NP-MRD: Showing NP-Card for 2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde (NP0146042)

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Record Information

Version

2.0

Created at

2022-09-02 01:21:54 UTC

Updated at

2022-09-02 01:21:55 UTC

NP-MRD ID

NP0146042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde

Description

Gamma-Bicyclohomofarnesal belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde is found in Alpinia calcarata and Hedychium spicatum. 2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde was first documented in 2019 (PMID: 30794339). Based on a literature review very few articles have been published on Gamma-Bicyclohomofarnesal.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.6381    2.0979   -1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9007    1.4749   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    2.2272    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    1.6916    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4569    0.1897    0.5909 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8969   -0.1622    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554   -1.1655    1.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078    1.0289    0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345   -0.6531   -0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501   -0.7024   -1.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0190   -0.0959   -1.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726   -0.5106   -0.3792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4498   -1.9898   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671   -0.0050   -0.2822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6395   -0.3408    0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -1.7421    1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4246   -2.5307    0.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6074    3.1836   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876    1.5979   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    3.3073    0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297    2.1493    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342    2.1088   -0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8781    2.1037    1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683   -0.0530    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607   -0.7652    2.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8783   -2.1671    1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -1.2029    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    1.3257    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7835    1.8259    0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.5908    0.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782   -1.6950   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2245   -0.0723   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1757   -1.7629   -2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7419   -0.2064   -2.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7042   -0.5584   -2.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075    0.9763   -1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762   -2.3978   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5148   -2.4495   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -2.3584    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -0.4269   -1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601    0.1633    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    0.1445    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -2.1731    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 14  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5 12  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  6
 15 41  1  0
 15 42  1  0
 16 43  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  1
M  END


  Mrv1652309022203212D          

 17 18  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
    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  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 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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0146042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H](CC=O)C(=C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O/c1-12-6-7-14-15(2,3)9-5-10-16(14,4)13(12)8-11-17/h11,13-14H,1,5-10H2,2-4H3/t13-,14?,16+/m0/s1

> <INCHI_KEY>
BFWKKBSHTOEBHL-XWDNMSNZSA-N

> <FORMULA>
C16H26O

> <MOLECULAR_WEIGHT>
234.383

> <EXACT_MASS>
234.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.36223895511572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]acetaldehyde

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
3.746077975666668

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.8570643585021

> <JCHEM_PKA_STRONGEST_BASIC>
-6.958197247776823

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
71.8175

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]acetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
g-Bicyclohomofarnesal	Generator
Γ-bicyclohomofarnesal	Generator

Chemical Formula

C₁₆H₂₆O

Average Mass

234.3830 Da

Monoisotopic Mass

234.19837 Da

IUPAC Name

2-[(1S,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]acetaldehyde

Traditional Name

2-[(1S,8aS)-5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]acetaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H](CC=O)C(=C)CCC12

InChI Identifier

InChI=1S/C16H26O/c1-12-6-7-14-15(2,3)9-5-10-16(14,4)13(12)8-11-17/h11,13-14H,1,5-10H2,2-4H3/t13-,14?,16+/m0/s1

InChI Key

BFWKKBSHTOEBHL-XWDNMSNZSA-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
Alpinia calcarata	LOTUS Database	35616633
Hedychium spicatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
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	4.62	ALOGPS
logP	3.75	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	17.86	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.82 m³·mol⁻¹	ChemAxon
Polarizability	28.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00046745

Chemspider ID

26352490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46937288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Doungchawee J, Kulsing C, Suekaew N, Na Pombejra S, Chavasiri W, Plabutong N, Thammahong A, Khotavivattana T: Volatile Chemical Composition, Antibacterial and Antifungal Activities of Extracts from Different Parts of Globba schomburgkii Hook.f. Chem Biodivers. 2019 May;16(5):e1900057. doi: 10.1002/cbdv.201900057. Epub 2019 Apr 4. [PubMed:30794339 ]
LOTUS database [Link]

Showing NP-Card for 2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde (NP0146042)

MOL for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

3D MOL for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

3D SDF for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

3D-SDF for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

PDB for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

3D PDB for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

SMILES for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

INCHI for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

Structure for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)

3D Structure for NP0146042 (2-[(1s,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]acetaldehyde)