NP-MRD: Showing NP-Card for 5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one (NP0336764)

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Record Information

Version

2.0

Created at

2024-09-11 07:43:57 UTC

Updated at

2024-09-11 07:43:57 UTC

NP-MRD ID

NP0336764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one

Description

5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-B']dipyran-2-one belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. 5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-B']dipyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-B']dipyran-2-one has been detected, but not quantified in, fruits. This could make 5-hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-B']dipyran-2-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307362D          

 29 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8151   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 19  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  2  0  0  0  0
 24  4  1  0  0  0  0
 24  5  1  0  0  0  0
 24 11  1  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 21  1  0  0  0  0
 28 18  1  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
M  END


  Mrv0541 05061307362D          

 29 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8151   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 19  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  2  0  0  0  0
 24  4  1  0  0  0  0
 24  5  1  0  0  0  0
 24 11  1  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 21  1  0  0  0  0
 28 18  1  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(=O)OC2=C3C=CC(C)(C)OC3=C(C(=O)CC(C)C)C(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O5/c1-6-7-8-9-15-13-18(26)28-22-16-10-11-24(4,5)29-23(16)20(21(27)19(15)22)17(25)12-14(2)3/h10-11,13-14,27H,6-9,12H2,1-5H3

> <INCHI_KEY>
UIZLWUQKSKSCTK-UHFFFAOYSA-N

> <FORMULA>
C24H30O5

> <MOLECULAR_WEIGHT>
398.492

> <EXACT_MASS>
398.20932407

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.929380754662205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-pentyl-2H,8H-pyrano[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
6.097858087666666

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.768183249541142

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.478750763128737

> <JCHEM_PKA_STRONGEST_BASIC>
-4.963535725099872

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
114.78819999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-pentylpyrano[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.671  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.188  -1.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.198  -2.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.671  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.671   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672  -1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      14.671   2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   24                                                            
CONECT    5   24                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   15                                                       
CONECT   10   11   16                                                       
CONECT   11   10   24                                                       
CONECT   12   14   17                                                       
CONECT   13   15   18                                                       
CONECT   14    2    3   12                                                  
CONECT   15    9   13   19                                                  
CONECT   16   10   22   23                                                  
CONECT   17   12   20   25                                                  
CONECT   18   13   26   28                                                  
CONECT   19   15   21   22                                                  
CONECT   20   17   21   23                                                  
CONECT   21   19   20   27                                                  
CONECT   22   16   19   28                                                  
CONECT   23   16   20   29                                                  
CONECT   24    4    5   11   29                                             
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27   21                                                            
CONECT   28   18   22                                                       
CONECT   29   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₅

Average Mass

398.4920 Da

Monoisotopic Mass

398.20932 Da

IUPAC Name

5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-pentyl-2H,8H-pyrano[2,3-h]chromen-2-one

Traditional Name

5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-pentylpyrano[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(=O)OC2=C3C=CC(C)(C)OC3=C(C(=O)CC(C)C)C(O)=C12

InChI Identifier

InChI=1S/C24H30O5/c1-6-7-8-9-15-13-18(26)28-22-16-10-11-24(4,5)29-23(16)20(21(27)19(15)22)17(25)12-14(2)3/h10-11,13-14,27H,6-9,12H2,1-5H3

InChI Key

UIZLWUQKSKSCTK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Butyrophenone
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Ether
Oxacycle
Organoheterocyclic compound
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	5.47	ALOGPS
logP	6.1	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.79 m³·mol⁻¹	ChemAxon
Polarizability	44.93 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

HMDB0034142

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012417

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

131751529

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one (NP0336764)

MOL for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

3D MOL for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

3D SDF for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

3D-SDF for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

PDB for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

3D PDB for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

SMILES for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

INCHI for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

Structure for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)

3D Structure for NP0336764 (5-Hydroxy-8,8-dimethyl-6-(3-methyl-1-oxobutyl)-4-pentyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one)