Filipin III - Moligand™, ≥95% , CAS No.480-49-9

CAS: 480-49-9 Cat. No.: F286897 Molecular Weight: 654.83 EC Number: 637-175-3

GRADE & PURITY Moligand™, ≥95%

Synonyms

1',26-dihydroxyfilipin | U-5956 | Filimarisin | TK-336 | NSC3364 | NSC-3364 | 14-Deoxylagosin | FILIPIN DERIVATIVE | 1'-epi-filipin iv | GUDVQJXODNJRIJ-CALCHBBNSA-N | 4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-oxacyclooctacosa-17,1

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Filipin III is the major component of Filipin, a 28-membered ring pentaene macrolide antifungal antibiotic produced by S. filipinensis, S. avermitilis and S. miharaensis. Filipin interacts with membrane sterols causing the alteration of membrane structure

Specifications

Synonyms

1', 26-dihydroxyfilipin | U-5956 | Filimarisin | TK-336 | NSC3364 | NSC-3364 | 14-Deoxylagosin | FILIPIN DERIVATIVE | 1'-epi-filipin iv | GUDVQJXODNJRIJ-CALCHBBNSA-N | 4, 6, 8, 10, 12, 14, 16, 27-Octahydroxy-3-(1-hydroxyhexyl)-17, 28-dimethyl-oxacyclooctacosa-17, 1

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Polyene antibiotic. Binds sterols in fungal membranes. Also inhibits formation of the pathological form of prion protein (PrP-res) from the normal membrane-bound (PrP-sen) form. Also fluorescent cholesterol stain.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CCCCCC(C1C(CC(CC(CC(CC(CC(CC(C(=CC=CC=CC=CC=CC(C(OC1=O)C)O)C)O)O)O)O)O)O)O)O
• IUPAC Name: (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• InChIKey: IMQSIXYSKPIGPD-YQRUMEKGSA-N
• INCHI: 1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1
• Isomeric SMILES: CCCCC[C@H]([C@@H]1[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@@H](/C(=C/C=C/C=C/C=C/C=C/[C@@H]([C@H](OC1=O)C)O)/C)O)O)O)O)O)O)O)O
• Molecular Weight: 654.83
• Reaxy-Rn: 1339814
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1339814&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolides and analogues

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolides and analogues
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolides and analogues
• Alternative Parents: Fatty alcohols Secondary alcohols Lactones Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Macrolide - Fatty alcohol - Fatty acyl - Carboxylic acid ester - Lactone - Secondary alcohol - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Oxacycle - Carbonyl group - Organooxygen compound - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
• External Descriptors: olefinic compound - macrolide - polyol

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)

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

Associated Targets(non-human)

Escherichia coli (133304 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Bacillus cereus (7522 Activities)

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Candida albicans (78123 Activities)

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Penicillium digitatum (260 Activities)

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Colletotrichum (56 Activities)

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Botrytis (43 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 3.27, Max Conc. mM: 5
• Sensitivity: light sensitive；Moisture sensitive
• Molecular Weight: 654.800 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 654.398 Da
• Monoisotopic Mass: 654.398 Da
• Topological Polar Surface Area: 208.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 991.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 5
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 5
• Covalently-Bonded Unit Count: 1

References

1. Xucan Yang, Lulu Cheng, Yile Zhao, Haoran Ma, Haitao Song, Xuanmin Yang, Kang-Nan Wang, Yanrong Zhang.  (2023)  Aggregation-induced emission-active iridium (III)-based mitochondria-targeting nanoparticle for two-photon imaging-guided photodynamic therapy.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:38176241] [10.1016/j.jcis.2023.12.172]

2. Jianbo Li, Yaru Xu, Jieke Zhang, Qinglian Li, Chenxu Wang, Zhe Wu, Weijing Yang, Meng Xu, Zhenzhong Zhang, Lei Wang, Jinjie Zhang.  (2023)  Bioinspired fine-tuning of the mechanical rigidity of SNEDDS for the efficient crossing of multiple gastrointestinal barriers.  JOURNAL OF CONTROLLED RELEASE,      [PMID:37625600] [10.1016/j.jconrel.2023.08.044]

3. Peifu Xiao, Xiaoguang Tao, Hanxun Wang, Hongbing Liu, Yupeng Feng, Yueqi Zhu, Zhengzhen Jiang, Tian Yin, Yu Zhang, Haibing He, Jingxin Gou, Xing Tang.  (2023)  Enzyme/pH dual stimuli-responsive nanoplatform co-deliver disulfiram and doxorubicin for effective treatment of breast cancer lung metastasis.  Expert Opinion on Drug Delivery,      [PMID:37452715] [10.1080/17425247.2023.2237888]

4. Zhuxian Wang, Yaqi Xue, Quanfu Zeng, Zhaoming Zhu, Yuan Wang, Yufan Wu, Chunyan Shen, Hongxia Zhu, Cuiping Jiang, Li Liu, Qiang Liu.  (2021)  Glycyrrhiza acid-Licochalcone A complexes for enhanced bioavailability and anti-melanogenic effect of Licochalcone A: cellular uptake and in vitro experiments.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2021.103037]

5. Li Wu, Yan Shi, Zihui Ni, Tao Yu, Zhipeng Chen.  (2021)  Preparation of a Self-Assembled Rhein–Doxorubicin Nanogel Targeting Mitochondria and Investigation on Its Antihepatoma Activity.  MOLECULAR PHARMACEUTICS,      [PMID:34890210] [10.1021/acs.molpharmaceut.1c00565]

6. Dan Li, Gaoyang Yi, Guifang Cao, Adam C. Midgley, Yongli Yang, Dan Yang, Wenguang Liu, Yujuan He, Xiaolin Yao, Guoliang Li.  (2025)  Dual-Carriers of Tartary Buckwheat-Derived Exosome-Like Nanovesicles Synergistically Regulate Glucose Metabolism in the Intestine-Liver Axis.  Small,      [PMID:40079102] [10.1002/smll.202410124]

7. Yuxin Huang, Wenya Zhu, Jiaxin Zhang, Yichen Zhang, Yuxin Liu, Guowei Wang, Wuli Yang.  (2025)  Mitochondrial-Targeting Zwitterionic Nanomedicine Based on Tertiary Amine N-oxide Polymers for Triple-Negative Breast Cancer Therapy.  BIOMACROMOLECULES,      [PMID:40920025] [10.1021/acs.biomac.5c01461]