Livestock Metabolome Database: Showing metabocard for Lanosterin (LMDB00309)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:00 UTC

Update Date

2016-07-20 20:52:58 UTC

Lmdb

LMDB00309

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lanosterin

Description

Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide.(wikipedia).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta)-Lanosta-8,24-dien-3-ol	ChEBI
(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-ol	ChEBI
4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol	ChEBI
(3b)-Lanosta-8,24-dien-3-ol	Generator
(3β)-Lanosta-8,24-dien-3-ol	Generator
(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-ol	Generator
(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-ol	Generator
4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-ol	Generator
4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-ol	Generator
(3 beta)-Lanosta-8,24-dien-3-ol	HMDB
(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol	HMDB
(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol	HMDB
Botalan base 138	HMDB
Lanosta-8,24-dien-3-ol	HMDB
Lanosta-8,24-dien-3beta-ol	HMDB
Lanosta-8,24-dienol	HMDB
Lanosterol	HMDB
Lanster	HMDB
4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol	MeSH, HMDB
Kryptosterol	MeSH, HMDB
Lanosterin	ChEBI
3beta-Hydroxy-lansota-8,24-dien-21-oic acid	HMDB
3beta-Hydroxylanosta-8,24-diene	HMDB
3β-Hydroxy-lansota-8,24-dien-21-oic acid	HMDB
3β-Hydroxylanosta-8,24-diene	HMDB
4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-ol	HMDB
4,4,14α-Trimethylcholesta-8,24-dien-3β-ol	HMDB
5alpha-Lanosta-8,24-dien-3beta-ol	HMDB
5α-Lanosta-8,24-dien-3β-ol	HMDB
Lanosta-8,24-dien-3β-ol	HMDB
Lanostadien-3beta-ol	HMDB
Lanostadien-3β-ol	HMDB

Chemical Formula

C₃₀H₅₀O

Average Molecular Weight

426.7174

Monoisotopic Molecular Weight

426.386166222

IUPAC Name

(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

Traditional Name

(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

CAS Registry Number

79-63-0

SMILES

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

InChI Identifier

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

InChI Key

CAHGCLMLTWQZNJ-BQNIITSRSA-N

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
14-alpha-methylsteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:16521 )
tetracyclic triterpenoid (CHEBI:16521 )
Cholesterol and derivatives (C01724 )
Cholesterol and derivatives (LMST01010017 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

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	7.72	ALOGPS
logP	7.71	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	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	4	ChemAxon
Refractivity	134.54 m³·mol⁻¹	ChemAxon
Polarizability	55.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-2953300000-ae1832f19369485ff53c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0aou-9820200000-573525b346ad3c9eef59	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4l-4910000000-0fe7f84c95ab0a849fe9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-2910000000-c67a1f122f33698a14f6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dj-1009400000-e2b516142f5128a7b5f6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-3002900000-35e63c0bf6f033cb847c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 1V, positive	splash10-0a6r-0110900000-5e42e1f2d9ad534c003c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0a4i-0230900000-10f58fa6e118cd7c5997	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, positive	splash10-0a4i-1791800000-178153ad92eececb33c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, positive	splash10-0a4i-2980300000-6ce95c7f8b15b35475af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, positive	splash10-0a4j-2950100000-48f86ff7a22c596aa44d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-0592-3940000000-c35d0cb6a2e4e291e8f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, positive	splash10-0592-3920000000-d717fdd3322a881bef99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, positive	splash10-0592-4910000000-4c6d07e3a8e48ae88580	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, positive	splash10-0a4j-5900000000-4c8b72037dbeae9a46d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 52V, positive	splash10-067m-8900000000-522b8688d50362297c41	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 62V, positive	splash10-0aou-9700000000-70d433827c1a6dab0c41	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 76V, positive	splash10-05ox-9500000000-5b122dea636d3e3b5916	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 90V, positive	splash10-05r3-9500000000-0c1c5cbd994f8406f30e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 111V, positive	splash10-05r3-9600000000-5cb8ae11d071fa19f206	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 29V, positive	splash10-0ktf-0392000000-03cda521ce6e102d92e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 29V, positive	splash10-059j-2900000000-8086693fb040e5ed7501	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 29V, positive	splash10-0a4i-4900000000-c58ff2dc28c6ba639997	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 29V, positive	splash10-01vk-0900000000-805937445cceda0cd70a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 29V, positive	splash10-0aor-0900000000-22d304b445b737121aa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0002900000-2cfcf7ce4b5b21140eae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pdi-2139500000-9a25961000db9796d6da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-4259100000-9f7f26265abec4122e35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-77a57cecc2069bee1926	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-5b0f06bf8120e780e30c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-1009400000-421e305d47b29da427d2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05mo-9731200000-b1bc6bb68e352e3bd687	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected and Quantified	9.75+/-1.64 mg/100g fat	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	Park, Y. W; Juáre...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details