NP-MRD: Showing NP-Card for w-hydroxyemodin (NP0006407)

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Record Information

Version

2.0

Created at

2020-12-09 03:25:54 UTC

Updated at

2021-08-19 23:59:39 UTC

NP-MRD ID

NP0006407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

w-hydroxyemodin

Provided By

NPAtlas

Description

Citreorosein, also known as W-hydroxyemodin, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, citreorosein is considered to be an aromatic polyketide. w-hydroxyemodin is found in Cassia fistula, Eriococcus coriaceus, Hamigera avellanea, Penicillium cyclopium, Penicillium restrictum, Polygonum sachalinensis, Rumex acetosella, Rumex aquaticus , Rumex cristatus, Rumex nepalensis, Talaromyces islandicus, Triangularia longicaudata and Xanthoria parietina. w-hydroxyemodin was first documented in 1940 (PMID: 16747151). Based on a literature review a small amount of articles have been published on Citreorosein (PMID: 32190053) (PMID: 34090405) (PMID: 31549123) (PMID: 31164126).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 31 33  0  0  0  0            999 V2000
    0.0656   -2.6508   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.4448   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -1.0319   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -1.9203   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -1.5133   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -2.3740   -0.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -0.1824   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258    0.7384    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    2.0891    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.2906   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.2663    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451    2.4906    0.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167    0.8262    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.7802    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    3.1053    0.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    1.4074    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1044   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -0.2155   -0.1600 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8934   -1.5563   -0.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.8235   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.4941   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.9641   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958   -2.5039   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.1835   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    2.3912    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    3.7912    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.2020    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.4444   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055    0.0368    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148   -1.6269   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -1.8461   -0.4500 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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21  2  1  0  0  0  0
 10  3  1  0  0  0  0
 21 13  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  0  0  0  0
 20 31  1  0  0  0  0
M  END

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0656   -2.6508   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.4448   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -1.0319   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -1.9203   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -1.5133   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -2.3740   -0.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -0.1824   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258    0.7384    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    2.0891    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.2906   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.2663    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451    2.4906    0.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167    0.8262    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.7802    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    3.1053    0.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    1.4074    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1044   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -0.2155   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934   -1.5563   -0.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.8235   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.4941   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.9641   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958   -2.5039   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.1835   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    2.3912    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    3.7912    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.2020    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.4444   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055    0.0368    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148   -1.6269   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -1.8461   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END


  Mrv1652306242118273D          

 31 33  0  0  0  0            999 V2000
    0.0656   -2.6508   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.4448   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -1.0319   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -1.9203   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -1.5133   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -2.3740   -0.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -0.1824   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258    0.7384    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    2.0891    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.2906   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.2663    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451    2.4906    0.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167    0.8262    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.7802    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    3.1053    0.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    1.4074    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1044   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -0.2155   -0.1600 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8934   -1.5563   -0.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.8235   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.4941   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.9641   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958   -2.5039   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.1835   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    2.3912    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    3.7912    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.2020    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.4444   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055    0.0368    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148   -1.6269   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -1.8461   -0.4500 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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21  2  1  0  0  0  0
 10  3  1  0  0  0  0
 21 13  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  9 25  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  0  0  0  0
 20 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(O[H])C([H])=C(C([H])=C3C(=O)C2=C1[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

> <INCHI_KEY>
YQHZABGPIPECSQ-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.575050316587237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-trihydroxy-6-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.540660342333333

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.100842287672915

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2492020630650815

> <JCHEM_PKA_STRONGEST_BASIC>
-2.945292474132076

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
73.9096

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0656   -2.6508   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.4448   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2513   -0.1824   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258    0.7384    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    2.0891    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.2906   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.2663    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451    2.4906    0.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167    0.8262    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.7802    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    3.1053    0.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    1.4074    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1044   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -0.2155   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934   -1.5563   -0.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.8235   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.4941   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.9641   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958   -2.5039   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.1835   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    2.3912    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    3.7912    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.2020    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.4444   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055    0.0368    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148   -1.6269   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -1.8461   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  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       0.066  -2.651  -0.590  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.209  -1.445  -0.370  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.609  -1.032  -0.292  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.650  -1.920  -0.450  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.965  -1.513  -0.373  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.031  -2.374  -0.526  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.251  -0.182  -0.131  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.226   0.738   0.033  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.490   2.089   0.279  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.938   0.291  -0.051  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.862   1.266   0.123  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.145   2.491   0.345  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.517   0.826   0.039  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.517   1.780   0.210  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.167   3.105   0.451  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.847   1.407   0.139  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.207   0.104  -0.098  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.649  -0.216  -0.160  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.893  -1.556  -0.404  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.207  -0.824  -0.264  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.872  -0.494  -0.201  0.00  0.00           C+0
HETATM   22  H   UNK     0      -2.460  -2.964  -0.640  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.396  -2.504  -1.475  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.281   0.184  -0.062  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.448   2.391   0.336  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.887   3.791   0.573  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.572   2.202   0.281  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.163   0.444  -0.913  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.106   0.037   0.819  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.815  -1.627  -0.741  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.478  -1.846  -0.450  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   23                                                       
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   25                                                       
CONECT   10    8   11    3                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   26                                                       
CONECT   16   14   17   27                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19   28   29                                             
CONECT   19   18   30                                                       
CONECT   20   17   21   31                                                  
CONECT   21   20    2   13                                                  
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   18                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   20                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

RDKit          3D

31 33  0  0  0  0  0  0  0  0999 V2000
    0.0656   -2.6508   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.4448   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -1.0319   -0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -1.9203   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -1.5133   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -2.3740   -0.5262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2513   -0.1824   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258    0.7384    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    2.0891    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9381    0.2906   -0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.2663    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1451    2.4906    0.3454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167    0.8262    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    1.7802    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    3.1053    0.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8474    1.4074    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.1044   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -0.2155   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934   -1.5563   -0.4035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.8235   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.4941   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.9641   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958   -2.5039   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.1835   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    2.3912    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869    3.7912    0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.2020    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    0.4444   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055    0.0368    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8148   -1.6269   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776   -1.8461   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Omega-hydroxyemodin	Kegg
.omega.-hydroxyemodin	HMDB
1,3,8-Trihydroxy-6-(hydroxymethyl)-9,10-anthracenedione	HMDB
1,3,8-Trihydroxy-6-(hydroxymethyl)anthra-9,10-quinone	HMDB
W-Hydroxyemodin	HMDB
1,3,8-Trihydroxy-6-hydroxymethylanthraquinone	HMDB

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2363 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

1,3,8-trihydroxy-6-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

OCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

InChI Key

YQHZABGPIPECSQ-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
Cassia fistula	LOTUS Database	35616633
Eriococcus coriaceus	LOTUS Database	35616633
Hamigera avellanea	LOTUS Database	35616633
Penicillium cyclopium	NPAtlas	16747151
Penicillium restrictum	LOTUS Database	35616633
Polygonum cuspidatum	KNApSAcK Database	22123792
Polygonum sachalinensis	Plant	KNApSAcK
Rumex acetosella	LOTUS Database	35616633
Rumex aquaticus	Plant	KNApSAcK
Rumex cristatus	LOTUS Database	35616633
Rumex nepalensis	LOTUS Database	35616633
Talaromyces islandicus	LOTUS Database	35616633
Triangularia longicaudata	LOTUS Database	35616633
Xanthoria parietina	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Zopfiella longicaudata	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthraquinones

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Not Available

Substituents

Not Available

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	672.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	95.38 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.380 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.02	ALOGPS
logP	2.54	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.91 m³·mol⁻¹	ChemAxon
Polarizability	27.58 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

NPA020086

HMDB ID

HMDB0034444

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citreorosein

METLIN ID

Not Available

PubChem Compound

361512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1534991

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 ]
Cheng W, Li Y, Yang W, Wu S, Wei M, Gao Y, Kang C, Zhang S, Li Y: Simultaneous Determination of 13 Constituents of Radix Polygoni Multiflori in Rat Plasma and Its Application in a Pharmacokinetic Study. Int J Anal Chem. 2020 Mar 3;2020:4508374. doi: 10.1155/2020/4508374. eCollection 2020. [PubMed:32190053 ]
Kengne IC, Feugap LDT, Njouendou AJ, Ngnokam CDJ, Djamalladine MD, Ngnokam D, Voutquenne-Nazabadioko L, Tamokou JD: Antibacterial, antifungal and antioxidant activities of whole plant chemical constituents of Rumex abyssinicus. BMC Complement Med Ther. 2021 Jun 5;21(1):164. doi: 10.1186/s12906-021-03325-y. [PubMed:34090405 ]
Mondal A, Saha N, Rajput A, Singh SK, Roy B, Husain SM: Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis. Org Biomol Chem. 2019 Oct 14;17(38):8711-8715. doi: 10.1039/c9ob01690b. Epub 2019 Sep 24. [PubMed:31549123 ]
Kong W, Huang C, Shi J, Li Y, Jiang X, Duan Q, Huang Y, Duan Y, Zhu X: Recycling of Chinese herb residues by endophytic and probiotic fungus Aspergillus cristatus CB10002 for the production of medicinal valuable anthraquinones. Microb Cell Fact. 2019 Jun 4;18(1):102. doi: 10.1186/s12934-019-1150-9. [PubMed:31164126 ]

Showing NP-Card for w-hydroxyemodin (NP0006407)

MOL for NP0006407 (w-hydroxyemodin)

3D MOL for NP0006407 (w-hydroxyemodin)

3D SDF for NP0006407 (w-hydroxyemodin)

3D-SDF for NP0006407 (w-hydroxyemodin)

PDB for NP0006407 (w-hydroxyemodin)

3D PDB for NP0006407 (w-hydroxyemodin)

SMILES for NP0006407 (w-hydroxyemodin)

INCHI for NP0006407 (w-hydroxyemodin)

Structure for NP0006407 (w-hydroxyemodin)

3D Structure for NP0006407 (w-hydroxyemodin)