NP-MRD: Showing NP-Card for (-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol (NP0074610)

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Record Information

Version

2.0

Created at

2022-04-28 19:54:25 UTC

Updated at

2022-04-28 19:54:25 UTC

NP-MRD ID

NP0074610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol

Description

5Alpha,8alpha-epidioxycholest-6-en-3beta-ol, also known as 5α,8α-epidioxycholest-6-en-3β-ol or ee-D-beta-ol, belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. Thus, 5alpha,8alpha-epidioxycholest-6-en-3beta-ol is considered to be a sterol. (-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol is found in Aplysia dactylomela, Aplysia juliana, Diadema setosum, Glyptocidaris crenularis, Metridium senile and Psammaplysilla purpurea. (-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol was first documented in 2003 (PMID: 12913243). Based on a literature review a small amount of articles have been published on 5alpha,8alpha-epidioxycholest-6-en-3beta-ol (PMID: 31163615) (PMID: 24427935).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221542D          

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M  END

     RDKit          3D

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M  END
> <DATABASE_ID>
NP0074610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1

> <INCHI_KEY>
FOISYVRNZSWLHL-MEKQHADNSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.646

> <EXACT_MASS>
416.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.38212380133541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(2R)-6-methylheptan-2-yl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol

> <ALOGPS_LOGP>
6.24

> <JCHEM_LOGP>
6.422841408

> <ALOGPS_LOGS>
-7.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.1490254826832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7336162538743682

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
121.15889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(2R)-6-methylheptan-2-yl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.238   4.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.794   4.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.765   2.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.743   1.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.210   1.687   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.633   3.156   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.907   3.175   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.434   2.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.753   3.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.827   5.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.093   5.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.367   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.558   2.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.608   0.806   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.091   1.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.071   1.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.814   3.143   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.761   4.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.725   0.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.844  -0.863   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.259   0.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.913  -1.125   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.448  -1.256   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.102  -2.650   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.636  -2.781   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.221  -3.913   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.116   0.650   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.494   3.995   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.107   4.186   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.940   3.740   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11   29                                             
CONECT    3    2    4    8   30                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9   15                                                  
CONECT    9    8   10   12   28                                             
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    9   13   18                                                  
CONECT   13   12   14   16   27                                             
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   13                                                            
CONECT   28    9   29                                                       
CONECT   29   28    2                                                       
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
5a,8a-Epidioxycholest-6-en-3b-ol	Generator
5Α,8α-epidioxycholest-6-en-3β-ol	Generator
5alpha,8alpha-Epidioxyergosta-6,22-dien-3-beta-ol	MeSH
5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-ol	MeSH
EE-D-beta-ol	MeSH

Chemical Formula

C₂₇H₄₄O₃

Average Mass

416.6460 Da

Monoisotopic Mass

416.32905 Da

IUPAC Name

(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(2R)-6-methylheptan-2-yl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol

Traditional Name

(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(2R)-6-methylheptan-2-yl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3

InChI Identifier

InChI=1S/C27H44O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1

InChI Key

FOISYVRNZSWLHL-MEKQHADNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysia dactylomela	LOTUS Database	35616633
Aplysia juliana	LOTUS Database	35616633
Diadema setosum	LOTUS Database	35616633
Glyptocidaris crenularis	LOTUS Database	35616633
Metridium senile	LOTUS Database	35616633
Pseudoceratina purpurea	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Cholane-skeleton
Ortho-dioxane
Cyclic alcohol
Dialkyl peroxide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cholestanoid (CHEBI:65851 )
3beta-sterol (CHEBI:65851 )
organic peroxide (CHEBI:65851 )
Cholesterol and derivatives (LMST01010358 )

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	6.24	ALOGPS
logP	6.42	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.16 m³·mol⁻¹	ChemAxon
Polarizability	51.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00035953

Chemspider ID

9604856

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11429981

PDB ID

Not Available

ChEBI ID

65851

Good Scents ID

Not Available

References

General References

Pereira RB, Pereira DM, Jimenez C, Rodriguez J, Nieto RM, Videira RA, Silva O, Andrade PB, Valentao P: Anti-Inflammatory Effects of 5alpha,8alpha-Epidioxycholest-6-en-3beta-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis. Mar Drugs. 2019 Jun 3;17(6). pii: md17060330. doi: 10.3390/md17060330. [PubMed:31163615 ]
Clark KE, Capper A, Della Togna G, Paul VJ, Romero LI, Johns T, Cubilla-Rios L, Capson TL: Ecology- and bioassay-guided drug discovery for treatments of tropical parasitic disease: 5alpha,8alpha-epidioxycholest-6-en-3beta-ol isolated from the mollusk Dolabrifera dolabrifera shows significant activity against Leishmania donovani. Nat Prod Commun. 2013 Nov;8(11):1537-40. [PubMed:24427935 ]
Goud TV, Srinivasulu M, Reddy VL, Reddy AV, Rao TP, Kumar DS, Murty US, Venkateswarlu Y: Two new bromotyrosine-derived metabolites from the sponge Psammaplysilla purpurea. Chem Pharm Bull (Tokyo). 2003 Aug;51(8):990-3. doi: 10.1248/cpb.51.990. [PubMed:12913243 ]

Showing NP-Card for (-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol (NP0074610)

MOL for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

3D MOL for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

3D SDF for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

3D-SDF for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

PDB for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

3D PDB for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

SMILES for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

INCHI for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

Structure for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)

3D Structure for NP0074610 ((-)-5alpha,8alpha-Epidioxycholest-6-en-3beta-ol)