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Showing NP-Card for (2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial (NP0243755)

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Record Information
Version1.0
Created at2022-09-07 04:22:36 UTC
Updated at2022-09-07 04:22:37 UTC
NP-MRD IDNP0243755
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial
Description(2E)-2-{2-[(1S,2S,4aS,8aR)-2-formyl-5,5,8a-trimethyl-decahydronaphthalen-1-yl]ethylidene}butanedial belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial is found in Zingiber mioga. It was first documented in 2022 (PMID: 36088123). Based on a literature review a significant number of articles have been published on (2E)-2-{2-[(1S,2S,4aS,8aR)-2-formyl-5,5,8a-trimethyl-decahydronaphthalen-1-yl]ethylidene}butanedial (PMID: 36088122) (PMID: 36088121) (PMID: 36088120) (PMID: 36088119) (PMID: 36088116) (PMID: 36088118).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)


  Mrv1652309072206222D          

 23 24  0  0  1  0            999 V2000
    0.8986   -2.2820    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
    1.9592   -2.2820    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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
  2 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
Download

3D MOL for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)

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3D SDF for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)

  Mrv1652309072206222D          

 23 24  0  0  1  0            999 V2000
    0.8986   -2.2820    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
    1.9592   -2.2820    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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
  2 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243755

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-19(2)10-4-11-20(3)17(7-5-15(13-22)9-12-21)16(14-23)6-8-18(19)20/h5,12-14,16-18H,4,6-11H2,1-3H3/b15-5+/t16-,17+,18+,20-/m1/s1

> <INCHI_KEY>
VOEKGBXENFNRQW-LHFGOLARSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.10281792118066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-{2-[(1S,2S,4aS,8aR)-2-formyl-5,5,8a-trimethyl-decahydronaphthalen-1-yl]ethylidene}butanedial

> <JCHEM_LOGP>
3.1190549080000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.463928414369715

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.40098457191478

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788757486576693

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
92.79929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-{2-[(1S,2S,4aS,8aR)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)
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PDB for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)
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       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   23                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    9   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

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3D PDB for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)
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SMILES for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)
CC1(C)CCC[C@]2(C)[C@@H](C\C=C(/CC=O)C=O)[C@H](CC[C@@H]12)C=O
Download
INCHI for NP0243755 ((2e)-2-{2-[(1s,2s,4as,8ar)-2-formyl-5,5,8a-trimethyl-octahydronaphthalen-1-yl]ethylidene}butanedial)
InChI=1S/C20H30O3/c1-19(2)10-4-11-20(3)17(7-5-15(13-22)9-12-21)16(14-23)6-8-18(19)20/h5,12-14,16-18H,4,6-11H2,1-3H3/b15-5+/t16-,17+,18+,20-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H30O3
Average Mass318.4570 Da
Monoisotopic Mass318.21949 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1(C)CCC[C@]2(C)[C@@H](C\C=C(/CC=O)C=O)[C@H](CC[C@@H]12)C=O
InChI Identifier
InChI=1S/C20H30O3/c1-19(2)10-4-11-20(3)17(7-5-15(13-22)9-12-21)16(14-23)6-8-18(19)20/h5,12-14,16-18H,4,6-11H2,1-3H3/b15-5+/t16-,17+,18+,20-/m1/s1
InChI KeyVOEKGBXENFNRQW-LHFGOLARSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Zingiber miogaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentDiterpenoids  
Alternative Parents
Substituents
  • Diterpenoid
    • 

  • Labdane diterpenoid
    • 

  • Enal
    • 

  • Alpha-hydrogen aldehyde
    • 

  • Alpha,beta-unsaturated aldehyde
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00057648  
Chemspider ID10032401  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11857930  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Xu X, Rothrock MJ Jr, Reeves J, Kumar GD, Mishra A: Using E. coli population to predict foodborne pathogens in pastured poultry farms. Food Microbiol. 2022 Dec;108:104092. doi: 10.1016/j.fm.2022.104092. Epub 2022 Jul 14. [PubMed:36088123  ] 
  2. Lanzl MI, Zwietering MH, Abee T, den Besten HMW: Combining enrichment with multiplex real-time PCR leads to faster detection and identification of Campylobacter spp. in food compared to ISO 10272-1:2017. Food Microbiol. 2022 Dec;108:104117. doi: 10.1016/j.fm.2022.104117. Epub 2022 Aug 19. [PubMed:36088122  ] 
  3. Cacciatore FA, Maders C, Alexandre B, Barreto Pinilla CM, Brandelli A, da Silva Malheiros P: Carvacrol encapsulation into nanoparticles produced from chia and flaxseed mucilage: Characterization, stability and antimicrobial activity against Salmonella and Listeria monocytogenes. Food Microbiol. 2022 Dec;108:104116. doi: 10.1016/j.fm.2022.104116. Epub 2022 Aug 18. [PubMed:36088121  ] 
  4. Liu X, Li Y, Micallef SA: Developmentally related and drought-induced shifts in the kale metabolome limited Salmonella enterica association, providing novel insights to enhance food safety. Food Microbiol. 2022 Dec;108:104113. doi: 10.1016/j.fm.2022.104113. Epub 2022 Aug 18. [PubMed:36088120  ] 
  5. Dos Santos AMP, Panzenhagen P, Ferrari RG, Conte-Junior CA: Large-scale genomic analysis reveals the pESI-like megaplasmid presence in Salmonella Agona, Muenchen, Schwarzengrund, and Senftenberg. Food Microbiol. 2022 Dec;108:104112. doi: 10.1016/j.fm.2022.104112. Epub 2022 Aug 12. [PubMed:36088119  ] 
  6. Centeno JA, Lorenzo JM, Carballo J: Effects of autochthonous Kluyveromyces lactis and commercial Enterococcus faecium adjunct cultures on the volatile profile and the sensory characteristics of short-ripened acid-curd Cebreiro cheese. Food Microbiol. 2022 Dec;108:104101. doi: 10.1016/j.fm.2022.104101. Epub 2022 Aug 1. [PubMed:36088116  ] 
  7. Chen J, Yang R, Wang Y, Koseki S, Fu L, Wang Y: Inhibitory effect of d-Tryptophan on the spoilage potential of Shewanella baltica and Pseudomonas fluorescens and its potential application in salmon fillet preservation. Food Microbiol. 2022 Dec;108:104104. doi: 10.1016/j.fm.2022.104104. Epub 2022 Aug 9. [PubMed:36088118  ] 
  8. Wicaksono WA, Buko A, Kusstatscher P, Sinkkonen A, Laitinen OH, Virtanen SM, Hyoty H, Cernava T, Berg G: Modulation of the food microbiome by apple fruit processing. Food Microbiol. 2022 Dec;108:104103. doi: 10.1016/j.fm.2022.104103. Epub 2022 Aug 4. [PubMed:36088117  ] 
  9. Jyung S, Kang JW, Kang DH: L. monocytogens exhibited less cell membrane damage, lipid peroxidation, and intracellular reactive oxygen species accumulation after plasma-activated water treatment compared to E. coli O157:H7 and S. Typhimurium. Food Microbiol. 2022 Dec;108:104098. doi: 10.1016/j.fm.2022.104098. Epub 2022 Jul 30. [PubMed:36088114  ] 
  10. Parafati L, Restuccia C, Cirvilleri G: Efficacy and mechanism of action of food isolated yeasts in the control of Aspergillus flavus growth on pistachio nuts. Food Microbiol. 2022 Dec;108:104100. doi: 10.1016/j.fm.2022.104100. Epub 2022 Aug 6. [PubMed:36088115  ] 
  11. LOTUS database [Link]