NP-MRD: Showing NP-Card for Tachysterol 3 (NP0087547)

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Record Information

Version

2.0

Created at

2022-05-11 16:52:43 UTC

Updated at

2022-05-11 16:52:43 UTC

NP-MRD ID

NP0087547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tachysterol 3

Description

Tachysterol 3, also known as previtamin D(3) or precalciferol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, tachysterol 3 is considered to be a secosteroid lipid molecule. Tachysterol 3 was first documented in 1981 (PMID: 6256855). Tachysterol 3 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 10876100).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220432D          

 30 32  0  0  1  0            999 V2000
   16.9519  -11.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9519   -6.8722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7324   -6.6209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9519   -7.6972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2140   -7.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7324   -7.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2374   -6.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9887   -5.8367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9519   -6.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2374   -8.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230   -6.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7960   -5.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230   -7.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4378   -5.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0524   -4.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2374   -8.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8596   -4.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230   -9.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1159   -3.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230  -10.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2374  -10.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5649   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9232   -3.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8084  -10.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2374  -11.4097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8084  -11.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5230  -11.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0939  -10.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3844   -6.5185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0217   -8.3535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 25  1  1  1  0  0  0
  2  3  1  0  0  0  0
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  2  7  1  0  0  0  0
  2  9  1  1  0  0  0
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  3 29  1  6  0  0  0
  4  6  1  0  0  0  0
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  5  6  1  0  0  0  0
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 24 26  1  0  0  0  0
 24 28  1  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
   -4.2896    2.8814   -1.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2453    0.8943   -2.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8569    0.5348    1.3069 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8680    1.5637    2.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2112    0.6350    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6228    0.0045   -3.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6468    0.5182   -4.4874 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.5778    1.4780   -3.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7661    2.6236   -3.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02231220432D          

 30 32  0  0  1  0            999 V2000
   16.9519  -11.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9519   -6.8722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   16.9519   -7.6972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CC[C@H](O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12+/t21-,24+,25-,26+,27-/m1/s1

> <INCHI_KEY>
YUGCAAVRZWBXEQ-FMCTZRJNSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.2299639128137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-3-[(E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

> <ALOGPS_LOGP>
7.38

> <JCHEM_LOGP>
7.067527084333333

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.3144263764392

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3490699029454927

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.29699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tachysterol3

> <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      31.644 -22.068   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      31.644 -12.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.100 -12.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.644 -14.368   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.999 -13.598   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.100 -14.837   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.310 -12.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.579 -10.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.644 -11.288   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.310 -15.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.976 -12.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.086 -10.577   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.976 -14.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.551  -9.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.564  -9.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.310 -16.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.071  -8.796   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.976 -17.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.550  -7.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.976 -18.988   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.310 -19.758   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.521  -6.186   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.057  -7.015   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.642 -19.758   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      30.310 -21.298   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.642 -21.298   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.976 -22.068   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.309 -18.988   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      34.318 -12.168   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      31.774 -15.593   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2    3    4    7    9                                             
CONECT    3    2    5    8   29                                             
CONECT    4    2    6   10   30                                             
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    2   11                                                       
CONECT    8    3   12   14                                                  
CONECT    9    2                                                            
CONECT   10    4   13   16                                                  
CONECT   11    7   13                                                       
CONECT   12    8   15                                                       
CONECT   13   10   11                                                       
CONECT   14    8                                                            
CONECT   15   12   17                                                       
CONECT   16   10   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   22   23                                                  
CONECT   20   18   21   24                                                  
CONECT   21   20   25                                                       
CONECT   22   19                                                            
CONECT   23   19                                                            
CONECT   24   20   26   28                                                  
CONECT   25    1   21   27                                                  
CONECT   26   24   27                                                       
CONECT   27   25   26                                                       
CONECT   28   24                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3b,6E)-9,10-Secocholesta-5(10),6,8-trien-3-ol	HMDB
(6E)-(3S)-9,10-Seco-5(10),6,8-cholestatrien-3-ol	HMDB
Tachysterol_3	HMDB
1,25-Dihydroxy-3-epi-19-nor-previtamin D3	HMDB
14-Epi-19-nortachysterol	HMDB
Previtamin D(3)	HMDB
Previtamin D(3), (3alpha,6Z)-isomer	HMDB
Tachysterol(3)	HMDB
Previtamin D(3), (3beta,6E)-isomer	HMDB
Previtamin D3	HMDB
Precholecalciferol	HMDB
Precalciferol	HMDB
Tachysterol 3	MeSH

Chemical Formula

C₂₇H₄₄O

Average Mass

384.6377 Da

Monoisotopic Mass

384.33922 Da

IUPAC Name

(1S)-3-[(E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

Traditional Name

tachysterol3

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CC[C@H](O)C1

InChI Identifier

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12+/t21-,24+,25-,26+,27-/m1/s1

InChI Key

YUGCAAVRZWBXEQ-FMCTZRJNSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Vitamin D3 and derivatives (LMST03020223 )

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	7.38	ALOGPS
logP	7.07	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.31	ChemAxon
pKa (Strongest Basic)	-1.3	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	7	ChemAxon
Refractivity	124.3 m³·mol⁻¹	ChemAxon
Polarizability	50.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0006560

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023972

KNApSAcK ID

Not Available

Chemspider ID

4446802

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2288996

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
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 ]

Showing NP-Card for Tachysterol 3 (NP0087547)

MOL for NP0087547 (Tachysterol 3)

3D MOL for NP0087547 (Tachysterol 3)

3D SDF for NP0087547 (Tachysterol 3)

3D-SDF for NP0087547 (Tachysterol 3)

PDB for NP0087547 (Tachysterol 3)

3D PDB for NP0087547 (Tachysterol 3)

SMILES for NP0087547 (Tachysterol 3)

INCHI for NP0087547 (Tachysterol 3)

Structure for NP0087547 (Tachysterol 3)

3D Structure for NP0087547 (Tachysterol 3)