NP-MRD: Showing NP-Card for (R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol (NP0057210)

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Record Information

Version

2.0

Created at

2022-04-28 02:42:42 UTC

Updated at

2022-04-28 02:42:42 UTC

NP-MRD ID

NP0057210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol

Description

Latifolin belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Thus, latifolin is considered to be a flavonoid. (R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol is found in Dalbergia cochinchinensis, Dalbergia latifolia , Dalbergia odorifera , Dalbergia parviflora and Dalbergia sissoides. (R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol was first documented in 2017 (PMID: 29243436). Based on a literature review a small amount of articles have been published on Latifolin (PMID: 35285195) (PMID: 33222562) (PMID: 32404543) (PMID: 32217949).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.0746   -0.9625    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351   -0.6225    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    0.6017    0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5617    1.4205   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920    0.9948   -2.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    1.8238   -3.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    3.0399   -2.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4791    3.4436   -1.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    2.6304   -0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601    3.0345    0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1329    0.1426    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.0157    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701    0.6757    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275    1.6291   -0.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -0.5943    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -0.9924    0.5204 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6017   -2.2447    0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -1.4918    0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4710   -1.1512    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345   -2.0204    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3251   -3.3521    1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -0.3458    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651   -1.8598    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -1.2697   -0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5933    1.1030    1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7037    0.0632   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840    1.4812   -4.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3432    3.6925   -3.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    4.3972   -1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0183    3.9001    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8480    2.0382   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4097    1.3587   -0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -2.5368    1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7140   -2.3180    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1416   -3.0036    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0683   -2.5168    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399   -3.3589    2.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844   -3.8906    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462   -3.9546    0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 11  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 13 15  1  0
  9  4  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 12 31  1  0
 14 32  1  0
  3 25  1  1
  2 24  1  0
  1 22  1  0
  1 23  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
M  END


  Mrv1652304282204422D          

 21 22  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057210

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O4/c1-4-11(12-7-5-6-8-14(12)18)13-9-15(19)17(21-3)10-16(13)20-2/h4-11,18-19H,1H2,2-3H3/t11-/m1/s1

> <INCHI_KEY>
OJVQOGDGFIJYPN-LLVKDONJSA-N

> <FORMULA>
C17H18O4

> <MOLECULAR_WEIGHT>
286.327

> <EXACT_MASS>
286.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.458303468142255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1R)-1-(2-hydroxyphenyl)prop-2-en-1-yl]-2,4-dimethoxyphenol

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.570166443333333

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.322954663248822

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.219869794287359

> <JCHEM_PKA_STRONGEST_BASIC>
-4.566880802880777

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
81.87709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
latifolin

> <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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2   16   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    4   16                                                       
CONECT   16   15    1   17                                                  
CONECT   17   16                                                            
CONECT   18    3   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₄

Average Mass

286.3270 Da

Monoisotopic Mass

286.12051 Da

IUPAC Name

5-[(1R)-1-(2-hydroxyphenyl)prop-2-en-1-yl]-2,4-dimethoxyphenol

Traditional Name

latifolin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H18O4/c1-4-11(12-7-5-6-8-14(12)18)13-9-15(19)17(21-3)10-16(13)20-2/h4-11,18-19H,1H2,2-3H3/t11-/m1/s1

InChI Key

OJVQOGDGFIJYPN-LLVKDONJSA-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
Dalbergia cochinchinensis	LOTUS Database	35616633
Dalbergia latifolia	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia parviflora	Plant	KNApSAcK
Dalbergia sissoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
4-alkoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Neoflavonoids (LMPK12100064 )

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	3.18	ALOGPS
logP	3.57	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.88 m³·mol⁻¹	ChemAxon
Polarizability	30.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00002098

Chemspider ID

301597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

340211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu RH, Yin QQ, Meng XW, Zhu Q, Liu Y, Yu HH, Lin LH, Shao F, Chen LY: [Quality evaluation of Dalbergiae Odoriferae Lignum by HPLC fingerprint and multi-component quantitative analysis]. Zhongguo Zhong Yao Za Zhi. 2022 Feb;47(4):959-966. doi: 10.19540/j.cnki.cjcmm.20210319.301. [PubMed:35285195 ]
Lai XX, Zhang N, Chen LY, Luo YY, Shou BY, Xie XX, Liu RH: Latifolin protects against myocardial infarction by alleviating myocardial inflammatory via the HIF-1alpha/NF-kappaB/IL-6 pathway. Pharm Biol. 2020 Dec;58(1):1156-1166. doi: 10.1080/13880209.2020.1840597. [PubMed:33222562 ]
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Showing NP-Card for (R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol (NP0057210)

MOL for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

3D MOL for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

3D SDF for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

3D-SDF for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

PDB for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

3D PDB for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

SMILES for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

INCHI for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

Structure for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)

3D Structure for NP0057210 ((R)-5,2'-Dihydroxy-2,4-dimethoxydalbergiquinol)