NP-MRD: Showing NP-Card for Erythrolic acid E (NP0010680)

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Record Information

Version

2.0

Created at

2021-01-05 20:07:02 UTC

Updated at

2021-07-15 17:06:46 UTC

NP-MRD ID

NP0010680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erythrolic acid E

Provided By

NPAtlas

Description

3-(11-Carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl)-4-hydroxybenzoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Erythrolic acid E is found in Erythrobacter sp. Based on a literature review very few articles have been published on 3-(11-carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl)-4-hydroxybenzoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107403D          

 58 58  0  0  0  0            999 V2000
    0.7280   -0.2778    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    0.5498    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0056    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    0.6223   -0.5885 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5239    0.3589   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348   -0.6647   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -1.0223   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876   -2.1070   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4287   -2.7512   -2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4074   -2.4468   -1.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1771   -0.3035    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083    0.7257    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674    1.0463    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    2.0706    1.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    1.9509    1.1211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4940    2.1222    0.8041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8693    1.4707   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    0.4991   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0263   -2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.0991    0.5106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9092    0.1243    0.5256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6074   -0.4949   -0.6321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3580   -1.8675   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1329   -0.2950   -0.5091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6470   -0.9249    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7262   -0.9211   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5310   -1.8717   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583   -0.5348   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -1.1250    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0297    0.3257    2.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7138    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286   -1.0794    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    1.6993   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.1319   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568   -1.2272   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7830   -2.4609   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247   -0.5971    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    1.2914    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    2.3928    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223    2.4610    2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.5084    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061    3.2561    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3403   -0.2673    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3381    0.7758   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7589   -0.9214    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3604   -0.3272    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529   -0.5606   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 13  5  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
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  3 32  1  0  0  0  0
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  6 35  1  0  0  0  0
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 28 58  1  0  0  0  0
M  END

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
    0.7280   -0.2778    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    0.5498    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0056    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5239    0.3589   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348   -0.6647   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -1.0223   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1771   -0.3035    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083    0.7257    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674    1.0463    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7707    2.3928    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13  5  1  0
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M  END


  Mrv1652306242107403D          

 58 58  0  0  0  0            999 V2000
    0.7280   -0.2778    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    0.5498    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0056    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    0.6223   -0.5885 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.5350   -0.7138    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286   -1.0794    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    1.6993   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.1319   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568   -1.2272   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7830   -2.4609   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247   -0.5971    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    1.2914    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    2.3928    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223    2.4610    2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.5084    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061    3.2561    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    1.8762    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    1.8199   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.7785   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802    0.0178   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -0.9918   -2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.2498    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.2090    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -0.2673    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.2373    0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630   -0.0855   -1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931   -2.1457    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3381    0.7758   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3697   -2.0077    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7589   -0.9214    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3604   -0.3272    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529   -0.5606   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 13  5  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 22 52  1  6  0  0  0
 23 53  1  0  0  0  0
 24 54  1  1  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 25 57  1  0  0  0  0
 28 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010680

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O6/c1-14(7-9-17-13-18(22(27)28)10-12-20(17)24)5-4-6-15(2)8-11-19(23)16(3)21(25)26/h6-7,10,12-13,16,19,23-24H,4-5,8-9,11H2,1-3H3,(H,25,26)(H,27,28)/b14-7-,15-6-/t16-,19+/m0/s1

> <INCHI_KEY>
NTUPPVZJNOAYQQ-UHFFFAOYSA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.476

> <EXACT_MASS>
390.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.71818649300627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2Z,6Z,10R,11S)-11-carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl]-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
4.4857527830000015

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.892736062251135

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.202090594716347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.932535118020457

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
109.49989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2Z,6Z,10R,11S)-11-carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl]-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 58  0  0  0  0  0  0  0  0999 V2000
    0.7280   -0.2778    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    0.5498    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0056    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    0.6223   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5239    0.3589   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348   -0.6647   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -1.0223   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876   -2.1070   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4287   -2.7512   -2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4074   -2.4468   -1.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1771   -0.3035    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083    0.7257    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674    1.0463    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    2.0706    1.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    1.9509    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940    2.1222    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    1.4707   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    0.4991   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0263   -2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.0991    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    0.1243    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6074   -0.4949   -0.6321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3580   -1.8675   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1329   -0.2950   -0.5091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6470   -0.9249    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7262   -0.9211   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5310   -1.8717   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583   -0.5348   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -1.1250    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0297    0.3257    2.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7138    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286   -1.0794    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    1.6993   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.1319   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568   -1.2272   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7830   -2.4609   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247   -0.5971    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    1.2914    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    2.3928    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223    2.4610    2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.5084    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061    3.2561    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    1.8762    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    1.8199   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.7785   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802    0.0178   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -0.9918   -2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.2498    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.2090    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -0.2673    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.2373    0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630   -0.0855   -1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931   -2.1457    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3381    0.7758   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3697   -2.0077    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7589   -0.9214    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3604   -0.3272    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529   -0.5606   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 13  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  6
 23 53  1  0
 24 54  1  1
 25 55  1  0
 25 56  1  0
 25 57  1  0
 28 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       0.728  -0.278   2.332  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.407   0.550   1.256  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.312  -0.006   0.499  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080   0.622  -0.589  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.524   0.359  -0.287  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.135  -0.665  -0.976  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.450  -1.022  -0.779  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.088  -2.107  -1.511  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.429  -2.751  -2.357  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.407  -2.447  -1.296  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.177  -0.304   0.165  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.608   0.726   0.875  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.267   1.046   0.634  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.704   2.071   1.339  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.985   1.951   1.121  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.494   2.122   0.804  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.869   1.471  -0.467  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.760   0.499  -0.633  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.941   0.026  -2.046  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.438  -0.099   0.511  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.909   0.124   0.526  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.607  -0.495  -0.632  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.358  -1.867  -0.597  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.133  -0.295  -0.509  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.647  -0.925   0.745  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.726  -0.921  -1.706  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.531  -1.872  -1.539  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.458  -0.535  -2.994  0.00  0.00           O+0
HETATM   29  H   UNK     0       0.178  -1.125   1.900  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.030   0.326   2.926  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.535  -0.714   2.964  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.529  -1.079   0.698  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.915   1.699  -0.690  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.836   0.132  -1.575  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.557  -1.227  -1.718  0.00  0.00           H+0
HETATM   36  H   UNK     0       8.783  -2.461  -0.352  0.00  0.00           H+0
HETATM   37  H   UNK     0       8.225  -0.597   0.314  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.181   1.291   1.618  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.771   2.393   1.246  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.222   2.461   2.087  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.520   2.508   0.341  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.606   3.256   0.698  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.150   1.876   1.634  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.361   1.820  -1.394  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.497   0.779  -2.606  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.880   0.018  -2.472  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.308  -0.992  -2.113  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.334  -1.250   0.442  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.948   0.209   1.461  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.340  -0.267   1.505  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.149   1.237   0.592  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.363  -0.086  -1.613  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.393  -2.146   0.351  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.338   0.776  -0.470  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.370  -2.008   0.830  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.759  -0.921   0.696  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.360  -0.327   1.615  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.553  -0.561  -3.445  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3   15                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   33   34                                             
CONECT    5    4    6   13                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   36                                                       
CONECT   11    7   12   37                                                  
CONECT   12   11   13   38                                                  
CONECT   13   12   14    5                                                  
CONECT   14   13   39                                                       
CONECT   15    2   16   40   41                                             
CONECT   16   15   17   42   43                                             
CONECT   17   16   18   44                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   45   46   47                                             
CONECT   20   18   21   48   49                                             
CONECT   21   20   22   50   51                                             
CONECT   22   21   23   24   52                                             
CONECT   23   22   53                                                       
CONECT   24   22   25   26   54                                             
CONECT   25   24   55   56   57                                             
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   58                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   25                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  116    0
END

RDKit          3D

58 58  0  0  0  0  0  0  0  0999 V2000
    0.7280   -0.2778    2.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    0.5498    1.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0056    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    0.6223   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5239    0.3589   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348   -0.6647   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -1.0223   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876   -2.1070   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4287   -2.7512   -2.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4074   -2.4468   -1.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1771   -0.3035    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083    0.7257    0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674    1.0463    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    2.0706    1.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847    1.9509    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940    2.1222    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    1.4707   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    0.4991   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0263   -2.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.0991    0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    0.1243    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6074   -0.4949   -0.6321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3580   -1.8675   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1329   -0.2950   -0.5091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6470   -0.9249    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7262   -0.9211   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5310   -1.8717   -1.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583   -0.5348   -2.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -1.1250    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0297    0.3257    2.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350   -0.7138    2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5286   -1.0794    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    1.6993   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.1319   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568   -1.2272   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7830   -2.4609   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247   -0.5971    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    1.2914    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    2.3928    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223    2.4610    2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.5084    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6061    3.2561    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    1.8762    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610    1.8199   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.7785   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802    0.0178   -2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084   -0.9918   -2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.2498    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477    0.2090    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3403   -0.2673    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    1.2373    0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3630   -0.0855   -1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931   -2.1457    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3381    0.7758   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3697   -2.0077    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7589   -0.9214    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3604   -0.3272    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5529   -0.5606   -3.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 13  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  6
 23 53  1  0
 24 54  1  1
 25 55  1  0
 25 56  1  0
 25 57  1  0
 28 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-(11-Carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl)-4-hydroxybenzoate	Generator
Erythrolate e	Generator

Chemical Formula

C₂₂H₃₀O₆

Average Mass

390.4760 Da

Monoisotopic Mass

390.20424 Da

IUPAC Name

3-[(2Z,6Z,10R,11S)-11-carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl]-4-hydroxybenzoic acid

Traditional Name

3-[(2Z,6Z,10R,11S)-11-carboxy-10-hydroxy-3,7,11-trimethylundeca-2,6-dien-1-yl]-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)CCC(C)=CCCC(C)=CCC1=C(O)C=CC(=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C22H30O6/c1-14(7-9-17-13-18(22(27)28)10-12-20(17)24)5-4-6-15(2)8-11-19(23)16(3)21(25)26/h6-7,10,12-13,16,19,23-24H,4-5,8-9,11H2,1-3H3,(H,25,26)(H,27,28)

InChI Key

NTUPPVZJNOAYQQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythrobacter sp.	NPAtlas	22384985

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
Long-chain fatty acid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Phenol
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Benzenoid
Fatty acid
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.43	ALOGPS
logP	4.49	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	109.5 m³·mol⁻¹	ChemAxon
Polarizability	42.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA018278

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76530656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Erythrolic acid E (NP0010680)

MOL for NP0010680 (Erythrolic acid E)

3D MOL for NP0010680 (Erythrolic acid E)

3D SDF for NP0010680 (Erythrolic acid E)

3D-SDF for NP0010680 (Erythrolic acid E)

PDB for NP0010680 (Erythrolic acid E)

3D PDB for NP0010680 (Erythrolic acid E)

SMILES for NP0010680 (Erythrolic acid E)

INCHI for NP0010680 (Erythrolic acid E)

Structure for NP0010680 (Erythrolic acid E)

3D Structure for NP0010680 (Erythrolic acid E)