NP-MRD: Showing NP-Card for 4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate (NP0312449)

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Record Information

Version

2.0

Created at

2022-09-11 09:14:43 UTC

Updated at

2022-09-11 09:14:44 UTC

NP-MRD ID

NP0312449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate

Description

4-[4-Hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl]phenyl acetate belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. 4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate is found in Deguelia spruceana. 4-[4-Hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl]phenyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171506202D          

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M  END

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M  END


  Mrv1533004171506202D          

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M  END
> <DATABASE_ID>
NP0312449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C2=C(C=CC(C)(C)O2)C2=C1C(O)=C(C(=O)O2)C1=CC=C(OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O7/c1-15(2)7-12-19-24-20(13-14-28(4,5)35-24)26-22(25(19)32-6)23(30)21(27(31)34-26)17-8-10-18(11-9-17)33-16(3)29/h7-11,13-14,30H,12H2,1-6H3

> <INCHI_KEY>
KKKBGQVXKVNICK-UHFFFAOYSA-N

> <FORMULA>
C28H28O7

> <MOLECULAR_WEIGHT>
476.525

> <EXACT_MASS>
476.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.207903597332916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl]phenyl acetate

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
4.776680621666666

> <ALOGPS_LOGS>
-5.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.328282990780558

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6099703190489425

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
134.12479999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate

> <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       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.826   0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.366   0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.136   2.104   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.676   2.104   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.366   3.437   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    3   18                                                  
CONECT   26   22   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35                                                       
CONECT   35   34   26                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
4-[4-Hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-F]chromen-3-yl]phenyl acetic acid	Generator

Chemical Formula

C₂₈H₂₈O₇

Average Mass

476.5250 Da

Monoisotopic Mass

476.18350 Da

IUPAC Name

4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxo-2H,8H-pyrano[2,3-f]chromen-3-yl]phenyl acetate

Traditional Name

4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C2=C(C=CC(C)(C)O2)C2=C1C(O)=C(C(=O)O2)C1=CC=C(OC(C)=O)C=C1

InChI Identifier

InChI=1S/C28H28O7/c1-15(2)7-12-19-24-20(13-14-28(4,5)35-24)26-22(25(19)32-6)23(30)21(27(31)34-26)17-8-10-18(11-9-17)33-16(3)29/h7-11,13-14,30H,12H2,1-6H3

InChI Key

KKKBGQVXKVNICK-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
Deguelia spruceana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Hydroxyisoflavonoid
Isoflav-3-enone skeleton
Angular pyranocoumarin
Pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Benzopyran
Phenol ester
1-benzopyran
Phenoxy compound
Anisole
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
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	4.71	ALOGPS
logP	4.78	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	6.33	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.12 m³·mol⁻¹	ChemAxon
Polarizability	51.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

118984490

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate (NP0312449)

MOL for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

3D MOL for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

3D SDF for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

3D-SDF for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

PDB for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

3D PDB for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

SMILES for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

INCHI for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

Structure for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)

3D Structure for NP0312449 (4-[4-hydroxy-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2-oxopyrano[2,3-f]chromen-3-yl]phenyl acetate)