NP-MRD: Showing NP-Card for Euserotin (NP0050208)

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Record Information

Version

2.0

Created at

2022-04-27 20:48:09 UTC

Updated at

2022-04-27 20:48:09 UTC

NP-MRD ID

NP0050208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euserotin

Description

(3AR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid 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. Euserotin is found in Eupatorium serotinum. Based on a literature review very few articles have been published on (3aR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222482D          

 27 28  0  0  1  0            999 V2000
    3.1925   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4589   -0.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7958    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -1.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132    1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    3.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    4.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6761    4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    3.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832   -0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -1.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241   -3.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -2.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
  6 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  1  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END


  Mrv1652304272222482D          

 27 28  0  0  1  0            999 V2000
    3.1925   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4589   -0.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7958    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -1.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132    1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    3.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    4.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6761    4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    3.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832   -0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -1.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241   -3.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187   -2.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
  6 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  1  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(C)=C\C(=O)O[C@@H]1C\C(C)=C\CC\C(=C\[C@H]2OC(=O)C(=C)[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O6/c1-5-12(2)10-18(22)26-16-9-13(3)7-6-8-15(20(23)24)11-17-19(16)14(4)21(25)27-17/h7,10-11,16-17,19H,4-6,8-9H2,1-3H3,(H,23,24)/b12-10+,13-7+,15-11-/t16-,17-,19-/m1/s1

> <INCHI_KEY>
ILNNCSSDKBHGFO-NLWYCLMBSA-N

> <FORMULA>
C21H26O6

> <MOLECULAR_WEIGHT>
374.433

> <EXACT_MASS>
374.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.90104310670961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
4.168014127666666

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.270978235474846

> <JCHEM_PKA_STRONGEST_BASIC>
-6.543665194934022

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
101.58999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       5.959  -2.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.983  -3.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.464  -3.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.920  -1.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.400  -1.649   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.857  -0.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.832   0.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.352   0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.896  -0.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.416  -0.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.807  -2.245   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.289   2.424   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.265   3.615   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.784   3.366   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.721   5.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.697   6.247   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.153   7.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.129   8.879   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.216   5.998   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.682  -0.280   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.644   0.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.089  -1.765   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.529  -2.309   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.198  -2.611   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.488  -4.531   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.032  -5.971   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.968  -4.281   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5                                                       
CONECT   25    3   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4R,11ar)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-10-carboxylate	Generator

Chemical Formula

C₂₁H₂₆O₆

Average Mass

374.4330 Da

Monoisotopic Mass

374.17294 Da

IUPAC Name

(3aR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid

Traditional Name

(3aR,4R,11aR)-6-methyl-3-methylidene-4-{[(2E)-3-methylpent-2-enoyl]oxy}-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC\C(C)=C\C(=O)O[C@@H]1C\C(C)=C\CC\C(=C\[C@H]2OC(=O)C(=C)[C@H]12)C(O)=O

InChI Identifier

InChI=1S/C21H26O6/c1-5-12(2)10-18(22)26-16-9-13(3)7-6-8-15(20(23)24)11-17-19(16)14(4)21(25)27-17/h7,10-11,16-17,19H,4-6,8-9H2,1-3H3,(H,23,24)/b12-10+,13-7+,15-11-/t16-,17-,19-/m1/s1

InChI Key

ILNNCSSDKBHGFO-NLWYCLMBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eupatorium serotinum	Plant	KNApSAcK

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
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	3.29	ALOGPS
logP	4.17	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.59 m³·mol⁻¹	ChemAxon
Polarizability	38.9 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

162988047

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Euserotin (NP0050208)

MOL for NP0050208 (Euserotin)

3D MOL for NP0050208 (Euserotin)

3D SDF for NP0050208 (Euserotin)

3D-SDF for NP0050208 (Euserotin)

PDB for NP0050208 (Euserotin)

3D PDB for NP0050208 (Euserotin)

SMILES for NP0050208 (Euserotin)

INCHI for NP0050208 (Euserotin)

Structure for NP0050208 (Euserotin)

3D Structure for NP0050208 (Euserotin)