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Showing NP-Card for (2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one (NP0188334)

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Record Information
Version2.0
Created at2022-09-04 04:39:02 UTC
Updated at2022-09-04 04:39:02 UTC
NP-MRD IDNP0188334
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one
DescriptionMaxima flavanone A belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. (2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one is found in Tephrosia maxima. Based on a literature review very few articles have been published on Maxima flavanone A.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)


  Mrv1652309042206392D          

 28 31  0  0  1  0            999 V2000
    0.3020   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
Download

3D MOL for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)

Download
3D SDF for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)

  Mrv1652309042206392D          

 28 31  0  0  1  0            999 V2000
    0.3020   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0188334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(O[C@@H](CC2=O)C2=CC=CC=C2)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O3/c1-16(2)10-11-18-14-20-21(26)15-22(17-8-6-5-7-9-17)27-24(20)19-12-13-25(3,4)28-23(18)19/h5-10,12-14,22H,11,15H2,1-4H3/t22-/m0/s1

> <INCHI_KEY>
LGHPWLOMYSXCFG-QFIPXVFZSA-N

> <FORMULA>
C25H26O3

> <MOLECULAR_WEIGHT>
374.48

> <EXACT_MASS>
374.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.70325498334208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-phenyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <JCHEM_LOGP>
5.724994416666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.513020821858081

> <JCHEM_PKA_STRONGEST_BASIC>
-4.643987668232717

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
113.98330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-phenyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)
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PDB for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.564  -5.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.494  -1.897   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   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   10                                                       
CONECT   18    9   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   19   27                                                       
CONECT   27   26    8   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

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3D PDB for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)
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SMILES for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)
CC(C)=CCC1=CC2=C(O[C@@H](CC2=O)C2=CC=CC=C2)C2=C1OC(C)(C)C=C2
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INCHI for NP0188334 ((2s)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-phenyl-2h,3h-pyrano[2,3-f]chromen-4-one)
InChI=1S/C25H26O3/c1-16(2)10-11-18-14-20-21(26)15-22(17-8-6-5-7-9-17)27-24(20)19-12-13-25(3,4)28-23(18)19/h5-10,12-14,22H,11,15H2,1-4H3/t22-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC25H26O3
Average Mass374.4800 Da
Monoisotopic Mass374.18819 Da
IUPAC Name(4S)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-phenyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one
Traditional Name(4S)-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-phenyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8,13-tetraen-6-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=CC2=C(O[C@@H](CC2=O)C2=CC=CC=C2)C2=C1OC(C)(C)C=C2
InChI Identifier
InChI=1S/C25H26O3/c1-16(2)10-11-18-14-20-21(26)15-22(17-8-6-5-7-9-17)27-24(20)19-12-13-25(3,4)28-23(18)19/h5-10,12-14,22H,11,15H2,1-4H3/t22-/m0/s1
InChI KeyLGHPWLOMYSXCFG-QFIPXVFZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tephrosia maximaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavans  
Direct Parent6-prenylated flavanones  
Alternative Parents
Substituents
  • 6-prenylated flavanone
    • 

  • Pyranoflavonoid
    • 

  • Flavanone
    • 

  • Pyranochromene
    • 

  • 2,2-dimethyl-1-benzopyran
    • 

  • Chromone
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Ketone
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.72ChemAxon
pKa (Strongest Acidic)14.51ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.98 m³·mol⁻¹ChemAxon
Polarizability42.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101673958  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]