NP-MRD: Showing NP-Card for 4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate (NP0230675)

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Record Information

Version

2.0

Created at

2022-09-06 11:12:11 UTC

Updated at

2022-09-06 11:12:11 UTC

NP-MRD ID

NP0230675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate

Description

4,5-Dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-decahydronaphthalen-1-yl]oxy}oxan-3-yl acetate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate is found in Eunicea fusca. 4,5-Dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-decahydronaphthalen-1-yl]oxy}oxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241513522D          

 34 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241513522D          

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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  4  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 26 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230675

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(OC2OCC(O)C(O)C2OC(C)=O)C2CCC(CC12C)C(C)=CC=CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O7/c1-16(8-7-13-26(4,5)31)19-10-11-20-22(12-9-17(2)27(20,6)14-19)34-25-24(33-18(3)28)23(30)21(29)15-32-25/h7-8,13,17,19-25,29-31H,9-12,14-15H2,1-6H3

> <INCHI_KEY>
MRYOFKDORPTZIE-UHFFFAOYSA-N

> <FORMULA>
C27H44O7

> <MOLECULAR_WEIGHT>
480.642

> <EXACT_MASS>
480.308703757

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.70327540987356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-decahydronaphthalen-1-yl]oxy}oxan-3-yl acetate

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
3.2469799869999996

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.32590510142796

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.812766934272425

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5240163514572953

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
130.62099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1H-naphthalen-1-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.899  -9.034   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.439  -6.366   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23    2   19   25                                             
CONECT   25   24                                                            
CONECT   26   22   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-decahydronaphthalen-1-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₇H₄₄O₇

Average Mass

480.6420 Da

Monoisotopic Mass

480.30870 Da

IUPAC Name

4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-decahydronaphthalen-1-yl]oxy}oxan-3-yl acetate

Traditional Name

4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1H-naphthalen-1-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC1CCC(OC2OCC(O)C(O)C2OC(C)=O)C2CCC(CC12C)C(C)=CC=CC(C)(C)O

InChI Identifier

InChI=1S/C27H44O7/c1-16(8-7-13-26(4,5)31)19-10-11-20-22(12-9-17(2)27(20,6)14-19)34-25-24(33-18(3)28)23(30)21(29)15-32-25/h7-8,13,17,19-25,29-31H,9-12,14-15H2,1-6H3

InChI Key

MRYOFKDORPTZIE-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
Eunicea fusca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	4.38	ALOGPS
logP	3.25	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.62 m³·mol⁻¹	ChemAxon
Polarizability	54.7 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	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

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 4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate (NP0230675)

MOL for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

PDB for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

SMILES for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

INCHI for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

Structure for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0230675 (4,5-dihydroxy-2-{[6-(6-hydroxy-6-methylhepta-2,4-dien-2-yl)-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}oxan-3-yl acetate)