NP-MRD: Showing NP-Card for (2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one (NP0233593)

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Record Information

Version

2.0

Created at

2022-09-06 15:15:15 UTC

Updated at

2022-09-06 15:15:16 UTC

NP-MRD ID

NP0233593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2'-Methoxykurarinone 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)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-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)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one was first documented in 2009 (PMID: 19169950). Based on a literature review a small amount of articles have been published on 2'-Methoxykurarinone (PMID: 34592853) (PMID: 24782228) (PMID: 24492722) (PMID: 20883179).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217152D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062217152D          

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M  END
> <DATABASE_ID>
NP0233593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC=C1[C@H]1CC(=O)C2=C(O1)C(C[C@H](CC=C(C)C)C(C)=C)=C(O)C=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-15(2)7-8-17(16(3)4)11-20-21(29)13-25(32-6)26-22(30)14-24(33-27(20)26)19-10-9-18(28)12-23(19)31-5/h7,9-10,12-13,17,24,28-29H,3,8,11,14H2,1-2,4-6H3/t17-,24+/m0/s1

> <INCHI_KEY>
KTAQQSUPNZAWEY-BXKMTCNYSA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.057940105538194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
5.461996216666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.448564484023994

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.108846686261172

> <JCHEM_PKA_STRONGEST_BASIC>
-4.418319767062681

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
129.15579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2S)-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                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-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   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   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      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -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      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   32                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   21   32                                                       
CONECT   32   31   18   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2'-Methoxykurarinone	MeSH

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

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

Traditional Name

(2R)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2S)-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=CC(O)=CC=C1[C@H]1CC(=O)C2=C(O1)C(C[C@H](CC=C(C)C)C(C)=C)=C(O)C=C2OC

InChI Identifier

InChI=1S/C27H32O6/c1-15(2)7-8-17(16(3)4)11-20-21(29)13-25(32-6)26-22(30)14-24(33-27(20)26)19-10-9-18(28)12-23(19)31-5/h7,9-10,12-13,17,24,28-29H,3,8,11,14H2,1-2,4-6H3/t17-,24+/m0/s1

InChI Key

KTAQQSUPNZAWEY-BXKMTCNYSA-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
2p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Aromatic monoterpenoid
Chromane
Benzopyran
Bicyclic monoterpenoid
1-benzopyran
Methoxyphenol
Monoterpenoid
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
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	5.46	ChemAxon
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.16 m³·mol⁻¹	ChemAxon
Polarizability	50.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00014196

Chemspider ID

82964380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133561937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li P, Chai WC, Wang ZY, Tang KJ, Chen JY, Venter H, Semple SJ, Xiang L: Bioactivity-guided isolation of compounds from Sophora flavescens with antibacterial activity against Acinetobacter baumannii. Nat Prod Res. 2022 Sep;36(17):4340-4348. doi: 10.1080/14786419.2021.1983570. Epub 2021 Oct 1. [PubMed:34592853 ]
Sasaki T, Li W, Higai K, Quang TH, Kim YH, Koike K: Protein tyrosine phosphatase 1B inhibitory activity of lavandulyl flavonoids from roots of Sophora flavescens. Planta Med. 2014 May;80(7):557-60. doi: 10.1055/s-0034-1368400. Epub 2014 Apr 29. [PubMed:24782228 ]
Kim JY, Kim JY, Kim JJ, Oh J, Kim YC, Lee MS: (2S)-2'-Methoxykurarinone inhibits osteoclastogenesis and bone resorption through down-regulation of RANKL signaling. Biol Pharm Bull. 2014;37(2):255-61. doi: 10.1248/bpb.b13-00695. [PubMed:24492722 ]
Jeong SI, Lee YE, Jang SI: (2S)-2'-methoxykurarinone from Sophora flavescens suppresses cutaneous T cell-attracting chemokine/CCL27 expression induced by interleukin-ss/tumor necrosis factor-alpha via heme oxygenase-1 in human keratinocytes. J Med Food. 2010 Oct;13(5):1116-24. doi: 10.1089/jmf.2009.1333. [PubMed:20883179 ]
Feng DQ, Ke CH, Lu CY, Li SJ: Herbal plants as a promising source of natural antifoulants: evidence from barnacle settlement inhibition. Biofouling. 2009;25(3):181-90. doi: 10.1080/08927010802669210. [PubMed:19169950 ]
LOTUS database [Link]

Showing NP-Card for (2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one (NP0233593)

MOL for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0233593 ((2r)-7-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-2,3-dihydro-1-benzopyran-4-one)