Didemnin B - ≥99% , CAS No.77327-05-0

CAS: 77327-05-0 Cat. No.: D647942 Molecular Weight: 1112.35 PubChem CID: 122651

GRADE & PURITY ≥99%

Synonyms

SCHEMBL1346816 | (2S)-N-[(1R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-12-hydroxy-3-isobutyl-8-isopropyl-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-13-[(1S)-1-methylpropyl]-2,5,7,10,15,19,22-heptaoxo-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-

Storage

Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Didemnin B is a depsipeptide extracted from the marine tunicate Trididemnin cyanophorum. Didemnin B can be used for the research of cancer.

In Vitro

Didemnin B has activity against miirine B16 melanoma, P388 leukemia, and M5076 sarcoma. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Didemnin B is a potent inhibitor of L1210 growth . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

SCHEMBL1346816 | (2S)-N-[(1R)-1-[[(3S, 6S, 8S, 12S, 13R, 16S, 17R, 20S, 23S)-12-hydroxy-3-isobutyl-8-isopropyl-20-[(4-methoxyphenyl)methyl]-6, 17, 21-trimethyl-13-[(1S)-1-methylpropyl]-2, 5, 7, 10, 15, 19, 22-heptaoxo-9, 18-dioxa-1, 4, 14, 21-tetrazabicyclo[21.3.0]hexacosan-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Didemnin B is a depsipeptide extracted from the marine tunicate Trididemnin cyanophorum. Didemnin B can be used for the research of cancer.

Storage

Desiccated, Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCC(C)C1C(CC(=O)OC(C(=O)C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)N1)NC(=O)C(CC(C)C)N(C)C(=O)C3CCCN3C(=O)C(C)O)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
• IUPAC Name: (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-[(2S)-2-hydroxypropanoyl]-N-methylpyrrolidine-2-carboxamide
• InChIKey: KYHUYMLIVQFXRI-SJPGYWQQSA-N
• INCHI: 1S/C57H89N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-36,39-44,46-47,49,65-66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,35-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
• Isomeric SMILES: CC[C@H](C)[C@@H]1[C@H](CC(=O)O[C@H](C(=O)[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]3CCCN3C(=O)[C@H](C)O)C)CC4=CC=C(C=C4)OC)C)CC(C)C)C)C(C)C)O
• Alternate CAS: 77327-05-0
• PubChem CID: 122651
• MeSH Entry Terms: didemnin A;didemnin A, N-(1-(2-hydroxy-1-oxopropyl)-L-prolyl)-, (S)-;didemnin A, N-(2-hydroxy-1-oxopropyl)-, (S)-;didemnin B;didemnin C;didemnin D;didemnin E;didemnins;NSC 325319;oncoprecipitin A
• Molecular Weight: 1112.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Depsipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Depsipeptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic depsipeptides
• Alternative Parents: Macrolide lactams Alpha amino acid esters Macrolactams Proline and derivatives Alpha amino acid amides Anisoles Pyrrolidinecarboxamides Methoxybenzenes N-acylpyrrolidines Phenoxy compounds Alkyl aryl ethers Alpha-acyloxy ketones Dicarboxylic acids and derivatives Cyclic carboximidic acids Tertiary carboxylic acid amides Lactones Lactams Secondary alcohols Cyclic ketones Carboxylic acid esters Polyols Azacyclic compounds Oxacyclic compounds Propargyl-type 1,3-dipolar organic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cyclic depsipeptide - Macrolide lactam - Alpha-amino acid ester - Proline or derivatives - Macrolactam - Alpha-amino acid amide - Alpha-amino acid or derivatives - Phenoxy compound - Anisole - Methoxybenzene - N-acylpyrrolidine - Phenol ether - Pyrrolidine carboxylic acid or derivatives - Pyrrolidine-2-carboxamide - Alkyl aryl ether - Alpha-acyloxy ketone - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Pyrrolidine - Cyclic carboximidic acid - Tertiary carboxylic acid amide - Carboxylic acid ester - Carboxamide group - Ketone - Lactam - Lactone - Secondary alcohol - Cyclic ketone - Oxacycle - Carboximidic acid - Carboximidic acid derivative - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Ether - Polyol - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
• External Descriptors: cyclodepsipeptide

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)

HT-29 (80576 Activities)

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

SK-MEL-28 (48833 Activities)

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

Associated Targets(non-human)

Oryctolagus cuniculus (11301 Activities)

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

P388 (20296 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (89.90 mM; Need ultrasonic)
• Molecular Weight: 1112.400 g/mol
• XLogP3: 5.500
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 15
• Exact Mass: 1111.64 Da
• Monoisotopic Mass: 1111.64 Da
• Topological Polar Surface Area: 288.000 Ų
• Heavy Atom Count: 79
• Formal Charge: 0
• Complexity: 2150.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 13
• 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