NP-MRD: Showing NP-Card for dinosterol (NP0217372)

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Record Information

Version

2.0

Created at

2022-09-05 17:42:10 UTC

Updated at

2022-09-05 17:42:10 UTC

NP-MRD ID

NP0217372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dinosterol

Description

Dinosterol 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, dinosterol is considered to be a sterol. dinosterol is found in Crypthecodinium cohnii, Gorgonia mariae, Gymnodinium catenatum, Peridinium foliaceum, Phallusia nigra, Plexaura homomalla, Prorocentrum cordatum and Scrippsiella trochoidea. dinosterol was first documented in 2019 (PMID: 31703423). Based on a literature review a small amount of articles have been published on Dinosterol (PMID: 34198015) (PMID: 36039683) (PMID: 35880372) (PMID: 34142408).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219422D          

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 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
  2 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217372

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O/c1-18(2)21(5)19(3)17-20(4)24-11-12-26-23-9-10-25-22(6)28(31)14-16-30(25,8)27(23)13-15-29(24,26)7/h17-18,20-28,31H,9-16H2,1-8H3/b19-17+/t20-,21-,22+,23+,24-,25+,26+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
LPFIPZJIWTZLEY-DAABMGJCSA-N

> <FORMULA>
C30H52O

> <MOLECULAR_WEIGHT>
428.745

> <EXACT_MASS>
428.401816294

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.971816129087216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6S,7S,10S,11S,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_LOGP>
8.051900049666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.89260677614785

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0961737961129305

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
134.18529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,7S,10S,11S,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.377  -0.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.523 -10.142   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    9    6   26                                             
CONECT   26   25                                                            
CONECT   27    2   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂O

Average Mass

428.7450 Da

Monoisotopic Mass

428.40182 Da

IUPAC Name

(1S,2R,5S,6S,7S,10S,11S,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

Traditional Name

(1S,2R,5S,6S,7S,10S,11S,14R,15R)-2,6,15-trimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H52O/c1-18(2)21(5)19(3)17-20(4)24-11-12-26-23-9-10-25-22(6)28(31)14-16-30(25,8)27(23)13-15-29(24,26)7/h17-18,20-28,31H,9-16H2,1-8H3/b19-17+/t20-,21-,22+,23+,24-,25+,26+,27+,28+,29-,30+/m1/s1

InChI Key

LPFIPZJIWTZLEY-DAABMGJCSA-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
Crypthecodinium cohnii	LOTUS Database	35616633
Gorgonia mariae	LOTUS Database	35616633
Gymnodinium catenatum	LOTUS Database	35616633
Peridinium foliaceum	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Plexaura homomalla	LOTUS Database	35616633
Prorocentrum cordatum	LOTUS Database	35616633
Scrippsiella trochoidea	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
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

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	8.05	ChemAxon
pKa (Strongest Acidic)	18.89	ChemAxon
pKa (Strongest Basic)	-1.1	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	134.19 m³·mol⁻¹	ChemAxon
Polarizability	55.97 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	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

4945298

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dinosterol

METLIN ID

Not Available

PubChem Compound

6441076

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Leblond JD, Elkins LC, Sabir K: Sterols of Amphidinium species in the Operculatum Clade: Predominance of cholesterol instead of Delta(8) ((14)) sterols previously considered Amphidinium-specific biomarkers. J Eukaryot Microbiol. 2023 Jan;70(1):e12942. doi: 10.1111/jeu.12942. Epub 2022 Sep 5. [PubMed:36039683 ]
Leblond JD, Lowrie SD, Myers CS: Sterols of morphologically distinct, okadaic acid-producing Prorocentrum texanum var. texanum and var. cuspidatum isolated from the Gulf of Mexico. J Eukaryot Microbiol. 2023 Jan;70(1):e12937. doi: 10.1111/jeu.12937. Epub 2022 Aug 9. [PubMed:35880372 ]
Vandergrift SL, Elkins LC, Alves-de-Souza C, Leblond JD: First examination of sterols in the marine dinoflagellate genus Vulcanodinium. J Eukaryot Microbiol. 2021 Nov;68(6):e12863. doi: 10.1111/jeu.12863. Epub 2021 Jul 11. [PubMed:34142408 ]
Nakakuni M, Yamasaki Y, Yoshitake N, Takehara K, Yamamoto S: Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH). Molecules. 2019 Nov 7;24(22):4040. doi: 10.3390/molecules24224040. [PubMed:31703423 ]
LOTUS database [Link]

Showing NP-Card for dinosterol (NP0217372)

MOL for NP0217372 (dinosterol)

3D MOL for NP0217372 (dinosterol)

3D SDF for NP0217372 (dinosterol)

3D-SDF for NP0217372 (dinosterol)

PDB for NP0217372 (dinosterol)

3D PDB for NP0217372 (dinosterol)

SMILES for NP0217372 (dinosterol)

INCHI for NP0217372 (dinosterol)

Structure for NP0217372 (dinosterol)

3D Structure for NP0217372 (dinosterol)