NP-MRD: Showing NP-Card for (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+ (NP0033770)

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Record Information

Version

2.0

Created at

2021-06-20 17:41:41 UTC

Updated at

2021-06-30 00:03:45 UTC

NP-MRD ID

NP0033770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+

Provided By

JEOL Database JEOL Logo

Description

CHEMBL463850 belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+ is found in Pimenta dioica. It was first documented in 2008 (Kikuzaki, H., et al.). Based on a literature review very few articles have been published on CHEMBL463850.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119413D          

 70 72  0  0  0  0            999 V2000
   -1.7461   -1.1994   -4.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732   -1.7827   -4.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2962   -1.4341   -2.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7639   -0.1171   -2.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4141    1.1279   -2.8720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2173    2.2595   -2.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
   -1.7461   -1.1994   -4.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732   -1.7827   -4.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
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 12 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
M  END


  Mrv1652306202119413D          

 70 72  0  0  0  0            999 V2000
   -1.7461   -1.1994   -4.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732   -1.7827   -4.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -2.8963   -4.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962   -1.4341   -2.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7639   -0.1171   -2.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4141    1.1279   -2.8720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2173    2.2595   -2.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3498    1.5287   -1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    2.0996   -0.8752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.0307   -1.8017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8784   -0.8662   -0.7197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4296   -0.5846    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448   -1.3173    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -2.6297    1.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5365   -2.5556    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2354   -2.1832    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -1.6695    0.5789 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4419   -0.2784    0.8653 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024    0.2909    1.2564 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5301    1.7851    1.5884 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3233    2.0057    2.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    2.3793    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    2.6247    0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    2.4413    2.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    2.1368    3.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382    2.1766    4.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2773    1.8758    5.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4124    2.4992    3.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    2.5020    4.4545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    2.7906    2.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5668    3.0322    1.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    2.7884    1.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    0.1183    0.1436 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0400    0.5441    0.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -1.3420   -0.3097 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6905   -1.4317   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4413   -1.8840   -0.6418 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5541   -3.2747   -0.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561   -3.0238   -5.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5332   -2.2623   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -1.3932   -2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.0195   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    1.3408   -2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109    1.0174   -3.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027    2.9521   -2.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204    2.7942   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8368   -0.1388   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111   -1.9157   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9689   -0.7357   -0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.3216    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -0.9319    2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -3.3657    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604   -2.9750    0.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -3.5488    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577   -1.8607    2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.2167    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -0.2138    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3690    2.1283    2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    2.4021    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    1.8663    4.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198    1.9748    6.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607    2.7547    3.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    2.8839    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1470    3.0427    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869    0.7401   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6585    0.2768   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -1.9549    0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5602   -2.3381   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.3759   -1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6333   -3.5920   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 33  1  0  0  0  0
 33 19  1  0  0  0  0
 19 18  1  0  0  0  0
 18 17  1  0  0  0  0
 33 34  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 20 21  1  0  0  0  0
  8  7  1  0  0  0  0
 26 28  2  0  0  0  0
 22 21  1  0  0  0  0
 22 24  1  0  0  0  0
 28 30  1  0  0  0  0
 24 25  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5 10  1  0  0  0  0
 10  8  1  0  0  0  0
 30 32  2  0  0  0  0
 10 11  1  0  0  0  0
 32 24  1  0  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
 28 29  1  0  0  0  0
  2  3  1  0  0  0  0
 25 26  1  0  0  0  0
  8  9  2  0  0  0  0
 26 27  1  0  0  0  0
 11 12  1  0  0  0  0
 22 23  2  0  0  0  0
 12 13  2  0  0  0  0
 30 31  1  0  0  0  0
  2  1  2  0  0  0  0
 17 37  1  0  0  0  0
 13 14  1  0  0  0  0
 37 35  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 19 20  1  0  0  0  0
 17 16  1  0  0  0  0
 25 60  1  0  0  0  0
 32 64  1  0  0  0  0
 29 62  1  0  0  0  0
 27 61  1  0  0  0  0
 31 63  1  0  0  0  0
 17 56  1  1  0  0  0
 33 65  1  6  0  0  0
 34 66  1  0  0  0  0
 35 67  1  1  0  0  0
 36 68  1  0  0  0  0
 37 69  1  6  0  0  0
 38 70  1  0  0  0  0
 20 58  1  0  0  0  0
 20 59  1  0  0  0  0
 19 57  1  1  0  0  0
  7 45  1  0  0  0  0
  7 46  1  0  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
  5 42  1  1  0  0  0
 10 47  1  6  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  3 39  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  0  0  0  0
 14 52  1  0  0  0  0
 14 53  1  0  0  0  0
 15 54  1  0  0  0  0
 15 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033770

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])C([H])([H])C([H])([H])C(=O)[C@]1([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])O[C@]1([H])O[C@]([H])(C([H])([H])OC(=O)C2=C([H])C(O[H])=C(O[H])C(O[H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O13/c26-15-6-5-12(10-19(29)30)14(15)4-2-1-3-7-36-25-23(34)22(33)21(32)18(38-25)11-37-24(35)13-8-16(27)20(31)17(28)9-13/h1-2,8-9,12,14,18,21-23,25,27-28,31-34H,3-7,10-11H2,(H,29,30)/b2-1-/t12-,14-,18-,21-,22+,23-,25-/m1/s1

> <INCHI_KEY>
YNGJOPKAULIOQY-QUZKLYMESA-N

> <FORMULA>
C25H32O13

> <MOLECULAR_WEIGHT>
540.518

> <EXACT_MASS>
540.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.67120496398458

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
0.7914004989999996

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.10796476602828

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.462530432825825

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490924340554898

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
128.66320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
   -1.7461   -1.1994   -4.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732   -1.7827   -4.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -2.8963   -4.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962   -1.4341   -2.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -0.1171   -2.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4141    1.1279   -2.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173    2.2595   -2.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3498    1.5287   -1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    2.0996   -0.8752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.0307   -1.8017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8784   -0.8662   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4296   -0.5846    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448   -1.3173    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -2.6297    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5365   -2.5556    1.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354   -2.1832    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5355   -1.6695    0.5789 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4419   -0.2784    0.8653 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024    0.2909    1.2564 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5301    1.7851    1.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233    2.0057    2.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    2.3793    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    2.6247    0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    2.4413    2.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    2.1368    3.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382    2.1766    4.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2773    1.8758    5.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4124    2.4992    3.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    2.5020    4.4545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    2.7906    2.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5668    3.0322    1.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    2.7884    1.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    0.1183    0.1436 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0400    0.5441    0.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300   -1.3420   -0.3097 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6905   -1.4317   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4413   -1.8840   -0.6418 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5541   -3.2747   -0.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7561   -3.0238   -5.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5332   -2.2623   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -1.3932   -2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.0195   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    1.3408   -2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109    1.0174   -3.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6027    2.9521   -2.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204    2.7942   -1.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8368   -0.1388   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111   -1.9157   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9689   -0.7357   -0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.3216    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -0.9319    2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -3.3657    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604   -2.9750    0.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -3.5488    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577   -1.8607    2.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430   -2.2167    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -0.2138    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3690    2.1283    2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5466    2.4021    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    1.8663    4.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198    1.9748    6.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2607    2.7547    3.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    2.8839    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1470    3.0427    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869    0.7401   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6585    0.2768   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -1.9549    0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5602   -2.3381   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.3759   -1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6333   -3.5920   -1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 33  1  0
 33 19  1  0
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 18 17  1  0
 33 34  1  0
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  8  7  1  0
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 10  8  1  0
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 14 53  1  0
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 15 55  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.746  -1.199  -4.635  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.873  -1.783  -4.018  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.307  -2.896  -4.526  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.296  -1.434  -2.670  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.764  -0.117  -2.045  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.414   1.128  -2.872  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.217   2.260  -2.236  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.350   1.529  -1.549  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.204   2.100  -0.875  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.278   0.031  -1.802  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.878  -0.866  -0.720  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.430  -0.585   0.683  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.645  -1.317   1.486  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.969  -2.630   1.198  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.537  -2.556   1.463  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.235  -2.183   0.270  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.535  -1.670   0.579  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.442  -0.278   0.865  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.702   0.291   1.256  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.530   1.785   1.588  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.323   2.006   2.342  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.255   2.379   1.591  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.267   2.625   0.393  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.012   2.441   2.401  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.021   2.137   3.769  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.238   2.177   4.440  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.277   1.876   5.772  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.412   2.499   3.769  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.596   2.502   4.455  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.384   2.791   2.412  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.567   3.032   1.772  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.175   2.788   1.732  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.751   0.118   0.144  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.040   0.544   0.590  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.830  -1.342  -0.310  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.691  -1.432  -1.456  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.441  -1.884  -0.642  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.554  -3.275  -0.980  0.00  0.00           O+0
HETATM   39  H   UNK     0      -0.756  -3.024  -5.388  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.533  -2.262  -1.995  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.794  -1.393  -2.784  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.241  -0.020  -1.083  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.660   1.341  -2.857  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.711   1.017  -3.920  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.603   2.952  -2.988  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.620   2.794  -1.496  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.837  -0.139  -2.729  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.711  -1.916  -0.983  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.969  -0.736  -0.732  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.854   0.322   1.111  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.485  -0.932   2.494  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.408  -3.366   1.883  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.160  -2.975   0.179  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.900  -3.549   1.751  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.758  -1.861   2.283  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.943  -2.217   1.441  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.026  -0.214   2.176  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.369   2.128   2.204  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.547   2.402   0.682  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.879   1.866   4.313  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.220   1.975   6.019  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.261   2.755   3.779  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.439   2.884   0.805  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.147   3.043   0.679  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.487   0.740  -0.722  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.659   0.277  -0.121  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.308  -1.955   0.465  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.560  -2.338  -1.803  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.038  -1.376  -1.526  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.633  -3.592  -1.072  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   39                                                       
CONECT    4    5    2   40   41                                             
CONECT    5    6   10    4   42                                             
CONECT    6    7    5   43   44                                             
CONECT    7    8    6   45   46                                             
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    5    8   11   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   11   13   50                                                  
CONECT   13   12   14   51                                                  
CONECT   14   13   15   52   53                                             
CONECT   15   14   16   54   55                                             
CONECT   16   15   17                                                       
CONECT   17   18   37   16   56                                             
CONECT   18   19   17                                                       
CONECT   19   33   18   20   57                                             
CONECT   20   21   19   58   59                                             
CONECT   21   20   22                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26   60                                                  
CONECT   26   28   25   27                                                  
CONECT   27   26   61                                                       
CONECT   28   26   30   29                                                  
CONECT   29   28   62                                                       
CONECT   30   28   32   31                                                  
CONECT   31   30   63                                                       
CONECT   32   30   24   64                                                  
CONECT   33   35   19   34   65                                             
CONECT   34   33   66                                                       
CONECT   35   33   36   37   67                                             
CONECT   36   35   68                                                       
CONECT   37   38   17   35   69                                             
CONECT   38   37   70                                                       
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46    7                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   17                                                            
CONECT   57   19                                                            
CONECT   58   20                                                            
CONECT   59   20                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   29                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  144    0
END

RDKit          3D

70 72  0  0  0  0  0  0  0  0999 V2000
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  7 45  1  0
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  6 43  1  0
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  5 42  1  1
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  4 40  1  0
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 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₃

Average Mass

540.5180 Da

Monoisotopic Mass

540.18429 Da

IUPAC Name

2-[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

Traditional Name

[(1R,2R)-3-oxo-2-[(2Z)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@]1([H])C([H])([H])C([H])([H])C(=O)[C@]1([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])O[C@]1([H])O[C@]([H])(C([H])([H])OC(=O)C2=C([H])C(O[H])=C(O[H])C(O[H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C25H32O13/c26-15-6-5-12(10-19(29)30)14(15)4-2-1-3-7-36-25-23(34)22(33)21(32)18(38-25)11-37-24(35)13-8-16(27)20(31)17(28)9-13/h1-2,8-9,12,14,18,21-23,25,27-28,31-34H,3-7,10-11H2,(H,29,30)/b2-1-/t12-,14-,18-,21-,22+,23-,25-/m1/s1

InChI Key

YNGJOPKAULIOQY-QUZKLYMESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pimenta dioica	JEOL database	Kikuzaki, H., et al, J. Nat. Prod. 71, 861 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Jasmonic acid
Fatty acyl glycoside of mono- or disaccharide
Galloyl ester
Alkyl glycoside
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Carbonyl group
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.14	ALOGPS
logP	0.79	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	128.66 m³·mol⁻¹	ChemAxon
Polarizability	51.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23340701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kikuzaki, H., et al. (2008). Kikuzaki, H., et al, J. Nat. Prod. 71, 861 (2008) . J. Nat. Prod..

Showing NP-Card for (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+ (NP0033770)

MOL for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

3D MOL for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

3D SDF for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

3D-SDF for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

PDB for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

3D PDB for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

SMILES for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

INCHI for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

Structure for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)

3D Structure for NP0033770 ((1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-g+)