20,21)

InChI Key

BNKCVLYEVLBHCL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170058 )

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	2.6	ALOGPS
logP	3.55	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	80.42 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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

HMDB0037830

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016979

KNApSAcK ID

Not Available

Chemspider ID

21237667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14259008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for xi-7-Hydroxyhexadecanedioic acid (NP0048899)

MOL for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

3D MOL for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

3D SDF for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

3D-SDF for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

PDB for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

3D PDB for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

SMILES for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

INCHI for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

Structure for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)

3D Structure for NP0048899 (xi-7-Hydroxyhexadecanedioic acid)