NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one (NP0269823)

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Record Information

Version

2.0

Created at

2022-09-08 15:25:48 UTC

Updated at

2022-09-08 15:25:48 UTC

NP-MRD ID

NP0269823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Ugonin k 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-hydroxy-7-methoxychromen-4-one is found in Helminthostachys zeylanica. 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one was first documented in 2012 (PMID: 22192930). Based on a literature review a small amount of articles have been published on ugonin k (PMID: 29887353) (PMID: 28169537) (PMID: 35671862) (PMID: 25979512).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217252D          

 32 35  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    0.7145   -2.8875    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


  Mrv1652309082217252D          

 32 35  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
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M  END
> <DATABASE_ID>
NP0269823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@@H]2C(=C)CCCC2(C)C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O6/c1-14-6-5-9-26(2,3)17(14)11-16-22(31-4)13-23-24(25(16)30)20(29)12-21(32-23)15-7-8-18(27)19(28)10-15/h7-8,10,12-13,17,27-28,30H,1,5-6,9,11H2,2-4H3/t17-/m1/s1

> <INCHI_KEY>
ROCKAKPPZWGROR-QGZVFWFLSA-N

> <FORMULA>
C26H28O6

> <MOLECULAR_WEIGHT>
436.504

> <EXACT_MASS>
436.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.750557411821205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.635015277666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.740702940685953

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.61479688897592

> <JCHEM_PKA_STRONGEST_BASIC>
-4.743146752993726

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
123.51949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  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   31                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19                                                       
CONECT   27   18   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   16   31                                                  
CONECT   31   30   11   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₆

Average Mass

436.5040 Da

Monoisotopic Mass

436.18859 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@@H]2C(=C)CCCC2(C)C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H28O6/c1-14-6-5-9-26(2,3)17(14)11-16-22(31-4)13-23-24(25(16)30)20(29)12-21(32-23)15-7-8-18(27)19(28)10-15/h7-8,10,12-13,17,27-28,30H,1,5-6,9,11H2,2-4H3/t17-/m1/s1

InChI Key

ROCKAKPPZWGROR-QGZVFWFLSA-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
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.64	ChemAxon
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.52 m³·mol⁻¹	ChemAxon
Polarizability	47.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00048214

Chemspider ID

24628328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12114698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Huang YL, Shen CC, Shen YC, Chiou WF, Chen CC: Anti-inflammatory and Antiosteoporosis Flavonoids from the Rhizomes of Helminthostachys zeylanica. J Nat Prod. 2017 Feb 24;80(2):246-253. doi: 10.1021/acs.jnatprod.5b01164. Epub 2017 Feb 7. [PubMed:28169537 ]
Su CH, Chen YC, Yang YH, Wang CY, Ko PW, Huang PJ, Liaw CC, Liao WL, Cheng TL, Lee DY, Lo LC, Hsieh CL: Effect of the traditional Chinese herb Helminthostachys zeylanica on postsurgical recovery in patients with ankle fracture: A double-blinded randomized controlled clinical trial. J Ethnopharmacol. 2022 Sep 15;295:115435. doi: 10.1016/j.jep.2022.115435. Epub 2022 Jun 6. [PubMed:35671862 ]
Yamauchi K, Mitsunaga T, Itakura Y, Batubara I: Extracellular melanogenesis inhibitory activity and the structure-activity relationships of ugonins from Helminthostachys zeylanica roots. Fitoterapia. 2015 Jul;104:69-74. doi: 10.1016/j.fitote.2015.05.006. Epub 2015 May 12. [PubMed:25979512 ]
Lee CH, Huang YL, Liao JF, Chiou WF: Ugonin K-stimulated osteogenesis involves estrogen receptor-dependent activation of non-classical Src signaling pathway and classical pathway. Eur J Pharmacol. 2012 Feb 15;676(1-3):26-33. doi: 10.1016/j.ejphar.2011.12.001. Epub 2011 Dec 14. [PubMed:22192930 ]
LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one (NP0269823)

MOL for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

3D MOL for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

3D SDF for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

3D-SDF for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

PDB for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

3D PDB for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

SMILES for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

INCHI for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

Structure for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)

3D Structure for NP0269823 (2-(3,4-dihydroxyphenyl)-6-{[(1s)-2,2-dimethyl-6-methylidenecyclohexyl]methyl}-5-hydroxy-7-methoxychromen-4-one)