NP-MRD: Showing NP-Card for hispolon (NP0201948)

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Record Information

Version

2.0

Created at

2022-09-04 21:04:30 UTC

Updated at

2022-09-04 21:04:30 UTC

NP-MRD ID

NP0201948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hispolon

Description

Hispolon belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. hispolon is found in Inonotus hispidus, Phellinus igniarius, Phellinus merrillii, Pistacia atlantica and Tropicoporus linteus. hispolon was first documented in 2022 (PMID: 35837379). Based on a literature review a small amount of articles have been published on hispolon (PMID: 35890318) (PMID: 35660410) (PMID: 35350323) (PMID: 34763936).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223042D          

 16 16  0  0  0  0            999 V2000
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.7145    1.2375    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C(/O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O4/c1-8(13)6-10(14)4-2-9-3-5-11(15)12(16)7-9/h2-7,14-16H,1H3/b4-2+,10-6-

> <INCHI_KEY>
QDVIEIMMEUCFMW-QXYPORFMSA-N

> <FORMULA>
C12H12O4

> <MOLECULAR_WEIGHT>
220.224

> <EXACT_MASS>
220.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.870345945688488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-one

> <JCHEM_LOGP>
1.7149499136666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.771519129386226

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.803714997663246

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3323824967263205

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
62.78370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₂O₄

Average Mass

220.2240 Da

Monoisotopic Mass

220.07356 Da

IUPAC Name

(3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-one

Traditional Name

(3Z,5E)-6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-dien-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C(/O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C12H12O4/c1-8(13)6-10(14)4-2-9-3-5-11(15)12(16)7-9/h2-7,14-16H,1H3/b4-2+,10-6-

InChI Key

QDVIEIMMEUCFMW-QXYPORFMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Inonotus hispidus	LOTUS Database	35616633
Phellinus igniarius	LOTUS Database	35616633
Phellinus merrillii	LOTUS Database	35616633
Pistacia atlantica	LOTUS Database	35616633
Tropicoporus linteus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Acryloyl-group
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Ketone
Enol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.71	ChemAxon
pKa (Strongest Acidic)	8.8	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.78 m³·mol⁻¹	ChemAxon
Polarizability	22.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043576

Chemspider ID

8257726

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hispolon

METLIN ID

Not Available

PubChem Compound

10082188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hossain R, Ray P, Sarkar C, Islam MS, Khan RA, Khalipha ABR, Islam MT, Cho WC, Martorell M, Sharifi-Rad J, Butnariu M, Umbetova A, Calina D: Natural Compounds or Their Derivatives against Breast Cancer: A Computational Study. Biomed Res Int. 2022 Jul 5;2022:5886269. doi: 10.1155/2022/5886269. eCollection 2022. [PubMed:35837379 ]
Lee EK, Koh EM, Kim YN, Song J, Song CH, Jung KJ: Immunomodulatory Effect of Hispolon on LPS-Induced RAW264.7 Cells and Mitogen/Alloantigen-Stimulated Spleen Lymphocytes of Mice. Pharmaceutics. 2022 Jul 6;14(7):1423. doi: 10.3390/pharmaceutics14071423. [PubMed:35890318 ]
Peng S, Hou Y, Chen Z: Hispolon alleviates oxidative damage by stimulating the Nrf2 signaling pathway in PC12 cells. Arch Biochem Biophys. 2022 Sep 30;727:109303. doi: 10.1016/j.abb.2022.109303. Epub 2022 May 31. [PubMed:35660410 ]
Ansari MJ, Rahman M, Alharbi KS, Altowayan WM, Ali AMA, Almalki WH, Barkat MA, Singh T, Nasar S, Akhter MH, Beg S, Choudhry H: Hispolon-Loaded Liquid Crystalline Nanoparticles: Development, Stability, In Vitro Delivery Profile, and Assessment of Hepatoprotective Activity in Hepatocellular Carcinoma. ACS Omega. 2022 Mar 10;7(11):9452-9464. doi: 10.1021/acsomega.1c06796. eCollection 2022 Mar 22. [PubMed:35350323 ]
Purushothaman A, Teena Rose KS, Jacob JM, Varatharaj R, Shashikala K, Janardanan D: Curcumin analogues with improved antioxidant properties: A theoretical exploration. Food Chem. 2022 Mar 30;373(Pt B):131499. doi: 10.1016/j.foodchem.2021.131499. Epub 2021 Oct 30. [PubMed:34763936 ]
LOTUS database [Link]

Showing NP-Card for hispolon (NP0201948)

MOL for NP0201948 (hispolon)

3D MOL for NP0201948 (hispolon)

3D SDF for NP0201948 (hispolon)

3D-SDF for NP0201948 (hispolon)

PDB for NP0201948 (hispolon)

3D PDB for NP0201948 (hispolon)

SMILES for NP0201948 (hispolon)

INCHI for NP0201948 (hispolon)

Structure for NP0201948 (hispolon)

3D Structure for NP0201948 (hispolon)