Phorbol 12,13-dibutyrate - Moligand™,≥98% , CAS No.37558-16-0

CAS: 37558-16-0 Cat. No.: P276207 Molecular Weight: 504.61 EC Number: 636-433-2 PubChem CID: 37783

GRADE & PURITY Moligand™, ≥98%

Synonyms

Butanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa[3,4]benz[1,2-e]azulene-9,9a-diyl ester | PDBU | Phorbol dibutyrate

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Phorbol 12,13-dibutyrate (Phorbol dibutyrate) is a PKC activator and a potent skin tumor promoter.

Specifications

Synonyms

Butanoic acid, (1aR, 1bS, 4aR, 7aS, 7bS, 8R, 9R, 9aS)-1, 1a, 1b, 4, 4a, 5, 7a, 7b, 8, 9-decahydro-4a, 7b-dihydroxy-3-(hydroxymethyl)-1, 1, 6, 8-tetramethyl-5-oxo-9aH-cyclopropa[3, 4]benz[1, 2-e]azulene-9, 9a-diyl ester | PDBU | Phorbol dibutyrate

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

12, 13-Dibutyrate (PDBu) is a potent activator of protein kinase C (PKC). Its hydrophilicity is higher than that of phorbol 12 myristate 13 acetate (PMA), which facilitates the washing of PDBu out of cells in tissue culture. PDBu can activate the expressi

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

ACTIVATOR

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: CCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)CCC)O)C
• IUPAC Name: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
• InChIKey: BQJRUJTZSGYBEZ-YVQNUNKESA-N
• INCHI: 1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1
• Isomeric SMILES: CCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)CCC)O)C
• PubChem CID: 37783
• UN Number: 2928
• Packing Group: I
• Molecular Weight: 504.61

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids
        • Level5 Tigliane and ingenane diterpenoids
          • Level6 Phorbol esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Tigliane and ingenane diterpenoids
• Direct Parent: Phorbol esters
• Alternative Parents: Fatty acid esters Dicarboxylic acids and derivatives Tertiary alcohols Ketones Cyclic alcohols and derivatives Carboxylic acid esters Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Phorbol ester - Fatty acid ester - Dicarboxylic acid or derivatives - Fatty acyl - Cyclic alcohol - Tertiary alcohol - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Carbonyl group - Organooxygen compound - Primary alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.
• External Descriptors: Tigliane and ingenane diterpenoids

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)

PRKCD Tclin Protein kinase C delta type (10 Activities)

Discover Target: PRKCD

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

PRKCB Tchem Protein kinase C beta type (9 Activities)

Discover Target: PRKCB

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

PRKCE Tchem Protein kinase C epsilon type (11 Activities)

Discover Target: PRKCE

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

PRKCH Tchem Protein kinase C eta type (9 Activities)

Discover Target: PRKCH

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

VAV1 Tchem Proto-oncogene vav (1 Activities)

Discover Target: VAV1

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

PRKCG Tchem Protein kinase C gamma type (8 Activities)

Discover Target: PRKCG

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

PRKCA Tchem Protein kinase C alpha type (13 Activities)

Discover Target: PRKCA

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

PRKCQ Tchem Protein kinase C theta type (5 Activities)

Discover Target: PRKCQ

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

PRKCE Tchem Protein kinase C epsilon (1520 Activities)

Discover Target: PRKCE

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

PRKCG Tchem Protein kinase C gamma (2471 Activities)

Discover Target: PRKCG

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

PRKCH Tchem Protein kinase C eta (1863 Activities)

Discover Target: PRKCH

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

PRKCA Tchem Protein kinase C alpha (5923 Activities)

Discover Target: PRKCA

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

TRPV4 Tchem Transient receptor potential cation channel subfamily V member 4 (774 Activities)

Discover Target: TRPV4

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

PRKCQ Tchem Protein kinase C theta (3319 Activities)

Discover Target: PRKCQ

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

HL-60 (67320 Activities)

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

RASGRP3 Tchem RAS guanyl releasing protein 3 (130 Activities)

Discover Target: RASGRP3

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

Discover Target: ATAD5

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

Associated Targets(non-human)

Prkcd Protein kinase C delta (192 Activities)

Discover Target: Prkcd

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

Prkcb Protein kinase C beta (2 Activities)

Discover Target: Prkcb

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

Human immunodeficiency virus 1 (70413 Activities)

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

Human immunodeficiency virus 2 (5592 Activities)

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

C3H 10T1/2 (488 Activities)

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

W4 (10 Activities)

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

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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 DMSO to 50 mM and in ethanol to 25 mM
• Sensitivity: Light sensitive
• Molecular Weight: 504.600 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 504.272 Da
• Monoisotopic Mass: 504.272 Da
• Topological Polar Surface Area: 130.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 1030.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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