12-O-tetradecanoylphorbol-13-acetate (Q416716)

diester of an unsaturated, polycyclic compound

phorbol 12-myristate 13-acetate
tetradecanoylphorbol acetate
tetradecanoyl phorbol acetate
TPA
PMA
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate
Tetradecanoylphorbol Acetate
phorbol 13-acetate 12-myristate
phorbol myristate acetate
12-O-Tetradecanoylphorbol-13-acetate
12-myristate 13-acetate phorbol

Language	Label	Description	Also known as
English	12-O-tetradecanoylphorbol-13-acetate	diester of an unsaturated, polycyclic compound	phorbol 12-myristate 13-acetate tetradecanoylphorbol acetate tetradecanoyl phorbol acetate TPA PMA (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate Tetradecanoylphorbol Acetate phorbol 13-acetate 12-myristate phorbol myristate acetate 12-O-Tetradecanoylphorbol-13-acetate 12-myristate 13-acetate phorbol

Statements

instance of

type of chemical entity

0 references

0 references

0 references

response to phorbol 13-acetate 12-myristate

subject has role

reactant

1 reference

stated in

Gene Ontology release 2019-11-16

cellular response to phorbol 13-acetate 12-myristate

subject has role

reactant

1 reference

stated in

Gene Ontology release 2019-11-16

chemical structure

12-O-Tetradecanoylphorbol-13-acetate.svg
798 × 365; 39 KB

1 reference

imported from Wikimedia project

German Wikipedia

Phorbol 12-myristate 13-acetate.png
1,241 × 921; 24 KB

0 references

mass

616.397519±0 dalton

1 reference

language of work or name

English

retrieved

26 September 2016

chemical formula

C₃₆H₅₆O₈

1 reference

language of work or name

English

retrieved

26 September 2016

canonical SMILES

O=C(OC12C(OC(=O)CCCCCCCCCCCCC)C(C)C3(O)C(C=C(CO)CC4(O)C(=O)C(=CC43)C)C1C2(C)C)C

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isomeric SMILES

C=1[C@]2([C@]3([C@@]([C@H](OC(=O)CCCCCCCCCCCCC)[C@H]([C@@]2([C@]4([C@@](C(=O)C(=C4)C)(CC1CO)O)[H])O)C)(C3(C)C)OC(=O)C)[H])[H]

0 references

1 reference

24 September 2016

http://identifiers.org/wikipathways/WP1984_r82941

Croton tiglium

8 references

stated in

Anti-HIV-1 phorbol esters from the seeds of Croton tiglium

stated in

Effects of diterpene esters of tigliane, daphnane, ingenane, and lathyrane types on pink bollworm,Pectinophora gossypiella saunders (Lepidoptera: Gelechiidae).

stated in

Anti-HIV-1 phorbol esters from the seeds of Croton tiglium

stated in

Phorbol diester constituents of croton oil: separation by two-dimensional TLC and rapid purification utilizing reversed-phase overpressure layer chromatography (RP-OPLC)

stated in

Rotation Locular Countercurrent Chromatography and Quantitative1H-Nuclear Magnetic Resonance Spectroscopy of the Phorbol Ester Constituents of Croton Oil

stated in

Cytotoxic phorbol esters of Croton tiglium

stated in

Detoxification of Croton tiglium L. seeds by Ayurvedic process of Śodhana

stated in

Anti-HIV-1 phorbol esters from the seeds of Croton tiglium

Croton alnifolius

1 reference

stated in

Isolation of cytotoxic metabolites from targeted peruvian amazonian medicinal plants.

Euphorbia turczaninowii

1 reference

stated in

New jatrophane diterpenoid esters from Euphorbia turczaninowii

Wisteria brachybotrys

1 reference

stated in

Studies on inhibitors of skin tumor promotion, III. Inhibitory effects of isoflavonoids from Wisteria brachybotrys on Epstein-Barr virus activation

Leptolyngbya tenuis

1 reference

stated in

Inhibition of 12-O-tetradecanoylphorbol-13-acetate promoted mouse skin papilloma by digalactosyl diacylglycerols from the fresh water cyanobacterium Phormidium tenue

Iris tectorum

1 reference

stated in

28-deacetylbelamcandal, a tumor-promoting triterpenoid from Iris tectorum

subject has role

carcinogen

1 reference

stated in

Medical Subject Headings

MeSH descriptor ID

D013755

retrieved

15 March 2018

Identifiers

InChI

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

0 references

InChIKey

PHEDXBVPIONUQT-RGYGYFBISA-N

1 reference

stated in

ChEBI release 2020-09-01

CAS Registry Number

16561-29-8

2 references

imported from Wikimedia project

German Wikipedia

InChIKey

PHEDXBVPIONUQT-RGYGYFBISA-N

10 April 2021

https://commonchemistry.cas.org/detail?cas_rn=16561-29-8

0 references

1 reference

language of work or name

English

retrieved

26 September 2016

Reaxys registry number

2407201

0 references

ChEBI ID

37537

mapping relation type

exact match

0 references

ChEMBL ID

CHEMBL279115

1 reference

imported from Wikimedia project

1 reference

splash10-0wmi-1149300000-bafadaacebce41f7afbe

0 references

splash10-03dl-0391000000-f82f8da69357b2c4a9b0

0 references

splash10-03xv-1491000000-6b07269ecbd450e38fe7

0 references

0 references

1 reference

Hazardous Substances Data Bank

28 October 2019

12-O-TETRADECANOYLPHORBOL-13-ACETATE (English)

10 May 2021

1 reference

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

DTXCID30819884

0 references

EC number

605-413-5

1 reference

stated in

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.109.485

retrieved

27 December 2018

title

(1S,2S,6R,10S,11S,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate (English)

quotation

CAS no.: 16561-29-8 (English)

ECHA Substance Infocard ID

100.109.485

1 reference

stated in

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.109.485

retrieved

27 December 2018

title

(1S,2S,6R,10S,11S,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate (English)

quotation

CAS no.: 16561-29-8 (English)

Guide to Pharmacology Ligand ID

2341

1 reference

stated in

IUPHAR/BPS Guide to PHARMACOLOGY

5 February 2021