zymosterol intermediate 1c (YMDB00607)

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Identification

YMDB ID

YMDB00607

Name

zymosterol intermediate 1c

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

zymosterol intermediate 1c belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. zymosterol intermediate 1c is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Zymosterol intermediic acid 1C

CAS number

Not Available

Weight

Average: 426.6743
Monoisotopic: 426.349780716

InChI Key

GGLAWNOISZYLHT-FICDAWEZSA-N

InChI

InChI=1S/C29H46O2/c1-18(2)8-7-9-19(3)22-12-13-23-21-10-11-25-27(20(4)30)26(31)15-17-29(25,6)24(21)14-16-28(22,23)5/h8,19,22-23,25-27,31H,7,9-17H2,1-6H3/t19-,22-,23+,25+,26+,27?,28-,29-/m1/s1

IUPAC Name

1-[(2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-6-yl]ethan-1-one

Traditional IUPAC Name

zymosterol intermediate 1c

Chemical Formula

C₂₉H₄₆O₂

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C(C)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-hydroxysteroid
Hydroxysteroid
15-oxosteroid
Oxosteroid
3-beta-hydroxysteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

ketone (CHEBI:52389 )
Cholesterol and derivatives (LMST01010170 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.08	ALOGPS
logP	6.37	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.84 m³·mol⁻¹	ChemAxon
Polarizability	53.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

NADP + zymosterol intermediate 1c ↔ zymosterol intermediate 2 + Carbon dioxide + NADPH + hydron

zymosterol intermediate 1b + NADPH + hydron + oxygen ↔ NADP + zymosterol intermediate 1c + water

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0003900000-c8633ce99b3bd2ab4e4c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ar0-2139500000-2495705d9c6b28c661ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0hg9-3129100000-aa1b66ad19cbc07b9875	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-8d6e236c0015809927c0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0002900000-290ba0316ce1561ed4f5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-1009300000-68c0c7e47f186c76e998	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	52389
HMDB ID	Not Available
Pubchem Compound ID	25271596
Kegg ID	Not Available
ChemSpider ID	23107010
FOODB ID	Not Available
Wikipedia	Zymosterol
BioCyc ID	Not Available

Enzymes

Protein Details

1. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest- 7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha- cholest-7-en-3-one + CO(2) + NAD(P)H
Gene Name:: ERG26
Uniprot ID:: P53199
Molecular weight:: 38706.10156

Reactions

3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + CO(2) + NAD(P)H.

Protein Details

2. C-4 methylsterol oxidase

General function:: Involved in iron ion binding
Specific function:: Catalyzes the first step in the removal of the two C-4 methyl groups of 4,4-dimethylzymosterol
Gene Name:: ERG25
Uniprot ID:: P53045
Molecular weight:: 36478.89844

Reactions

4,4-dimethyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)(+) + H(2)O.
4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)(+) + 2 H(2)O.
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) + H(2)O.

Structure for #<Compound:0xab9c4ec8>

Enzymes

Reactions

Reactions