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Showing NP-Card for Lumisterol 3 (NP0334762)

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Record Information
Version2.0
Created at2024-09-10 19:51:10 UTC
Updated at2024-09-10 19:51:10 UTC
NP-MRD IDNP0334762
Secondary Accession NumbersNone
Natural Product Identification
Common NameLumisterol 3
DescriptionLumisterol 3 belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, lumisterol 3 is considered to be a sterol lipid molecule. It was first documented in 1981 (PMID: 6256855). Lumisterol 3 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 10876100).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334762 (Lumisterol 3)


  Mrv0541 02231220412D          

 31 34  0  0  1  0            999 V2000
   13.2979   -9.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7472   -6.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -7.6921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5277   -6.6158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3183   -7.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0327   -6.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5277   -7.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0327   -8.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0092   -7.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5675   -8.1103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3183   -6.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7841   -5.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -6.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5608   -8.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8028   -7.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0459   -8.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5739   -7.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5913   -5.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3051   -9.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7891   -9.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0209   -8.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2332   -5.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139   -8.9756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8477   -4.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6550   -4.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9112   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3603   -3.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8171   -8.3484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1798   -6.5133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3123   -8.4896    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 29  1  6  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 30  1  6  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 31  1  1  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  6  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
Download

3D MOL for NP0334762 (Lumisterol 3)

Download
3D SDF for NP0334762 (Lumisterol 3)

  Mrv0541 02231220412D          

 31 34  0  0  1  0            999 V2000
   13.2979   -9.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7472   -6.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -7.6921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5277   -6.6158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3183   -7.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0327   -6.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5277   -7.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0327   -8.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0092   -7.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5675   -8.1103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3183   -6.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7841   -5.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -6.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5608   -8.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8028   -7.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0459   -8.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5739   -7.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5913   -5.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3051   -9.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7891   -9.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0209   -8.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2332   -5.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139   -8.9756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8477   -4.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6550   -4.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9112   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3603   -3.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8171   -8.3484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1798   -6.5133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3123   -8.4896    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 29  1  6  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 30  1  6  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 31  1  1  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  6  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
UCTLRSWJYQTBFZ-XMVWLVNMSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.925206486825644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
6.707309549333335

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.46649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lumisterol 3

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0334762 (Lumisterol 3)
Download
PDB for NP0334762 (Lumisterol 3)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      24.823 -17.519   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      33.128 -12.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.128 -14.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.585 -12.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.461 -14.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.794 -12.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.585 -14.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.794 -15.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.484 -13.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.059 -15.139   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.461 -12.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.064 -10.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.128 -11.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.047 -16.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.632 -14.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.819 -16.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.071 -13.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.570 -10.568   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.436 -17.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.606 -17.590   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.172 -15.084   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.035  -9.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.159 -16.754   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.049  -9.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.556  -8.787   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.034  -7.323   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      38.006  -6.177   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.541  -7.006   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.259 -15.584   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      35.802 -12.158   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      30.450 -15.847   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2    3    4    6   13                                             
CONECT    3    2    7    8   29                                             
CONECT    4    2    9   12   30                                             
CONECT    5    8   10   11   31                                             
CONECT    6    2   11                                                       
CONECT    7    3    9                                                       
CONECT    8    3    5   16                                                  
CONECT    9    4    7                                                       
CONECT   10    5   14   15   17                                             
CONECT   11    5    6                                                       
CONECT   12    4   18   22                                                  
CONECT   13    2                                                            
CONECT   14   10   19   20                                                  
CONECT   15   10   21                                                       
CONECT   16    8   19                                                       
CONECT   17   10                                                            
CONECT   18   12   24                                                       
CONECT   19   14   16                                                       
CONECT   20   14   23                                                       
CONECT   21   15   23                                                       
CONECT   22   12                                                            
CONECT   23    1   20   21                                                  
CONECT   24   18   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0334762 (Lumisterol 3)
Download
SMILES for NP0334762 (Lumisterol 3)
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Download
INCHI for NP0334762 (Lumisterol 3)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(3b,9b,10a)-Cholesta-5,7-dien-3-olHMDB
9b,10a-Cholesta-5,7-dien-3b-olHMDB
9beta,10alpha-Cholesta-5,7-dien-3beta-olHMDB
Chemical FormulaC27H44O
Average Mass384.6377 Da
Monoisotopic Mass384.33922 Da
IUPAC Name(1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Namelumisterol 3
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1
InChI KeyUCTLRSWJYQTBFZ-XMVWLVNMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassCholestane steroids  
Direct ParentCholesterols and derivatives  
Alternative Parents
Substituents
  • Cholesterol
    • 

  • Cholesterol-skeleton
    • 

  • 3-hydroxy-delta-5-steroid
    • 

  • 3-hydroxy-delta-7-steroid
    • 

  • 3-beta-hydroxysteroid
    • 

  • 3-beta-hydroxy-delta-5-steroid
    • 

  • 3-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • Delta-7-steroid
    • 

  • Delta-5-steroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP7.3ALOGPS
logP6.71ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability49.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006505  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023946  
KNApSAcK IDNot Available
Chemspider ID99690  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2288990  
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound111049  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Holick MF, MacLaughlin JA, Doppelt SH: Regulation of cutaneous previtamin D3 photosynthesis in man: skin pigment is not an essential regulator. Science. 1981 Feb 6;211(4482):590-3. doi: 10.1126/science.6256855. [PubMed:6256855  ] 
  2. Chen TC, Persons KS, Lu Z, Mathieu JS, Holick MF: An evaluation of the biologic activity and vitamin D receptor binding affinity of the photoisomers of vitamin D3 and previtamin D3. J Nutr Biochem. 2000 May;11(5):267-72. doi: 10.1016/s0955-2863(00)00077-2. [PubMed:10876100  ]