NP-MRD: Showing NP-Card for epoxycoraxeniolide A (NP0332898)

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Record Information

Version

2.0

Created at

2024-05-01 22:07:28 UTC

Updated at

2026-01-03 22:35:06 UTC

NP-MRD ID

NP0332898

Natural Product DOI

https://doi.org/10.57994/2178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epoxycoraxeniolide A

Description

Epoxycoraxeniolide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on epoxycoraxeniolide A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142300442D          

 25 27  0  0  1  0            999 V2000
    0.8170    0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.5814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8564   -0.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -0.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2990   -0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5740   -1.0296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446   -0.1222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8226    0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550    0.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330    1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    2.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197    1.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    2.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7122   -0.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8343   -1.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887   -1.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210   -1.4518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0666   -0.9382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3578    0.0891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0464   -1.3898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4284   -0.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401   -2.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077   -2.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5037   -2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  0  0  0
  2 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12COC(=O)[C@@H](C\C=C\C(C)C)[C@@]1([H])CC[C@]1(C)O[C@H]1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-13(2)6-5-7-16-15-10-11-20(4)18(23-20)9-8-14(3)17(15)12-22-19(16)21/h5-6,13,15-18H,3,7-12H2,1-2,4H3/b6-5+/t15-,16+,17+,18+,20+/m1/s1

> <INCHI_KEY>
OQCCTFCKIHZESM-DUUHCLTNSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.62240872389611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6S,10R,14S)-4-methyl-9-methylidene-14-[(2E)-4-methylpent-2-en-1-yl]-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

> <JCHEM_LOGP>
4.171619085666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223842158818267

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
92.261

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S,10R,14S)-4-methyl-9-methylidene-14-[(2E)-4-methylpent-2-en-1-yl]-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  C   UNK     0       1.525   0.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.260  -1.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.465  -0.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.005  -0.167   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.158  -1.187   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       4.805  -1.922   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       7.363  -0.228   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.136   1.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.703   1.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.475   3.382   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.042   3.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.837   2.988   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.814   5.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.796  -0.792   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.024  -2.315   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.819  -3.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.386  -2.710   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       7.591  -1.751   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0      10.001   0.166   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.953  -2.594   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.800  -1.574   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.688  -3.948   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.121  -4.512   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.581  -4.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.540  -5.228   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    5   18   24                                             
CONECT   18   17                                                            
CONECT   19   14                                                            
CONECT   20    2   21   22                                                  
CONECT   21   20    2                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(1S,4S,6S,10R,14S)-4-methyl-9-methylidene-14-[(2E)-4-methylpent-2-en-1-yl]-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

Traditional Name

(1S,4S,6S,10R,14S)-4-methyl-9-methylidene-14-[(2E)-4-methylpent-2-en-1-yl]-5,12-dioxatricyclo[8.4.0.0^{4,6}]tetradecan-13-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12COC(=O)[C@@H](C\C=C\C(C)C)[C@@]1([H])CC[C@]1(C)O[C@H]1CCC2=C

InChI Identifier

InChI=1S/C20H30O3/c1-13(2)6-5-7-16-15-10-11-20(4)18(23-20)9-8-14(3)17(15)12-22-19(16)21/h5-6,13,15-18H,3,7-12H2,1-2,4H3/b6-5+/t15-,16+,17+,18+,20+/m1/s1

InChI Key

OQCCTFCKIHZESM-DUUHCLTNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	samafoullouss@usf.edu	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paragorgia arborea		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Fatty alcohol ester
Secoiridoid-skeleton
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Oxane
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.26 m³·mol⁻¹	ChemAxon
Polarizability	36.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for epoxycoraxeniolide A (NP0332898)

MOL for NP0332898 (epoxycoraxeniolide A )

3D MOL for NP0332898 (epoxycoraxeniolide A )

3D SDF for NP0332898 (epoxycoraxeniolide A )

3D-SDF for NP0332898 (epoxycoraxeniolide A )

PDB for NP0332898 (epoxycoraxeniolide A )

3D PDB for NP0332898 (epoxycoraxeniolide A )

SMILES for NP0332898 (epoxycoraxeniolide A )

INCHI for NP0332898 (epoxycoraxeniolide A )

Structure for NP0332898 (epoxycoraxeniolide A )

3D Structure for NP0332898 (epoxycoraxeniolide A )