NP-MRD: Showing NP-Card for (3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate (NP0221603)

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Record Information

Version

1.0

Created at

2022-09-05 23:13:46 UTC

Updated at

2022-09-05 23:13:46 UTC

NP-MRD ID

NP0221603

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate

Description

Ineupatorolide A 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. (3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate is found in Allagopappus dichotomus, Allagopappus viscosissimus, Carpesium glossophyllum and Carpesium nepalense. Based on a literature review very few articles have been published on Ineupatorolide A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201132D          

 26 27  0  0  1  0            999 V2000
   -1.4738   -0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8652   -2.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -1.2726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935   -0.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0305   -0.0664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0501    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785    0.7923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3634    1.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830    1.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220   -0.4280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0865   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587   -0.7387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980   -0.0325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8326   -0.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942   -2.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732   -1.0108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3259   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -0.9571    0.0000 C   0  0  0  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  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1652309062201132D          

 26 27  0  0  1  0            999 V2000
   -1.4738   -0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8652   -2.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -1.2726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935   -0.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0305   -0.0664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0501    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    1.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662    1.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785    0.7923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3634    1.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830    1.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220   -0.4280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0865   -1.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587   -0.7387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980   -0.0325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8326   -0.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7855   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942   -2.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732   -1.0108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3259   -0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -0.9571    0.0000 C   0  0  0  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  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221603

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O6/c1-6-11(2)18(22)26-17-16-14(13(4)19(23)25-16)10-15(21)12(3)8-7-9-20(17,5)24/h11-12,14,16-17,24H,4,6-10H2,1-3,5H3/t11-,12-,14+,16+,17-,20+/m1/s1

> <INCHI_KEY>
OVXUCZUDXTYPCU-DUGSKPGWSA-N

> <FORMULA>
C20H30O6

> <MOLECULAR_WEIGHT>
366.454

> <EXACT_MASS>
366.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.019152717273286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-dodecahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate

> <JCHEM_LOGP>
3.521134164666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.623385302702324

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.94663935035831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.259097834993092

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
94.83419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.751  -0.906   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.177  -1.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.517  -2.573   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.615  -3.746   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.010  -2.376   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.295  -0.862   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.057  -0.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.093   1.416   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.222   2.217   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.310   3.570   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.573   1.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.545   3.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.888   2.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.240   1.542   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.276   0.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.961  -0.799   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.895  -2.635   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.523  -1.379   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.610  -0.061   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.421  -1.679   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.200  -2.469   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.403  -4.146   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.043  -1.887   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.075  -0.641   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.617  -2.469   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.084  -1.787   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16    6   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₆

Average Mass

366.4540 Da

Monoisotopic Mass

366.20424 Da

IUPAC Name

(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-dodecahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate

Traditional Name

(3aS,6R,10S,11R,11aS)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O6/c1-6-11(2)18(22)26-17-16-14(13(4)19(23)25-16)10-15(21)12(3)8-7-9-20(17,5)24/h11-12,14,16-17,24H,4,6-10H2,1-3,5H3/t11-,12-,14+,16+,17-,20+/m1/s1

InChI Key

OVXUCZUDXTYPCU-DUGSKPGWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allagopappus dichotomus	LOTUS Database	35616633
Allagopappus viscosissimus	LOTUS Database	35616633
Carpesium glossophyllum	LOTUS Database	35616633
Carpesium nepalense	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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Oxolane
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
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	3.52	ChemAxon
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.83 m³·mol⁻¹	ChemAxon
Polarizability	39.02 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

C00012341

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

101688205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate (NP0221603)

MOL for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

3D MOL for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

3D SDF for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

3D-SDF for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

PDB for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

3D PDB for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

SMILES for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

INCHI for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

Structure for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)

3D Structure for NP0221603 ((3as,6r,10s,11r,11as)-10-hydroxy-6,10-dimethyl-3-methylidene-2,5-dioxo-octahydrocyclodeca[b]furan-11-yl (2r)-2-methylbutanoate)