NP-MRD: Showing NP-Card for Tetrahymanol (NP0087654)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:55 UTC

Updated at

2022-05-11 16:55:55 UTC

NP-MRD ID

NP0087654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetrahymanol

Description

Tetrahymanol, also known as gammaceran-3b-ol or wallichiniol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, tetrahymanol is considered to be an isoprenoid lipid molecule. Tetrahymanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetrahymanol is found in Adiantum pedatum, Alsophila spinulosa, Fossombronia pusilla, Oleandra wallichii and Tetrahymena pyriformis. A pentacyclic triterpenoid having a 3beta- (21alpha-) hydroxy-substituted gammacerane structure.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220532D          

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   18.1689   -4.5043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231220532D          

 35 39  0  0  1  0            999 V2000
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   16.1097   -6.5515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4560   -4.2942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3642   -7.5799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8532   -3.9498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.3184   -3.2293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  1 19  1  1  0  0  0
  2  4  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  6  0  0  0
  3  5  1  0  0  0  0
  3 10  1  0  0  0  0
  3 31  1  6  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 32  1  1  0  0  0
  5  7  1  0  0  0  0
  5 17  1  0  0  0  0
  5 21  1  1  0  0  0
  6  8  1  0  0  0  0
  6 18  1  0  0  0  0
  6 22  1  6  0  0  0
  7 13  1  0  0  0  0
  7 15  1  0  0  0  0
  7 33  1  6  0  0  0
  8 14  1  0  0  0  0
  8 16  1  0  0  0  0
  8 34  1  1  0  0  0
  9 13  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 15 23  1  0  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 16 25  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 24  1  0  0  0  0
 18 26  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O/c1-25(2)15-9-16-27(5)20(25)12-18-29(7)22(27)10-11-23-28(6)17-14-24(31)26(3,4)21(28)13-19-30(23,29)8/h20-24,31H,9-19H2,1-8H3/t20-,21-,22+,23+,24-,27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
BFNSRKHIVITRJP-VJBYBJRLSA-N

> <FORMULA>
C30H52O

> <MOLECULAR_WEIGHT>
428.7333

> <EXACT_MASS>
428.401816286

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.72896026218448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4aR,6aR,6bR,8aS,12aS,12bR,14aR,14bR)-4,4,6a,6b,9,9,12a,14b-octamethyl-docosahydropicen-3-ol

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
7.808720315666667

> <ALOGPS_LOGS>
-7.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.48943339017772

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351218351362649

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
131.0573

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahymanol

> <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  C   UNK     0      31.313 -11.416   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.593 -10.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.033 -10.677   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.593  -9.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.687 -11.426   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.915  -8.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.675 -12.966   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.255  -9.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.337 -12.956   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.033  -9.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.915 -11.467   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.313  -8.459   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.009 -13.736   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.255 -10.708   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.292 -13.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.650  -8.376   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.317 -10.592   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.878  -6.804   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.401  -9.789   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.631 -12.140   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.699  -9.948   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.861  -9.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.903 -12.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.915 -11.373   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      36.650  -6.772   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.255  -5.981   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.037 -15.057   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.558 -15.063   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      37.384  -9.660   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      38.129  -8.382   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      30.071 -12.229   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      32.585  -8.016   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      28.680 -14.149   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      35.193  -7.373   0.000  0.00  0.00           H+0
HETATM   35  O   UNK     0      37.928  -6.028   0.000  0.00  0.00           O+0
CONECT    1    2    3    9   19                                             
CONECT    2    1    4   11   20                                             
CONECT    3    1    5   10   31                                             
CONECT    4    2    6   12   32                                             
CONECT    5    3    7   17   21                                             
CONECT    6    4    8   18   22                                             
CONECT    7    5   13   15   33                                             
CONECT    8    6   14   16   34                                             
CONECT    9    1   13                                                       
CONECT   10    3   12                                                       
CONECT   11    2   14                                                       
CONECT   12    4   10                                                       
CONECT   13    7    9                                                       
CONECT   14    8   11                                                       
CONECT   15    7   23   27   28                                             
CONECT   16    8   25   29   30                                             
CONECT   17    5   24                                                       
CONECT   18    6   26                                                       
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23   15   24                                                       
CONECT   24   17   23                                                       
CONECT   25   16   26   35                                                  
CONECT   26   18   25                                                       
CONECT   27   15                                                            
CONECT   28   15                                                            
CONECT   29   16                                                            
CONECT   30   16                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35   25                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Gammaceran-3beta-ol	ChEBI
Gammaceran-3b-ol	Generator
Gammaceran-3β-ol	Generator
Wallichiniol	HMDB
Gammaceran-3-ol	HMDB

Chemical Formula

C₃₀H₅₂O

Average Mass

428.7333 Da

Monoisotopic Mass

428.40182 Da

IUPAC Name

(3S,4aR,6aR,6bR,8aS,12aS,12bR,14aR,14bR)-4,4,6a,6b,9,9,12a,14b-octamethyl-docosahydropicen-3-ol

Traditional Name

tetrahymanol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C30H52O/c1-25(2)15-9-16-27(5)20(25)12-18-29(7)22(27)10-11-23-28(6)17-14-24(31)26(3,4)21(28)13-19-30(23,29)8/h20-24,31H,9-19H2,1-8H3/t20-,21-,22+,23+,24-,27-,28-,29+,30+/m0/s1

InChI Key

BFNSRKHIVITRJP-VJBYBJRLSA-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
Adiantum pedatum	LOTUS Database	35616633
Alsophila spinulosa	LOTUS Database	35616633
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
Fossombronia pusilla	LOTUS Database	35616633
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
Oleandra wallichii	LOTUS Database	35616633
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
Tetrahymena pyriformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

pentacyclic triterpenoid (CHEBI:9493 )
Arborinane and stictane triterpenoids (C06083 )
Hopanes (C06083 )
Arborinane and stictane triterpenoids (LMPR0106210001 )

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	6.56	ALOGPS
logP	7.81	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	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	0	ChemAxon
Refractivity	131.06 m³·mol⁻¹	ChemAxon
Polarizability	54.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon