NP-MRD: Showing NP-Card for [(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate (NP0217682)

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Record Information

Version

2.0

Created at

2022-09-05 18:06:30 UTC

Updated at

2022-09-05 18:06:30 UTC

NP-MRD ID

NP0217682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

Description

[(3AR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate 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,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate is found in Centaurea paui. Based on a literature review very few articles have been published on [(3aR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220062D          

 22 23  0  0  1  0            999 V2000
    0.2172   -2.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -2.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908   -0.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -0.9274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7639   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -0.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8472    1.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545    2.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437    2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726    2.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331   -0.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -1.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -2.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273   -2.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -2.4240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2541   -3.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -1.7524    0.0000 C   0  0  1  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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22  2  1  1  0  0  0
  6 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217682

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-10-5-4-6-13(9-21-12(3)18)8-15-16(14(19)7-10)11(2)17(20)22-15/h5,8,14-16,19H,2,4,6-7,9H2,1,3H3/b10-5+,13-8+/t14-,15-,16+/m0/s1

> <INCHI_KEY>
PENVAWWEHIPEFZ-GQGLPCBOSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.45287104109201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3aR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate

> <JCHEM_LOGP>
1.6313591003333339

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.70390164204225

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9283134217707163

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
82.4433

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3aR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.405  -5.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.894  -3.734   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -2.480   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.540  -2.467   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.916  -1.242   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.377  -1.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.293  -0.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.761  -0.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.775   1.510   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.448   2.291   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.462   3.831   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.135   4.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.802   4.590   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.222  -0.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.116  -1.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.200  -3.011   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.186  -4.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.424  -5.467   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.718  -5.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.257  -4.525   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.341  -5.763   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.363  -3.271   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
[(3AR,4S,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-10-yl]methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

[(3aR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate

Traditional Name

[(3aR,4S,11aS)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H22O5/c1-10-5-4-6-13(9-21-12(3)18)8-15-16(14(19)7-10)11(2)17(20)22-15/h5,8,14-16,19H,2,4,6-7,9H2,1,3H3/b10-5+,13-8+/t14-,15-,16+/m0/s1

InChI Key

PENVAWWEHIPEFZ-GQGLPCBOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea paui	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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.63	ChemAxon
pKa (Strongest Acidic)	14.7	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.44 m³·mol⁻¹	ChemAxon
Polarizability	32.45 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

162949968

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate (NP0217682)

MOL for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

3D MOL for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

3D SDF for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

3D-SDF for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

PDB for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

3D PDB for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

SMILES for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

INCHI for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

Structure for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)

3D Structure for NP0217682 ([(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate)