NP-MRD: Showing NP-Card for (3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate (NP0177826)

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Record Information

Version

2.0

Created at

2022-09-03 15:43:17 UTC

Updated at

2022-09-03 15:43:17 UTC

NP-MRD ID

NP0177826

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(3AR,4R,9S,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl 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,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate is found in Ageratina ligustrina, Disynaphia multicrenulata, Eupatorium chinense, Eupatorium glehni, Schkuhria pinnata and Urolepis hecatantha. Based on a literature review very few articles have been published on (3aR,4R,9S,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032217432D          

 22 23  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
    6.4863    1.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776    2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0091    0.7940    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  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 16 15  1  4  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  1  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>
NP0177826

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC=C(C)C[C@@H](O)[C@@H]2[C@H](OC(=O)C2=C)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-9-5-6-14(21-12(4)18)10(2)8-15-16(13(19)7-9)11(3)17(20)22-15/h5,8,13-16,19H,3,6-7H2,1-2,4H3/t13-,14+,15-,16-/m1/s1

> <INCHI_KEY>
UYVDDCCDZKMLBM-QKPAOTATSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.820467109941845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.681319190000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.703899725209407

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9283142601934014

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
82.1841

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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      12.108   2.673   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.652   4.114   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.084   1.482   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.350  -5.030   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.917  -2.397   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   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   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,4R,9S,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-9-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC=C(C)C[C@@H](O)[C@@H]2[C@H](OC(=O)C2=C)C=C1C

InChI Identifier

InChI=1S/C17H22O5/c1-9-5-6-14(21-12(4)18)10(2)8-15-16(13(19)7-9)11(3)17(20)22-15/h5,8,13-16,19H,3,6-7H2,1-2,4H3/t13-,14+,15-,16-/m1/s1

InChI Key

UYVDDCCDZKMLBM-QKPAOTATSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina ligustrina	LOTUS Database	35616633
Disynaphia multicrenulata	LOTUS Database	35616633
Eupatorium chinense	LOTUS Database	35616633
Eupatorium glehni	LOTUS Database	35616633
Schkuhria pinnata	LOTUS Database	35616633
Urolepis hecatantha	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
Sesquiterpenoid
Germacrane sesquiterpenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.68	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	2	ChemAxon
Refractivity	82.18 m³·mol⁻¹	ChemAxon
Polarizability	31.82 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

163029818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate (NP0177826)

MOL for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

3D MOL for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

3D SDF for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

3D-SDF for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

PDB for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

3D PDB for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

SMILES for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

INCHI for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

Structure for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)

3D Structure for NP0177826 ((3ar,4r,9s,11ar)-4-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-9-yl acetate)