NP-MRD: Showing NP-Card for 3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate (NP0176924)

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Record Information

Version

2.0

Created at

2022-09-03 14:40:18 UTC

Updated at

2022-09-03 14:40:18 UTC

NP-MRD ID

NP0176924

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate

Description

Manoalide monoacetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate is found in Luffariella variabilis and Thorectandra excavatus. 3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate was first documented in 2007 (PMID: 17295541). Based on a literature review a small amount of articles have been published on Manoalide monoacetate (PMID: 17952508) (PMID: 20161977) (PMID: 19078858) (PMID: 17899268).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032216402D          

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  Mrv1652309032216402D          

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 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 11 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176924

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1OC(=O)C=C1C1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)C(O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+

> <INCHI_KEY>
IBDCHSSSHBQBDQ-CAOOACKPSA-N

> <FORMULA>
C27H38O6

> <MOLECULAR_WEIGHT>
458.595

> <EXACT_MASS>
458.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.65199600348241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-5-oxo-2,5-dihydrofuran-2-yl acetate

> <JCHEM_LOGP>
5.377757476333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.841402053530727

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7695762081970754

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1813791836745215

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
128.6341

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-5-oxo-2H-furan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.246 -14.765   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.770 -16.230   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.675 -17.476   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.770 -16.230   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.246 -14.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.711 -14.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.855 -15.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.320 -14.844   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.640 -13.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.104 -12.862   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.425 -11.355   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.889 -10.879   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.209  -9.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.065  -8.343   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.674  -8.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.818  -9.928   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.283  -9.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.428 -10.482   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.107 -11.989   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -15.892 -10.006   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -16.212  -8.500   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -15.068  -7.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -13.603  -7.945   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.077  -6.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -12.109  -7.573   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.495 -12.307   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.816 -10.801   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -3.031 -12.783   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   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   14   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   11                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Manoalide monoacetic acid	Generator

Chemical Formula

C₂₇H₃₈O₆

Average Mass

458.5950 Da

Monoisotopic Mass

458.26684 Da

IUPAC Name

3-{6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-5-oxo-2,5-dihydrofuran-2-yl acetate

Traditional Name

3-{6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-5-oxo-2H-furan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1OC(=O)C=C1C1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)C(O)O1

InChI Identifier

InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+

InChI Key

IBDCHSSSHBQBDQ-CAOOACKPSA-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
Luffariella variabilis	LOTUS Database	35616633
Thorectandra excavatus	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
Diterpenoid
Acylal
2-furanone
Dicarboxylic acid or derivatives
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.38	ChemAxon
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.63 m³·mol⁻¹	ChemAxon
Polarizability	52.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00039733

Chemspider ID

10208708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14059492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Skindersoe ME, Ettinger-Epstein P, Rasmussen TB, Bjarnsholt T, de Nys R, Givskov M: Quorum sensing antagonism from marine organisms. Mar Biotechnol (NY). 2008 Jan-Feb;10(1):56-63. doi: 10.1007/s10126-007-9036-y. Epub 2007 Oct 20. [PubMed:17952508 ]
Motti CA, Ettinger-Epstein P, Willis RH, Tapiolas DM: ESI FTICR-MS analysis of larvae from the marine sponge Luffariella variabilis. Mar Drugs. 2010 Jan 22;8(1):190-9. doi: 10.3390/md8010190. [PubMed:20161977 ]
Gauvin-Bialecki A, Aknin M, Smadja J: 24-O-ethylmanoalide, a manoalide-related sesterterpene from the marine sponge Luffariella cf. variabilis. Molecules. 2008 Dec 15;13(12):3184-91. doi: 10.3390/molecules13123184. [PubMed:19078858 ]
Ettinger-Epstein P, Tapiolas DM, Motti CA, Wright AD, Battershill CN, de Nys R: Production of manoalide and its analogues by the sponge Luffariella variabilis Is hardwired. Mar Biotechnol (NY). 2008 Jan-Feb;10(1):64-74. doi: 10.1007/s10126-007-9037-x. Epub 2007 Sep 25. [PubMed:17899268 ]
Ettinger-Epstein P, Motti CA, Nys Rd, Wright AD, Battershill CN, Tapiolas DM: Acetylated sesterterpenes from the Great Barrier Reef sponge Luffariella variabilis. J Nat Prod. 2007 Apr;70(4):648-51. doi: 10.1021/np060240d. Epub 2007 Feb 13. [PubMed:17295541 ]
LOTUS database [Link]

Showing NP-Card for 3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate (NP0176924)

MOL for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

3D MOL for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

3D SDF for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

3D-SDF for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

PDB for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

3D PDB for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

SMILES for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

INCHI for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

Structure for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)

3D Structure for NP0176924 (3-{6-hydroxy-5-[(3e)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl}-5-oxo-2h-furan-2-yl acetate)