NP-MRD: Showing NP-Card for (+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan (NP0057033)

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Record Information

Version

2.0

Created at

2022-04-28 02:36:10 UTC

Updated at

2022-04-28 02:36:10 UTC

NP-MRD ID

NP0057033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan

Description

Licorisoflavan A belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. (+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan is found in Glycyrrhiza aspera and Glycyrrhiza uralensis . (+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan was first documented in 2015 (PMID: 25963162). Based on a literature review a small amount of articles have been published on Licorisoflavan A (PMID: 31278631) (PMID: 30391123) (PMID: 27735870) (PMID: 25531232).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204362D          

 32 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282204362D          

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M  END
> <DATABASE_ID>
NP0057033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C(OC)=C2C[C@H](COC2=C1)C1=CC=C(O)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O5/c1-16(2)7-9-20-23(28)12-11-19(26(20)29)18-13-22-25(32-15-18)14-24(30-5)21(27(22)31-6)10-8-17(3)4/h7-8,11-12,14,18,28-29H,9-10,13,15H2,1-6H3/t18-/m1/s1

> <INCHI_KEY>
GDAAEAXMNLVRCZ-GOSISDBHSA-N

> <FORMULA>
C27H34O5

> <MOLECULAR_WEIGHT>
438.564

> <EXACT_MASS>
438.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.50730023184576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(3S)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
6.333469344666667

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.664505061561451

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.318991034720215

> <JCHEM_PKA_STRONGEST_BASIC>
-4.380578615777177

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
130.37220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(3S)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <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  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    1   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₅

Average Mass

438.5640 Da

Monoisotopic Mass

438.24062 Da

IUPAC Name

4-[(3S)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

Traditional Name

4-[(3S)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C(OC)=C2C[C@H](COC2=C1)C1=CC=C(O)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C27H34O5/c1-16(2)7-9-20-23(28)12-11-19(26(20)29)18-13-22-25(32-15-18)14-24(30-5)21(27(22)31-6)10-8-17(3)4/h7-8,11-12,14,18,28-29H,9-10,13,15H2,1-6H3/t18-/m1/s1

InChI Key

GDAAEAXMNLVRCZ-GOSISDBHSA-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
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylated isoflavonoids

Alternative Parents

Substituents

5-methoxyisoflavonoid-skeleton
7-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
1-benzopyran
Chromane
Benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	5.31	ALOGPS
logP	6.33	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.37 m³·mol⁻¹	ChemAxon
Polarizability	49.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00010036

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133269766

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao D, Liu L, Li Y, Ruan J, Wang H: Licorisoflavan A Exerts Antidepressant-Like Effect in Mice: Involvement of BDNF-TrkB Pathway and AMPA Receptors. Neurochem Res. 2019 Sep;44(9):2044-2056. doi: 10.1007/s11064-019-02840-2. Epub 2019 Jul 5. [PubMed:31278631 ]
Sidhu P, Shankargouda S, Rath A, Hesarghatta Ramamurthy P, Fernandes B, Kumar Singh A: Therapeutic benefits of liquorice in dentistry. J Ayurveda Integr Med. 2020 Jan-Mar;11(1):82-88. doi: 10.1016/j.jaim.2017.12.004. Epub 2018 Nov 1. [PubMed:30391123 ]
Liu N, Li L, Zhu X, Ling Z, Feng J, Hu Y, Wang Y, Mou L, Wang Y: A High Content Screening Assay to Identify Compounds with Anti-Epithelial-Mesenchymal Transition Effects from the Chinese Herbal Medicine Tong-Mai-Yang-Xin-Wan. Molecules. 2016 Oct 10;21(10):1340. doi: 10.3390/molecules21101340. [PubMed:27735870 ]
Kirmizibekmez H, Uysal GB, Masullo M, Demirci F, Bagci Y, Kan Y, Piacente S: Prenylated polyphenolic compounds from Glycyrrhiza iconica and their antimicrobial and antioxidant activities. Fitoterapia. 2015 Jun;103:289-93. doi: 10.1016/j.fitote.2015.05.003. Epub 2015 May 8. [PubMed:25963162 ]
Ahn SJ, Park SN, Lee YJ, Cho EJ, Lim YK, Li XM, Choi MH, Seo YW, Kook JK: In vitro antimicrobial activities of 1-methoxyficifolinol, licorisoflavan A, and 6,8-diprenylgenistein against Streptococcus mutans. Caries Res. 2015;49(1):78-89. doi: 10.1159/000362676. Epub 2014 Dec 18. [PubMed:25531232 ]

Showing NP-Card for (+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan (NP0057033)

MOL for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

3D MOL for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

3D SDF for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

3D-SDF for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

PDB for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

3D PDB for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

SMILES for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

INCHI for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

Structure for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)

3D Structure for NP0057033 ((+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan)