Plinabulin (NPI-2358) - ≥97% , Tubulin inhibitor, CAS No.714272-27-2, Tubulin inhibitor

CAS: 714272-27-2 Cat. No.: P126141 Molecular Weight: 336.39

GRADE & PURITY ≥97%

Synonyms

TRIBENOSIDE [MI] | DB05992 | 986FY7F8XR | HMS3884P14 | plinabulinum | Dibenzyl N, N-diisopropyl-phosphoramidite | Plinabulin(NPI-2358) | 2,5-Piperazinedione, 3-((5-(1,1-dimethylethyl)-1H-imidazol-4-yl)methylene)-6-(phenylmethylene)-, (3Z,6Z)- | BPI 2358 |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Plinabulin (NPI-2358) is a vascular disrupting agent (VDA) against tubulin-depolymerizing with IC50 of 9.8~18 nM in tumor cells. Phase 1/2.

Specifications

Synonyms

TRIBENOSIDE [MI] | DB05992 | 986FY7F8XR | HMS3884P14 | plinabulinum | Dibenzyl N, N-diisopropyl-phosphoramidite | Plinabulin(NPI-2358) | 2, 5-Piperazinedione, 3-((5-(1, 1-dimethylethyl)-1H-imidazol-4-yl)methylene)-6-(phenylmethylene)-, (3Z, 6Z)- | BPI 2358 |

Specifications & Purity

≥97%

Biochemical and Physiological Mechanisms

NPI-2358 (Plinabulin) is a novel vascular disrupting agent (VDA) with an IC50 of 15 nM against HT-29 cells. NPI-2358 binds to the colchicine-binding site of tubulin. NPI-2358 has potent in-vitro anti-tumor activity against various human t

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Mechanism of action

Tubulin inhibitor

Purity

≥97%

Product Properties

• ALogP: 2.8

Names and Identifiers

• Pubchem Sid: 504765142
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765142
• Canonical Smiles: CC(C)(C)C1=C(N=CN1)C=C2C(=O)NC(=CC3=CC=CC=C3)C(=O)N2
• IUPAC Name: (3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
• InChIKey: UNRCMCRRFYFGFX-TYPNBTCFSA-N
• INCHI: 1S/C19H20N4O2/c1-19(2,3)16-13(20-11-21-16)10-15-18(25)22-14(17(24)23-15)9-12-7-5-4-6-8-12/h4-11H,1-3H3,(H,20,21)(H,22,25)(H,23,24)/b14-9-,15-10-
• Isomeric SMILES: CC(C)(C)C1=C(N=CN1)/C=C\2/C(=O)N/C(=C\C3=CC=CC=C3)/C(=O)N2
• Molecular Weight: 336.39
• Reaxy-Rn: 21120913
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21120913&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrazines
• Alternative Parents: Benzene and substituted derivatives Imidazoles Heteroaromatic compounds Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Monocyclic benzene moiety - Pyrazine - Benzenoid - Azole - Imidazole - Heteroaromatic compound - Lactam - Azacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
• External Descriptors: Not available

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)

CYP2C9 Tchem Cytochrome P450 2C9 (1 Activities)

Discover Target: CYP2C9

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

RAF1 Tclin Serine/threonine-protein kinase RAF (4169 Activities)

Discover Target: RAF1

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)

Discover Target: MAPK10

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

LYN Tclin Tyrosine-protein kinase Lyn (4251 Activities)

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

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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BXPC-3 (2997 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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MES-SA (905 Activities)

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MES-SA/Dx5 (643 Activities)

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NCI-H1975 (4994 Activities)

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MOLT-4 (49676 Activities)

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PC-3 (62116 Activities)

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U-937 (7138 Activities)

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A549 (127892 Activities)

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NCI-H292 (733 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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HUVEC (11049 Activities)

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Jurkat (10389 Activities)

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NCI-H446 (443 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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CDK1 Tchem Cyclin-dependent kinase 1/cyclin B1 (1887 Activities)

Discover Target: CDK1

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

TUBA3C Tchem Tubulin alpha (84 Activities)

Discover Target: TUBA3C

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Carboxylesterase (379 Activities)

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Aspergillus fumigatus (16427 Activities)

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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Trichophyton rubrum (3646 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Epidermophyton floccosum (561 Activities)

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B16-F10 (4610 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Trichophyton mentagrophytes (4846 Activities)

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TUBB2B Tubulin (2175 Activities)

Discover Target: TUBB2B

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 67 mg/mL Water <1 mg/mL Ethanol <1 mg/mL
• Molecular Weight: 336.400 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 336.159 Da
• Monoisotopic Mass: 336.159 Da
• Topological Polar Surface Area: 86.900 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 597.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Shengrong Liao, Xiaochu Qin, Ding Li, Zhengchao Tu, Jinsheng Li, Xuefeng Zhou, Junfeng Wang, Bin Yang, Xiuping Lin, Juan Liu, Xianwen Yang, Yonghong Liu.  (2014)  Design and synthesis of novel soluble 2,5-diketopiperazine derivatives as potential anticancer agents.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:24960627] [10.1016/j.ejmech.2014.06.030]