NP-MRD: Showing NP-Card for beta-Sinensal (NP0048283)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:00 UTC

Updated at

2022-03-17 20:54:00 UTC

NP-MRD ID

NP0048283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Sinensal

Description

Beta-Sinensal, also known as β-sinensal, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. beta-Sinensal is found in Ageratina conyzoides, Citrus chinensis, Citrus paradisi , Citrus reticulata , Citrus spp., Poncirus trifoliate x Citrus sinensis and var.Citrus spp.. Beta-Sinensal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920262D          

 18 17  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  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
    5.0013    2.8875    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
    3.5724    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
    2.1434    0.4125    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
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    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
    2.8579    0.0000    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
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 13  2  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 14  3  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 12  2  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCC(=C)C=C)=C(\C)CC\C([H])=C(\C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11-

> <INCHI_KEY>
NOPLRNXKHZRXHT-PVMFERMNSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.956760298189465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
4.229890758333334

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.173217367722673

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
72.9734

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   5.390   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   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       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       4.001   2.310   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       9.336   2.310   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    1   13                                                       
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    6   13                                                       
CONECT    9    6   14   17                                                  
CONECT   10    7   14                                                       
CONECT   11    7   15   18                                                  
CONECT   12   15   16                                                       
CONECT   13    2    5    8                                                  
CONECT   14    3    9   10                                                  
CONECT   15    4   11   12                                                  
CONECT   16   12                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
b-Sinensal	Generator
Β-sinensal	Generator
b-Sinensal?	HMDB
FEMA 3141	HMDB

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3346 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

(2Z,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

Traditional Name

(2Z,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal

CAS Registry Number

3779-62-2

SMILES

[H]\C(CCC(=C)C=C)=C(\C)CC\C([H])=C(\C)C=O

InChI Identifier

InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11-

InChI Key

NOPLRNXKHZRXHT-PVMFERMNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina conyzoides	Plant	KNApSAcK
Citrus chinensis	Plant	KNApSAcK
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus paradisi	Plant	KNApSAcK
Citrus reticulata	Plant	KNApSAcK
Citrus spp.	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Poncirus trifoliate x Citrus sinensis	Plant	KNApSAcK
var.Citrus spp.	-	KNApSAcK

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

Farsesane sesquiterpenoid
Sesquiterpenoid
Medium-chain aldehyde
Enal
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	4.81	ALOGPS
logP	4.23	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.2	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	8	ChemAxon
Refractivity	72.97 m³·mol⁻¹	ChemAxon
Polarizability	26.96 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

FDB014353

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

24976875

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for beta-Sinensal (NP0048283)

MOL for NP0048283 (beta-Sinensal)

3D MOL for NP0048283 (beta-Sinensal)

3D SDF for NP0048283 (beta-Sinensal)

3D-SDF for NP0048283 (beta-Sinensal)

PDB for NP0048283 (beta-Sinensal)

3D PDB for NP0048283 (beta-Sinensal)

SMILES for NP0048283 (beta-Sinensal)

INCHI for NP0048283 (beta-Sinensal)

Structure for NP0048283 (beta-Sinensal)

3D Structure for NP0048283 (beta-Sinensal)