NP-MRD: Showing NP-Card for 5α,8α-epidioxysterol (NP0148527)

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Record Information

Version

2.0

Created at

2022-09-02 04:17:27 UTC

Updated at

2022-09-02 04:17:27 UTC

NP-MRD ID

NP0148527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5α,8α-epidioxysterol

Description

5Alpha,8alpha-epidioxysterol, also known as 5α,8α-epidioxysterol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5α,8α-epidioxysterol is found in Lobophytum sarcophytoides. 5α,8α-epidioxysterol was first documented in 2000 (PMID: 10650100). Based on a literature review a small amount of articles have been published on 5alpha,8alpha-epidioxysterol (PMID: 30691285) (PMID: 24427934) (PMID: 23459300) (PMID: 12377225).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206172D          

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     RDKit          3D

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 14 29  1  0  0  0  0
 29 30  1  1  0  0  0
 18 31  1  6  0  0  0
 31 32  1  0  0  0  0
 15 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0148527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)[C@H]1C[C@@H]1[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/C29H46O3/c1-17(2)18(3)21-15-22(21)19(4)23-7-8-24-26(23,5)11-10-25-27(6)12-9-20(30)16-28(27)13-14-29(24,25)32-31-28/h13-14,17-25,30H,7-12,15-16H2,1-6H3/t18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
FYNMKNFAKCHMLL-PPXWZDJSSA-N

> <FORMULA>
C29H46O3

> <MOLECULAR_WEIGHT>
442.684

> <EXACT_MASS>
442.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.10425763980396

> <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-[(1R)-1-[(1R,2R)-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
6.375604129333333

> <ALOGPS_LOGS>
-7.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.1490254826832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7336162538743682

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
128.40149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(1R)-1-[(1R,2R)-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      19.814   8.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.160   7.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.040   6.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.626   7.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.745   8.442   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.972   5.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.102   4.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.708   4.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.174   4.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.293   6.037   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.520   3.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.263   2.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.210   0.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.816   1.561   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.202   1.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.276   0.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.542  -0.194   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.243   1.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.687   0.579   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.082   2.017   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.542   1.999   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.659   3.487   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.191   3.639   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.214   2.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.389   1.433   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.882   2.658   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.540   4.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.056   4.368   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.007   3.089   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.565   4.524   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.556   0.988   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.943   1.179   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   26   32                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24   31                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   11   14   30                                             
CONECT   30   29                                                            
CONECT   31   18   32                                                       
CONECT   32   31   15                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
22R,23R,24R-5alpha,8alpha-Epidioxy-22,23-methylene-24-methylcholest-6-en-3beta-ol	ChEBI
22R,23R,24R-5a,8a-Epidioxy-22,23-methylene-24-methylcholest-6-en-3b-ol	Generator
22R,23R,24R-5Α,8α-epidioxy-22,23-methylene-24-methylcholest-6-en-3β-ol	Generator
5a,8a-Epidioxysterol	Generator
5Α,8α-epidioxysterol	Generator

Chemical Formula

C₂₉H₄₆O₃

Average Mass

442.6840 Da

Monoisotopic Mass

442.34470 Da

IUPAC Name

(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(1R)-1-[(1R,2R)-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-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-[(1R)-1-[(1R,2R)-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]-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)[C@@H](C)[C@H]1C[C@@H]1[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/C29H46O3/c1-17(2)18(3)21-15-22(21)19(4)23-7-8-24-26(23,5)11-10-25-27(6)12-9-20(30)16-28(27)13-14-29(24,25)32-31-28/h13-14,17-25,30H,7-12,15-16H2,1-6H3/t18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29+/m1/s1

InChI Key

FYNMKNFAKCHMLL-PPXWZDJSSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Lobophytum sarcophytoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
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

cyclopropanes (CHEBI:65853 )
3beta-sterol (CHEBI:65853 )
organic peroxide (CHEBI:65853 )

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	5.35	ALOGPS
logP	6.38	ChemAxon
logS	-7.5	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	4	ChemAxon
Refractivity	128.4 m³·mol⁻¹	ChemAxon
Polarizability	54.1 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

8964658

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10789345

PDB ID

Not Available

ChEBI ID

65853

Good Scents ID

Not Available

References

General References

Yang M, Liang LF, Li H, Tang W, Guo YW: A new 5alpha,8alpha-epidioxysterol with immunosuppressive activity from the South China Sea soft coral Sinularia sp. Nat Prod Res. 2020 Jul;34(13):1814-1819. doi: 10.1080/14786419.2018.1561683. Epub 2019 Jan 29. [PubMed:30691285 ]
Su TR, Liang KJ, Chiang MY, Lu MC, Wue YJ, Su JH: 5alpha,8alpha-epidioxysterols from a Formosan sponge, Axinyssa sp. Nat Prod Commun. 2013 Nov;8(11):1535-6. [PubMed:24427934 ]
Yen WH, Chen WF, Cheng CH, Dai CF, Lu MC, Su JH, Su YD, Chen YH, Chang YC, Chen YH, Sheu JH, Lin CH, Wen ZH, Sung PJ: A new 5alpha,8alpha-Epidioxysterol from the soft coral Sinularia gaweli. Molecules. 2013 Mar 4;18(3):2895-903. doi: 10.3390/molecules18032895. [PubMed:23459300 ]
Toume K, Ishibashi M: 5alpha, 8alpha-Epidioxysterol sulfate from a diatom Odontella aurita. Phytochemistry. 2002 Oct;61(4):359-60. doi: 10.1016/s0031-9422(02)00224-8. [PubMed:12377225 ]
Sheu JH, Chang KC, Duh CY: A cytotoxic 5alpha,8alpha-epidioxysterol from a soft coral Sinularia species. J Nat Prod. 2000 Jan;63(1):149-51. doi: 10.1021/np9903954. [PubMed:10650100 ]
LOTUS database [Link]

Showing NP-Card for 5α,8α-epidioxysterol (NP0148527)

MOL for NP0148527 (5α,8α-epidioxysterol)

3D MOL for NP0148527 (5α,8α-epidioxysterol)

3D SDF for NP0148527 (5α,8α-epidioxysterol)

3D-SDF for NP0148527 (5α,8α-epidioxysterol)

PDB for NP0148527 (5α,8α-epidioxysterol)

3D PDB for NP0148527 (5α,8α-epidioxysterol)

SMILES for NP0148527 (5α,8α-epidioxysterol)

INCHI for NP0148527 (5α,8α-epidioxysterol)

Structure for NP0148527 (5α,8α-epidioxysterol)

3D Structure for NP0148527 (5α,8α-epidioxysterol)