NP-MRD: Showing NP-Card for Theonellasterol (NP0081289)

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Record Information

Version

2.0

Created at

2022-04-29 02:14:47 UTC

Updated at

2022-04-29 02:14:47 UTC

NP-MRD ID

NP0081289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Theonellasterol

Description

Theonellasterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, theonellasterol is considered to be a sterol. Theonellasterol is found in Theonella swinhoei. Theonellasterol was first documented in 2011 (PMID: 21428459). Based on a literature review a significant number of articles have been published on Theonellasterol (PMID: 22851924) (PMID: 34436473) (PMID: 33265994) (PMID: 23203270) (PMID: 23000093) (PMID: 22291955).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292204142D          

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 11 27  1  6  0  0  0
  9 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  6  0  0  0
  2 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](CC[C@@H](C)[C@H]1CCC2=C3CC[C@H]4C(=C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h19-20,22,24-25,27-28,31H,5,8-18H2,1-4,6-7H3/t20-,22+,24-,25+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
CVZFQTIJNREPCP-HFLKTIQXSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.53133877363007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,7R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

> <ALOGPS_LOGP>
7.35

> <JCHEM_LOGP>
7.8960997126666665

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.09585379735507

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4446735490368923

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
133.67159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.10e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -7.261   7.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.581   8.835   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.436   9.865   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.756  11.372   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.972   9.389   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.651   7.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.796   6.853   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.187   7.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.042   8.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.578   7.962   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.258   6.455   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.402   5.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.867   5.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.274   6.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.900   7.701   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.756   8.732   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.044   4.961   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.584   4.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.354   3.627   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.894   3.627   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.664   2.293   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.204   2.293   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.664   4.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.894   6.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.204   4.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.274   3.627   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.218   4.991   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.363   9.944   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.827  10.420   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.331   6.377   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.045   9.311   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   29                                                  
CONECT    6    5    7    8   30                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10   28                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   14   27                                             
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   10                                                       
CONECT   17   14   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17                                                            
CONECT   27   11                                                            
CONECT   28    9   29                                                       
CONECT   29   28    5                                                       
CONECT   30    6                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxytheonellasterol	MeSH
7alpha-Hydroxytheonellasterol	MeSH

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(1R,2R,5S,7R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

Traditional Name

(1R,2R,5S,7R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-6-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-5-ol

CAS Registry Number

Not Available

SMILES

CC[C@@H](CC[C@@H](C)[C@H]1CCC2=C3CC[C@H]4C(=C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h19-20,22,24-25,27-28,31H,5,8-18H2,1-4,6-7H3/t20-,22+,24-,25+,27+,28+,29-,30+/m1/s1

InChI Key

CVZFQTIJNREPCP-HFLKTIQXSA-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
Theonella swinhoei	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Stigmasterols and C24-ethyl derivatives (LMST01040180 )

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	7.35	ALOGPS
logP	7.9	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.1	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.67 m³·mol⁻¹	ChemAxon
Polarizability	55.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046997

Chemspider ID

29212465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52931395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guo JK, Chiang CY, Lu MC, Chang WB, Su JH: 4-Methylenesterols from a sponge Theonella swinhoei. Mar Drugs. 2012 Jul;10(7):1536-1544. doi: 10.3390/md10071536. Epub 2012 Jul 19. [PubMed:22851924 ]
Lai KH, Peng BR, Su CH, El-Shazly M, Sun YL, Shih MC, Huang YT, Yen PT, Wang LS, Su JH: Anti-Proliferative Potential of Secondary Metabolites from the Marine Sponge Theonella sp.: Moving from Correlation toward Causation. Metabolites. 2021 Aug 10;11(8):532. doi: 10.3390/metabo11080532. [PubMed:34436473 ]
Shin AY, Lee HS, Lee YJ, Lee JS, Son A, Choi C, Lee J: Oxygenated Theonellastrols: Interpretation of Unusual Chemical Behaviors Using Quantum Mechanical Calculations and Stereochemical Reassignment of 7alpha-Hydroxytheonellasterol. Mar Drugs. 2020 Nov 30;18(12):607. doi: 10.3390/md18120607. [PubMed:33265994 ]
Sepe V, Ummarino R, D'Auria MV, Taglialatela-Scafati O, Marino SD, D'Amore C, Renga B, Chini MG, Bifulco G, Nakao Y, Fusetani N, Fiorucci S, Zampella A: Preliminary structure-activity relationship on theonellasterol, a new chemotype of FXR antagonist, from the marine sponge Theonella swinhoei. Mar Drugs. 2012 Nov 5;10(11):2448-66. doi: 10.3390/md10112448. [PubMed:23203270 ]
Fiorucci S, Distrutti E, Bifulco G, D'Auria MV, Zampella A: Marine sponge steroids as nuclear receptor ligands. Trends Pharmacol Sci. 2012 Nov;33(11):591-601. doi: 10.1016/j.tips.2012.08.004. Epub 2012 Sep 21. [PubMed:23000093 ]
Renga B, Mencarelli A, D'Amore C, Cipriani S, D'Auria MV, Sepe V, Chini MG, Monti MC, Bifulco G, Zampella A, Fiorucci S: Discovery that theonellasterol a marine sponge sterol is a highly selective FXR antagonist that protects against liver injury in cholestasis. PLoS One. 2012;7(1):e30443. doi: 10.1371/journal.pone.0030443. Epub 2012 Jan 23. [PubMed:22291955 ]
Chini MG, Jones CR, Zampella A, D'Auria MV, Renga B, Fiorucci S, Butts CP, Bifulco G: Quantitative NMR-derived interproton distances combined with quantum mechanical calculations of 13C chemical shifts in the stereochemical determination of conicasterol F, a nuclear receptor ligand from Theonella swinhoei. J Org Chem. 2012 Feb 3;77(3):1489-96. doi: 10.1021/jo2023763. Epub 2012 Jan 23. [PubMed:22201476 ]
De Marino S, Ummarino R, D'Auria MV, Chini MG, Bifulco G, Renga B, D'Amore C, Fiorucci S, Debitus C, Zampella A: Theonellasterols and conicasterols from Theonella swinhoei. Novel marine natural ligands for human nuclear receptors. J Med Chem. 2011 Apr 28;54(8):3065-75. doi: 10.1021/jm200169t. Epub 2011 Apr 5. [PubMed:21428459 ]

Showing NP-Card for Theonellasterol (NP0081289)

MOL for NP0081289 (Theonellasterol)

3D MOL for NP0081289 (Theonellasterol)

3D SDF for NP0081289 (Theonellasterol)

3D-SDF for NP0081289 (Theonellasterol)

PDB for NP0081289 (Theonellasterol)

3D PDB for NP0081289 (Theonellasterol)

SMILES for NP0081289 (Theonellasterol)

INCHI for NP0081289 (Theonellasterol)

Structure for NP0081289 (Theonellasterol)

3D Structure for NP0081289 (Theonellasterol)