NP-MRD: Showing NP-Card for parietin (NP0332836)

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Record Information

Version

2.0

Created at

2024-04-23 00:06:47 UTC

Updated at

2024-09-16 20:03:37 UTC

NP-MRD ID

NP0332836

Natural Product DOI

https://doi.org/10.57994/2111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

parietin

Description

Physcion, also known as parienin or rheochrysidin, 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. Physcion is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Physcion has been detected, but not quantified in, a few different foods, such as common sages, garden rhubarbs, and sorrels. This could make physcion a potential biomarker for the consumption of these foods. It was first documented in 2005 (PMID: 16272711). A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6 (PMID: 17091434) (PMID: 17125234) (PMID: 17397111) (PMID: 17917292).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310101713232D          

 21 23  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  2  0  0  0  0
 12  6  2  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
 21  2  1  0  0  0  0
 21  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3

> <INCHI_KEY>
FFWOKTFYGVYKIR-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.690022907157772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.9673255549999995

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.561546847343456

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.894089363631251

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855742429849496

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
76.6172

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
physcion

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   21                                                            
CONECT    3    7    9                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    8   12                                                       
CONECT    7    1    3    4                                                  
CONECT    8    5    6   21                                                  
CONECT    9    3   13   15                                                  
CONECT   10    5   14   15                                                  
CONECT   11    4   13   17                                                  
CONECT   12    6   14   18                                                  
CONECT   13    9   11   16                                                  
CONECT   14   10   12   16                                                  
CONECT   15    9   10   19                                                  
CONECT   16   13   14   20                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione	ChEBI
1,8-Dihydroxy-3-methoxy-6-methylanthraquinone	ChEBI
1,8-Dihydroxy-3-methyl-6-methoxyanthraquinone	ChEBI
Emodin monomethyl ether	ChEBI
Parienin	ChEBI
Parietin	ChEBI
Physcione	ChEBI
Rheochrysidin	ChEBI
Emodin 3-methyl ether	MeSH

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

physcion

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O

InChI Identifier

InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3

InChI Key

FFWOKTFYGVYKIR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	Not Available	Université de Rennes	Solenn Ferron	2024-04-23	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
flavicans		Not Available

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

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Anthraquinone type (C17045 )

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	2.95	ALOGPS
logP	3.97	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	28.69 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

HMDB0180733

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014824

KNApSAcK ID

C00019420

Chemspider ID

Not Available

KEGG Compound ID

C17045

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Parietin

METLIN ID

Not Available

PubChem Compound

10639

PDB ID

Not Available

ChEBI ID

38167

Good Scents ID

Not Available

References

General References

Lee NJ, Choi JH, Koo BS, Ryu SY, Han YH, Lee SI, Lee DU: Antimutagenicity and cytotoxicity of the constituents from the aerial parts of Rumex acetosa. Biol Pharm Bull. 2005 Nov;28(11):2158-61. doi: 10.1248/bpb.28.2158. [PubMed:16272711 ]
Reutrakul V, Chanakul W, Pohmakotr M, Jaipetch T, Yoosook C, Kasisit J, Napaswat C, Santisuk T, Prabpai S, Kongsaeree P, Tuchinda P: Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens. Planta Med. 2006 Dec;72(15):1433-5. doi: 10.1055/s-2006-951725. Epub 2006 Nov 7. [PubMed:17091434 ]
Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG: Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J Nat Prod. 2006 Nov;69(11):1622-5. doi: 10.1021/np060248n. [PubMed:17125234 ]
Yang X, Yang L, Wang S, Yu D, Ni H: Synergistic interaction of physcion and chrysophanol on plant powdery mildew. Pest Manag Sci. 2007 May;63(5):511-5. doi: 10.1002/ps.1362. [PubMed:17397111 ]
El-Halawany AM, Chung MH, Nakamura N, Ma CM, Nishihara T, Hattori M: Estrogenic and anti-estrogenic activities of Cassia tora phenolic constituents. Chem Pharm Bull (Tokyo). 2007 Oct;55(10):1476-82. doi: 10.1248/cpb.55.1476. [PubMed:17917292 ]

Showing NP-Card for parietin (NP0332836)

MOL for NP0332836 (parietin)

3D MOL for NP0332836 (parietin)

3D SDF for NP0332836 (parietin)

3D-SDF for NP0332836 (parietin)

PDB for NP0332836 (parietin)

3D PDB for NP0332836 (parietin)

SMILES for NP0332836 (parietin)

INCHI for NP0332836 (parietin)

Structure for NP0332836 (parietin)

3D Structure for NP0332836 (parietin)