NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate (NP0303844)

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Record Information

Version

2.0

Created at

2022-09-10 18:32:05 UTC

Updated at

2022-09-10 18:32:05 UTC

NP-MRD ID

NP0303844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate

Description

3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate is found in Citrus junos, Prunus domestica and Salacia chinensis. 3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161509152D          

 30 31  0  0  0  0            999 V2000
   -2.2310   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -2.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -3.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -3.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -4.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -3.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -4.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -3.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034   -3.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -2.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034   -2.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455    0.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    2.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    2.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    2.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    3.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219    4.1158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4791    3.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488    2.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    3.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256    1.3013    0.0000 C   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  4  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18  2  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 30  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -4.2907    1.6985   -1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2738    0.2605   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4143   -0.5468   -1.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796   -1.9695   -1.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553   -2.8012   -2.2578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3232   -2.4124   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5347   -1.2555    0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5876   -0.3048   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8032   -1.7307    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977   -0.4113    0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3796    0.5092    1.5071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0870   -1.3171    0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309   -1.2618    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329   -0.2714    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.1094    0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258   -0.6717    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5744    0.1216    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494    1.3222   -0.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767   -0.4131    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311    0.3359    0.1106 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7669    0.4509    1.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7305    1.4357    1.2203 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6124    1.3232    2.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5786    2.3271    2.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5198    1.4278   -0.0639 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3850    2.6127   -0.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    0.2103   -0.8954 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9472   -0.9125   -0.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -0.1628   -1.0465 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6723   -1.5438   -1.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5407    1.9569   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818    1.9761   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1068    2.3251   -0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4689   -0.2028   -2.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3562   -2.6970   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269   -3.2807    0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365   -0.3828   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3001    0.7596    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5410   -0.5431    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1415   -1.2559    2.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7762   -2.8357    1.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8369   -1.4314    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6899    0.3733    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -2.3865    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -2.2744    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117    1.3922    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.8715    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5098    1.1002   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -1.7288    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    1.3834   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    2.4148    1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933    1.4468    3.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0694    0.3162    2.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7651    2.6642    3.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6079    1.3914    0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    2.4164   -1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7490    0.4046   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9103   -0.7162   -0.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4551    0.3181   -1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4719   -1.9338   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  1
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  7 10  1  0
 29 20  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 13 45  1  0
 12 44  1  0
 11 43  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 16 49  1  0
 20 50  1  6
 22 51  1  1
 23 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  1
 26 56  1  0
 27 57  1  6
 28 58  1  0
 29 59  1  6
 30 60  1  0
M  END


  Mrv1533004161509152D          

 30 31  0  0  0  0            999 V2000
   -2.2310   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -2.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600   -3.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -3.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455   -4.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -3.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -4.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -3.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034   -3.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -2.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8034   -2.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9455    0.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    2.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0435    2.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    2.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916    3.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219    4.1158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4791    3.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488    2.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    3.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256    1.3013    0.0000 C   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  4  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18  2  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303844

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=CC1(O)C(C)=CC(=O)CC1(C)C)=CC(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O9/c1-11(5-6-21(28)12(2)8-13(23)9-20(21,3)4)7-15(24)30-19-18(27)17(26)16(25)14(10-22)29-19/h5-8,14,16-19,22,25-28H,9-10H2,1-4H3

> <INCHI_KEY>
HLVPIMVSSMJFPS-UHFFFAOYSA-N

> <FORMULA>
C21H30O9

> <MOLECULAR_WEIGHT>
426.462

> <EXACT_MASS>
426.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.75288685055706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.058540733333333414

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.011190554228733

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.169544155561752

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220316903

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
107.40759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.165  -0.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.498   0.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.832  -0.476   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.832  -2.016   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.498  -2.786   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.166  -2.786   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -8.166  -4.326   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.832  -5.096   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.832  -6.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.498  -7.406   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.498  -8.946   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.166  -7.406   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.166  -8.946   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.499  -6.636   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.833  -7.406   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -9.499  -5.096   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.833  -4.326   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.498   1.834   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.165   2.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.165   4.144   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.648   3.876   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.681   3.876   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.671   5.056   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.144   6.503   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.134   7.683   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.628   6.771   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.638   5.591   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.424   6.539   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.173   5.115   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.208   2.429   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
CONECT   18    2   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   22                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid	Generator
(+/-)-cis,trans-abscisate glucosyl ester	Generator

Chemical Formula

C₂₁H₃₀O₉

Average Mass

426.4620 Da

Monoisotopic Mass

426.18898 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

CC(C=CC1(O)C(C)=CC(=O)CC1(C)C)=CC(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H30O9/c1-11(5-6-21(28)12(2)8-13(23)9-20(21,3)4)7-15(24)30-19-18(27)17(26)16(25)14(10-22)29-19/h5-8,14,16-19,22,25-28H,9-10H2,1-4H3

InChI Key

HLVPIMVSSMJFPS-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
Citrus junos	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Terpene glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Fatty acid ester
Cyclohexenone
Fatty acyl
Monosaccharide
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aldehyde
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

an abscisic acid conjugate (CPD-7727 )

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	0.08	ALOGPS
logP	0.059	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.41 m³·mol⁻¹	ChemAxon
Polarizability	43.75 Å³	ChemAxon
Number of Rings	2	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

72727935

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate (NP0303844)

MOL for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

3D MOL for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

3D SDF for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

3D-SDF for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

PDB for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

3D PDB for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

SMILES for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

INCHI for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

Structure for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)

3D Structure for NP0303844 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate)