NP-MRD: Showing NP-Card for 22-Dehydroclerosterol (NP0137008)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:51 UTC

Updated at

2022-05-30 16:38:51 UTC

NP-MRD ID

NP0137008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-Dehydroclerosterol

Description

22-Dehydroclerosterol, also known as ethylbenzylamine or N,N-dibenzyl ethyl amine, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 22-Dehydroclerosterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 22-dehydroclerosterol has been detected, but not quantified in, green vegetables. This could make 22-dehydroclerosterol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241216042D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241216042D          

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M  END
> <DATABASE_ID>
NP0137008

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,20-21,23-27,30H,2,7,11-18H2,1,3-6H3/b9-8+

> <INCHI_KEY>
ZTJFINKUHDHOSM-CMDGGOBGSA-N

> <FORMULA>
C29H46O

> <MOLECULAR_WEIGHT>
410.6749

> <EXACT_MASS>
410.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.52449750623356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-[(3E)-5-ethyl-6-methylhepta-3,6-dien-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
7.19

> <JCHEM_LOGP>
7.134909324333332

> <ALOGPS_LOGS>
-6.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.66019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-[(3E)-5-ethyl-6-methylhepta-3,6-dien-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.929  -1.991   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.595  -1.221   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.258  -1.991   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.258  -0.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.613  -3.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.934  -4.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.258  -3.541   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.595  -4.305   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.929  -3.526   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.269  -4.305   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.203   2.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.230   1.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.736   1.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.218   3.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.195   4.305   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.083   1.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.245   0.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.590   1.078   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.934   0.303   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.934  -1.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.613  -2.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.245  -1.252   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.202  -1.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.113  -0.493   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.202   0.757   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.697   2.219   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.673   3.369   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.277  -0.916   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.760   0.544   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.269   0.857   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7   20                                             
CONECT    4    3                                                            
CONECT    5    6   21                                                       
CONECT    6    5    7                                                       
CONECT    7    3    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12   26                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22   25                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    3   19   21                                                  
CONECT   21    5   20   22                                                  
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   17   24   26                                                  
CONECT   26   11   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   13   28   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Ethylbenzylamine	HMDB
N,N-Dibenzyl ethyl amine	HMDB
N,N-Dibenzyl-N-ethylamine	HMDB
N-Ethyl-N-(phenylmethyl)-benzenemethanamine	HMDB
N-Ethyldibenzylamine	HMDB
Poriferasta-5,22E,25-trien-3b-ol	HMDB

Chemical Formula

C₂₉H₄₆O

Average Mass

410.6749 Da

Monoisotopic Mass

410.35487 Da

IUPAC Name

14-[(3E)-5-ethyl-6-methylhepta-3,6-dien-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

14-[(3E)-5-ethyl-6-methylhepta-3,6-dien-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

CCC(\C=C\C(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)=C

InChI Identifier

InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,20-21,23-27,30H,2,7,11-18H2,1,3-6H3/b9-8+

InChI Key

ZTJFINKUHDHOSM-CMDGGOBGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	7.19	ALOGPS
logP	7.13	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	18.2	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	130.66 m³·mol⁻¹	ChemAxon
Polarizability	51.52 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

HMDB0034078

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012337

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15608664

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 22-Dehydroclerosterol (NP0137008)

MOL for NP0137008 (22-Dehydroclerosterol)

3D MOL for NP0137008 (22-Dehydroclerosterol)

3D SDF for NP0137008 (22-Dehydroclerosterol)

3D-SDF for NP0137008 (22-Dehydroclerosterol)

PDB for NP0137008 (22-Dehydroclerosterol)

3D PDB for NP0137008 (22-Dehydroclerosterol)

SMILES for NP0137008 (22-Dehydroclerosterol)

INCHI for NP0137008 (22-Dehydroclerosterol)

Structure for NP0137008 (22-Dehydroclerosterol)

3D Structure for NP0137008 (22-Dehydroclerosterol)