NP-MRD: Showing NP-Card for Kurarinol (NP0062557)

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Record Information

Version

2.0

Created at

2022-04-28 07:11:18 UTC

Updated at

2022-04-28 07:11:18 UTC

NP-MRD ID

NP0062557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kurarinol

Description

Kurarinol 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. Kurarinol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Kurarinol is found in Albizia julibrissin and Sophora flavescens . Kurarinol was first documented in 2014 (PMID: 24997323). Based on a literature review a small amount of articles have been published on kurarinol (PMID: 34592853) (PMID: 27483227) (PMID: 34885820) (PMID: 26996023).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209112D          

 33 35  0  0  1  0            999 V2000
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   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    1.5395    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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    2.1912   -1.1695    1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3465   -2.0637    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883   -1.0679   -0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    0.2914   -0.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    0.3942   -0.1035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8813    1.7273   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287    2.6232    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282209112D          

 33 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0062557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C[C@H](OC2=C(C[C@@H](CCC(C)(C)O)C(C)=C)C(O)=C1)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O7/c1-14(2)15(8-9-26(3,4)31)10-18-20(29)12-23(32-5)24-21(30)13-22(33-25(18)24)17-7-6-16(27)11-19(17)28/h6-7,11-12,15,22,27-29,31H,1,8-10,13H2,2-5H3/t15-,22+/m1/s1

> <INCHI_KEY>
XMUPAAIHKAIUSU-QRQCRPRQSA-N

> <FORMULA>
C26H32O7

> <MOLECULAR_WEIGHT>
456.535

> <EXACT_MASS>
456.21480337

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.128527827384815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
4.250566956999999

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.023015113129409

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.072080366504515

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2597505042970738

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
125.65959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.565   0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.105   2.874   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+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  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   26                                                            
CONECT   31    3   32                                                       
CONECT   32   31                                                            
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₇

Average Mass

456.5350 Da

Monoisotopic Mass

456.21480 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C[C@H](OC2=C(C[C@@H](CCC(C)(C)O)C(C)=C)C(O)=C1)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C26H32O7/c1-14(2)15(8-9-26(3,4)31)10-18-20(29)12-23(32-5)24-21(30)13-22(33-25(18)24)17-7-6-16(27)11-19(17)28/h6-7,11-12,15,22,27-29,31H,1,8-10,13H2,2-5H3/t15-,22+/m1/s1

InChI Key

XMUPAAIHKAIUSU-QRQCRPRQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Albizia julibrissin	LOTUS Database	35616633
Sophora flavescens	Plant	KNApSAcK

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
Hydroxyflavonoid
Flavanone
4'-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Chromane
Resorcinol
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary 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

trihydroxyflavanone (CHEBI:81093 )
monomethoxyflavanone (CHEBI:81093 )

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	3.6	ALOGPS
logP	4.25	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-1.3	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	8	ChemAxon
Refractivity	125.66 m³·mol⁻¹	ChemAxon
Polarizability	48.13 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

C00019181

Chemspider ID

23332653

KEGG Compound ID

C17444

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44563198

PDB ID

Not Available

ChEBI ID

81093

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 ]
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 ]
Li J, Lin Y, He L, Ou R, Chen T, Zhang X, Li Q, Zeng Z, Long Q: Two New Isoprenoid Flavonoids from Sophora flavescens with Antioxidant and Cytotoxic Activities. Molecules. 2021 Nov 29;26(23):7228. doi: 10.3390/molecules26237228. [PubMed:34885820 ]
Suzuki R, Kai H, Uesawa Y, Matsuno K, Okada Y, Shirataki Y: Electron Ionization Mass Spectrometry-based Metabolomics Studies of Sophoraflavescens can Identify the Geographical Origin of Root Samples. Nat Prod Commun. 2016 Jan;11(1):73-5. [PubMed:26996023 ]
Shu G, Yang J, Zhao W, Xu C, Hong Z, Mei Z, Yang X: Kurarinol induces hepatocellular carcinoma cell apoptosis through suppressing cellular signal transducer and activator of transcription 3 signaling. Toxicol Appl Pharmacol. 2014 Dec 1;281(2):157-65. doi: 10.1016/j.taap.2014.06.021. Epub 2014 Jul 2. [PubMed:24997323 ]

Showing NP-Card for Kurarinol (NP0062557)

MOL for NP0062557 (Kurarinol)

3D MOL for NP0062557 (Kurarinol)

3D SDF for NP0062557 (Kurarinol)

3D-SDF for NP0062557 (Kurarinol)

PDB for NP0062557 (Kurarinol)

3D PDB for NP0062557 (Kurarinol)

SMILES for NP0062557 (Kurarinol)

INCHI for NP0062557 (Kurarinol)

Structure for NP0062557 (Kurarinol)

3D Structure for NP0062557 (Kurarinol)