Nomilin - analytical standard, ≥98% , CAS No.1063-77-0

CAS: 1063-77-0 Cat. No.: N115725 Molecular Weight: 514.56

GRADE & PURITY Analytical standard, ≥98%

Synonyms

CHEBI:7609 | NSC 297134 | AI3-00994 | (1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B,7,7,11A,13A-PENTAMETHYLOXIRENO(4,4A)-2-BENZOPYRAN(6,5-G)(2)BENZOXEPIN-3,5,9(3AH,4BH,6H)-TRIONE | C08773 | UNII-3AYA9KEC48 | n-Octadecano

Storage

Room temperature

Shipped In

Normal

Overview

Nomilin is a natural product isolated from grapefruit seed and varying Citrus fruits. The compound Nomilin is an inducer of Phase II detoxifying enzymes and inhibitor of chemically induced carcinogenesis. The compound has been observed to have 2.9-8.3 times the antioxidant activity when compared to Vitamin C. Nomilin has also been documented to inhibit HIV-1 injection in human mononuclear cells. In a dose dependent manner Nomilin has increased the activity of GST in the liver of rats.
A inducer of phase II detoxifying enzymes

Specifications

Synonyms

CHEBI:7609 | NSC 297134 | AI3-00994 | (1S, 3AS, 4AR, 4BR, 6AR, 11S, 11AR, 11BR, 13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B, 7, 7, 11A, 13A-PENTAMETHYLOXIRENO(4, 4A)-2-BENZOPYRAN(6, 5-G)(2)BENZOXEPIN-3, 5, 9(3AH, 4BH, 6H)-TRIONE | C08773 | UNII-3AYA9KEC48 | n-Octadecano

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Antiangiogenic and chemopreventive effects. Shows antitumor and immunomodulatory effects in vivo. Reduces serum VEGF. Orally active.

Storage

Room temperature

Shipped In

Normal

Grade

Analytical standard

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=O)OC1CC(=O)OC(C2C1(C3CCC4(C(OC(=O)C5C4(C3(C(=O)C2)C)O5)C6=COC=C6)C)C)(C)C
• IUPAC Name: [(1R,2R,4S,7S,8S,11R,12R,13S,18R)-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
• InChIKey: KPDOJFFZKAUIOE-WNGDLQANSA-N
• 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/t16-,17+,19+,21+,22-,25+,26-,27+,28-/m1/s1
• Isomeric SMILES: CC(=O)O[C@H]1CC(=O)OC([C@H]2[C@]1([C@H]3CC[C@]4([C@@H](OC(=O)[C@@H]5[C@@]4([C@@]3(C(=O)C2)C)O5)C6=COC=C6)C)C)(C)C
• Molecular Weight: 514.56
• Reaxy-Rn: 1673900
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1673900&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Limonoids
• Alternative Parents: Naphthopyrans Naphthalenes Tricarboxylic acids and derivatives Oxepanes 1,4-dioxepanes Delta valerolactones Pyrans Oxanes Heteroaromatic compounds Furans Carboxylic acid esters Ketones Oxacyclic compounds Dialkyl ethers Epoxides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: Triterpenoids (C30)

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in acetone, 100% ethanol (slightly), methanol (slightly), and ethyl acetate (slightly). Insoluble in water.
• Molecular Weight: 514.600 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 514.22 Da
• Monoisotopic Mass: 514.22 Da
• Topological Polar Surface Area: 122.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 1080.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Dan Yu, Fei Liu, Changdong Zou, Xiao Yang.  (2022)  Municipal green waste promotes iron release from steelmaking slag in water.  RESOURCES CONSERVATION AND RECYCLING,      [PMID:] [10.1016/j.resconrec.2022.106722]

2. Xing Liu, Mingzhu Xia, Xinyi Wu, Ruobing Chen, Yuting Peng, Yi Fan, Junjie Han, Yichun Zhao, Man Qu.  (2025)  Nomilin ameliorates perfluorooctanoic acid (PFOA)-induced impairment of zebrafish (Danio rerio) ocular development and visual function through PIK3CA activation.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:41297770] [10.1016/j.taap.2025.117660]