NP-MRD: Showing NP-Card for 12-methyltetradecanoic acid (NP0272959)

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Record Information

Version

2.0

Created at

2022-09-08 19:48:49 UTC

Updated at

2022-09-08 19:48:50 UTC

NP-MRD ID

NP0272959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-methyltetradecanoic acid

Description

12-Methyltetradecanoic acid, also known as 15:0Ai or anteiso-15:0, 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. A branched-chain saturated fatty acid comprising tetradecanoic acid carrying a 12-methyl substituent. 12-methyltetradecanoic acid is found in Agelas conifera, Antirrhinum majus, Callyspongia fallax, Erylus formosus, Mycale laevis, Myrmekioderma rea, Solanum lycopersicum, Streptomyces endophyticus, Streptomyces indicus, Suberites massa and Xestospongia muta. 12-methyltetradecanoic acid was first documented in 2005 (PMID: 15750056). 12-Methyltetradecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 17295090).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 46  0  0  0  0  0  0  0  0999 V2000
   -5.4535    0.2474   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276   -0.3418   -0.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9963    0.5627    0.7375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1224   -0.1345    2.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444    0.9220    0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -0.3071    0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190    0.1402    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2807   -1.0490    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -0.4916    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208   -1.6223    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153   -1.0750    0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141   -0.3118   -1.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193    0.2209   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    1.1537   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8787    1.6482   -0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0768    2.5624   -1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9628    1.1505    0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1730    1.0787   -1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7726   -0.5654   -2.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4397    0.5374   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0143   -1.3252   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5970   -0.5301   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5809    1.4902    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1064   -0.0187    2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584   -1.2116    1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799    0.2962    2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628    1.5605   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    1.5290    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -1.0026   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7643   -0.8110    1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    0.8244    1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    0.6429   -0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2812   -1.5833    1.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525   -1.7337   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970    0.0442   -0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422    0.1789    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -2.3081   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764   -2.1145    1.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -0.4026    0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.9205    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -0.9588   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999    0.5474   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.7344   -2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8231   -0.6421   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737    1.9870   -0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761    0.5464    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8117    0.3153    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 17 47  1  0
M  END

LMFA01020008
  Mrv1652304032018322D          

 17 16  0  0  0  0            999 V2000
    7.8577    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2867    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5722    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0012    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7157    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4302    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1447    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8592    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5737    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2882    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0027    5.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2882    7.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1433    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4288    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144    6.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4288    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000    5.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  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  1  0  0  0  0
 11 10  1  0  0  0  0
 10 12  2  0  0  0  0
 13  1  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H30O2/c1-3-14(2)12-10-8-6-4-5-7-9-11-13-15(16)17/h14H,3-13H2,1-2H3,(H,16,17)

> <INCHI_KEY>
XKLJLHAPJBUBNL-UHFFFAOYSA-N

> <FORMULA>
C15H30O2

> <MOLECULAR_WEIGHT>
242.403

> <EXACT_MASS>
242.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
31.79356551161832

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-methyltetradecanoic acid

> <ALOGPS_LOGP>
6.48

> <JCHEM_LOGP>
5.6544645440000005

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
72.4302

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-methyltetradecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01020008                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      14.668  10.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.335  10.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.001  11.643   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.669  11.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.003  10.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.336  11.643   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.670  10.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.004  11.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.338  10.873   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.671  11.643   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      28.005  10.873   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.671  13.183   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.334  11.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.000  10.873   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.667  11.643   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.000   9.333   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.333  10.873   0.000  0.00  0.00           C+0
CONECT    1    3   13                                                       
CONECT    2    3    4                                                       
CONECT    3    2    1                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
12-Methyl myristic acid	ChEBI
12-Methyl-tetradecanoic acid	ChEBI
12-Methyl-tetradecansaeure	ChEBI
12-Methyltetradecansaeure	ChEBI
12-MTA	ChEBI
15:0 Anteiso	ChEBI
15:0Ai	ChEBI
a15:0	ChEBI
AC15:0	ChEBI
Anteiso-15:0	ChEBI
Anteiso-C15	ChEBI
Anteiso-C15:0	ChEBI
Anteisopentadecanoic acid	ChEBI
Aseanostatin P5	ChEBI
C15:0Ai	ChEBI
Sarcinic acid	ChEBI
12-Methyl myristate	Generator
12-Methyl-tetradecanoate	Generator
Anteisopentadecanoate	Generator
Sarcinate	Generator
12-Methyltetradecanoate	Generator
(+)-12-Methyl myristate	Generator
12-MTA CPD	MeSH
Aseanostatin P5, (S)-isomer	MeSH
(+)-12-Methyltetradecanoate	Generator

Chemical Formula

C₁₅H₃₀O₂

Average Mass

242.4030 Da

Monoisotopic Mass

242.22458 Da

IUPAC Name

12-methyltetradecanoic acid

Traditional Name

12-methyltetradecanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)CCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C15H30O2/c1-3-14(2)12-10-8-6-4-5-7-9-11-13-15(16)17/h14H,3-13H2,1-2H3,(H,16,17)

InChI Key

XKLJLHAPJBUBNL-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
Agelas conifera	LOTUS Database	35616633
Antirrhinum majus	LOTUS Database	35616633
Callyspongia fallax	LOTUS Database	35616633
Erylus formosus	LOTUS Database	35616633
Mycale laevis	LOTUS Database	35616633
Myrmekioderma rea	LOTUS Database	35616633
Solanum lycopersicum	LOTUS Database	35616633
Streptomyces endophyticus	LOTUS Database	35616633
Streptomyces indicus	LOTUS Database	35616633
Suberites massa	LOTUS Database	35616633
Xestospongia muta	LOTUS Database	35616633

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
Methyl-branched fatty acid
Branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:39251 )
branched-chain saturated fatty acid (CHEBI:39251 )
Branched fatty acids (C16665 )
Branched fatty acids (LMFA01020008 )

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	6.48	ALOGPS
logP	5.65	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	72.43 m³·mol⁻¹	ChemAxon
Polarizability	31.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062084

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

C16665

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21672

PDB ID

Not Available

ChEBI ID

39251

Good Scents ID

Not Available

References

General References

Funke G, Aravena-Roman M, Frodl R: First description of Curtobacterium spp. isolated from human clinical specimens. J Clin Microbiol. 2005 Mar;43(3):1032-6. doi: 10.1128/JCM.43.3.1032-1036.2005. [PubMed:15750056 ]
Cole N, Hume EB, Jalbert I, Vijay AK, Krishnan R, Willcox MD: Effects of topical administration of 12-methyl tetradecanoic acid (12-MTA) on the development of corneal angiogenesis. Angiogenesis. 2007;10(1):47-54. doi: 10.1007/s10456-007-9063-3. Epub 2007 Feb 13. [PubMed:17295090 ]
LOTUS database [Link]

Showing NP-Card for 12-methyltetradecanoic acid (NP0272959)

MOL for NP0272959 (12-methyltetradecanoic acid)

3D MOL for NP0272959 (12-methyltetradecanoic acid)

3D SDF for NP0272959 (12-methyltetradecanoic acid)

3D-SDF for NP0272959 (12-methyltetradecanoic acid)

PDB for NP0272959 (12-methyltetradecanoic acid)

3D PDB for NP0272959 (12-methyltetradecanoic acid)

SMILES for NP0272959 (12-methyltetradecanoic acid)

INCHI for NP0272959 (12-methyltetradecanoic acid)

Structure for NP0272959 (12-methyltetradecanoic acid)

3D Structure for NP0272959 (12-methyltetradecanoic acid)