NP-MRD: Showing NP-Card for 4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid (NP0039890)

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Record Information

Version

2.0

Created at

2021-06-20 22:11:51 UTC

Updated at

2021-06-30 00:13:28 UTC

NP-MRD ID

NP0039890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid

Provided By

JEOL Database JEOL Logo

Description

4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid is found in Convolvulus dorycnium L. 4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid was first documented in 2010 (Nacef, S., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100113D          

 45 46  0  0  0  0            999 V2000
    0.3238    3.1934    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8185    0.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.2056    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.8180    1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.0951    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.7092    3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.1528    3.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    2.9956    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -0.2414    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815   -0.8583    2.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -0.1436    1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.7828    1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261   -1.2351   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2167   -1.0546   -0.9325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5335    0.3406   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6334   -2.3453 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8143   -3.0883   -2.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -3.8687   -1.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -3.5915   -3.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -4.4121   -4.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8827   -2.9997   -4.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -3.4219   -5.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -3.2554   -1.7784 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3609   -2.7060   -0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -3.5419    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774    3.5216   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    3.3394   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.8039    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    2.8559    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8595   -1.8906    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3120   -1.5497   -2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6911   -4.4974   -6.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -2.8933   -6.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -3.1642   -6.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -4.3223   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372   -2.7445   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -2.7695    0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -3.7876    0.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  3  4  2  0  0  0  0
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  6  8  1  0  0  0  0
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  6  7  2  0  0  0  0
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  5  9  2  0  0  0  0
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  4 29  1  0  0  0  0
  9 31  1  0  0  0  0
  8 30  1  0  0  0  0
  1 26  1  0  0  0  0
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 18 38  1  0  0  0  0
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 13 33  1  6  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 24 44  1  1  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
 15 35  1  0  0  0  0
 14 34  1  1  0  0  0
 22 39  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
M  END

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    0.3238    3.1934    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8185    0.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.2056    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.8180    1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.0951    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.7092    3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.1528    3.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    2.9956    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -0.2414    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815   -0.8583    2.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -0.1436    1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.7828    1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261   -1.2351   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2167   -1.0546   -0.9325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5335    0.3406   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6334   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -3.0883   -2.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -3.8687   -1.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8822   -3.4219   -5.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3609   -2.7060   -0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -3.5419    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774    3.5216   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    3.3394   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.8039    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    2.8559    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    3.2624    3.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.8022    3.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -1.8906    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -0.6132   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.5037   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104    0.7537   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.0097   -3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3860   -4.2470   -2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1603   -4.3223   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9556   -3.7876    0.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  3  4  2  0
  5  6  1  0
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  6  7  2  0
 11  3  1  0
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M  END


  Mrv1652306212100113D          

 45 46  0  0  0  0            999 V2000
    0.3238    3.1934    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8185    0.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.2056    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.8180    1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.0951    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.7092    3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.1528    3.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2335   -0.2414    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5335    0.3406   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8822   -3.4219   -5.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1291   -3.5419    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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  3  4  2  0  0  0  0
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 11  3  1  0  0  0  0
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  2  1  1  0  0  0  0
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 16 36  1  0  0  0  0
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 15 35  1  0  0  0  0
 14 34  1  1  0  0  0
 22 39  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(O[C@@]2([H])[C@]([H])(O[H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]2([H])O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O9/c1-23-12-5-8(14(19)20)3-4-11(12)25-13-9(17)6-16(22,7-10(13)18)15(21)24-2/h3-5,9-10,13,17-18,22H,6-7H2,1-2H3,(H,19,20)/t9-,10-,13-,16+/m1/s1

> <INCHI_KEY>
FJVABKOTOFTGEO-HTIIAEJPSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.327

> <EXACT_MASS>
356.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.66715342680687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methoxy-4-{[(1S,2R,4S,6R)-2,4,6-trihydroxy-4-(methoxycarbonyl)cyclohexyl]oxy}benzoic acid

> <ALOGPS_LOGP>
-0.34

> <JCHEM_LOGP>
-0.7153325153333333

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.177191832708642

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.127673830186161

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2435559333526705

> <JCHEM_POLAR_SURFACE_AREA>
142.75000000000003

> <JCHEM_REFRACTIVITY>
82.45359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxy-4-{[(1S,2R,4S,6R)-2,4,6-trihydroxy-4-(methoxycarbonyl)cyclohexyl]oxy}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    0.3238    3.1934    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8185    0.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.2056    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.8180    1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.0951    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.7092    3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.1528    3.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    2.9956    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -0.2414    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815   -0.8583    2.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -0.1436    1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.7828    1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261   -1.2351   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2167   -1.0546   -0.9325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5335    0.3406   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6334   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -3.0883   -2.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -3.8687   -1.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -3.5915   -3.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -4.4121   -4.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8827   -2.9997   -4.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -3.4219   -5.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -3.2554   -1.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3609   -2.7060   -0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -3.5419    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774    3.5216   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    3.3394   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.8039    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    2.8559    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    3.2624    3.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.8022    3.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -1.8906    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -0.6132   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.5037   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104    0.7537   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.0097   -3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -1.5497   -2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -4.2470   -2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911   -4.4974   -6.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -2.8933   -6.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -3.1642   -6.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -4.3223   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372   -2.7445   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -2.7695    0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -3.7876    0.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  3  4  2  0
  5  6  1  0
  6  8  1  0
  4  5  1  0
  6  7  2  0
 11  3  1  0
 17 23  1  0
 23 24  1  0
 24 13  1  0
 13 14  1  0
 14 16  1  0
 16 17  1  0
 13 12  1  0
  3  2  1  0
 19 21  1  0
  5  9  2  0
 21 22  1  0
  2  1  1  0
 19 20  2  0
 17 18  1  1
 17 19  1  0
 14 15  1  0
 24 25  1  0
 10 32  1  0
  4 29  1  0
  9 31  1  0
  8 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 38  1  0
 25 45  1  0
 13 33  1  6
 16 36  1  0
 16 37  1  0
 24 44  1  1
 23 42  1  0
 23 43  1  0
 15 35  1  0
 14 34  1  1
 22 39  1  0
 22 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.324   3.193   0.107  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.515   1.819   0.417  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.442   1.206   1.182  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.600   1.818   1.668  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.499   1.095   2.471  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.738   1.709   3.007  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.567   1.153   3.702  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.884   2.996   2.643  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.233  -0.241   2.795  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.081  -0.858   2.313  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.209  -0.144   1.493  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.928  -0.783   1.072  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.826  -1.235  -0.296  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.217  -1.055  -0.933  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.534   0.341  -1.033  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.280  -1.633  -2.345  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.814  -3.088  -2.398  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.732  -3.869  -1.607  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.840  -3.591  -3.851  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.660  -4.412  -4.250  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.883  -3.000  -4.614  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.882  -3.422  -5.978  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.418  -3.255  -1.778  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.361  -2.706  -0.349  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.129  -3.542   0.522  0.00  0.00           O+0
HETATM   26  H   UNK     0       1.177   3.522  -0.494  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.581   3.339  -0.493  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.302   3.804   1.015  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.821   2.856   1.443  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.727   3.262   3.067  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.918  -0.802   3.429  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.860  -1.891   2.574  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.115  -0.613  -0.859  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.987  -1.504  -0.295  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.210   0.754  -0.204  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.679  -1.010  -3.021  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.312  -1.550  -2.711  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.386  -4.247  -2.234  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.691  -4.497  -6.047  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.077  -2.893  -6.496  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.831  -3.164  -6.459  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.160  -4.322  -1.759  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.337  -2.744  -2.388  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.669  -2.769   0.017  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.956  -3.788   0.054  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    4   11    2                                                  
CONECT    4    3    5   29                                                  
CONECT    5    6    4    9                                                  
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6   30                                                       
CONECT    9   10    5   31                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12    3                                                  
CONECT   12   11   13                                                       
CONECT   13   24   14   12   33                                             
CONECT   14   13   16   15   34                                             
CONECT   15   14   35                                                       
CONECT   16   14   17   36   37                                             
CONECT   17   23   16   18   19                                             
CONECT   18   17   38                                                       
CONECT   19   21   20   17                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   39   40   41                                             
CONECT   23   17   24   42   43                                             
CONECT   24   23   13   25   44                                             
CONECT   25   24   45                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   18                                                            
CONECT   39   22                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   23                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   92    0
END

RDKit          3D

45 46  0  0  0  0  0  0  0  0999 V2000
    0.3238    3.1934    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8185    0.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.2056    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.8180    1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.0951    2.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    1.7092    3.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    1.1528    3.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8841    2.9956    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -0.2414    2.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0815   -0.8583    2.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -0.1436    1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -0.7828    1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261   -1.2351   -0.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2167   -1.0546   -0.9325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5335    0.3406   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797   -1.6334   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -3.0883   -2.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -3.8687   -1.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -3.5915   -3.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -4.4121   -4.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8827   -2.9997   -4.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -3.4219   -5.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182   -3.2554   -1.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3609   -2.7060   -0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -3.5419    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774    3.5216   -0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    3.3394   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    3.8039    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    2.8559    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    3.2624    3.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.8022    3.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -1.8906    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -0.6132   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.5037   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104    0.7537   -0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.0097   -3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3120   -1.5497   -2.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -4.2470   -2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911   -4.4974   -6.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -2.8933   -6.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -3.1642   -6.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -4.3223   -1.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372   -2.7445   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -2.7695    0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -3.7876    0.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  3  4  2  0
  5  6  1  0
  6  8  1  0
  4  5  1  0
  6  7  2  0
 11  3  1  0
 17 23  1  0
 23 24  1  0
 24 13  1  0
 13 14  1  0
 14 16  1  0
 16 17  1  0
 13 12  1  0
  3  2  1  0
 19 21  1  0
  5  9  2  0
 21 22  1  0
  2  1  1  0
 19 20  2  0
 17 18  1  1
 17 19  1  0
 14 15  1  0
 24 25  1  0
 10 32  1  0
  4 29  1  0
  9 31  1  0
  8 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 38  1  0
 25 45  1  0
 13 33  1  6
 16 36  1  0
 16 37  1  0
 24 44  1  1
 23 42  1  0
 23 43  1  0
 15 35  1  0
 14 34  1  1
 22 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₉

Average Mass

356.3270 Da

Monoisotopic Mass

356.11073 Da

IUPAC Name

3-methoxy-4-{[(1S,2R,4S,6R)-2,4,6-trihydroxy-4-(methoxycarbonyl)cyclohexyl]oxy}benzoic acid

Traditional Name

3-methoxy-4-{[(1S,2R,4S,6R)-2,4,6-trihydroxy-4-(methoxycarbonyl)cyclohexyl]oxy}benzoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])=C(O[C@@]2([H])[C@]([H])(O[H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]2([H])O[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C16H20O9/c1-23-12-5-8(14(19)20)3-4-11(12)25-13-9(17)6-16(22,7-10(13)18)15(21)24-2/h3-5,9-10,13,17-18,22H,6-7H2,1-2H3,(H,19,20)/t9-,10-,13-,16+/m1/s1

InChI Key

FJVABKOTOFTGEO-HTIIAEJPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Convolvulus dorycnium	JEOL database	Nacef, S., et al, Phytochem. Lett. 3, 66 (2010)

Chemical Taxonomy

Classification

Not classified

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	-0.34	ALOGPS
logP	-0.72	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.45 m³·mol⁻¹	ChemAxon
Polarizability	34.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Nacef, S., et al. (2010). Nacef, S., et al, Phytochem. Lett. 3, 66 (2010). Phytochem..

Showing NP-Card for 4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid (NP0039890)

MOL for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

3D MOL for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

3D SDF for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

3D-SDF for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

PDB for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

3D PDB for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

SMILES for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

INCHI for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

Structure for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)

3D Structure for NP0039890 (4-O-(4'-carboxymethyl-2',4',6'-trihydroxycyclohexyl)-vanillic acid)