Np mrd loader

Showing NP-Card for Dihydrobrassicasterol (NP0336682)

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Record Information
Version2.0
Created at2024-09-11 07:23:35 UTC
Updated at2024-09-11 07:23:35 UTC
NP-MRD IDNP0336682
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrobrassicasterol
Description Dihydrobrassicasterol was first documented in 2016 (PMID: 26872973). Based on a literature review a small amount of articles have been published on Dihydrobrassicasterol (PMID: 37523212) (PMID: 32918703) (PMID: 32144288).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336682 (Dihydrobrassicasterol)


  Mrv2104 05262309552D          

 29 32  0  0  0  0            999 V2000
   -3.7126   -1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5710   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710    0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2812    1.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969    2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7126    0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283   -2.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 29  1  0  0  0  0
  2  3  1  0  0  0  0
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 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
Download

3D MOL for NP0336682 (Dihydrobrassicasterol)

Download
3D SDF for NP0336682 (Dihydrobrassicasterol)

  Mrv2104 05262309552D          

 29 32  0  0  0  0            999 V2000
   -3.7126   -1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126   -1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710    0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582    0.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    0.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365    0.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -0.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853   -0.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    0.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    1.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969    2.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    1.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283   -2.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 29  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3

> <INCHI_KEY>
SGNBVLSWZMBQTH-UHFFFAOYNA-N

> <FORMULA>
C28H48O

> <MOLECULAR_WEIGHT>
400.691

> <EXACT_MASS>
400.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
51.09207285104034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
7.399908127000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.397243770292629

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
125.16509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
campesterol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0336682 (Dihydrobrassicasterol)
Download
PDB for NP0336682 (Dihydrobrassicasterol)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -6.930  -3.680   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.930  -2.139   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.597  -1.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.266  -2.139   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.266  -3.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.597  -4.448   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.933  -1.368   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.602  -2.139   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.602  -3.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.933  -4.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.933   0.171   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.602   0.939   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.274   0.171   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.274  -1.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.188   0.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.087  -0.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.188  -1.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.266  -0.597   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.274   1.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.586   2.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.250   2.907   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.922   2.907   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.258   2.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.594   2.907   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.594   4.448   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.930   2.136   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.930   0.595   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.266   2.907   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.266  -4.448   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7   18                                             
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14    8   13   17                                                  
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   14   16                                                       
CONECT   18    4                                                            
CONECT   19   13                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    1                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

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3D PDB for NP0336682 (Dihydrobrassicasterol)
Download
SMILES for NP0336682 (Dihydrobrassicasterol)
CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C
Download
INCHI for NP0336682 (Dihydrobrassicasterol)
InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC28H48O
Average Mass400.6910 Da
Monoisotopic Mass400.37052 Da
IUPAC Name1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
Traditional Namecampesterol
CAS Registry NumberNot Available
SMILES
CC(C)C(C)CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3
InChI KeySGNBVLSWZMBQTH-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ChemAxon
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.17 m³·mol⁻¹ChemAxon
Polarizability51.09 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tsukagoshi Y, Suzuki H, Seki H, Muranaka T, Ohyama K, Fujimoto Y: Ajuga Delta24-Sterol Reductase Catalyzes the Direct Reductive Conversion of 24-Methylenecholesterol to Campesterol. J Biol Chem. 2016 Apr 8;291(15):8189-98. doi: 10.1074/jbc.M115.703470. Epub 2016  Feb 12. [PubMed:26872973  ] 
  2. Recsei C, Russell RA, Cagnes M, Darwish T: Deuterated squalene and sterols from modified Saccharomyces cerevisiae. Org Biomol Chem. 2023 Aug 16;21(32):6537-6548. doi: 10.1039/d3ob00754e. [PubMed:37523212  ] 
  3. Begum SA, Hira K, Pal PP, Nessa S, Kulkarni OP, Danaraj J, Shaik AB, Araya H, Fujimoto Y: Halodule pinifolia (Seagrass) attenuated lipopolysaccharide-, carrageenan-, and crystal-induced secretion of pro-inflammatory cytokines: mechanism and chemistry. Inflammopharmacology. 2021 Feb;29(1):253-267. doi: 10.1007/s10787-020-00747-x.  Epub 2020 Sep 12. [PubMed:32918703  ] 
  4. Gallo C, Landi S, d'Ippolito G, Nuzzo G, Manzo E, Sardo A, Fontana A: Diatoms synthesize sterols by inclusion of animal and fungal genes in the plant pathway. Sci Rep. 2020 Mar 6;10(1):4204. doi: 10.1038/s41598-020-60993-5. [PubMed:32144288  ]