NP-MRD: Showing NP-Card for (1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate (NP0213498)

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Record Information

Version

2.0

Created at

2022-09-05 12:30:29 UTC

Updated at

2022-09-05 12:30:29 UTC

NP-MRD ID

NP0213498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate

Description

(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate 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. Based on a literature review very few articles have been published on (1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052214302D          

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 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 11 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  6  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0213498

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-7-9-10-11-23(28)32-19(8-2)12-15-24(29)33-22-14-13-21-26(31)25(30)20(17(3)4)16-27(21,6)18(22)5/h10-12,15,18-22,25-26,30-31H,3,7-9,13-14,16H2,1-2,4-6H3/b11-10-,15-12-/t18-,19-,20-,21-,22+,25+,26-,27+/m0/s1

> <INCHI_KEY>
XTHWIOVPLRZOBP-SGEFWGAZSA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.78937541904605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate

> <JCHEM_LOGP>
5.492646485666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.033098621143239

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.606948707909083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2676533421455183

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
129.9368

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1H-naphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate

> <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      -4.001  17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.000  15.400   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  16.170   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.334  17.710   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   28                                             
CONECT    7    6                                                            
CONECT    8    6    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   11    6   29                                                  
CONECT   29   28                                                            
CONECT   30    8   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4AR,5S,6R,7S,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoic acid	Generator

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate

Traditional Name

(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1H-naphthalen-2-yl (2Z,4S)-4-[(2Z)-hex-2-enoyloxy]hex-2-enoate

CAS Registry Number

Not Available

SMILES

CCC\C=C/C(=O)O[C@@H](CC)\C=C/C(=O)O[C@@H]1CC[C@H]2[C@H](O)[C@H](O)[C@@H](C[C@]2(C)[C@H]1C)C(C)=C

InChI Identifier

InChI=1S/C27H42O6/c1-7-9-10-11-23(28)32-19(8-2)12-15-24(29)33-22-14-13-21-26(31)25(30)20(17(3)4)16-27(21,6)18(22)5/h10-12,15,18-22,25-26,30-31H,3,7-9,13-14,16H2,1-2,4-6H3/b11-10-,15-12-/t18-,19-,20-,21-,22+,25+,26-,27+/m0/s1

InChI Key

XTHWIOVPLRZOBP-SGEFWGAZSA-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 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
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.49	ChemAxon
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	129.94 m³·mol⁻¹	ChemAxon
Polarizability	52.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

162998006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate (NP0213498)

MOL for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

3D MOL for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

3D SDF for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

3D-SDF for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

PDB for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

3D PDB for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

SMILES for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

INCHI for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

Structure for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)

3D Structure for NP0213498 ((1r,2r,4ar,5s,6r,7s,8ar)-5,6-dihydroxy-1,8a-dimethyl-7-(prop-1-en-2-yl)-octahydro-1h-naphthalen-2-yl (2z,4s)-4-[(2z)-hex-2-enoyloxy]hex-2-enoate)