NP-MRD: Showing NP-Card for {6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate (NP0318577)

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Record Information

Version

2.0

Created at

2022-09-11 19:09:32 UTC

Updated at

2022-09-11 19:09:32 UTC

NP-MRD ID

NP0318577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

Description

{6-[(6-Hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Based on a literature review very few articles have been published on {6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221092D          

 34 37  0  0  0  0            999 V2000
   -0.5230    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517    7.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    7.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    7.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2375    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112221092D          

 34 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0318577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(O)C(=O)OCC1=CC(=O)C2(CC3C(=C)CCC4C(C)(C)C(O)CCC34C)OC2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O8/c1-13-6-7-17-24(3,4)18(28)8-9-25(17,5)16(13)11-26-19(29)10-15(21(31)22(26)34-26)12-33-23(32)20(30)14(2)27/h10,14,16-18,20,22,27-28,30H,1,6-9,11-12H2,2-5H3

> <INCHI_KEY>
WTPCVDMJSKOJKE-UHFFFAOYSA-N

> <FORMULA>
C26H36O8

> <MOLECULAR_WEIGHT>
476.566

> <EXACT_MASS>
476.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.48192535649095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

> <JCHEM_LOGP>
2.2269991329999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.107453109450354

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.757965685639146

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349956408718809

> <JCHEM_POLAR_SURFACE_AREA>
133.66

> <JCHEM_REFRACTIVITY>
122.79209999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.976   7.851   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   9.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.976  10.518   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  11.852   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  11.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  13.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.657  13.712   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.371  14.702   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  13.186   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.414  14.519   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.414  11.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.644  10.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  10.518   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   9.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   9.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104   7.851   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.644   7.851   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.644   9.391   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.977   8.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.311   7.851   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.645   8.621   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.311   6.311   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.645   5.541   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.978   6.311   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.312   5.541   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.312   4.001   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.646   6.311   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.646   7.851   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.979   5.541   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.313   6.311   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.979   4.001   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.977   5.541   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.644   6.311   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.310   5.541   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   33                                             
CONECT   18   17   19                                                       
CONECT   19   18   17   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22   33                                                       
CONECT   33   32   17   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoic acid	Generator

Chemical Formula

C₂₆H₃₆O₈

Average Mass

476.5660 Da

Monoisotopic Mass

476.24102 Da

IUPAC Name

{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

Traditional Name

{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

CAS Registry Number

Not Available

SMILES

CC(O)C(O)C(=O)OCC1=CC(=O)C2(CC3C(=C)CCC4C(C)(C)C(O)CCC34C)OC2C1=O

InChI Identifier

InChI=1S/C26H36O8/c1-13-6-7-17-24(3,4)18(28)8-9-25(17,5)16(13)11-26-19(29)10-15(21(31)22(26)34-26)12-33-23(32)20(30)14(2)27/h10,14,16-18,20,22,27-28,30H,1,6-9,11-12H2,2-5H3

InChI Key

WTPCVDMJSKOJKE-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Cyclohexenone
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Monosaccharide
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.23	ChemAxon
pKa (Strongest Acidic)	11.76	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.79 m³·mol⁻¹	ChemAxon
Polarizability	50.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

78443912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate (NP0318577)

MOL for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

3D MOL for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

3D SDF for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

3D-SDF for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

PDB for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

3D PDB for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

SMILES for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

INCHI for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

Structure for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)

3D Structure for NP0318577 ({6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate)