NP-MRD: Showing NP-Card for (2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial (NP0330067)

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Record Information

Version

1.0

Created at

2022-09-12 15:04:42 UTC

Updated at

2022-09-12 15:04:42 UTC

NP-MRD ID

NP0330067

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial

Description

Oxytoxin 2 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. It was first documented in 2004 (PMID: 15505724). Based on a literature review a significant number of articles have been published on Oxytoxin 2 (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 30508332).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 34  0  0  0  0  0  0  0  0999 V2000
    4.4162    1.2228   -0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7621   -0.1206    0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1386   -0.3644    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -1.0513    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4863   -0.8133   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.6258   -0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155   -0.3784   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357    0.8845   -1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8694   -1.3417   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2865   -1.1638   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313   -1.3106   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -0.4175    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7399   -0.7162    1.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -1.8228    2.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086    0.9088   -0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7313    1.9638    0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712    3.1484    0.5439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889    2.0383    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6920    1.2304   -1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124    1.4082   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391    0.1743    1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9195    0.0271    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2622   -1.4697    0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531   -2.0352    0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586    0.6461   -2.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    1.3643   -0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    1.6037   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -2.2810   -0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2190   -1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4700   -1.9535   -1.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005   -2.2748    0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4155    0.0108    2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319    0.9890   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5781    1.0790   -1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4090    1.6602    1.7760 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  3  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 12 13  1  0
 13 14  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 13 32  1  0
M  END


  Mrv1652309122217042D          

 17 16  0  0  0  0            999 V2000
    6.1875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    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  3  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  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
M  END
> <DATABASE_ID>
NP0330067

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-13(2)6-4-7-14(3)8-5-9-15(12-17)10-11-16/h6,8-9,11-12H,5,10H2,1-3H3/b14-8+,15-9+

> <INCHI_KEY>
QRFWLZGUPBROQW-VOMDNODZSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.138606261155893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-[(3E)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial

> <JCHEM_LOGP>
2.5817937216666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.354601289790473

> <JCHEM_PKA_STRONGEST_BASIC>
-4.931004628981079

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
74.1032

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-[(3E)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      11.550  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.010  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.240  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.700  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   17  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    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(2E)-2-[(3E)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial

Traditional Name

(2E)-2-[(3E)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial

CAS Registry Number

Not Available

SMILES

CC(C)=CC#C\C(C)=C\C\C=C(/CC=O)C=O

InChI Identifier

InChI=1S/C15H18O2/c1-13(2)6-4-7-14(3)8-5-9-15(12-17)10-11-16/h6,8-9,11-12H,5,10H2,1-3H3/b14-8+,15-9+

InChI Key

QRFWLZGUPBROQW-VOMDNODZSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
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 Framework

Aliphatic acyclic 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	2.58	ChemAxon
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	0	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

Not Available

Chemspider ID

10472043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23426277

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Chen WF, Chang YC, Chiu YW, Fang LS, Chen YH, Su YD, Peng BR, Lu MC, Chen JJ, Wen ZH, Wu YC, Sung PJ: Oxytoxin-2, An Algal-Derived Molecule from a Cultured Mollusc Volvatella vigourouxi. Nat Prod Commun. 2016 Dec;11(12):1783-1784. [PubMed:30508332 ]
Cutignano A, Notti V, d'Ippolito G, Coll AD, Cimino G, Fontana A: Lipase-mediated production of defensive toxins in the marine mollusc Oxynoe olivacea. Org Biomol Chem. 2004 Nov 7;2(21):3167-71. doi: 10.1039/B410454D. Epub 2004 Oct 7. [PubMed:15505724 ]
LOTUS database [Link]

Showing NP-Card for (2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial (NP0330067)

MOL for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

3D MOL for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

3D SDF for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

3D-SDF for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

PDB for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

3D PDB for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

SMILES for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

INCHI for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

Structure for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)

3D Structure for NP0330067 ((2e)-2-[(3e)-4,8-dimethylnona-3,7-dien-5-yn-1-ylidene]butanedial)