NP-MRD: Showing NP-Card for (2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate (NP0209029)

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Record Information

Version

2.0

Created at

2022-09-05 06:16:39 UTC

Updated at

2022-09-05 06:16:39 UTC

NP-MRD ID

NP0209029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate

Description

Fuscoside E 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. (2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate is found in Eunicea fusca. (2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate was first documented in 2011 (PMID: 21865038). Based on a literature review very few articles have been published on Fuscoside E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208162D          

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  Mrv1652309052208162D          

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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
  8 27  1  0  0  0  0
 13 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0209029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@H]2CC[C@@H](C[C@]12C)C(\C)=C\CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O6/c1-16(2)8-7-9-17(3)20-11-12-21-23(13-10-18(4)27(21,6)14-20)33-26-25(32-19(5)28)24(30)22(29)15-31-26/h8-9,18,20-26,29-30H,7,10-15H2,1-6H3/b17-9+/t18-,20-,21+,22+,23-,24+,25-,26-,27+/m0/s1

> <INCHI_KEY>
IDBOOCJKJVAGAO-DESIZGQRSA-N

> <FORMULA>
C27H44O6

> <MOLECULAR_WEIGHT>
464.643

> <EXACT_MASS>
464.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.78350751876616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R)-2-{[(1S,4S,4aR,6S,8aS)-4,4a-dimethyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-decahydronaphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate

> <JCHEM_LOGP>
4.518529387333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.32590510142796

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.812766934272421

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5273027443159233

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
128.6723

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R)-2-{[(1S,4S,4aR,6S,8aS)-4,4a-dimethyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-octahydro-1H-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+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  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   27                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    8   13                                                  
CONECT   28    6   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    5   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₆

Average Mass

464.6430 Da

Monoisotopic Mass

464.31379 Da

IUPAC Name

(2S,3S,4R,5R)-2-{[(1S,4S,4aR,6S,8aS)-4,4a-dimethyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-decahydronaphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate

Traditional Name

(2S,3S,4R,5R)-2-{[(1S,4S,4aR,6S,8aS)-4,4a-dimethyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-octahydro-1H-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@H]2CC[C@@H](C[C@]12C)C(\C)=C\CC=C(C)C

InChI Identifier

InChI=1S/C27H44O6/c1-16(2)8-7-9-17(3)20-11-12-21-23(13-10-18(4)27(21,6)14-20)33-26-25(32-19(5)28)24(30)22(29)15-31-26/h8-9,18,20-26,29-30H,7,10-15H2,1-6H3/b17-9+/t18-,20-,21+,22+,23-,24+,25-,26-,27+/m0/s1

InChI Key

IDBOOCJKJVAGAO-DESIZGQRSA-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
1,2-diol
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
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	4.52	ChemAxon
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.67 m³·mol⁻¹	ChemAxon
Polarizability	53.78 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

26616693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53484199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Reina E, Puentes C, Rojas J, Garcia J, Ramos FA, Castellanos L, Aragon M, Ospina LF: Fuscoside E: a strong anti-inflammatory diterpene from Caribbean octocoral Eunicea fusca. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5888-91. doi: 10.1016/j.bmcl.2011.07.092. Epub 2011 Aug 4. [PubMed:21865038 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate (NP0209029)

MOL for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

3D MOL for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

3D SDF for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

3D-SDF for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

PDB for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

3D PDB for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

SMILES for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

INCHI for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

Structure for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)

3D Structure for NP0209029 ((2s,3s,4r,5r)-2-{[(1s,4s,4ar,6s,8as)-4,4a-dimethyl-6-[(2e)-6-methylhepta-2,5-dien-2-yl]-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate)