NP-MRD: Showing NP-Card for 6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one (NP0157908)

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Record Information

Version

2.0

Created at

2022-09-02 15:24:08 UTC

Updated at

2022-09-02 15:24:08 UTC

NP-MRD ID

NP0157908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one

Description

6-{1-[6-Hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-decahydro-1H-indeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. 6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one is found in Jaborosa magellanica. 6-{1-[6-Hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-decahydro-1H-indeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517092D          

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 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CC(C)=C(C)C(=O)O1)C1(O)CCC2C3CC(OC3CC(=O)C12C)C1=CC=CC(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O6/c1-14-11-22(34-26(31)15(14)2)17(4)28(32)10-9-20-19-12-23(18-7-6-8-21(29)16(18)3)33-24(19)13-25(30)27(20,28)5/h6-8,17,19-20,22-24,29,32H,9-13H2,1-5H3

> <INCHI_KEY>
NRUXYXNJOQUZGB-UHFFFAOYSA-N

> <FORMULA>
C28H36O6

> <MOLECULAR_WEIGHT>
468.59

> <EXACT_MASS>
468.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.325310469732926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-decahydro-1H-indeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
4.737579965

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.931123995517602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.751312255869603

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2662303713141467

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
128.01149999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one

> <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      -0.753  -3.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.017  -2.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.753  -0.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.293  -0.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.063   0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.293   1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.063   3.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.753   1.822   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.017   3.155   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.017   0.488   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.603   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.557  -2.179   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.396  -3.711   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.396  -0.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.803  -0.021   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.833  -1.166   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.373  -1.166   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.404  -0.021   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.811  -0.648   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.650  -2.179   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.143  -2.500   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.373  -3.833   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.833  -3.833   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.063  -5.167   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.063  -2.500   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.158  -3.745   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.144   0.122   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.144   1.662   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.478   2.432   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.812   1.662   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.812   0.122   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.145  -0.648   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.478  -0.648   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.478  -2.188   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3                                                       
CONECT   11    5                                                            
CONECT   12    2   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   12   16   26                                             
CONECT   26   25                                                            
CONECT   27   19   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   27   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₆

Average Mass

468.5900 Da

Monoisotopic Mass

468.25119 Da

IUPAC Name

6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-decahydro-1H-indeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CC(C1CC(C)=C(C)C(=O)O1)C1(O)CCC2C3CC(OC3CC(=O)C12C)C1=CC=CC(O)=C1C

InChI Identifier

InChI=1S/C28H36O6/c1-14-11-22(34-26(31)15(14)2)17(4)28(32)10-9-20-19-12-23(18-7-6-8-21(29)16(18)3)33-24(19)13-25(30)27(20,28)5/h6-8,17,19-20,22-24,29,32H,9-13H2,1-5H3

InChI Key

NRUXYXNJOQUZGB-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
Jaborosa magellanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Toluene
Monocyclic benzene moiety
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen 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	3.22	ALOGPS
logP	4.74	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	128.01 m³·mol⁻¹	ChemAxon
Polarizability	52.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

73824992

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one (NP0157908)

MOL for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

3D MOL for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

3D SDF for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

3D-SDF for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

PDB for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

3D PDB for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

SMILES for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

INCHI for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

Structure for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)

3D Structure for NP0157908 (6-{1-[6-hydroxy-2-(3-hydroxy-2-methylphenyl)-5a-methyl-5-oxo-octahydroindeno[5,4-b]furan-6-yl]ethyl}-3,4-dimethyl-5,6-dihydropyran-2-one)