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Showing NP-Card for (2z)-2-(4-methylpent-3-en-1-ylidene)butanedial (NP0278322)

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Record Information
Version2.0
Created at2022-09-09 03:18:07 UTC
Updated at2022-09-09 03:18:07 UTC
NP-MRD IDNP0278322
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2z)-2-(4-methylpent-3-en-1-ylidene)butanedial
DescriptionBeta-Acaridial, also known as β-acaridial or alpha-acaridial, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. (2z)-2-(4-methylpent-3-en-1-ylidene)butanedial is found in Tyrophagus putrescentiae. (2z)-2-(4-methylpent-3-en-1-ylidene)butanedial was first documented in 2003 (PMID: 12951507). Based on a literature review a small amount of articles have been published on beta-Acaridial (PMID: 15112732) (PMID: 12728991).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)


  Mrv1652309092205182D          

 12 11  0  0  0  0            999 V2000
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)

     RDKit          3D

 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.8544   -1.3887    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524   -0.0028    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182    0.7674    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    0.5738    0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4382   -0.1513   -0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8396   -0.2129    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    0.3434   -0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135    1.1360   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011    1.3708   -2.3641 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525    0.1503    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183   -0.5358   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2471   -1.7353   -0.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1202   -2.0983    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764   -1.6885    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7854   -1.4726   -1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    1.7783    0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460    0.8616    2.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4632    0.2229    1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    1.6197    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075    0.2208   -1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164   -1.2425   -0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -0.7871    0.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    1.5580   -1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105   -0.4522    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    1.1210    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    0.0440   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
  7  8  1  0
  8  9  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
  8 23  1  0
M  END
Download

3D SDF for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)


  Mrv1652309092205182D          

 12 11  0  0  0  0            999 V2000
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC\C=C(\CC=O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-9(2)4-3-5-10(8-12)6-7-11/h4-5,7-8H,3,6H2,1-2H3/b10-5-

> <INCHI_KEY>
WFMDNHSSEXHQAN-YHYXMXQVSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.22842214520749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-(4-methylpent-3-en-1-ylidene)butanedial

> <JCHEM_LOGP>
1.3373727819999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.355022320751473

> <JCHEM_PKA_STRONGEST_BASIC>
-4.923914677557704

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
50.9392

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-(4-methylpent-3-en-1-ylidene)butanedial

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)

Download
PDB for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)
Download
SMILES for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)
CC(C)=CC\C=C(\CC=O)C=O
Download
INCHI for NP0278322 ((2z)-2-(4-methylpent-3-en-1-ylidene)butanedial)
InChI=1S/C10H14O2/c1-9(2)4-3-5-10(8-12)6-7-11/h4-5,7-8H,3,6H2,1-2H3/b10-5-
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View in JSmol
Synonyms
ValueSource
b-AcaridialGenerator
Β-acaridialGenerator
2(e)-(4-Methyl-3-pentenylidene)butanedialMeSH
alpha-AcaridialMeSH
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name(2Z)-2-(4-methylpent-3-en-1-ylidene)butanedial
Traditional Name(2Z)-2-(4-methylpent-3-en-1-ylidene)butanedial
CAS Registry NumberNot Available
SMILES
CC(C)=CC\C=C(\CC=O)C=O
InChI Identifier
InChI=1S/C10H14O2/c1-9(2)4-3-5-10(8-12)6-7-11/h4-5,7-8H,3,6H2,1-2H3/b10-5-
InChI KeyWFMDNHSSEXHQAN-YHYXMXQVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tyrophagus putrescentiaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAcyclic monoterpenoids  
Alternative Parents
Substituents
  • Acyclic monoterpenoid
    • 

  • Medium-chain aldehyde
    • 

  • Enal
    • 

  • Alpha-hydrogen aldehyde
    • 

  • Alpha,beta-unsaturated aldehyde
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP1.34ChemAxon
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.94 m³·mol⁻¹ChemAxon
Polarizability18.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID75125864  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87224935  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Suzuki T, Haga K, Tsutsumi T, Matsuyama S: Analysis of anal secretions from phlaeothripine thrips. J Chem Ecol. 2004 Feb;30(2):409-23. doi: 10.1023/b:joec.0000017985.89897.c3. [PubMed:15112732  ] 
  2. Shimizu N, Mori N, Kuwahara Y: Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae). Biosci Biotechnol Biochem. 2003 Aug;67(8):1732-6. doi: 10.1271/bbb.67.1732. [PubMed:12951507  ] 
  3. Shimizu N, Tarui H, Mori N, Nishida R, Kuwahara Y: (E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (alpha-acariolal) and (E)-2-(2-hydroxyethyl)-6-methyl-2,5-heptadienal (beta-acariolal), two new types of isomeric monoterpenes from Caloglyphus polyphyllae (Acari: Acaridae). Biosci Biotechnol Biochem. 2003 Feb;67(2):308-13. doi: 10.1271/bbb.67.308. [PubMed:12728991  ] 
  4. LOTUS database [Link]