NP-MRD: Showing NP-Card for Diuvaretin (NP0055328)

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Record Information

Version

2.0

Created at

2022-04-28 01:24:59 UTC

Updated at

2022-04-28 01:24:59 UTC

NP-MRD ID

NP0055328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diuvaretin

Description

Diuvaretin belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. Thus, diuvaretin is considered to be a flavonoid lipid molecule. Diuvaretin is found in Uvaria acuminata , Uvaria angolensis, Uvaria chamae , Uvaria kirkii, Uvaria leptocladon , Uvaria tanzaniae and Xylopia africana. Diuvaretin was first documented in 1991 (PMID: 1775574). Diuvaretin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12168763) (PMID: 14709883) (PMID: 15635168).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171501442D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171501442D          

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M  END
> <DATABASE_ID>
NP0055328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC2=CC=CC=C2O)C(O)=C(CC2=CC=CC=C2O)C(O)=C1C(=O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O6/c1-36-30-23(18-21-12-6-8-14-25(21)32)28(34)22(17-20-11-5-7-13-24(20)31)29(35)27(30)26(33)16-15-19-9-3-2-4-10-19/h2-14,31-32,34-35H,15-18H2,1H3

> <INCHI_KEY>
KDEMELRYKGOXDL-UHFFFAOYSA-N

> <FORMULA>
C30H28O6

> <MOLECULAR_WEIGHT>
484.548

> <EXACT_MASS>
484.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.26783702125556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2,4-dihydroxy-3,5-bis[(2-hydroxyphenyl)methyl]-6-methoxyphenyl}-3-phenylpropan-1-one

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
7.271457321

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8747773749122585

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3162316494348625

> <JCHEM_PKA_STRONGEST_BASIC>
-4.635755742730425

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
139.64489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diuvaretin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -5.390   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  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   15   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₈O₆

Average Mass

484.5480 Da

Monoisotopic Mass

484.18859 Da

IUPAC Name

1-{2,4-dihydroxy-3,5-bis[(2-hydroxyphenyl)methyl]-6-methoxyphenyl}-3-phenylpropan-1-one

Traditional Name

diuvaretin

CAS Registry Number

Not Available

SMILES

COC1=C(CC2=CC=CC=C2O)C(O)=C(CC2=CC=CC=C2O)C(O)=C1C(=O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C30H28O6/c1-36-30-23(18-21-12-6-8-14-25(21)32)28(34)22(17-20-11-5-7-13-24(20)31)29(35)27(30)26(33)16-15-19-9-3-2-4-10-19/h2-14,31-32,34-35H,15-18H2,1H3

InChI Key

KDEMELRYKGOXDL-UHFFFAOYSA-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
Uvaria acuminata	Plant	KNApSAcK
Uvaria angolensis	Plant	KNApSAcK
Uvaria chamae	Plant	KNApSAcK
Uvaria kirkii	Plant	KNApSAcK
Uvaria leptocladon	Plant	KNApSAcK
Uvaria tanzaniae	LOTUS Database	35616633
Xylopia africana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Diphenylmethane
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Phenylketone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Resorcinol
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:65802 )
monomethoxybenzene (CHEBI:65802 )
dihydrochalcones (CHEBI:65802 )
Chalcones and dihydrochalcones (LMPK12120472 )

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	4.78	ALOGPS
logP	7.27	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.32	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.64 m³·mol⁻¹	ChemAxon
Polarizability	51.27 Å³	ChemAxon
Number of Rings	4	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

Not Available

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

3085222

PDB ID

Not Available

ChEBI ID

65802

Good Scents ID

Not Available

References

General References

Makangara JJ, Jonker SA, Nkunya MH: A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis. Nat Prod Lett. 2002 Aug;16(4):267-72. doi: 10.1080/10575630290020604. [PubMed:12168763 ]
Ichimaru M, Nakatani N, Takahashi T, Nishiyama Y, Moriyasu M, Kato A, Mathenge SG, Juma FD, Nganga JN: Cytotoxic C-benzylated dihydrochalcones from Uvaria acuminata. Chem Pharm Bull (Tokyo). 2004 Jan;52(1):138-41. doi: 10.1248/cpb.52.138. [PubMed:14709883 ]
Nakatani N, Ichimaru M, Moriyasu M, Kato A: Induction of apoptosis in human promyelocytic leukemia cell line HL-60 by C-benzylated dihydrochalcones, uvaretin, isouvaretin and diuvaretin. Biol Pharm Bull. 2005 Jan;28(1):83-6. doi: 10.1248/bpb.28.83. [PubMed:15635168 ]
Nkunya MH, Weenen H, Bray DH, Mgani QA, Mwasumbi LB: Antimalarial activity of Tanzanian plants and their active constituents: the genus Uvaria. Planta Med. 1991 Aug;57(4):341-3. doi: 10.1055/s-2006-960113. [PubMed:1775574 ]

Showing NP-Card for Diuvaretin (NP0055328)

MOL for NP0055328 (Diuvaretin)

3D MOL for NP0055328 (Diuvaretin)

3D SDF for NP0055328 (Diuvaretin)

3D-SDF for NP0055328 (Diuvaretin)

PDB for NP0055328 (Diuvaretin)

3D PDB for NP0055328 (Diuvaretin)

SMILES for NP0055328 (Diuvaretin)

INCHI for NP0055328 (Diuvaretin)

Structure for NP0055328 (Diuvaretin)

3D Structure for NP0055328 (Diuvaretin)