NP-MRD: Showing NP-Card for 5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate (NP0208225)

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Record Information

Version

2.0

Created at

2022-09-05 05:08:38 UTC

Updated at

2022-09-05 05:08:38 UTC

NP-MRD ID

NP0208225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate

Description

5-Hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl acetate belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. 5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate is found in Lonchocarpus atropurpureus. Based on a literature review very few articles have been published on 5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207082D          

 33 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052207082D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0208225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C(OC(C)=O)C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O6/c1-15(2)11-12-19-24-18(13-14-27(4,5)33-24)21(29)20-22(30)26(31-16(3)28)23(32-25(19)20)17-9-7-6-8-10-17/h6-11,13-14,23,26,29H,12H2,1-5H3

> <INCHI_KEY>
ODHBZKZVTFSCIW-UHFFFAOYSA-N

> <FORMULA>
C27H28O6

> <MOLECULAR_WEIGHT>
448.515

> <EXACT_MASS>
448.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.565395819775134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-7-oxo-5-phenyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,8,11-tetraen-6-yl acetate

> <JCHEM_LOGP>
5.797396044666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.901450363209177

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.433682624000452

> <JCHEM_PKA_STRONGEST_BASIC>
-4.657334583204425

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
126.45390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-7-oxo-5-phenyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,8,11-tetraen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.861  -1.633   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.851  -3.347   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   12   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33                                                       
CONECT   33   32   11                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl acetic acid	Generator

Chemical Formula

C₂₇H₂₈O₆

Average Mass

448.5150 Da

Monoisotopic Mass

448.18859 Da

IUPAC Name

9-hydroxy-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-7-oxo-5-phenyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,8,11-tetraen-6-yl acetate

Traditional Name

9-hydroxy-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-7-oxo-5-phenyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,8,11-tetraen-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C(OC(C)=O)C(=O)C2=C(O)C2=C1OC(C)(C)C=C2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H28O6/c1-15(2)11-12-19-24-18(13-14-27(4,5)33-24)21(29)20-22(30)26(31-16(3)28)23(32-25(19)20)17-9-7-6-8-10-17/h6-11,13-14,23,26,29H,12H2,1-5H3

InChI Key

ODHBZKZVTFSCIW-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
Lonchocarpus atropurpureus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
Pyranoflavonoid
Hydroxyflavonoid
Flavanonol
Flavanone
5-hydroxyflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Alpha-acyloxy ketone
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.8	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.45 m³·mol⁻¹	ChemAxon
Polarizability	48.57 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	No	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

162820417

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate (NP0208225)

MOL for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

3D MOL for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

3D SDF for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

3D-SDF for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

PDB for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

3D PDB for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

SMILES for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

INCHI for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

Structure for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)

3D Structure for NP0208225 (5-hydroxy-8,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-oxo-2-phenyl-2h,3h-pyrano[3,2-g]chromen-3-yl acetate)