NP-MRD: Showing NP-Card for Gorgosterol (NP0081085)

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Record Information

Version

2.0

Created at

2022-04-29 02:03:46 UTC

Updated at

2022-04-29 02:03:46 UTC

NP-MRD ID

NP0081085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gorgosterol

Description

Gorgosterol belongs to the class of organic compounds known as gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence. Thus, gorgosterol is considered to be a sterol. Gorgosterol is found in Acanthaster planci, Axinella aruensis, Eunicea laciniata, Palythoa caribaeorum, Sarcophyton glaucum, Sarcophyton trocheliophorum, Sinularia brassica and Sinularia molesta. Gorgosterol was first documented in 2016 (PMID: 26134487). Based on a literature review a small amount of articles have been published on Gorgosterol (PMID: 34585632) (PMID: 34564185) (PMID: 34198015) (PMID: 28648587).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292204032D          

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M  END

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 21 22  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  6  0  0  0
 21 28  1  6  0  0  0
 19 29  1  6  0  0  0
 14 30  1  1  0  0  0
  2 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)[C@@]1(C)C[C@@H]1[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-18(2)20(4)30(7)17-27(30)19(3)24-10-11-25-23-9-8-21-16-22(31)12-14-28(21,5)26(23)13-15-29(24,25)6/h8,18-20,22-27,31H,9-17H2,1-7H3/t19-,20+,22-,23-,24+,25-,26-,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
YRPMZHRSQIFCLR-PVNJCSFGSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.21286883261021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(1S)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
7.365698872000002

> <ALOGPS_LOGS>
-7.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
132.33419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(1S)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-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      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.974  -1.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.763  -0.324   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.051  -3.388   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.421  -4.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.498  -5.628   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.715  -3.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.243  -4.223   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.446  -2.304   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   30                                             
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   22   23   28                                             
CONECT   22   21   20                                                       
CONECT   23   21   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28   21                                                            
CONECT   29   19                                                            
CONECT   30   14                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Gorgost-5-en-3beta-ol	Kegg
Gorgost-5-en-3b-ol	Generator
Gorgost-5-en-3β-ol	Generator

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(1S)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(1S)-1-[(1R,2R)-2-methyl-2-[(2R)-3-methylbutan-2-yl]cyclopropyl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)[C@@]1(C)C[C@@H]1[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C30H50O/c1-18(2)20(4)30(7)17-27(30)19(3)24-10-11-25-23-9-8-21-16-22(31)12-14-28(21,5)26(23)13-15-29(24,25)6/h8,18-20,22-27,31H,9-17H2,1-7H3/t19-,20+,22-,23-,24+,25-,26-,27+,28-,29+,30+/m0/s1

InChI Key

YRPMZHRSQIFCLR-PVNJCSFGSA-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
Acanthaster planci	LOTUS Database	35616633
Axinella aruensis	LOTUS Database	35616633
Eunicea laciniata	-	KNApSAcK
Palythoa caribaeorum	LOTUS Database	35616633
Sarcophyton glaucum	LOTUS Database	35616633
Sarcophyton trocheliophorum	LOTUS Database	35616633
Sinularia brassica	LOTUS Database	35616633
Sinularia molesta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Gorgostanes and derivatives

Direct Parent

Gorgostanes and derivatives

Alternative Parents

Substituents

Gorgostane-skeleton
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Gorgosterols and derivatives (LMST01060001 )

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	5.91	ALOGPS
logP	7.37	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	18.2	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	4	ChemAxon
Refractivity	132.33 m³·mol⁻¹	ChemAxon
Polarizability	55.21 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

C00046756

Chemspider ID

27025878

KEGG Compound ID

C19655

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52931413

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1509701

References

General References

Hegazy ME, Mohamed TA, Elshamy AI, Hassanien AA, Abdel-Azim NS, Shreadah MA, Abdelgawad II, Elkady EM, Pare PW: A new steroid from the Red Sea soft coral Lobophytum lobophytum. Nat Prod Res. 2016;30(3):340-4. doi: 10.1080/14786419.2015.1046871. Epub 2015 Jul 2. [PubMed:26134487 ]
Zidan SAH, Abdelhamid RA, Alian A, Fouad MA, Matsunami K, Orabi MAA: Diterpenes and sterols from the Red Sea soft coral Sarcophyton trocheliophorum and their cytotoxicity and anti-leishmanial activities. J Asian Nat Prod Res. 2021 Sep 29:1-9. doi: 10.1080/10286020.2021.1979522. [PubMed:34585632 ]
Pham GN, Kang DY, Kim MJ, Han SJ, Lee JH, Na M: Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration. Mar Drugs. 2021 Sep 17;19(9). pii: md19090523. doi: 10.3390/md19090523. [PubMed:34564185 ]
Graeff JE, Leblond JD: Sterol Composition of the Peridinioid Dinoflagellate Zooxanthella nutricula, A Symbiont of Polycystine Radiolarians. Protist. 2021 Jul;172(3):125817. doi: 10.1016/j.protis.2021.125817. Epub 2021 May 20. [PubMed:34198015 ]
He YQ, Lee Caplan S, Scesa P, West LM: Cyclized 9,11-secosterol enol-ethers from the gorgonian Pseudopterogorgia americana. Steroids. 2017 Sep;125:47-53. doi: 10.1016/j.steroids.2017.06.008. Epub 2017 Jun 23. [PubMed:28648587 ]

Showing NP-Card for Gorgosterol (NP0081085)

MOL for NP0081085 (Gorgosterol)

3D MOL for NP0081085 (Gorgosterol)

3D SDF for NP0081085 (Gorgosterol)

3D-SDF for NP0081085 (Gorgosterol)

PDB for NP0081085 (Gorgosterol)

3D PDB for NP0081085 (Gorgosterol)

SMILES for NP0081085 (Gorgosterol)

INCHI for NP0081085 (Gorgosterol)

Structure for NP0081085 (Gorgosterol)

3D Structure for NP0081085 (Gorgosterol)