NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one (NP0322185)

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Record Information

Version

2.0

Created at

2022-09-12 00:48:59 UTC

Updated at

2022-09-12 00:48:59 UTC

NP-MRD ID

NP0322185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one

Description

Ugonin J belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one is found in Helminthostachys zeylanica. 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one was first documented in 2018 (PMID: 29887353). Based on a literature review a small amount of articles have been published on ugonin J (PMID: 33220422) (PMID: 33075336) (PMID: 35645800) (PMID: 34512347).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202492D          

 31 34  0  0  1  0            999 V2000
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   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122202492D          

 31 34  0  0  1  0            999 V2000
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   -0.7145   -2.8875    0.0000 C   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   -4.1250    0.0000 C   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
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M  END
> <DATABASE_ID>
NP0322185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC(=C)[C@H]1CC1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O6/c1-13-5-4-8-25(2,3)16(13)10-15-18(27)11-22-23(24(15)30)20(29)12-21(31-22)14-6-7-17(26)19(28)9-14/h6-7,9,11-12,16,26-28,30H,1,4-5,8,10H2,2-3H3/t16-/m1/s1

> <INCHI_KEY>
VCPZVNMTXCALPA-MRXNPFEDSA-N

> <FORMULA>
C25H26O6

> <MOLECULAR_WEIGHT>
422.477

> <EXACT_MASS>
422.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.64817794947777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-6-{[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxy-4H-chromen-4-one

> <JCHEM_LOGP>
5.489121221666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.204577948873476

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.846492526506607

> <JCHEM_PKA_STRONGEST_BASIC>
-5.373213005745121

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
119.03719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-6-{[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.850  -5.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.860  -3.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   17   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   15   30                                                  
CONECT   30   29   11   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₆

Average Mass

422.4770 Da

Monoisotopic Mass

422.17294 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-6-{[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-6-{[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC(=C)[C@H]1CC1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C25H26O6/c1-13-5-4-8-25(2,3)16(13)10-15-18(27)11-22-23(24(15)30)20(29)12-21(31-22)14-6-7-17(26)19(28)9-14/h6-7,9,11-12,16,26-28,30H,1,4-5,8,10H2,2-3H3/t16-/m1/s1

InChI Key

VCPZVNMTXCALPA-MRXNPFEDSA-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
Helminthostachys zeylanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

6-prenylated flavones

Alternative Parents

Substituents

6-prenylated flavone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.49	ChemAxon
pKa (Strongest Acidic)	6.85	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.04 m³·mol⁻¹	ChemAxon
Polarizability	45.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00048213

Chemspider ID

24626491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12114697

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang TC, Chiou WC, Lai WH, Huang HC, Huang YL, Liu HK, Liang YC, Huang C: Ugonin J improves metabolic disorder and ameliorates nonalcoholic fatty liver disease by regulating the AMPK/AKT signaling pathway. Pharmacol Res. 2021 Jan;163:105298. doi: 10.1016/j.phrs.2020.105298. Epub 2020 Nov 18. [PubMed:33220422 ]
Shah AB, Yoon S, Kim JH, Zhumanova K, Ban YJ, Lee KW, Park KH: Effectiveness of cyclohexyl functionality in ugonins from Helminthostachys zeylanica to PTP1B and alpha-glucosidase inhibitions. Int J Biol Macromol. 2020 Dec 15;165(Pt B):1822-1831. doi: 10.1016/j.ijbiomac.2020.10.061. Epub 2020 Oct 17. [PubMed:33075336 ]
Yamauchi K, Fujieda A, Mitsunaga T: Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells. Bioorg Med Chem Lett. 2018 Aug 1;28(14):2518-2522. doi: 10.1016/j.bmcl.2018.05.051. Epub 2018 May 28. [PubMed:29887353 ]
Shah AB, Baiseitova A, Kim JH, Lee YH, Park KH: Inhibition of Bacterial Neuraminidase and Biofilm Formation by Ugonins Isolated From Helminthostachys Zeylanica (L.) Hook. Front Pharmacol. 2022 May 11;13:890649. doi: 10.3389/fphar.2022.890649. eCollection 2022. [PubMed:35645800 ]
Chiou WC, Lu HF, Hsu NY, Chang TY, Chin YF, Liu PC, Lo JM, Wu YB, Yang JM, Huang C: Ugonin J Acts as a SARS-CoV-2 3C-like Protease Inhibitor and Exhibits Anti-inflammatory Properties. Front Pharmacol. 2021 Aug 26;12:720018. doi: 10.3389/fphar.2021.720018. eCollection 2021. [PubMed:34512347 ]
LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one (NP0322185)

MOL for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

3D MOL for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

3D SDF for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

3D-SDF for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

PDB for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

3D PDB for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

SMILES for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

INCHI for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

Structure for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)

3D Structure for NP0322185 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5,7-dihydroxychromen-4-one)