NP-MRD: Showing NP-Card for fucosterol (NP0264127)

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Record Information

Version

2.0

Created at

2022-09-08 07:33:04 UTC

Updated at

2022-09-08 07:33:05 UTC

NP-MRD ID

NP0264127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fucosterol

Description

Fucosterol 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. Thus, fucosterol is considered to be a sterol lipid molecule. fucosterol is found in Acanthus ilicifolius, Alitta succinea, Amaranthus tricolor, Amphilectus fucorum, Apis cerana, Arabidopsis thaliana, Carthamus tinctorius, Caulerpa taxifolia, Chara australis, Cystoseira barbata, Dictyopteris divaricata, Dictyota dichotoma, Dictyota fasciola, Dictyota mertensii, Dictyuchus monosporus, Diplopterygium glaucum, Dragmacidon lunaecharta, Durvillaea potatorum, Ecklonia cava, Ectyoplasia ferox, Eisenia bicyclis, Fucus vesiculosus, Fucus virsoides, Haliclona oculata, Helianthus annuus, Hydrodictyon reticulatum, Hymeniacidon perlevis, Kalanchoe petitiana, Leptogorgia viminalis, Olea europaea, Padina gymnospora, Panax quinquefolius, Petrosia ficiformis, Phaseolus vulgaris, Salpa thompsoni, Sarcophyton crassocaule, Sargassum fusiforme, Sargassum siliquastrum, Sargassum vachellianum, Setaria italica, Sinapis alba, Stypopodium flabelliforme, Tanacetum parthenium, Thalassiosira eccentrica, Thalassiosira pseudonana, Tridax procumbens, Trigonella caerulea, Turbinaria conoides, Turbinaria ornata, Tydemania expeditionis, Ulva lactuca, Ulva pertusa, Ulva rigida, Vanilla planifolia, Xestospongia testudinaria and Zea mays. fucosterol was first documented in 2003 (PMID: 14560919). Fucosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

fucosterol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
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 18 24  1  0  0  0  0
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 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
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M  END

fucosterol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
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 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0264127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/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/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
OSELKOCHBMDKEJ-JUGJNGJRSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.693184798774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R,5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
7.60

> <JCHEM_LOGP>
7.4388973106666665

> <ALOGPS_LOGS>
-6.74

> <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>
130.61609999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.48e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fucosterol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: fucosterol                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.421  -9.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.685  -7.662   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.311  -6.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.338  -2.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.815  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   11   14   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(24E)-24-N-Propylidenecholesterol	ChEBI
(3beta,24E)-Stigmasta-5,24(28)-dien-3-ol	ChEBI
(3beta,24E)-Stigmasta-5,24(28)-dien-ol	ChEBI
(e)-Stigmasta-5,24(28)-dien-3beta-ol	ChEBI
24E-Ethylidene-cholest-5-en-3beta-ol	ChEBI
Fucosterin	ChEBI
trans-24-Ethylidenecholesterol	ChEBI
(3b,24E)-Stigmasta-5,24(28)-dien-3-ol	Generator
(3Β,24E)-stigmasta-5,24(28)-dien-3-ol	Generator
(3b,24E)-Stigmasta-5,24(28)-dien-ol	Generator
(3Β,24E)-stigmasta-5,24(28)-dien-ol	Generator
(e)-Stigmasta-5,24(28)-dien-3b-ol	Generator
(e)-Stigmasta-5,24(28)-dien-3β-ol	Generator
24E-Ethylidene-cholest-5-en-3b-ol	Generator
24E-Ethylidene-cholest-5-en-3β-ol	Generator
24Z-Ethylidenecholest-5-en-3b-ol	MeSH
Fucosterol, 28-(14)C-labeled CPD, (e)-isomer	MeSH
delta(5)-Avenasterol	MeSH
Fucosterol, (3beta)-isomer	MeSH
24-Isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterol	MeSH
Stigmasta-5,24-dien-3 beta-ol	MeSH
28-Isofucosterol	MeSH

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R,5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

fucosterol

CAS Registry Number

Not Available

SMILES

C\C=C(/CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H48O/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/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

OSELKOCHBMDKEJ-JUGJNGJRSA-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
Acanthus ilicifolius	LOTUS Database	35616633
Alitta succinea	LOTUS Database	35616633
Amaranthus tricolor	LOTUS Database	35616633
Amphilectus fucorum	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Carthamus tinctorius	LOTUS Database	35616633
Caulerpa taxifolia	LOTUS Database	35616633
Chara australis	LOTUS Database	35616633
Cystoseira barbata	LOTUS Database	35616633
Dictyopteris divaricata	LOTUS Database	35616633
Dictyota dichotoma	LOTUS Database	35616633
Dictyota fasciola	LOTUS Database	35616633
Dictyota mertensii	LOTUS Database	35616633
Dictyuchus monosporus	LOTUS Database	35616633
Diplopterygium glaucum	LOTUS Database	35616633
Dragmacidon lunaecharta	LOTUS Database	35616633
Durvillaea potatorum	LOTUS Database	35616633
Ecklonia cava	LOTUS Database	35616633
Ectyoplasia ferox	LOTUS Database	35616633
Eisenia bicyclis	LOTUS Database	35616633
Fucus vesiculosus	LOTUS Database	35616633
Fucus virsoides	LOTUS Database	35616633
Haliclona oculata	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Hydrodictyon reticulatum	LOTUS Database	35616633
Hymeniacidon perlevis	LOTUS Database	35616633
Kalanchoe petitiana	LOTUS Database	35616633
Leptogorgia viminalis	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Padina gymnospora	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Petrosia ficiformis	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633
Sarcophyton crassocaule	LOTUS Database	35616633
Sargassum fusiforme	LOTUS Database	35616633
Sargassum siliquastrum	LOTUS Database	35616633
Sargassum vachellianum	LOTUS Database	35616633
Setaria italica	LOTUS Database	35616633
Sinapis alba	LOTUS Database	35616633
Stypopodium flabelliforme	LOTUS Database	35616633
Tanacetum parthenium	LOTUS Database	35616633
Thalassiosira eccentrica	LOTUS Database	35616633
Thalassiosira pseudonana	LOTUS Database	35616633
Tridax procumbens	LOTUS Database	35616633
Trigonella caerulea	LOTUS Database	35616633
Turbinaria conoides	LOTUS Database	35616633
Turbinaria ornata	LOTUS Database	35616633
Tydemania expeditionis	LOTUS Database	35616633
Ulva lactuca	LOTUS Database	35616633
Ulva pertusa	LOTUS Database	35616633
Ulva rigida	LOTUS Database	35616633
Vanilla planifolia Jacks.	LOTUS Database	35616633
Xestospongia testudinaria	LOTUS Database	35616633
Zea mays	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

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:27865 )
phytosterols (CHEBI:27865 )
stigmastane (C08817 )
Stigmasterols and C24-ethyl derivatives (C08817 )
Stigmastane and derivatives (C08817 )

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	7.6	ALOGPS
logP	7.44	ChemAxon
logS	-6.7	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	130.62 m³·mol⁻¹	ChemAxon
Polarizability	53.69 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

C00003653

Chemspider ID

Not Available

KEGG Compound ID

C08817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fucosterol

METLIN ID

Not Available

PubChem Compound

5281328

PDB ID

Not Available

ChEBI ID

27865

Good Scents ID

Not Available

References

General References

Lee S, Lee YS, Jung SH, Kang SS, Shin KH: Anti-oxidant activities of fucosterol from the marine algae Pelvetia siliquosa. Arch Pharm Res. 2003 Sep;26(9):719-22. doi: 10.1007/BF02976680. [PubMed:14560919 ]
LOTUS database [Link]

Showing NP-Card for fucosterol (NP0264127)

MOL for NP0264127 (fucosterol)

3D MOL for NP0264127 (fucosterol)

3D SDF for NP0264127 (fucosterol)

3D-SDF for NP0264127 (fucosterol)

PDB for NP0264127 (fucosterol)

3D PDB for NP0264127 (fucosterol)

SMILES for NP0264127 (fucosterol)

INCHI for NP0264127 (fucosterol)

Structure for NP0264127 (fucosterol)

3D Structure for NP0264127 (fucosterol)