NP-MRD: Showing NP-Card for macaflavanone g (NP0221069)

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Record Information

Version

2.0

Created at

2022-09-05 22:33:07 UTC

Updated at

2022-09-05 22:33:07 UTC

NP-MRD ID

NP0221069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macaflavanone g

Description

Macaflavanone G belongs to the class of organic compounds known as 2'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 2'-position. Macaflavanone G 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. macaflavanone g is found in Macaranga tanarius. macaflavanone g was first documented in 2008 (PMID: 18844422). Based on a literature review very few articles have been published on macaflavanone G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200332D          

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M  END

     RDKit          3D

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  Mrv1652309062200332D          

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 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 30  1  0  0  0  0
 13 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 11 35  1  0  0  0  0
 35 36  1  0  0  0  0
  7 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@]1(C)CCC2=C(C=CC(O)=C2O1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O6/c1-17(2)7-6-13-30(5)14-12-20-19(10-11-22(31)29(20)36-30)25-16-24(33)27-26(35-25)15-23(32)21(28(27)34)9-8-18(3)4/h7-8,10-11,15,25,31-32,34H,6,9,12-14,16H2,1-5H3/t25-,30+/m0/s1

> <INCHI_KEY>
YDKQMGVESZZFGP-SETSBSEESA-N

> <FORMULA>
C30H36O6

> <MOLECULAR_WEIGHT>
492.612

> <EXACT_MASS>
492.251188879

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.56644704677874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5-yl]-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
7.3252806533333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.245131120964059

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.679284838734664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6430371719446715

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
142.68899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5,7-dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-3,4-dihydro-1-benzopyran-5-yl]-6-(3-methylbut-2-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     -12.272   1.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.755   1.119   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.765   2.299   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.228  -0.328   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.712  -0.595   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.185  -2.043   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.195  -3.757   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   36                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   17   29                                                  
CONECT   29   28                                                            
CONECT   30   18   13                                                       
CONECT   31   12   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   11   36                                                  
CONECT   36   35    7                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2S)-5,7-Dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-5-yl]-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one	ChEBI

Chemical Formula

C₃₀H₃₆O₆

Average Mass

492.6120 Da

Monoisotopic Mass

492.25119 Da

IUPAC Name

(2S)-5,7-dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5-yl]-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-5,7-dihydroxy-2-[(2R)-8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-3,4-dihydro-1-benzopyran-5-yl]-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@]1(C)CCC2=C(C=CC(O)=C2O1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C(CC=C(C)C)=C2O

InChI Identifier

InChI=1S/C30H36O6/c1-17(2)7-6-13-30(5)14-12-20-19(10-11-22(31)29(20)36-30)25-16-24(33)27-26(35-25)15-23(32)21(28(27)34)9-8-18(3)4/h7-8,10-11,15,25,31-32,34H,6,9,12-14,16H2,1-5H3/t25-,30+/m0/s1

InChI Key

YDKQMGVESZZFGP-SETSBSEESA-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
Macaranga tanarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

2'-prenylated flavanones

Alternative Parents

Substituents

2'-prenylated flavanone
6-prenylated flavanone
Pyranoflavonoid
6-prenylated flavan
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavanone (CHEBI:66647 )

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	7.33	ChemAxon
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	142.69 m³·mol⁻¹	ChemAxon
Polarizability	56.57 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

C00039689

Chemspider ID

24636438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25155335

PDB ID

Not Available

ChEBI ID

66647

Good Scents ID

Not Available

References

General References

Kawakami S, Harinantenaina L, Matsunami K, Otsuka H, Shinzato T, Takeda Y: Macaflavanones A-G, prenylated flavanones from the leaves of Macaranga tanarius. J Nat Prod. 2008 Nov;71(11):1872-6. doi: 10.1021/np800380d. Epub 2008 Oct 10. [PubMed:18844422 ]
LOTUS database [Link]

Showing NP-Card for macaflavanone g (NP0221069)

MOL for NP0221069 (macaflavanone g)

3D MOL for NP0221069 (macaflavanone g)

3D SDF for NP0221069 (macaflavanone g)

3D-SDF for NP0221069 (macaflavanone g)

PDB for NP0221069 (macaflavanone g)

3D PDB for NP0221069 (macaflavanone g)

SMILES for NP0221069 (macaflavanone g)

INCHI for NP0221069 (macaflavanone g)

Structure for NP0221069 (macaflavanone g)

3D Structure for NP0221069 (macaflavanone g)