NP-MRD: Showing NP-Card for (2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid (NP0155189)

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Record Information

Version

2.0

Created at

2022-09-02 12:12:29 UTC

Updated at

2022-09-02 12:12:29 UTC

NP-MRD ID

NP0155189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

Description

(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid is found in Robinia pseudoacacia. Based on a literature review very few articles have been published on (2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214122D          

 29 29  0  0  1  0            999 V2000
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    4.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8245    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871    2.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    2.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    3.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    4.3808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1627    4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366    3.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741    5.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868    5.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0240    6.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    5.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
   -4.5514    0.2885    2.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937   -0.8353    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8156   -1.9723    1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6097   -3.1678    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -3.2406   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3673   -4.3280    0.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1704   -0.6415    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357    0.5321    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    0.7606   -0.8470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6176   -0.3473   -0.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0612    1.0912   -2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589    2.0947   -2.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5808    2.9396   -2.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    4.0943   -2.8604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    2.3332   -1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995    1.8975   -0.3098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5307    3.1238   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412    1.5647    1.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588    0.4577    1.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9932    0.1901    0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    1.0494   -0.0456 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162   -1.0945    0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0549   -1.0574    0.2227 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8048   -0.8868   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    0.0268    0.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641   -2.2992    0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1680   -2.2264   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9933   -3.1598   -0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4971   -1.1213   -0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7197    1.2403    1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5047    0.0867    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7196    0.4965    2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5975   -2.0355    2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003   -4.4237    0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8358   -1.3790   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8382    1.3093    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -1.0828   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8659    0.4664   -2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342    2.2996   -3.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875    3.0469   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245    1.4117   -1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3660    3.1207   -0.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    3.1042    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739    4.0119   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261    1.5453    1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081    2.4979    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536   -1.9749    0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8871   -1.1762    2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383   -1.0394   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.6807   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1441    0.1046   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041   -0.1270    1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -3.1749    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0440   -2.3267    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1134   -0.3872   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  1
 23 26  1  0
 26 27  1  0
 27 29  1  0
 27 28  2  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
 16  9  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 29 55  1  0
  3 33  1  0
  6 34  1  0
M  END


  Mrv1652309022214122D          

 29 29  0  0  1  0            999 V2000
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    4.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8245    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871    2.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    2.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    3.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    4.3808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1627    4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366    3.9436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741    5.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868    5.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0240    6.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    5.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@@]1(O)C=CC(=O)C[C@]1(C)COC(=O)C[C@@](C)(O)CC(O)=O)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O9/c1-13(8-15(22)23)4-6-20(28)7-5-14(21)9-18(20,2)12-29-17(26)11-19(3,27)10-16(24)25/h4-8,27-28H,9-12H2,1-3H3,(H,22,23)(H,24,25)/b6-4+,13-8-/t18-,19+,20-/m1/s1

> <INCHI_KEY>
LQOHVNQOXUUPAV-NETYDWIQSA-N

> <FORMULA>
C20H26O9

> <MOLECULAR_WEIGHT>
410.419

> <EXACT_MASS>
410.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.934654388761814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.48537294866666647

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.604946156121347

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9025717933651913

> <JCHEM_PKA_STRONGEST_BASIC>
-3.008391398269846

> <JCHEM_POLAR_SURFACE_AREA>
158.43

> <JCHEM_REFRACTIVITY>
103.11459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.347   4.135   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.830   4.402   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.303   5.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.260   7.564   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.797   4.937   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.816   2.846   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.093   4.206   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.909   5.512   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.448   5.458   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.186   6.871   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.002   8.177   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.304   8.994   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.308   7.361   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.818   9.483   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.095  10.843   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.911  12.149   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.444  10.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Value	Source
(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate	Generator

Chemical Formula

C₂₀H₂₆O₉

Average Mass

410.4190 Da

Monoisotopic Mass

410.15768 Da

IUPAC Name

(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

Traditional Name

(2Z,4E)-5-[(1R,6R)-6-({[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@@]1(O)C=CC(=O)C[C@]1(C)COC(=O)C[C@@](C)(O)CC(O)=O)=C\C(O)=O

InChI Identifier

InChI=1S/C20H26O9/c1-13(8-15(22)23)4-6-20(28)7-5-14(21)9-18(20,2)12-29-17(26)11-19(3,27)10-16(24)25/h4-8,27-28H,9-12H2,1-3H3,(H,22,23)(H,24,25)/b6-4+,13-8-/t18-,19+,20-/m1/s1

InChI Key

LQOHVNQOXUUPAV-NETYDWIQSA-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
Robinia pseudoacacia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Cyclohexenone
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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	0.58	ALOGPS
logP	0.49	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	103.11 m³·mol⁻¹	ChemAxon
Polarizability	40.93 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

Not Available

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

162900616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid (NP0155189)

MOL for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

3D MOL for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

3D SDF for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

3D-SDF for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

PDB for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

3D PDB for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

SMILES for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

INCHI for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

Structure for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)

3D Structure for NP0155189 ((2z,4e)-5-[(1r,6r)-6-({[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxy}methyl)-1-hydroxy-6-methyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid)