NP-MRD: Showing NP-Card for (2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one (NP0242099)

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Record Information

Version

2.0

Created at

2022-09-07 02:19:48 UTC

Updated at

2022-09-07 02:19:48 UTC

NP-MRD ID

NP0242099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one

Description

Kushenol I belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. (2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one is found in Sophora flavescens. (2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one was first documented in 2013 (PMID: 24228588). Kushenol I is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 31001351) (PMID: 28936847) (PMID: 28278618) (PMID: 27483227).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006252D          

 33 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309272006252D          

 33 35  0  0  0  0            999 V2000
 9999.268010001.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0242099

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O7/c1-13(2)6-7-15(14(3)4)10-18-20(29)12-21(32-5)22-23(30)24(31)26(33-25(18)22)17-9-8-16(27)11-19(17)28/h6,8-9,11-12,15,24,26-29,31H,3,7,10H2,1-2,4-5H3/t15-,24+,26-/m1/s1

> <INCHI_KEY>
QKEDJCCCNZWOBS-SGOPFIAHSA-N

> <FORMULA>
C26H30O7

> <MOLECULAR_WEIGHT>
454.519

> <EXACT_MASS>
454.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.80879187089825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
4.6009437

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.99466351673929

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.975950345925509

> <JCHEM_PKA_STRONGEST_BASIC>
-4.054011988816929

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
126.01169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.3008668.635   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.9678669.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.6338668.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.2998669.405   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8659.9668668.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8658.6328669.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9668667.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.9678670.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6338671.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3008671.715   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8662.6378667.091   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8665.3008662.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8663.9598661.675   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8667.9588662.450   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8671.9588664.777   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8674.6278669.397   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8670.6238663.994   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8671.9588669.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6258668.629   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.6258667.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.9588666.319   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.2928667.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8673.2928668.629   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.3008667.082   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8663.9678666.312   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8663.9668664.772   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8665.3008664.002   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8667.9618667.082   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0    8666.6278666.312   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8666.6278664.772   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8667.9618664.002   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8669.2958664.772   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8669.2958666.312   0.000  0.00  0.00           C+0
CONECT    1    2   24                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   25                                                            
CONECT   12   13   27                                                       
CONECT   13   12                                                            
CONECT   14   31                                                            
CONECT   15   21                                                            
CONECT   16   23                                                            
CONECT   17   32                                                            
CONECT   18   19   23                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   15                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   16                                                  
CONECT   24   25    1   29                                                  
CONECT   25   24   26   11                                                  
CONECT   26   25   27                                                       
CONECT   27   26   12   30                                                  
CONECT   28   29   33                                                       
CONECT   29   30   28   24                                                  
CONECT   30   29   31   27                                                  
CONECT   31   30   32   14                                                  
CONECT   32   31   33   17                                                  
CONECT   33   32   28   20                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₇

Average Mass

454.5190 Da

Monoisotopic Mass

454.19915 Da

IUPAC Name

(2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H30O7/c1-13(2)6-7-15(14(3)4)10-18-20(29)12-21(32-5)22-23(30)24(31)26(33-25(18)22)17-9-8-16(27)11-19(17)28/h6,8-9,11-12,15,24,26-29,31H,3,7,10H2,1-2,4-5H3/t15-,24+,26-/m1/s1

InChI Key

QKEDJCCCNZWOBS-SGOPFIAHSA-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
Sophora flavescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
5-methoxyflavonoid-skeleton
Flavanone
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanonol
Hydroxyflavonoid
Chromone
Bicyclic monoterpenoid
Benzopyran
Monoterpenoid
Chromane
Aromatic monoterpenoid
1-benzopyran
Phenol ether
Resorcinol
Aryl alkyl ketone
Aryl ketone
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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	3.86	ALOGPS
logP	4.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.01 m³·mol⁻¹	ChemAxon
Polarizability	47.81 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20128940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20832634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yim D, Kim MJ, Shin Y, Lee SJ, Shin JG, Kim DH: Inhibition of Cytochrome P450 Activities by Sophora flavescens Extract and Its Prenylated Flavonoids in Human Liver Microsomes. Evid Based Complement Alternat Med. 2019 Mar 13;2019:2673769. doi: 10.1155/2019/2673769. eCollection 2019. [PubMed:31001351 ]
Ma HY, Zhou WS, Chu FJ, Wang D, Liang SW, Li S: [HPLC fingerprint of flavonoids in Sophora flavescens and determination of five components]. Zhongguo Zhong Yao Za Zhi. 2013 Aug;38(16):2690-5. [PubMed:24228588 ]
Zhang HQ, Zhu ZH, Qian DW, Weng ZB, Guo S, Duan JA, Lei ZH, Li AP: [Analysis and evaluation of alkaloids and flavonoids in flower of Sophora flavescens from Shanxi province]. Zhongguo Zhong Yao Za Zhi. 2016 Dec;41(24):4621-4627. doi: 10.4268/cjcmm20162422. [PubMed:28936847 ]
Huang R, Liu Y, Zhao LL, Chen XX, Wang F, Cai W, Chen L: A new flavonoid from Sophora flavescens Ait. Nat Prod Res. 2017 Oct;31(19):2228-2232. doi: 10.1080/14786419.2017.1297992. Epub 2017 Mar 6. [PubMed:28278618 ]
Zhang Q, Yu J, Wang Y, Su W: Selective Extraction of Flavonoids from Sophora flavescens Ait. by Mechanochemistry. Molecules. 2016 Jul 29;21(8):989. doi: 10.3390/molecules21080989. [PubMed:27483227 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one (NP0242099)

MOL for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0242099 ((2r,3r)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)