NP-MRD: Showing NP-Card for Eucannabinolide (NP0048575)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:37 UTC

Updated at

2022-03-17 20:58:37 UTC

NP-MRD ID

NP0048575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eucannabinolide

Description

Eucannabinolide 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. Eucannabinolide is found in Picradeniopsis absinthifolia, Disynaphia multicrenulata, Eupatorium cannabinum , Eupatorium chinense, Eupatorium formosanum, Eupatorium glehni, Eupatorium glehnii, Eupatorium sachalinense, Schkuhria pinnata and Urolepis hecatantha. Eucannabinolide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218052D          

 30 31  0  0  0  0            999 V2000
   -2.4985    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309   -1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -0.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878    0.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    1.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -0.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6454   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -0.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2168    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454    0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 16  2  0  0  0  0
 15 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END


  Mrv0541 02241218052D          

 30 31  0  0  0  0            999 V2000
   -2.4985    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6309   -1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640   -0.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878    0.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    1.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -0.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6454   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -0.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2168    0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6454    0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  2  0  0  0  0
  3 18  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 16  2  0  0  0  0
 15 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C\C=C(C)\CC(OC(=O)C(\CO)=C\CO)C2C(OC(=O)C2=C)\C=C1/C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+

> <INCHI_KEY>
XYPJAWWDSQFSQA-VISQRNLASA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.4529

> <EXACT_MASS>
420.178417872

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
43.301736997691194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.3327141113333325

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.791836944593676

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.184372055196134

> <JCHEM_PKA_STRONGEST_BASIC>
-2.557857287039238

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
109.56329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.664   1.116   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.664  -0.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.331  -1.196   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.000  -0.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.000   1.116   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.331   1.884   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -1.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.664  -0.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.664   1.116   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   1.884   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.348  -2.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.178  -2.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.799  -1.460   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.911   0.027   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.000   1.884   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.307  -1.144   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.948  -4.196   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.331  -2.737   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.000  -1.196   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.336  -0.425   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.671  -1.196   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.336   1.116   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.333   1.116   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.669   1.884   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.333  -0.425   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.005   1.116   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.669   3.426   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.338   1.884   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.333   4.196   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.671   1.114   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   15                                                  
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   16                                                  
CONECT   14    5                                                            
CONECT   15    9   23                                                       
CONECT   16   13                                                            
CONECT   17   12                                                            
CONECT   18    3                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   24   25                                                  
CONECT   24   23   26   27                                                  
CONECT   25   23                                                            
CONECT   26   24   28                                                       
CONECT   27   24   29                                                       
CONECT   28   26   30                                                       
CONECT   29   27                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4529 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

Traditional Name

9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

CAS Registry Number

38458-58-1

SMILES

CC(=O)OC1C\C=C(C)\CC(OC(=O)C(\CO)=C\CO)C2C(OC(=O)C2=C)\C=C1/C

InChI Identifier

InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10+,16-7+

InChI Key

XYPJAWWDSQFSQA-VISQRNLASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bahia absinthifolia	LOTUS Database	35616633
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Disynaphia multicrenulata	LOTUS Database	35616633
Eupatorium cannabinum	Plant	KNApSAcK
Eupatorium chinense	LOTUS Database	35616633
Eupatorium formosanum	Plant	KNApSAcK
Eupatorium glehni	LOTUS Database	35616633
Eupatorium glehnii	Plant	KNApSAcK
Eupatorium sachalinense	Plant	KNApSAcK
Schkuhria pinnata	Plant	KNApSAcK
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
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Organic oxygen compound
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	1.59	ALOGPS
logP	1.33	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.18	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.56 m³·mol⁻¹	ChemAxon
Polarizability	43.3 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

FDB015620

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

54600668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Eucannabinolide (NP0048575)

MOL for NP0048575 (Eucannabinolide)

3D MOL for NP0048575 (Eucannabinolide)

3D SDF for NP0048575 (Eucannabinolide)

3D-SDF for NP0048575 (Eucannabinolide)

PDB for NP0048575 (Eucannabinolide)

3D PDB for NP0048575 (Eucannabinolide)

SMILES for NP0048575 (Eucannabinolide)

INCHI for NP0048575 (Eucannabinolide)

Structure for NP0048575 (Eucannabinolide)

3D Structure for NP0048575 (Eucannabinolide)