NP-MRD: Showing NP-Card for Desacetyllaurenobiolide (NP0048591)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:54 UTC

Updated at

2022-03-17 20:58:54 UTC

NP-MRD ID

NP0048591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Desacetyllaurenobiolide

Description

Desacetyllaurenobiolide, also known as chamissellin, belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Desacetyllaurenobiolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Desacetyllaurenobiolide is found, on average, in the highest concentration within sweet bay. Desacetyllaurenobiolide has also been detected, but not quantified in, herbs and spices. Desacetyllaurenobiolide is found in Artemisia spp. , Cassinia subtropica, Cotula cinerea, Leucanthemopsis pulverulenta, Plagius grandis, Tanacetum argenteum, Tanacetum aureum, Tanacetum densum and Tanacetum polycephalum. This could make desacetyllaurenobiolide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309192D          

 18 19  0  0  0  0            999 V2000
    5.8628    3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    3.2398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-

> <INCHI_KEY>
FRDLPOYYWWRSPZ-ZVEIMFCASA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.78192610689755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.4710048466666663

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18268648207417

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.624850725106088

> <JCHEM_PKA_STRONGEST_BASIC>
-3.058393678865861

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.5171

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6,10-dimethyl-3-methylidene-3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.944   6.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.574  -1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.264   5.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.944   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.944   3.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.039   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.574   5.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.109   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.039   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.574   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.740   4.032   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.109   4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.204   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.204   3.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.835   2.786   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.204   6.048   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.295   2.786   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.740   1.540   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   10                                                       
CONECT    7    9   12                                                       
CONECT    8   10   13                                                       
CONECT    9    1    5    7                                                  
CONECT   10    2    6    8                                                  
CONECT   11    3   14   15                                                  
CONECT   12    7   14   16                                                  
CONECT   13    8   14   18                                                  
CONECT   14   11   12   13                                                  
CONECT   15   11   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Chamissellin	HMDB
Deacetyllaurenobiolide	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3175 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

4-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

Traditional Name

4-hydroxy-6,10-dimethyl-3-methylidene-3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

35001-24-2

SMILES

C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-

InChI Key

FRDLPOYYWWRSPZ-ZVEIMFCASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia spp.	Plant	KNApSAcK
Cassinia subtropica	LOTUS Database	35616633
Cotula cinerea	LOTUS Database	35616633
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Leucanthemopsis pulverulenta	LOTUS Database	35616633
Plagius grandis	LOTUS Database	35616633
Tanacetum argenteum	LOTUS Database	35616633
Tanacetum aureum	LOTUS Database	35616633
Tanacetum densum	LOTUS Database	35616633
Tanacetum polycephalum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.45	ALOGPS
logP	2.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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

HMDB0036770

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015712

KNApSAcK ID

C00012386

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

131752050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Desacetyllaurenobiolide (NP0048591)

MOL for NP0048591 (Desacetyllaurenobiolide)

3D MOL for NP0048591 (Desacetyllaurenobiolide)

3D SDF for NP0048591 (Desacetyllaurenobiolide)

3D-SDF for NP0048591 (Desacetyllaurenobiolide)

PDB for NP0048591 (Desacetyllaurenobiolide)

3D PDB for NP0048591 (Desacetyllaurenobiolide)

SMILES for NP0048591 (Desacetyllaurenobiolide)

INCHI for NP0048591 (Desacetyllaurenobiolide)

Structure for NP0048591 (Desacetyllaurenobiolide)

3D Structure for NP0048591 (Desacetyllaurenobiolide)