NP-MRD: Showing NP-Card for 5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal (NP0253579)

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Record Information

Version

2.0

Created at

2022-09-07 17:29:18 UTC

Updated at

2022-09-07 17:29:18 UTC

NP-MRD ID

NP0253579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal

Description

5-{4-Hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]Heptan-1-yl}-3-methylpenta-2,4-dienal belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal is found in Euphorbia bivonae and Pueraria montana. 5-{4-Hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]Heptan-1-yl}-3-methylpenta-2,4-dienal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161519472D          

 18 19  0  0  0  0            999 V2000
   -0.7612   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4112   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035   -1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  6  2  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=CC12OC1(C)CC(O)CC2(C)C)=CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-11(6-8-16)5-7-15-13(2,3)9-12(17)10-14(15,4)18-15/h5-8,12,17H,9-10H2,1-4H3

> <INCHI_KEY>
ZTALKMXOHWQNIA-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.20136595449737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.6246488456666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.13968403410598

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7377022034820433

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
72.30380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.421  -5.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.191  -4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.731  -4.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.501  -5.541   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.041  -5.541   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.421  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.119  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.119   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.890   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.946  -3.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.500  -3.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8   10                                                       
CONECT   10    9    8   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal

Traditional Name

5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal

CAS Registry Number

Not Available

SMILES

CC(C=CC12OC1(C)CC(O)CC2(C)C)=CC=O

InChI Identifier

InChI=1S/C15H22O3/c1-11(6-8-16)5-7-15-13(2,3)9-12(17)10-14(15,4)18-15/h5-8,12,17H,9-10H2,1-4H3

InChI Key

ZTALKMXOHWQNIA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia bivonae	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633

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

Cyclofarsesane sesquiterpenoid
Sesquiterpenoid
Oxepane
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-7279 )

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	2.56	ALOGPS
logP	1.62	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.3 m³·mol⁻¹	ChemAxon
Polarizability	28.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal (NP0253579)

MOL for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

3D MOL for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

3D SDF for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

3D-SDF for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

PDB for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

3D PDB for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

SMILES for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

INCHI for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

Structure for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)

3D Structure for NP0253579 (5-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-methylpenta-2,4-dienal)