NP-MRD: Showing NP-Card for (1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate (NP0247245)

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Record Information

Version

2.0

Created at

2022-09-07 09:01:35 UTC

Updated at

2022-09-07 09:01:35 UTC

NP-MRD ID

NP0247245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate

Description

(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-decahydronaphthalen-1-yl (2E)-3-methylpent-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. (1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate is found in Euryops algoensis. Based on a literature review very few articles have been published on (1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-decahydronaphthalen-1-yl (2E)-3-methylpent-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072211012D          

 26 28  0  0  1  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5303   -1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -2.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 24  1  6  0  0  0
 20 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END


  Mrv1652309072211012D          

 26 28  0  0  1  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5303   -1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -2.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 24  1  6  0  0  0
 20 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0247245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(C)=C\C(=O)O[C@@H]1[C@H](O)[C@H](C[C@]2(C)[C@@H](C)CC(=O)C[C@H]12)[C@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-6-12(2)7-17(23)26-19-15-9-14(22)8-13(3)20(15,4)10-16(18(19)24)21(5)11-25-21/h7,13,15-16,18-19,24H,6,8-11H2,1-5H3/b12-7+/t13-,15+,16-,18+,19-,20+,21-/m0/s1

> <INCHI_KEY>
WQPOYRBZCATNLX-LKERXJEMSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.85813292058978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-decahydronaphthalen-1-yl (2E)-3-methylpent-2-enoate

> <JCHEM_LOGP>
2.9781546143333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.24742580939334

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.825149904082917

> <JCHEM_PKA_STRONGEST_BASIC>
-3.312662754089212

> <JCHEM_POLAR_SURFACE_AREA>
76.13000000000001

> <JCHEM_REFRACTIVITY>
98.46990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2E)-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.990  -1.900   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.527  -4.527   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.990  -4.260   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   21                                                       
CONECT   25   20    9   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3S,4AR,5S,8as)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-decahydronaphthalen-1-yl (2E)-3-methylpent-2-enoic acid	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC\C(C)=C\C(=O)O[C@@H]1[C@H](O)[C@H](C[C@]2(C)[C@@H](C)CC(=O)C[C@H]12)[C@]1(C)CO1

InChI Identifier

InChI=1S/C21H32O5/c1-6-12(2)7-17(23)26-19-15-9-14(22)8-13(3)20(15,4)10-16(18(19)24)21(5)11-25-21/h7,13,15-16,18-19,24H,6,8-11H2,1-5H3/b12-7+/t13-,15+,16-,18+,19-,20+,21-/m0/s1

InChI Key

WQPOYRBZCATNLX-LKERXJEMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euryops algoensis	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
Fatty acid ester
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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

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

162842670

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate (NP0247245)

MOL for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

3D MOL for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

3D SDF for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

3D-SDF for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

PDB for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

3D PDB for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

SMILES for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

INCHI for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

Structure for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)

3D Structure for NP0247245 ((1s,2r,3s,4ar,5s,8as)-2-hydroxy-4a,5-dimethyl-3-[(2r)-2-methyloxiran-2-yl]-7-oxo-octahydronaphthalen-1-yl (2e)-3-methylpent-2-enoate)