NP-MRD: Showing NP-Card for (3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one (NP0331064)

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Record Information

Version

1.0

Created at

2022-09-12 17:02:33 UTC

Updated at

2022-09-12 17:02:34 UTC

NP-MRD ID

NP0331064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

Description

ZINC105223888 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. (3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one is found in Artemisia absinthium. Based on a literature review very few articles have been published on ZINC105223888.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122219022D          

 18 19  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6722    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18  2  1  6  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/C[C@H](O)\C(C)=C\[C@H]2OC(=O)C(=C)[C@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13+,14-/m1/s1

> <INCHI_KEY>
XQVSREKNQZKAKU-ZOAWPARFSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.710758317685347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,9S,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_LOGP>
2.585355579666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.55482788407284

> <JCHEM_PKA_STRONGEST_BASIC>
-2.993518283506539

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.4619

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,9S,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.379  -2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.588   2.424   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aR,9S,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

(3aR,9S,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C\C1=C/C[C@H](O)\C(C)=C\[C@H]2OC(=O)C(=C)[C@H]2CC1

InChI Identifier

InChI=1S/C15H20O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13+,14-/m1/s1

InChI Key

XQVSREKNQZKAKU-ZOAWPARFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia absinthium	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	2.59	ChemAxon
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	-3	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	71.46 m³·mol⁻¹	ChemAxon
Polarizability	26.71 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

124541845

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one (NP0331064)

MOL for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D MOL for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D SDF for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D-SDF for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

PDB for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D PDB for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

SMILES for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

INCHI for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

Structure for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D Structure for NP0331064 ((3ar,9s,11ar)-9-hydroxy-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)