NP-MRD: Showing NP-Card for 8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one (NP0150019)

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Record Information

Version

2.0

Created at

2022-09-02 06:00:26 UTC

Updated at

2022-09-02 06:00:26 UTC

NP-MRD ID

NP0150019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one

Description

8-(3,7-Dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. 8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one is found in Mesua ferrea. 8-(3,7-Dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519462D          

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  Mrv1533004231519462D          

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M  END
> <DATABASE_ID>
NP0150019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)CCC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O5/c1-18(2)10-9-11-20(5)14-15-22-28(33)27(24(31)16-19(3)4)29(34)26-23(17-25(32)35-30(22)26)21-12-7-6-8-13-21/h6-8,10,12-14,17,19,33-34H,9,11,15-16H2,1-5H3

> <INCHI_KEY>
VRRSSMIKCUVMEF-UHFFFAOYSA-N

> <FORMULA>
C30H34O5

> <MOLECULAR_WEIGHT>
474.597

> <EXACT_MASS>
474.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.939249903983594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
8.287479951

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.137236542583455

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.964745408971689

> <JCHEM_PKA_STRONGEST_BASIC>
-6.203973606119161

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
151.28779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -4.620   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   34                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   10   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   26   21   34                                                  
CONECT   34   33    7   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₅

Average Mass

474.5970 Da

Monoisotopic Mass

474.24062 Da

IUPAC Name

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one

Traditional Name

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)CCC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

InChI Identifier

InChI=1S/C30H34O5/c1-18(2)10-9-11-20(5)14-15-22-28(33)27(24(31)16-19(3)4)29(34)26-23(17-25(32)35-30(22)26)21-12-7-6-8-13-21/h6-8,10,12-14,17,19,33-34H,9,11,15-16H2,1-5H3

InChI Key

VRRSSMIKCUVMEF-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, 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
Mesua ferrea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
4-phenylcoumarin
Terpene lactone
7-hydroxycoumarin
Hydroxycoumarin
Butyrophenone
Coumarin
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	6.05	ALOGPS
logP	8.29	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	151.29 m³·mol⁻¹	ChemAxon
Polarizability	52.94 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

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

73803900

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one (NP0150019)

MOL for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

3D MOL for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

3D SDF for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

3D-SDF for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

PDB for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

3D PDB for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

SMILES for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

INCHI for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

Structure for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)

3D Structure for NP0150019 (8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one)