NP-MRD: Showing NP-Card for (z)-24-ethylidenelophenol (NP0248114)

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Record Information

Version

2.0

Created at

2022-09-07 10:14:18 UTC

Updated at

2022-09-07 10:14:18 UTC

NP-MRD ID

NP0248114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z)-24-ethylidenelophenol

Description

(Z)-24-ethylidenelophenol, also known as alpha1-sitosterol, 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. (z)-24-ethylidenelophenol is found in Baccharoides anthelmintica, Betula pendula, Bryonia dioica, Camellia sinensis, Canavalia ensiformis, Cheiropleuria bicuspis, Leucanthemum vulgare, Elaeagnus angustifolia, Euphorbia peplus, Euphorbia sapinii, Gleichenia japonica, Gynostemma pentaphyllum, Hippophae rhamnoides, Mangifera indica, Musa paradisiaca, Neolitsea aciculata, Nigella sativa, Olea europaea, Panax ginseng, Panax quinquefolius, Phaseolus vulgaris, Polypodium formosanum, Schisandra chinensis, Sesamum indicum, Sesamum radiatum, Solanum melongena, Symphoricarpos albus, Vigna angularis, Vitis vinifera and Yucca gloriosa. Thus, (Z)-24-ethylidenelophenol is considered to be a sterol lipid molecule (Z)-24-ethylidenelophenol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007332D          

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M  END

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M  END


  Mrv1652309272007332D          

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10000.049710001.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.763310000.4796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.478110000.8916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17  4  1  6  0  0  0
 16  5  1  1  0  0  0
 19  1  1  1  0  0  0
 18 12  1  0  0  0  0
 18  6  1  6  0  0  0
 10  7  1  6  0  0  0
 10 19  1  0  0  0  0
 13 11  2  0  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
 34 35  1  6  0  0  0
 34 24  1  0  0  0  0
 34 20  1  0  0  0  0
 34 23  1  0  0  0  0
 11 21  1  0  0  0  0
 21  3  1  6  0  0  0
  8 20  1  0  0  0  0
 20  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0248114

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24-,25+,26+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
LPZCCMIISIBREI-JXMPMKKESA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.66526384346601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.85

> <JCHEM_LOGP>
7.803870137000004

> <ALOGPS_LOGS>
-6.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.957638198850066

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0677290518229814

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
135.08769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.56e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8662.6338666.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6228668.634   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8666.6228664.004   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0    8661.3038660.897   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8658.6368662.445   0.000  0.00  0.00           O+0
HETATM    6  H   UNK     0    8662.6338661.673   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8663.9638664.004   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8665.2938667.856   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.9598667.086   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.9598665.546   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.2938664.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.9638662.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2978663.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.3018665.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8659.9678664.760   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.9678663.220   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.3018662.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.6348663.220   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.6348664.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278667.086   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6278665.546   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0918665.070   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.9978666.316   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918669.102   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4278669.872   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.7608669.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.0958669.872   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0958671.412   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4318672.182   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8670.7608672.182   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4318669.102   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8674.7648669.872   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.7598669.872   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8668.0918667.562   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0    8669.4268668.331   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   17                                                            
CONECT    5   16                                                            
CONECT    6   18                                                            
CONECT    7   10                                                            
CONECT    8    9   20                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    7   19                                             
CONECT   11   10   13   21                                                  
CONECT   12   13   18                                                       
CONECT   13   12   11                                                       
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    5                                                  
CONECT   17   16   18    4                                                  
CONECT   18   17   19   12    6                                             
CONECT   19   14   18    1   10                                             
CONECT   20   21   34    8    2                                             
CONECT   21   20   22   11    3                                             
CONECT   22   21   23                                                       
CONECT   23   22   34                                                       
CONECT   24   25   33   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34   35   24   20   23                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(3beta,5alpha)-4-Methylstigmasta-7,24(28)-dien-3-ol	ChEBI
alpha1-Sitosterol	ChEBI
4-alpha-Methyl-5-alpha-stigmasta-7,Z-24-dien-3-beta-ol	Kegg
(3b,5a)-4-Methylstigmasta-7,24(28)-dien-3-ol	Generator
(3Β,5α)-4-methylstigmasta-7,24(28)-dien-3-ol	Generator
a1-Sitosterol	Generator
Α1-sitosterol	Generator
4-a-Methyl-5-a-stigmasta-7,Z-24-dien-3-b-ol	Generator
4-Α-methyl-5-α-stigmasta-7,Z-24-dien-3-β-ol	Generator
(Z)-24-Ethylidenelophenol	KEGG
Citrostadienol	PhytoBank
(3beta,4alpha,5alpha,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol	PhytoBank
(3β,4α,5α,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol	PhytoBank
24-Ethylidenelophenol	PhytoBank
5alpha-Sitosterol	PhytoBank
5α-Sitosterol	PhytoBank
Citrastadienol	PhytoBank

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

Traditional Name

(1R,2S,5S,6S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C

InChI Identifier

InChI=1S/C30H50O/c1-8-22(19(2)3)10-9-20(4)24-13-14-26-23-11-12-25-21(5)28(31)16-18-30(25,7)27(23)15-17-29(24,26)6/h8,11,19-21,24-28,31H,9-10,12-18H2,1-7H3/b22-8-/t20-,21+,24-,25+,26+,27+,28+,29-,30+/m1/s1

InChI Key

LPZCCMIISIBREI-JXMPMKKESA-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

Species Name	Source	Reference
Baccharoides anthelmintica	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Bryonia dioica	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Canavalia ensiformis	LOTUS Database	35616633
Cheiropleuria bicuspis	LOTUS Database	35616633
Chrysanthemum vulgare	LOTUS Database	35616633
Elaeagnus angustifolia	LOTUS Database	35616633
Euphorbia Euphorbia peplus	LOTUS Database	35616633
Euphorbia sapinii	LOTUS Database	35616633
Gleichenia japonica	LOTUS Database	35616633
Gynostemma pentaphyllum	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Musa paradisiaca	LOTUS Database	35616633
Neolitsea aciculata	LOTUS Database	35616633
Nigella sativa	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Polypodium formosanum	LOTUS Database	35616633
Schisandra chinensis	LOTUS Database	35616633
Sesamum indicum	LOTUS Database	35616633
Sesamum radiatum	LOTUS Database	35616633
Solanum melongena	LOTUS Database	35616633
Symphoricarpos albus	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Yucca gloriosa	LOTUS Database	35616633

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
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:33203 )
Stigmasterols and C24-ethyl derivatives (C11523 )
Stigmasterols and C24-ethyl derivatives (LMST01040144 )

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	7.85	ALOGPS
logP	7.8	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-1.1	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	135.09 m³·mol⁻¹	ChemAxon
Polarizability	55.67 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007321

Chemspider ID

Not Available

KEGG Compound ID

C11523

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548595

PDB ID

Not Available

ChEBI ID

33203

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (z)-24-ethylidenelophenol (NP0248114)

MOL for NP0248114 ((z)-24-ethylidenelophenol)

3D MOL for NP0248114 ((z)-24-ethylidenelophenol)

3D SDF for NP0248114 ((z)-24-ethylidenelophenol)

3D-SDF for NP0248114 ((z)-24-ethylidenelophenol)

PDB for NP0248114 ((z)-24-ethylidenelophenol)

3D PDB for NP0248114 ((z)-24-ethylidenelophenol)

SMILES for NP0248114 ((z)-24-ethylidenelophenol)

INCHI for NP0248114 ((z)-24-ethylidenelophenol)

Structure for NP0248114 ((z)-24-ethylidenelophenol)

3D Structure for NP0248114 ((z)-24-ethylidenelophenol)