NP-MRD: Showing NP-Card for Lumisterol 3 (NP0334762)

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Record Information

Version

2.0

Created at

2024-09-10 19:51:10 UTC

Updated at

2024-09-10 19:51:10 UTC

NP-MRD ID

NP0334762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lumisterol 3

Description

Lumisterol 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. Lumisterol 3 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  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


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
(3b,9b,10a)-Cholesta-5,7-dien-3-ol	HMDB
9b,10a-Cholesta-5,7-dien-3b-ol	HMDB
9beta,10alpha-Cholesta-5,7-dien-3beta-ol	HMDB

Chemical Formula

C₂₇H₄₄O

Average Mass

384.6377 Da

Monoisotopic Mass

384.33922 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 Name

lumisterol 3

CAS Registry Number

Not 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 Key

UCTLRSWJYQTBFZ-XMVWLVNMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010247 )

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	7.3	ALOGPS
logP	6.71	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.27	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	5	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	49.93 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

HMDB0006505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023946

KNApSAcK ID

Not Available

Chemspider ID

99690

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2288990

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

111049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lumisterol 3 (NP0334762)

MOL for NP0334762 (Lumisterol 3)

3D MOL for NP0334762 (Lumisterol 3)

3D SDF for NP0334762 (Lumisterol 3)

3D-SDF for NP0334762 (Lumisterol 3)

PDB for NP0334762 (Lumisterol 3)

3D PDB for NP0334762 (Lumisterol 3)

SMILES for NP0334762 (Lumisterol 3)

INCHI for NP0334762 (Lumisterol 3)

Structure for NP0334762 (Lumisterol 3)

3D Structure for NP0334762 (Lumisterol 3)