ContaminantDB: Nomilin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 01:18:53 UTC

Update Date

2016-11-09 01:18:55 UTC

Accession Number

CHEM029654

Identification

Common Name

Nomilin

Class

Small Molecule

Description

Constituent of grapefruit (Citrus paradisi). Nomilin is found in lemon, sweet orange, and citrus.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(Acetyloxy)-1,2-dihydroobacunoic acid .epislon.-lactone	HMDB
1-(Acetyloxy)-1,2-dihydroobacunoic acid eta-lactone	HMDB
Obacunoic acid, 1-(acetyloxy)-1,2-dihydro-, eta-lactone	HMDB
7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetic acid	Generator
Nomilin	MeSH

Chemical Formula

C₂₈H₃₄O₉

Average Molecular Mass

514.564 g/mol

Monoisotopic Mass

514.220 g/mol

CAS Registry Number

1063-77-0

IUPAC Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetate

Traditional Name

7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetate

SMILES

CC(=O)OC1CC(=O)OC(C)(C)C2CC(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C

InChI Identifier

InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3

InChI Key

KPDOJFFZKAUIOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Caprolactone
1,4-dioxepane
Delta valerolactone
Dioxepane
Oxepane
Delta_valerolactone
Pyran
Oxane
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	3.59	ALOGPS
logP	3.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	17.84	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	125.61 m³·mol⁻¹	ChemAxon
Polarizability	52.45 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-075c-4042900000-fc535c0f11729f4239e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0000940000-e3c7abba890a6b92fd3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ac9-1005900000-c2ec1f5596e3673813d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9214300000-ac3dee9f3fded529d9f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02t9-1000930000-45a049d6ce0b3536f997	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0mxs-2000910000-3108b08c8b322c3f15c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4j-9004500000-4830d9a5ba4d4894b690	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000970000-6f49114931a3dd525b19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-0002910000-51b960020631aa9bcb47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q0-0589610000-2a37c04043727994c609	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0006690000-794552605e05e3cce0ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000100000-963e39539283fd2e73fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000300000-95c2c9a1289acbeb9a9c	Spectrum