NP-MRD: Showing NP-Card for cis-Vaccenic acid (NP0000281)

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Record Information

Version

1.0

Created at

2017-11-20 21:43:09 UTC

Updated at

2021-06-30 02:07:08 UTC

NP-MRD ID

NP0000281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cis-Vaccenic acid

Description

Cis-11-Octadecenoic acid, also known as (Z)-octadec-11-enoic acid or asclepic 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. Cis-11-Octadecenoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240219
     RDKit          3D
cis-Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    4.6293    1.7860   -1.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    0.2921   -1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056   -0.0800   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -1.5205   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -2.1601    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.7176    1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885   -0.3210    1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709    0.5299    2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    0.2006    2.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    1.0111    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.7242    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338   -0.6606    1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -1.1701    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.3516   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530   -0.3397   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430    0.5010   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7427    0.5502   -1.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1463    1.1333   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    0.4106    0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4491    2.5005   -0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163    2.3162   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    2.1871   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    2.0077   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303   -0.2611   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -0.0156   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102    0.1377   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510    0.6372   -0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -1.6985   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941   -2.0543   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -3.2889    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.1094    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.3569    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062   -2.0891    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4544   -0.0105    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    1.5669    2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -0.8370    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    0.6100    3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657    0.9234    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.0776    1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482    1.3943    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.0346    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -0.6889    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199   -1.4148    2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.1911   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182   -1.2938   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    0.6786   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -0.8400   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.3556   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.1391    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    1.5676   -1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.0821   -2.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127    1.2147   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2072   -0.4382   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9378    3.0506    0.1381 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  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 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END


  Mrv1652309042000412D          

 20 19  0  0  0  0            999 V2000
   -3.7393   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826   -0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5958   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826    0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3102   -0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8821   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5457   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464   -0.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6621   -0.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3765   -0.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -0.1986    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 16  1  0  0  0  0
 10 20  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC\C=C/CCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-

> <INCHI_KEY>
UWHZIFQPPBDJPM-FPLPWBNLSA-N

> <FORMULA>
C18H34O2

> <MOLECULAR_WEIGHT>
282.4614

> <EXACT_MASS>
282.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.09733266607341

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11Z)-octadec-11-enoic acid

> <ALOGPS_LOGP>
7.67

> <JCHEM_LOGP>
6.783798451000001

> <ALOGPS_LOGS>
-6.36

> <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>
87.40219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-vaccenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240219
     RDKit          3D
cis-Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    4.6293    1.7860   -1.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    0.2921   -1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056   -0.0800   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -1.5205   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -2.1601    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.7176    1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885   -0.3210    1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709    0.5299    2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    0.2006    2.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    1.0111    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.7242    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338   -0.6606    1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -1.1701    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.3516   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530   -0.3397   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430    0.5010   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7427    0.5502   -1.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1463    1.1333   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    0.4106    0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4491    2.5005   -0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163    2.3162   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    2.1871   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    2.0077   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303   -0.2611   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -0.0156   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102    0.1377   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510    0.6372   -0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -1.6985   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941   -2.0543   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -3.2889    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.1094    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.3569    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062   -2.0891    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4544   -0.0105    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    1.5669    2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -0.8370    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    0.6100    3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657    0.9234    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.0776    1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482    1.3943    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.0346    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -0.6889    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199   -1.4148    2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.1911   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182   -1.2938   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    0.6786   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -0.8400   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.3556   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.1391    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    1.5676   -1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.0821   -2.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127    1.2147   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2072   -0.4382   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9378    3.0506    0.1381 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  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 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -6.980  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.315  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.646  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.981  -0.386   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -12.312  -1.154   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0     -10.981   1.154   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.647  -0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.312  -1.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.980  -0.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.647  -1.144   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.895  -0.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.355  -0.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.019  -1.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.900  -1.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.564  -0.367   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.231  -1.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.233  -0.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.569  -1.131   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.903  -0.359   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.315  -0.371   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   20                                                       
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   20                                                       
CONECT   14   15   17                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0240219
HETATM    1  C1  UNL     1       4.629   1.786  -1.572  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.564   0.292  -1.340  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.106  -0.080  -1.155  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.890  -1.521  -0.912  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.507  -2.160   0.255  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.118  -1.718   1.631  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.389  -0.321   1.908  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.471   0.530   2.270  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.055   0.201   2.446  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.169   1.011   1.519  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.274   0.724   1.677  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.734  -0.661   1.434  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.470  -1.170   0.047  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.142  -0.352  -1.029  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.653  -0.340  -0.875  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.243   0.501  -1.985  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.743   0.550  -1.906  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.146   1.133  -0.622  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.219   0.411   0.391  1.00  0.00           O  
HETATM   20  O2  UNL     1      -6.449   2.500  -0.540  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.716   2.316  -1.214  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.545   2.187  -1.082  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.680   2.008  -2.678  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.930  -0.261  -2.249  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.157  -0.016  -0.465  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.610   0.138  -2.168  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.651   0.637  -0.488  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.782  -1.699  -0.997  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.294  -2.054  -1.837  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.329  -3.289   0.259  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.625  -2.109   0.111  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.786  -2.357   2.322  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.106  -2.089   1.910  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.454  -0.010   1.798  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.837   1.567   2.446  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.769  -0.837   2.485  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.795   0.610   3.483  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.466   0.923   0.458  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.334   2.078   1.795  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.848   1.394   0.988  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.630   1.035   2.704  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.833  -0.689   1.592  1.00  0.00           H  
HETATM   43  H23 UNL     1      -1.320  -1.415   2.136  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.954  -2.191  -0.002  1.00  0.00           H  
HETATM   45  H25 UNL     1      -0.418  -1.294  -0.194  1.00  0.00           H  
HETATM   46  H26 UNL     1      -1.740   0.679  -0.945  1.00  0.00           H  
HETATM   47  H27 UNL     1      -1.917  -0.840  -1.993  1.00  0.00           H  
HETATM   48  H28 UNL     1      -4.047  -1.356  -0.930  1.00  0.00           H  
HETATM   49  H29 UNL     1      -3.936   0.139   0.097  1.00  0.00           H  
HETATM   50  H30 UNL     1      -3.896   1.568  -1.881  1.00  0.00           H  
HETATM   51  H31 UNL     1      -3.895   0.082  -2.952  1.00  0.00           H  
HETATM   52  H32 UNL     1      -6.113   1.215  -2.717  1.00  0.00           H  
HETATM   53  H33 UNL     1      -6.207  -0.438  -2.093  1.00  0.00           H  
HETATM   54  H34 UNL     1      -5.938   3.051   0.138  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8    8   34
CONECT    8    9   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   19   20
CONECT   20   54
END

HMDB0240219
     RDKit          3D
cis-Vaccenic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
    4.6293    1.7860   -1.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    0.2921   -1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1056   -0.0800   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -1.5205   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -2.1601    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -1.7176    1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885   -0.3210    1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709    0.5299    2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    0.2006    2.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    1.0111    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736    0.7242    1.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338   -0.6606    1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -1.1701    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.3516   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530   -0.3397   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430    0.5010   -1.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7427    0.5502   -1.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1463    1.1333   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2189    0.4106    0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4491    2.5005   -0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7163    2.3162   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    2.1871   -1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798    2.0077   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303   -0.2611   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -0.0156   -0.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102    0.1377   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510    0.6372   -0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -1.6985   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941   -2.0543   -1.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -3.2889    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -2.1094    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.3569    2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062   -2.0891    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4544   -0.0105    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    1.5669    2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694   -0.8370    2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    0.6100    3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657    0.9234    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.0776    1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482    1.3943    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    1.0346    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -0.6889    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199   -1.4148    2.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.1911   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182   -1.2938   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    0.6786   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172   -0.8400   -1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -1.3556   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356    0.1391    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8959    1.5676   -1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8947    0.0821   -2.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127    1.2147   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2072   -0.4382   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9378    3.0506    0.1381 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  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 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(Z)-11-Octadecenoic acid	ChEBI
(Z)-Octadec-11-enoic acid	ChEBI
Asclepic acid	ChEBI
cis-11-Octadecenoic acid	ChEBI
cis-Octadec-11-enoic acid	ChEBI
VACCENIC ACID	ChEBI
(Z)-11-Octadecenoate	Generator
(Z)-Octadec-11-enoate	Generator
Asclepate	Generator
cis-11-Octadecenoate	Generator
cis-Octadec-11-enoate	Generator
VACCENate	Generator
cis-Vaccenate	Generator
(11Z)-Octadecenoate	HMDB
(11Z)-Octadecenoic acid	HMDB
11-Octadecenoate	HMDB
11-Octadecenoic acid	HMDB
11Z-Octadecenoate	HMDB
11Z-Octadecenoic acid	HMDB

Chemical Formula

C₁₈H₃₄O₂

Average Mass

282.4614 Da

Monoisotopic Mass

282.25588 Da

IUPAC Name

(11Z)-octadec-11-enoic acid

Traditional Name

cis-vaccenic acid

CAS Registry Number

506-17-2

SMILES

CCCCCC\C=C/CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-

InChI Key

UWHZIFQPPBDJPM-FPLPWBNLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
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, 25 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, 252 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, 50 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, 75 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, 101 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	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, 176 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, 201 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
Agaricus blazei	LOTUS Database	35616633
Anisophyllea laurina	LOTUS Database	35616633
Asclepias syriaca	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Elaeis oleifera	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Leptolyngbya tenuis	LOTUS Database	35616633
Lygodium japonicum	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Pinus koraiensis	LOTUS Database	35616633
Pinus radiata	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Sterculia tragacantha	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Lactobacillus plantarum	KNApSAcK Database	22123792

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
Unsaturated fatty acid
Straight chain 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

vaccenic acid (CHEBI:50464 )
Unsaturated fatty acids (LMFA01030076 )

Physical Properties

State

Liquid

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	7.67	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	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	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.1 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

HMDB0240219

DrugBank ID

DB04801

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012766

KNApSAcK ID

C00000347

Chemspider ID

4445888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282761

PDB ID

Not Available

ChEBI ID

50464

Good Scents ID

Not Available

References

General References

Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]

Showing NP-Card for cis-Vaccenic acid (NP0000281)

MOL for NP0000281 (cis-Vaccenic acid)

3D MOL for NP0000281 (cis-Vaccenic acid)

3D SDF for NP0000281 (cis-Vaccenic acid)

3D-SDF for NP0000281 (cis-Vaccenic acid)

PDB for NP0000281 (cis-Vaccenic acid)

3D PDB for NP0000281 (cis-Vaccenic acid)

SMILES for NP0000281 (cis-Vaccenic acid)

INCHI for NP0000281 (cis-Vaccenic acid)

Structure for NP0000281 (cis-Vaccenic acid)

3D Structure for NP0000281 (cis-Vaccenic acid)