NP-MRD: Showing NP-Card for chrysophanol (NP0033999)

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Record Information

Version

1.0

Created at

2021-06-20 17:51:28 UTC

Updated at

2021-08-20 00:00:28 UTC

NP-MRD ID

NP0033999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chrysophanol

Provided By

JEOL Database JEOL Logo

Description

Chrysophanol, also known as chrysophanic acid or 3-methylchrysazin, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Thus, chrysophanol is considered to be an aromatic polyketide. Chrysophanol has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and sorrels (Rumex acetosa). This could make chrysophanol a potential biomarker for the consumption of these foods. Chrysophanol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. chrysophanol is found in Abrus melanospermus, Aloe aculeata, Aloe arborescens, Aloe berhana, Aloe broomii, Aloe castellorum, Aloe debrana, Aloe graminicola, Aloe maculata, Aloe megalacantha, Aloe pulcherrima , Aloe purpurea, Aloe rivae, Aloe saponaria , Aloe succotrina, Aloe turkanensis, Aloe vaombe, Asahinea chrysantha, Asphodeline damascena, Asphodeline lutea, Asphodeline taurica, Asphodelus aestivus, Asphodelus albus, Asphodelus fistulosus, Bulbine abyssinica, Senna sulfurea, Cassia nodosa, Chromolaena odorata, Dendrobium fimbriatum, Dendrobium thyrsiflorum, Entodon luridus, Eremurus chinensis, Euphorbia hylonoma, Fallopia multiflora, Frangula alnus, Harungana madagascariensis, Hemerocallus minor, Schefflera rhododendrifolia, Karwinskia humboldtiana, Kniphofia foliosa, Kniphofia schimperi, Ligusticum sinense, Maesopsis eminii, Monilinia fructicola, Monodictys sp., Osmanthus armatus, Boeremia foveata, Phormium tenax, Picramnia hirsuta, Picramnia sellowii, Plantago lanceolata, Polyporus umbellatus, Psorospermum febrifugum, Pyrenophora catenaria, R. uredinicola., Ramularia uredinicola, Rhamnus cathartica, Rhamnus formosana, Rhamnus frangula , Rhamnus kurdica, Rhamnus pallasii, Rhamnus prinoides , Rhamnus wightii , Rheum emodi , Rheum palaestinum, Rumex abyssinicus, Rumex acetosella , Rumex aquaticus , Rumex chalepensis, Rumex confertus , Rumex crispus , Rumex hydrolapathum, Rumex obtusifolius , Rumex patientia L. , Rumex pictus, Rumex scutatus , Rumex vesicarius , Rumex,Rheum spp., Ruscus aculeatus, Sanguisorba alpina, Selaginella delicatula, Senna corymbosa, Senna longiracemosa, Senna villosa, Shefflera venulosa, Shorea worthingtonii, Simethis mattiazzii, Strossmayeria bakeriana, Trichoderma polysporum, Trichoderma viride, Trirhabda geminata, Trypanosoma brucei, Ventilago denticulata, Ventilago viminalis, Vismia cayennensis, Vismia latifolia and Xanthorrhoea australis. It was first documented in 2009 (PMID: 19742131). Based on a literature review a significant number of articles have been published on Chrysophanol (PMID: 24136708) (PMID: 24358188) (PMID: 24395532) (PMID: 20877234).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119513D          

 29 31  0  0  0  0            999 V2000
    3.8533    1.2110   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    1.4662   -2.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1175   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    2.3259   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713    2.9783    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    1.8790   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    1.2167   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    1.0057   -2.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    0.7276   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917    0.1429   -2.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    0.9505   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.4884   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.6908    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    1.3533    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.8120    1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.4515    3.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    1.6137    0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.0958    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.6797    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    1.1982   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    1.9990   -3.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    0.2481   -3.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    2.4685   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    3.0652    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.4805   -3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185   -0.0301   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    0.3324    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.5133    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7239    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 17  2  0  0  0  0
  3  4  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  2  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
 11 12  1  0  0  0  0
 17 15  1  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 13 12  2  0  0  0  0
  4  5  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 17  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  0  0  0  0
 15 16  1  0  0  0  0
  8 25  1  0  0  0  0
  3 23  1  0  0  0  0
 14 28  1  0  0  0  0
 13 27  1  0  0  0  0
 12 26  1  0  0  0  0
  5 24  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 16 29  1  0  0  0  0
M  END

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.8533    1.2110   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    1.4662   -2.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1175   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    2.3259   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713    2.9783    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    1.8790   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    1.2167   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    1.0057   -2.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    0.7276   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917    0.1429   -2.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    0.9505   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.4884   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.6908    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    1.3533    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.8120    1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.4515    3.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    1.6137    0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.0958    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.6797    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    1.1982   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    1.9990   -3.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    0.2481   -3.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    2.4685   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    3.0652    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.4805   -3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185   -0.0301   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    0.3324    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.5133    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7239    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 17  2  0
  3  4  2  0
  4  6  1  0
  7  6  2  0
  8  2  2  0
  7  8  1  0
  2  3  1  0
 11 12  1  0
 17 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  4  5  1  0
  7  9  1  0
  2  1  1  0
  6 18  1  0
 18 19  2  0
 18 17  1  0
  9 10  2  0
 11  9  1  0
 15 16  1  0
  8 25  1  0
  3 23  1  0
 14 28  1  0
 13 27  1  0
 12 26  1  0
  5 24  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 29  1  0
M  END


  Mrv1652306202119513D          

 29 31  0  0  0  0            999 V2000
    3.8533    1.2110   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    1.4662   -2.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1175   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    2.3259   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713    2.9783    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    1.8790   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    1.2167   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    1.0057   -2.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    0.7276   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917    0.1429   -2.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    0.9505   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.4884   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.6908    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    1.3533    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.8120    1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.4515    3.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    1.6137    0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.0958    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.6797    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    1.1982   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    1.9990   -3.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    0.2481   -3.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    2.4685   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    3.0652    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.4805   -3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185   -0.0301   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    0.3324    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.5133    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7239    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 17  2  0  0  0  0
  3  4  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  2  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
 11 12  1  0  0  0  0
 17 15  1  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 13 12  2  0  0  0  0
  4  5  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 17  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  0  0  0  0
 15 16  1  0  0  0  0
  8 25  1  0  0  0  0
  3 23  1  0  0  0  0
 14 28  1  0  0  0  0
 13 27  1  0  0  0  0
 12 26  1  0  0  0  0
  5 24  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 16 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)C1=C(C([H])=C(C([H])=C1O[H])C([H])([H])[H])C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

> <INCHI_KEY>
LQGUBLBATBMXHT-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.2375

> <EXACT_MASS>
254.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.51357626545222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
4.1249968206666665

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.594259866958376

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.940475575263968

> <JCHEM_PKA_STRONGEST_BASIC>
-5.646760342395251

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
70.15400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
turkey rhubarb

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.8533    1.2110   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    1.4662   -2.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1175   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    2.3259   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713    2.9783    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    1.8790   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    1.2167   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    1.0057   -2.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    0.7276   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917    0.1429   -2.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    0.9505   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.4884   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.6908    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    1.3533    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.8120    1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.4515    3.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    1.6137    0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.0958    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.6797    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    1.1982   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    1.9990   -3.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    0.2481   -3.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    2.4685   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    3.0652    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.4805   -3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185   -0.0301   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    0.3324    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.5133    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7239    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 17  2  0
  3  4  2  0
  4  6  1  0
  7  6  2  0
  8  2  2  0
  7  8  1  0
  2  3  1  0
 11 12  1  0
 17 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  4  5  1  0
  7  9  1  0
  2  1  1  0
  6 18  1  0
 18 19  2  0
 18 17  1  0
  9 10  2  0
 11  9  1  0
 15 16  1  0
  8 25  1  0
  3 23  1  0
 14 28  1  0
 13 27  1  0
 12 26  1  0
  5 24  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.853   1.211  -3.824  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.979   1.466  -2.631  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.490   2.118  -1.503  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.686   2.326  -0.384  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.271   2.978   0.667  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.359   1.879  -0.366  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.848   1.217  -1.481  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.656   1.006  -2.609  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.545   0.728  -1.489  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.992   0.143  -2.469  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.396   0.951  -0.303  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.720   0.488  -0.310  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.538   0.691   0.803  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.036   1.353   1.922  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.721   1.812   1.928  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.309   2.451   3.066  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.892   1.614   0.816  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.502   2.096   0.814  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.951   2.680   1.800  0.00  0.00           O+0
HETATM   20  H   UNK     0       3.262   1.198  -4.745  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.606   1.999  -3.932  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.362   0.248  -3.715  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.521   2.469  -1.489  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.608   3.065   1.387  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.251   0.481  -3.474  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.119  -0.030  -1.181  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.565   0.332   0.797  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.670   1.513   2.791  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.372   2.724   2.948  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    8    3    1                                                  
CONECT    3    4    2   23                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   24                                                       
CONECT    6    4    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    2    7   25                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11   17   12    9                                                  
CONECT   12   11   13   26                                                  
CONECT   13   14   12   27                                                  
CONECT   14   15   13   28                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15   29                                                       
CONECT   17   11   15   18                                                  
CONECT   18    6   19   17                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   16                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

RDKit          3D

29 31  0  0  0  0  0  0  0  0999 V2000
    3.8533    1.2110   -3.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789    1.4662   -2.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4905    2.1175   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    2.3259   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713    2.9783    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    1.8790   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    1.2167   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    1.0057   -2.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    0.7276   -1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917    0.1429   -2.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963    0.9505   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.4884   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.6908    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    1.3533    1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.8120    1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.4515    3.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    1.6137    0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5020    2.0958    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.6797    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    1.1982   -4.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    1.9990   -3.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    0.2481   -3.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    2.4685   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    3.0652    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    0.4805   -3.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1185   -0.0301   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5647    0.3324    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700    1.5133    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7239    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 17  2  0
  3  4  2  0
  4  6  1  0
  7  6  2  0
  8  2  2  0
  7  8  1  0
  2  3  1  0
 11 12  1  0
 17 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
  4  5  1  0
  7  9  1  0
  2  1  1  0
  6 18  1  0
 18 19  2  0
 18 17  1  0
  9 10  2  0
 11  9  1  0
 15 16  1  0
  8 25  1  0
  3 23  1  0
 14 28  1  0
 13 27  1  0
 12 26  1  0
  5 24  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
1,8-Dihydroxy-3-methyl-9,10-anthracenedione	ChEBI
1,8-Dihydroxy-3-methylanthraquinone	ChEBI
3-Methylchrysazin	ChEBI
Chrysophanic acid	ChEBI
Chrysophansaeure	ChEBI
Chrysophanate	Generator
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9ci	HMDB
1,8-Dihydroxy-3-methyl-9,10-anthraquinone	HMDB
1,8-Dihydroxy-3-methyl-anthraquinone	HMDB
1,8-Dihydroxy-3-methylanthra-9,10-quinone	HMDB
2-Methyl-4,5-dihydroxyanthraquinone	HMDB
3-Methyl-1, 8-dihydroxyanthraquinone	HMDB
3-Methyl-1,8-dihydroxyanthraquinone	HMDB
4, 5-Dihydroxy-2-methylanthraquinone	HMDB
4,5-Dihydroxy-2-methylanthraquinone	HMDB
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9ci)	HMDB
Archinin	HMDB
C.I. natural yellow 23	HMDB
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)	HMDB
Crysophanic acid	HMDB
Crysophanol	HMDB
Rheic acid	HMDB
Rumicin	HMDB
Turkey rhubarb	HMDB
Chrysophanic acid, ion (1-)	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Mass

254.2375 Da

Monoisotopic Mass

254.05791 Da

IUPAC Name

1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

turkey rhubarb

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)C1=C(C([H])=C(C([H])=C1O[H])C([H])([H])[H])C2=O

InChI Identifier

InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

InChI Key

LQGUBLBATBMXHT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃ at 50C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Abrus melanospermus	LOTUS Database	35616633
Abrus pulchellus	KNApSAcK Database	22123792
Achyranthes bidentata	KNApSAcK Database	22123792
Aloe aculeata	LOTUS Database	35616633
Aloe arborescens	LOTUS Database	35616633
Aloe berhana	Plant	KNApSAcK
Aloe broomii	LOTUS Database	35616633
Aloe castellorum	LOTUS Database	35616633
Aloe debrana	LOTUS Database	35616633
Aloe graminicola	Plant	KNApSAcK
Aloe maculata	LOTUS Database	35616633
Aloe megalacantha	Plant	KNApSAcK
Aloe pulcherrima	Plant	KNApSAcK
Aloe purpurea	LOTUS Database	35616633
Aloe rivae	Plant	KNApSAcK
Aloe saponaria	Plant	KNApSAcK
Aloe succotrina	LOTUS Database	35616633
Aloe turkanensis	Plant	KNApSAcK
Aloe vaombe	LOTUS Database	35616633
Aloe vera	KNApSAcK Database	22123792
Alvaradoa haitiensis	KNApSAcK Database	22123792
Alvaradoa jamaicensis	KNApSAcK Database	22123792
Asahinea chrysantha	LOTUS Database	35616633
Asphodeline damascena	LOTUS Database	35616633
Asphodeline globifera	KNApSAcK Database	22123792
Asphodeline lutea	LOTUS Database	35616633
Asphodeline taurica	LOTUS Database	35616633
Asphodelus aestivus	LOTUS Database	35616633
Asphodelus albus	LOTUS Database	35616633
Asphodelus fistulosus	LOTUS Database	35616633
Berchemia floribunda	KNApSAcK Database	22123792
Bulbine abyssinica	LOTUS Database	35616633
Bulbine capitata	KNApSAcK Database	22123792
Bulbine narcissifolia	KNApSAcK Database	22123792
Cassia acutifolia	KNApSAcK Database	22123792
Cassia alata L.	KNApSAcK Database	22123792
Cassia angolensis	KNApSAcK Database	22123792
Cassia angustifolia	KNApSAcK Database	22123792
Cassia fistula	KNApSAcK Database	22123792
Cassia glauca	LOTUS Database	35616633
Cassia grandis	KNApSAcK Database	22123792
Cassia javanica	KNApSAcK Database	22123792
Cassia mimosoides	KNApSAcK Database	22123792
Cassia nodosa	Plant	KNApSAcK
Cassia obtusifolia	KNApSAcK Database	22123792
Cassia occidentalis	KNApSAcK Database	22123792
Cassia quinquangulata	KNApSAcK Database	22123792
Cassia renigera	KNApSAcK Database	22123792
Cassia roxburghii	KNApSAcK Database	22123792
Cassia senna	KNApSAcK Database	22123792
Cassia siamea	KNApSAcK Database	22123792
Cassia sophora	KNApSAcK Database	22123792
Cassia speciosa	KNApSAcK Database	22123792
Cassia tora	KNApSAcK Database	22123792
Cassia torosa L.	KNApSAcK Database	22123792
Chamaecrista absus	KNApSAcK Database	22123792
Chamaecrista mimosoides	KNApSAcK Database	22123792
Chamaecrista nomame	KNApSAcK Database	22123792
Chamaecrista pumila	KNApSAcK Database	22123792
Chromolaena odorata	LOTUS Database	35616633
Dendrobium fimbriatum	LOTUS Database	35616633
Dendrobium thyrsiflorum	LOTUS Database	35616633
Entodon luridus	LOTUS Database	35616633
Eremurus chinensis	LOTUS Database	35616633
Euphorbia hylonoma	LOTUS Database	35616633
Fallopia multiflora	LOTUS Database	35616633
Frangula alnus	LOTUS Database	35616633
Harungana madagascariensis	LOTUS Database	35616633
Hemerocallis citriana	KNApSAcK Database	22123792
Hemerocallis fulva	KNApSAcK Database	22123792
Hemerocallis lilio-asphodelus	KNApSAcK Database	22123792
Hemerocallus minor	-	KNApSAcK
Heptapleurum rhododendrifolium	LOTUS Database	35616633
Karwinskia humboldtiana	LOTUS Database	35616633
Kniphofia foliosa	LOTUS Database	35616633
Kniphofia schimperi	LOTUS Database	35616633
Ligusticum chuanxiong	KNApSAcK Database	22123792
Ligusticum sinense	LOTUS Database	35616633
Luetzelburgia pallidiflora	KNApSAcK Database	22123792
Maesopsis eminii	LOTUS Database	35616633
Monilinia fructicola	LOTUS Database	35616633
Monodictys sp.	-	KNApSAcK
Osmanthus armatus	LOTUS Database	35616633
Phoma exigua var. foveata	LOTUS Database	35616633
Phormium tenax	LOTUS Database	35616633
Picramnia antidesma	KNApSAcK Database	22123792
Picramnia hirsuta	LOTUS Database	35616633
Picramnia latifolia	KNApSAcK Database	22123792
Picramnia sellowii	LOTUS Database	35616633
Plantago lanceolata	LOTUS Database	35616633
Polygonum cuspidatum	KNApSAcK Database	22123792
Polygonum multiflorum	KNApSAcK Database	22123792
Polyporus umbellatus	LOTUS Database	35616633
Psorospermum febrifugum	LOTUS Database	35616633
Pyrenophora catenaria	LOTUS Database	35616633
R. uredinicola.	JEOL database	Miethbauer, S., et al, J. Nat. Prod. 71, 1371 (2008)
Ramularia uredinicola	LOTUS Database	35616633
Rhamnus cathartica	LOTUS Database	35616633
Rhamnus davurica	KNApSAcK Database	22123792
Rhamnus formosana	LOTUS Database	35616633
Rhamnus frangula	Plant	KNApSAcK
Rhamnus kurdica	LOTUS Database	35616633
Rhamnus nepalensis	KNApSAcK Database	22123792
Rhamnus pallasii	LOTUS Database	35616633
Rhamnus prinoides	Plant	KNApSAcK
Rhamnus purshiana	KNApSAcK Database	22123792
Rhamnus wightii	Plant	KNApSAcK
Rheum australe	Plant	KNApSAcK
Rheum emodi	KNApSAcK Database	22123792
Rheum officinale	KNApSAcK Database	22123792
Rheum palaestinum	LOTUS Database	35616633
Rheum palmatum	KNApSAcK Database	22123792
Rheum rhabarbarum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rheum spp.	KNApSAcK Database	22123792
Rheum tanguticum	KNApSAcK Database	22123792
Rheum wittrocki	KNApSAcK Database	22123792
Rumex	FooDB	KNAPSACK
Rumex abyssinicus	LOTUS Database	35616633
Rumex acetosa	KNApSAcK Database	22123792
Rumex acetosella	Plant	KNApSAcK
Rumex alpinus	KNApSAcK Database	22123792
Rumex aquaticus	Plant	KNApSAcK
Rumex chalepensis	LOTUS Database	35616633
Rumex confertus	Plant	KNApSAcK
Rumex crispus	Plant	KNApSAcK
Rumex dentatus	KNApSAcK Database	22123792
Rumex hydrolapathum	Plant	KNApSAcK
Rumex japonicus	KNApSAcK Database	22123792
Rumex nepalensis	KNApSAcK Database	22123792
Rumex obtusifolius	Plant	KNApSAcK
Rumex patientia	Plant	KNApSAcK
Rumex patientia L.	KNApSAcK Database	22123792
Rumex pictus	LOTUS Database	35616633
Rumex scutatus	Plant	KNApSAcK
Rumex spp.	KNApSAcK Database	22123792
Rumex vesicarius	Plant	KNApSAcK
Rumex,Rheum spp.	-	KNApSAcK
Ruscus aculeatus	LOTUS Database	35616633
Sanguisorba alpina	LOTUS Database	35616633
Selaginella delicatula	LOTUS Database	35616633
Senna alata	KNApSAcK Database	22123792
Senna alexandrina	KNApSAcK Database	22123792
Senna angustisiliqua	KNApSAcK Database	22123792
Senna auriculata	KNApSAcK Database	22123792
Senna corymbosa	LOTUS Database	35616633
Senna didymobotrya	KNApSAcK Database	22123792
Senna garrettiana	KNApSAcK Database	22123792
Senna italica	KNApSAcK Database	22123792
Senna longiracemosa	LOTUS Database	35616633
Senna macranthera	KNApSAcK Database	22123792
Senna obtusifolia	KNApSAcK Database	22123792
Senna occidentalis	KNApSAcK Database	22123792
Senna podocarpa	KNApSAcK Database	22123792
Senna quinquangulata	KNApSAcK Database	22123792
Senna septemtrionalis	KNApSAcK Database	22123792
Senna siamea	KNApSAcK Database	22123792
Senna singueana	KNApSAcK Database	22123792
Senna sophera	KNApSAcK Database	22123792
Senna spectabilis	KNApSAcK Database	22123792
Senna tora	KNApSAcK Database	22123792
Senna villosa	LOTUS Database	35616633
Shefflera venulosa	-	KNApSAcK
Shorea worthingtonii	LOTUS Database	35616633
Simethis mattiazzii	LOTUS Database	35616633
Strossmayeria bakeriana	LOTUS Database	35616633
Tectona grandis	KNApSAcK Database	22123792
Trichoderma polysporum	LOTUS Database	35616633
Trichoderma viride	LOTUS Database	35616633
Trirhabda geminata	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633
Vatairea heteroptera	KNApSAcK Database	22123792
Ventilago denticulata	LOTUS Database	35616633
Ventilago leiocarpa	KNApSAcK Database	22123792
Ventilago viminalis	LOTUS Database	35616633
Vismia cayennensis	LOTUS Database	35616633
Vismia latifolia	LOTUS Database	35616633
Xanthorrhoea australis	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Pyrenochaeta terrestris	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthraquinones

Direct Parent

Anthraquinones

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	196.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	489.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.98 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.720 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.08	ALOGPS
logP	4.12	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.15 m³·mol⁻¹	ChemAxon
Polarizability	25.51 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

HMDB ID

HMDB0030670

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Chrysophanol

METLIN ID

Not Available

PubChem Compound

10208

PDB ID

Not Available

ChEBI ID

3687

Good Scents ID

rw1229821

References

General References

Zhao X, Zheng Z, Feng S, Shi Z, Chen D: A TD-DFT study on the photo-physicochemical properties of chrysophanol from rheum. Int J Mol Sci. 2009 Jul 13;10(7):3186-93. doi: 10.3390/ijms10073186. [PubMed:19742131 ]
Wu W, Yan R, Yao M, Zhan Y, Wang Y: Pharmacokinetics of anthraquinones in rat plasma after oral administration of a rhubarb extract. Biomed Chromatogr. 2014 Apr;28(4):564-72. doi: 10.1002/bmc.3070. Epub 2013 Oct 18. [PubMed:24136708 ]
Lee YS, Ju HK, Kim YJ, Lim TG, Uddin MR, Kim YB, Baek JH, Kwon SW, Lee KW, Seo HS, Park SU, Yang TJ: Enhancement of anti-inflammatory activity of Aloe vera adventitious root extracts through the alteration of primary and secondary metabolites via salicylic acid elicitation. PLoS One. 2013 Dec 16;8(12):e82479. doi: 10.1371/journal.pone.0082479. eCollection 2013. [PubMed:24358188 ]
Chang SJ, Huang SH, Lin YJ, Tsou YY, Lin CW: Antiviral activity of Rheum palmatum methanol extract and chrysophanol against Japanese encephalitis virus. Arch Pharm Res. 2014;37(9):1117-23. doi: 10.1007/s12272-013-0325-x. Epub 2014 Jan 7. [PubMed:24395532 ]
Kim SJ, Kim MC, Lee BJ, Park DH, Hong SH, Um JY: Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo. Molecules. 2010 Sep 16;15(9):6436-51. doi: 10.3390/molecules15096436. [PubMed:20877234 ]
Miethbauer, S., et al. (2008). Miethbauer, S., et al, J. Nat. Prod. 71, 1371 (2008). J. Nat. Prod..

Showing NP-Card for chrysophanol (NP0033999)

MOL for NP0033999 (chrysophanol)

3D MOL for NP0033999 (chrysophanol)

3D SDF for NP0033999 (chrysophanol)

3D-SDF for NP0033999 (chrysophanol)

PDB for NP0033999 (chrysophanol)

3D PDB for NP0033999 (chrysophanol)

SMILES for NP0033999 (chrysophanol)

INCHI for NP0033999 (chrysophanol)

Structure for NP0033999 (chrysophanol)

3D Structure for NP0033999 (chrysophanol)