NP-MRD: Showing NP-Card for (5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one (NP0225786)

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Record Information

Version

2.0

Created at

2022-09-06 04:36:51 UTC

Updated at

2022-09-06 04:36:51 UTC

NP-MRD ID

NP0225786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one

Description

(5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as diterpene lactones. (5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one is found in Salvia palaestina. These are diterpenoids containing a lactone moiety (5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methyl-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514212D          

 31 33  0  0  0  0            999 V2000
    1.4521   -6.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -6.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6674   -6.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
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  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
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 16 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191514212D          

 31 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0225786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)O\C1=C\C(O)C(C)(O)CCC1C(C)(O)CCC2C(C)(C)C(O)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O6/c1-15-13-21(28)31-16(15)14-20(27)25(6,30)12-8-18-23(4)10-9-19(26)22(2,3)17(23)7-11-24(18,5)29/h13-14,17-20,26-27,29-30H,7-12H2,1-6H3/b16-14+

> <INCHI_KEY>
FFAXSQPCILRGAU-JQIJEIRASA-N

> <FORMULA>
C25H40O6

> <MOLECULAR_WEIGHT>
436.589

> <EXACT_MASS>
436.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.51093858885065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.3690859456666673

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.926451565533078

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.383740909073879

> <JCHEM_PKA_STRONGEST_BASIC>
-0.30951821313917083

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
120.77719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.711 -11.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.246 -11.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770 -13.150   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770 -13.150   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.675 -14.396   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.246 -11.685   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.206  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   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       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.183  -2.043   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   16   22   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₆

Average Mass

436.5890 Da

Monoisotopic Mass

436.28249 Da

IUPAC Name

(5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5E)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1H-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)O\C1=C\C(O)C(C)(O)CCC1C(C)(O)CCC2C(C)(C)C(O)CCC12C

InChI Identifier

InChI=1S/C25H40O6/c1-15-13-21(28)31-16(15)14-20(27)25(6,30)12-8-18-23(4)10-9-19(26)22(2,3)17(23)7-11-24(18,5)29/h13-14,17-20,26-27,29-30H,7-12H2,1-6H3/b16-14+

InChI Key

FFAXSQPCILRGAU-JQIJEIRASA-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
Salvia palaestina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Labdane diterpenoid
Diterpenoid
2-furanone
Cyclic alcohol
Dihydrofuran
Enol ester
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
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	2.83	ALOGPS
logP	2.37	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.78 m³·mol⁻¹	ChemAxon
Polarizability	49.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one (NP0225786)

MOL for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

3D MOL for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

3D SDF for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

3D-SDF for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

PDB for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

3D PDB for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

SMILES for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

INCHI for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

Structure for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)

3D Structure for NP0225786 ((5e)-5-[5-(2,6-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)-2,3-dihydroxy-3-methylpentylidene]-4-methylfuran-2-one)