NP-MRD: Showing NP-Card for (3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one (NP0174492)

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Record Information

Version

2.0

Created at

2022-09-03 11:45:24 UTC

Updated at

2022-09-03 11:45:24 UTC

NP-MRD ID

NP0174492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one

Description

(3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one is found in Hedychium spicatum. Based on a literature review very few articles have been published on (3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032213452D          

 24 26  0  0  1  0            999 V2000
    0.0000   -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  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
    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
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    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
    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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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  1  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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6119   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0174492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H](C\C=C3/C[C@H](O)OC3=O)C(=C)CC(=O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-12-10-15(21)17-19(2,3)8-5-9-20(17,4)14(12)7-6-13-11-16(22)24-18(13)23/h6,14,16-17,22H,1,5,7-11H2,2-4H3/b13-6+/t14-,16+,17-,20+/m0/s1

> <INCHI_KEY>
GQEHHMNYGFNQSN-IMWRMOLGSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.72831854801538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
3.5767240923333334

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.2179927500743

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.242496712641094

> <JCHEM_PKA_STRONGEST_BASIC>
-4.004911836031611

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
92.24039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one

> <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       0.000  -3.080   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.580  -7.835   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.009 -10.546   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.564  -9.300   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.377  -7.359   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-decahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one

Traditional Name

(3E,5R)-3-{2-[(1S,4aS,8aR)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H](C\C=C3/C[C@H](O)OC3=O)C(=C)CC(=O)[C@@H]12

InChI Identifier

InChI=1S/C20H28O4/c1-12-10-15(21)17-19(2,3)8-5-9-20(17,4)14(12)7-6-13-11-16(22)24-18(13)23/h6,14,16-17,22H,1,5,7-11H2,2-4H3/b13-6+/t14-,16+,17-,20+/m0/s1

InChI Key

GQEHHMNYGFNQSN-IMWRMOLGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hedychium spicatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	2.5	ALOGPS
logP	3.58	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.24 m³·mol⁻¹	ChemAxon
Polarizability	36.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162905060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one (NP0174492)

MOL for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

3D MOL for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

3D SDF for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

3D-SDF for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

PDB for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

3D PDB for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

SMILES for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

INCHI for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

Structure for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)

3D Structure for NP0174492 ((3e,5r)-3-{2-[(1s,4as,8ar)-5,5,8a-trimethyl-2-methylidene-4-oxo-hexahydronaphthalen-1-yl]ethylidene}-5-hydroxyoxolan-2-one)