NP-MRD: Showing NP-Card for Emodic acid (NP0006406)

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Record Information

Version

2.0

Created at

2020-12-09 03:25:51 UTC

Updated at

2021-07-15 16:54:42 UTC

NP-MRD ID

NP0006406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Emodic acid

Provided By

NPAtlas

Description

Emodic acid is also known as emodate. Emodic acid is found in Flavocetraria cucullata, Holopus rangii, Penicillium aurantiogriseum, Penicillium cyclopium, Penicillium restrictum and Xanthoria parietina. Emodic acid was first documented in 1940 (PMID: 16747151). Based on a literature review very few articles have been published on Emodic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 30 32  0  0  0  0            999 V2000
   -4.7455   -1.9512    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -0.9084    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932   -0.3233   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -0.3474    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    0.7793   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.3455   -1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    2.4708   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682    0.7035   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -0.4450    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9437    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1454    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069   -2.1853    1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.6686    0.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.3618    1.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.8677    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -1.5619    1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    0.2514    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.9282   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.0379   -1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    0.4753   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.1718   -0.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.2040   -1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667   -0.8346   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.2829   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.9809   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.8428    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.2509    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -2.2972    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    0.6217   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.6823   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 10  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
 10 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 19 30  1  0  0  0  0
M  END

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.7455   -1.9512    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -0.9084    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932   -0.3233   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -0.3474    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    0.7793   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.3455   -1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    2.4708   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682    0.7035   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -0.4450    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9437    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1454    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069   -2.1853    1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.6686    0.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.3618    1.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.8677    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -1.5619    1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    0.2514    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.9282   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.0379   -1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    0.4753   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.1718   -0.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.2040   -1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667   -0.8346   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.2829   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.9809   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.8428    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.2509    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -2.2972    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    0.6217   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.6823   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10  4  1  0
 20 13  1  0
 21  8  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END


  Mrv1652306242118273D          

 30 32  0  0  0  0            999 V2000
   -4.7455   -1.9512    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -0.9084    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932   -0.3233   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -0.3474    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    0.7793   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.3455   -1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    2.4708   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682    0.7035   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -0.4450    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9437    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1454    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069   -2.1853    1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.6686    0.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.3618    1.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.8677    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -1.5619    1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    0.2514    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.9282   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.0379   -1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    0.4753   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.1718   -0.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.2040   -1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667   -0.8346   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.2829   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.9809   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.8428    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.2509    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -2.2972    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    0.6217   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.6823   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 10  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
 10 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
 19 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C(O[H])=C2C(=O)C3=C(O[H])C([H])=C(O[H])C([H])=C3C(=O)C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)

> <INCHI_KEY>
ZJXVNNSMRGTDBI-UHFFFAOYSA-N

> <FORMULA>
C15H8O7

> <MOLECULAR_WEIGHT>
300.222

> <EXACT_MASS>
300.027002598

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.74254549870453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,7-trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
2.9655930176666665

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.27480362816513

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.399011521731737

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3599474960957805

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
74.34989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
emodic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.7455   -1.9512    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -0.9084    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932   -0.3233   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -0.3474    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    0.7793   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.3455   -1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    2.4708   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682    0.7035   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -0.4450    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9437    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1454    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069   -2.1853    1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.6686    0.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.3618    1.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.8677    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -1.5619    1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    0.2514    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.9282   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.0379   -1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    0.4753   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.1718   -0.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.2040   -1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667   -0.8346   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.2829   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.9809   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.8428    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.2509    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -2.2972    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    0.6217   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.6823   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10  4  1  0
 20 13  1  0
 21  8  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  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  O   UNK     0      -4.745  -1.951   1.004  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.647  -0.908   0.306  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.793  -0.323  -0.160  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.318  -0.347   0.009  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.153   0.779  -0.742  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.895   1.345  -1.046  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.827   2.471  -1.802  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.768   0.704  -0.544  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.922  -0.445   0.223  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.176  -0.944   0.482  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.242  -1.145   0.767  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.107  -2.185   1.461  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.599  -0.669   0.529  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.686  -1.362   1.064  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.946  -0.868   0.808  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.024  -1.562   1.343  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.160   0.251   0.065  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.032   0.928  -0.461  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.273   2.038  -1.196  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.750   0.475  -0.234  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.575   1.172  -0.777  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.716   2.204  -1.466  0.00  0.00           O+0
HETATM   23  H   UNK     0      -6.367  -0.835  -0.837  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.027   1.283  -1.136  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.078   2.981  -2.101  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.262  -1.843   1.084  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.545  -2.251   1.656  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.427  -2.297   0.772  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.149   0.622  -0.124  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.749   2.682  -1.663  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   23                                                       
CONECT    4    2    5   10                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   25                                                       
CONECT    8    6    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4   26                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   28                                                       
CONECT   17   15   18   29                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   30                                                       
CONECT   20   18   21   13                                                  
CONECT   21   20   22    8                                                  
CONECT   22   21                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26   10                                                            
CONECT   27   14                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

RDKit          3D

30 32  0  0  0  0  0  0  0  0999 V2000
   -4.7455   -1.9512    1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -0.9084    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7932   -0.3233   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -0.3474    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    0.7793   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.3455   -1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8269    2.4708   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7682    0.7035   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215   -0.4450    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1765   -0.9437    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1454    0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069   -2.1853    1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5988   -0.6686    0.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.3618    1.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.8677    0.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0239   -1.5619    1.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    0.2514    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318    0.9282   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.0379   -1.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    0.4753   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.1718   -0.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.2040   -1.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3667   -0.8346   -0.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0270    1.2829   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.9809   -2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -1.8428    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -2.2509    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270   -2.2972    0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    0.6217   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.6823   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 10  4  1  0
 20 13  1  0
 21  8  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Emodate	Generator
4,5,7-Trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	Generator

Chemical Formula

C₁₅H₈O₇

Average Mass

300.2220 Da

Monoisotopic Mass

300.02700 Da

IUPAC Name

4,5,7-trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

emodic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)

InChI Key

ZJXVNNSMRGTDBI-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
Flavocetraria cucullata	LOTUS Database	35616633
Holopus rangii	LOTUS Database	35616633
Penicillium aurantiogriseum	LOTUS Database	35616633
Penicillium cyclopium	NPAtlas	16747151
Penicillium restrictum	LOTUS Database	35616633
Xanthoria parietina	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium sp.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
Hydroxyanthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.99	ALOGPS
logP	2.97	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	27.74 Å³	ChemAxon
Number of Rings	3	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

NPA020077

HMDB ID

HMDB0174949

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016317

Chemspider ID

320910

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

361510

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Anslow WK, Breen J, Raistrick H: Studies in the biochemistry of micro-organisms: Emodic acid (4:5:7-trihydroxyanthraquinone-2-carboxylic acid) and omega-hydroxyemodin (4:5:7-trihydroxy-2-(hydroxymethyl)-anthraquinone), metabolic products of a strain of Penicillium cyclopium Westling. Biochem J. 1940 Feb;34(2):159-68. doi: 10.1042/bj0340159. [PubMed:16747151 ]

Showing NP-Card for Emodic acid (NP0006406)

MOL for NP0006406 (Emodic acid)

3D MOL for NP0006406 (Emodic acid)

3D SDF for NP0006406 (Emodic acid)

3D-SDF for NP0006406 (Emodic acid)

PDB for NP0006406 (Emodic acid)

3D PDB for NP0006406 (Emodic acid)

SMILES for NP0006406 (Emodic acid)

INCHI for NP0006406 (Emodic acid)

Structure for NP0006406 (Emodic acid)

3D Structure for NP0006406 (Emodic acid)