NP-MRD: Showing NP-Card for Epoxymiolenol (NP0332897)

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Record Information

Version

2.0

Created at

2024-05-01 22:06:58 UTC

Updated at

2026-01-03 22:35:06 UTC

NP-MRD ID

NP0332897

Natural Product DOI

https://doi.org/10.57994/2177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epoxymiolenol

Description

Epoxymiolenol belongs to the class of organic compounds known as xeniaphyllane and xenicane diterpenoids. These are diterpenoids with a structure based either on the xeniaphyllane or the xenicane skeleton. Based on a literature review very few articles have been published on Epoxymiolenol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142300432D          

 24 26  0  0  1  0            999 V2000
    0.8002    0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.5765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8427   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940   -0.5985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5753   -1.0035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -0.4638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9733    0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6108    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4761    1.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137    2.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9790    3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8859    1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2427   -1.2778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9134   -1.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287   -1.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8948   -2.0932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534   -1.3874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4270   -0.8505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -2.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -2.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5323   -2.7601    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  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  6  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 15  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
  2 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(C)O[C@H]3CCC(=C)[C@]1([H])[C@@H](O)[C@]2(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-13(2)7-6-11-19(4)15-10-12-20(5)16(22-20)9-8-14(3)17(15)18(19)21/h7,15-18,21H,3,6,8-12H2,1-2,4-5H3/t15-,16-,17-,18+,19+,20-/m0/s1

> <INCHI_KEY>
PQHKZLDTSFDIIZ-KYRVCDIISA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.88847109354936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6S,10R,11R,12R)-4,12-dimethyl-9-methylidene-12-(4-methylpent-3-en-1-yl)-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-11-ol

> <JCHEM_LOGP>
4.125384821333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.878721682622377

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6647274278511621

> <JCHEM_POLAR_SURFACE_AREA>
32.76

> <JCHEM_REFRACTIVITY>
91.45400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S,10R,11R,12R)-4,12-dimethyl-9-methylidene-12-(4-methylpent-3-en-1-yl)-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-11-ol

> <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       1.494   0.266   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.250  -1.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.440  -0.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.980  -0.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.149  -1.117   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       4.807  -1.873   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       7.668  -0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.417   0.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.607   1.631   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.355   3.150   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.545   4.128   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.294   5.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.987   3.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.188  -0.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.920  -2.385   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.172  -3.282   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.400  -2.637   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       7.270  -3.907   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       1.966  -2.590   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.797  -1.588   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.722  -3.932   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.164  -4.474   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.616  -3.962   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.594  -5.152   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8   14   15                                             
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                                                            
CONECT   15    7   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18   23                                             
CONECT   18   17                                                            
CONECT   19    2   20   21                                                  
CONECT   20   19    2                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₂

Average Mass

304.4740 Da

Monoisotopic Mass

304.24023 Da

IUPAC Name

(1S,4S,6S,10R,11R,12R)-4,12-dimethyl-9-methylidene-12-(4-methylpent-3-en-1-yl)-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-11-ol

Traditional Name

(1S,4S,6S,10R,11R,12R)-4,12-dimethyl-9-methylidene-12-(4-methylpent-3-en-1-yl)-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-11-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(C)O[C@H]3CCC(=C)[C@]1([H])[C@@H](O)[C@]2(C)CCC=C(C)C

InChI Identifier

InChI=1S/C20H32O2/c1-13(2)7-6-11-19(4)15-10-12-20(5)16(22-20)9-8-14(3)17(15)18(19)21/h7,15-18,21H,3,6,8-12H2,1-2,4-5H3/t15-,16-,17-,18+,19+,20-/m0/s1

InChI Key

PQHKZLDTSFDIIZ-KYRVCDIISA-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)	[email protected]	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	[email protected]	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	[email protected]	University of South Florida	Sam Afoullouss	2024-05-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	[email protected]	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 xeniaphyllane and xenicane diterpenoids. These are diterpenoids with a structure based either on the xeniaphyllane or the xenicane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Xeniaphyllane and xenicane diterpenoids

Alternative Parents

Substituents

Xeniaphyllane diterpenoid
Secondary alcohol
Cyclobutanol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.13	ChemAxon
pKa (Strongest Acidic)	19.88	ChemAxon
pKa (Strongest Basic)	-0.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.45 m³·mol⁻¹	ChemAxon
Polarizability	36.89 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 Epoxymiolenol (NP0332897)

MOL for NP0332897 (Epoxymiolenol)

3D MOL for NP0332897 (Epoxymiolenol)

3D SDF for NP0332897 (Epoxymiolenol)

3D-SDF for NP0332897 (Epoxymiolenol)

PDB for NP0332897 (Epoxymiolenol)

3D PDB for NP0332897 (Epoxymiolenol)

SMILES for NP0332897 (Epoxymiolenol)

INCHI for NP0332897 (Epoxymiolenol)

Structure for NP0332897 (Epoxymiolenol)

3D Structure for NP0332897 (Epoxymiolenol)