all-trans-retinoic acid (CHEBI:15367)

ChEBI > Main

CHEBI:15367 - all-trans-retinoic acid

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	all-trans-retinoic acid

ChEBI ID	CHEBI:15367

ChEBI ASCII Name	all-trans-retinoic acid

Definition	A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45376, CHEBI:8815

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__925657037015077__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__925657037015077__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45376","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__925657037015077__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"925657037015077","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__925657037015077__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Marvin 10130717263D

starting HoverWatcher_5

Time for openFile(

Marvin 10130717263D

50 50 0 0 0 0 999 V2000

-3.1215 -1.3479 -0.2123 C 0 0 2 0 0 0 0 0 0 0 0 0

-4.2243 -2.1081 -1.0465 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8557 -2.1339 -0.0374 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8928 -3.4965 -0.0174 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8746 -4.2068 -0.8401 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.2980 -3.6267 -0.7679 C 0 0 0 0 0 0 0 0 0 0 0 0

4.9628 5.9553 -0.7427 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8998 5.1152 -0.6583 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8096 3.9044 -0.0544 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5928 3.2425 -0.0193 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2790 2.1736 0.7389 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1234 1.4625 0.7111 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0316 0.1094 0.7535 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6166 -1.5409 0.0805 C 0 0 0 0 0 0 0 0 0 0 0 0

5.1785 6.6268 -1.7453 O 0 0 0 0 0 0 0 0 0 0 0 0

5.7521 6.1217 0.1757 O 0 0 0 0 0 0 0 0 0 0 0 0

4.9953 3.2579 0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2350 -0.7351 0.7394 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.6984 -1.1123 1.2295 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.9586 0.0476 -0.9139 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2175 -0.4593 0.7724 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9666 -4.3386 0.7460 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.2221 -1.6891 -0.8805 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0350 -1.9988 -2.1195 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9241 -5.2831 -0.6525 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5194 -4.1181 -1.8735 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7252 -3.8320 0.2158 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9334 -4.1149 -1.5126 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0894 5.4786 -1.1128 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8668 3.5602 -0.6263 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9542 1.8400 1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2936 2.0123 0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0878 -1.9765 -0.4756 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6722 6.5508 -2.4611 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9886 3.3812 1.6141 H 0 0 0 0 0 0 0 0 0 0 0 0

5.9517 3.6161 0.1492 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0242 2.1906 0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8780 -0.5147 1.5929 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8013 -0.5535 -0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0503 -1.8091 0.7895 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9025 -2.0512 1.7498 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0272 -0.5467 1.8750 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6338 -0.5493 1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9222 0.5369 -1.0766 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3707 0.7609 -0.3384 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4746 -0.0626 -1.8869 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8940 -0.0064 1.3379 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5441 -5.0431 1.3514 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3680 -3.7874 1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2968 -4.9017 0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0

1 19 1 0 0 0 0

1 20 1 0 0 0 0

1 2 1 0 0 0 0

1 3 1 0 0 0 0

3 14 1 0 0 0 0

4 3 2 0 0 0 0

22 4 1 0 0 0 0

5 4 1 0 0 0 0

6 5 1 0 0 0 0

2 6 1 0 0 0 0

8 7 1 0 0 0 0

16 7 2 0 0 0 0

15 7 1 0 0 0 0

9 8 2 0 0 0 0

10 9 1 0 0 0 0

17 9 1 0 0 0 0

11 10 2 0 0 0 0

12 11 1 0 0 0 0

13 12 2 0 0 0 0

21 13 1 0 0 0 0

18 13 1 0 0 0 0

14 21 2 0 0 0 0

2 23 1 0 0 0 0

2 24 1 0 0 0 0

5 25 1 0 0 0 0

5 26 1 0 0 0 0

6 27 1 0 0 0 0

6 28 1 0 0 0 0

8 29 1 0 0 0 0

10 30 1 0 0 0 0

11 31 1 0 0 0 0

12 32 1 0 0 0 0

14 33 1 0 0 0 0

15 34 1 0 0 0 0

17 35 1 0 0 0 0

17 36 1 0 0 0 0

17 37 1 0 0 0 0

18 38 1 0 0 0 0

18 39 1 0 0 0 0

18 40 1 0 0 0 0

19 41 1 0 0 0 0

19 42 1 0 0 0 0

19 43 1 0 0 0 0

20 44 1 0 0 0 0

20 45 1 0 0 0 0

20 46 1 0 0 0 0

21 47 1 0 0 0 0

22 48 1 0 0 0 0

22 49 1 0 0 0 0

22 50 1 0 0 0 0

M END): 44 ms

reading 50 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

50 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Coumarin () or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and is considered a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. While coumarin is not an anticoagulant, its 3-alkyl-4-hydroxy derivatives, such as the fungal metabolite dicoumarol, inhibit synthesis of vitamin K, a key component in blood clotting. A related compound, the prescription drug anticoagulant warfarin, is used to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism.
Read full article at Wikipedia

Formula

C20H28O2

Net Charge

Average Mass

300.43512

Monoisotopic Mass

300.20893

InChI

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChIKey

SHGAZHPCJJPHSC-YCNIQYBTSA-N

SMILES

CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(O)=O

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	signalling molecule A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell. retinoid X receptor agonist An agonist that selectively binds to and activates a retinoid X receptor. AP-1 antagonist An antogonist that interferes with the action of activator protein 1 (AP-1). retinoic acid receptor agonist An agonist that selectively binds to and activates a retinoic acid receptor. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via retinoic acid ) metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via vitamin A ) fat-soluble vitamin (role) Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess. (via vitamin A )

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. anti-inflammatory agent Any compound that has anti-inflammatory effects. retinoic acid receptor agonist An agonist that selectively binds to and activates a retinoic acid receptor.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	all-trans-retinoic acid (CHEBI:15367) has role anti-inflammatory agent (CHEBI:67079) all-trans-retinoic acid (CHEBI:15367) has role antineoplastic agent (CHEBI:35610) all-trans-retinoic acid (CHEBI:15367) has role antioxidant (CHEBI:22586) all-trans-retinoic acid (CHEBI:15367) has role AP-1 antagonist (CHEBI:67199) all-trans-retinoic acid (CHEBI:15367) has role human metabolite (CHEBI:77746) all-trans-retinoic acid (CHEBI:15367) has role keratolytic drug (CHEBI:50176) all-trans-retinoic acid (CHEBI:15367) has role retinoic acid receptor agonist (CHEBI:67198) all-trans-retinoic acid (CHEBI:15367) has role retinoid X receptor agonist (CHEBI:63794) all-trans-retinoic acid (CHEBI:15367) has role signalling molecule (CHEBI:62488) all-trans-retinoic acid (CHEBI:15367) is a retinoic acid (CHEBI:26536) all-trans-retinoic acid (CHEBI:15367) is a vitamin A (CHEBI:12777) all-trans-retinoic acid (CHEBI:15367) is conjugate acid of all-trans-retinoate (CHEBI:35291)

Incoming	1-O-all-trans-retinoyl-β-glucuronic acid (CHEBI:28870) has functional parent all-trans-retinoic acid (CHEBI:15367) 4-hydroxyphenyl retinamide (CHEBI:42588) has functional parent all-trans-retinoic acid (CHEBI:15367) 5,6-epoxyretinoic acid (CHEBI:80658) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-13,14-dihydroretinoic acid (CHEBI:194189) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-16-hydroxyretinoic acid (CHEBI:139256) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-18-hydroxyretinoic acid (CHEBI:80657) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-3,4-didehydroretinoic acid (CHEBI:133794) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4,16-dihydroxyretinoic acid (CHEBI:139259) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4,18-dihydroxyretinoic acid (CHEBI:139261) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4-hydroxyretinoic acid (CHEBI:63795) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4-oxo-16-hydroxyretinoic acid (CHEBI:139263) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4-oxo-18-hydroxyretinoic acid (CHEBI:139265) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-4-oxoretinoic acid (CHEBI:80656) has functional parent all-trans-retinoic acid (CHEBI:15367) SR11302 (CHEBI:197438) has functional parent all-trans-retinoic acid (CHEBI:15367) all-trans-retinoate (CHEBI:35291) is conjugate base of all-trans-retinoic acid (CHEBI:15367)

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

INNs	Sources
tretinoin	WHO MedNet
tretinoína	WHO MedNet
trétinoïne	WHO MedNet
tretinoinum	WHO MedNet

Synonyms	Sources
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid	ChEBI
(all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	KEGG COMPOUND
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid	KEGG COMPOUND
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid	ChemIDplus
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid	LIPID MAPS
Acide retinoique (French)	KEGG COMPOUND
AGN 100335	KEGG COMPOUND
all-(E)-retinoic acid	KEGG COMPOUND
all-trans retinoic acid	ChemIDplus
all-trans-beta-Retinoic acid	KEGG COMPOUND
all-trans-retinoic acid	KEGG COMPOUND
all-trans-tretinoin	KEGG COMPOUND
all-trans-vitamin A acid	KEGG COMPOUND
all-trans-vitamin A₁ acid	KEGG COMPOUND
beta-Retinoic acid	KEGG COMPOUND
retinoic acid	KEGG COMPOUND
Ro 1-5488	KEGG COMPOUND
trans-retinoic acid	KEGG COMPOUND
Tretin M	KEGG COMPOUND
vitamin A acid	KEGG COMPOUND

Brand Names	Sources
Altreno	DrugBank
Atralin	ChemIDplus
Avita	ChemIDplus
Betarretin	ChemIDplus
Biacna	DrugBank
Cordes vas	ChemIDplus
Dermairol	ChemIDplus
Refissa	ChemIDplus
Renova	DrugBank
Retin-A	DrugBank
Retisol-A	DrugBank
Stieva-A	DrugBank
Tri-luma	DrugBank
Veltin	DrugBank
Vesanoid	DrugBank
Vitinoin	DrugBank

Manual Xrefs	Databases
2722	DrugCentral
C00777	KEGG COMPOUND
D00094	KEGG DRUG
DB00755	DrugBank
FDB022710	FooDB
HMDB0001852	HMDB
LMPR01090019	LIPID MAPS
REA	PDBeChem
Retinoic_acid	Wikipedia
Tretinoin	Wikipedia
View more database links

Registry Numbers	Types	Sources
2057223	Reaxys Registry Number	Reaxys
302-79-4	CAS Registry Number	KEGG COMPOUND
302-79-4	CAS Registry Number	ChemIDplus

Citations	Types	Sources
10022884	PubMed citation	Europe PMC
10970886	PubMed citation	Europe PMC
11073974	PubMed citation	Europe PMC
11214352	PubMed citation	Europe PMC
11332619	PubMed citation	Europe PMC
11343416	PubMed citation	Europe PMC
11437362	PubMed citation	Europe PMC
11556813	PubMed citation	Europe PMC
11722649	PubMed citation	Europe PMC
11896294	PubMed citation	Europe PMC
11904404	PubMed citation	Europe PMC
12958591	PubMed citation	Europe PMC
14581379	PubMed citation	Europe PMC
14605492	PubMed citation	Europe PMC
14627725	PubMed citation	Europe PMC
14704332	PubMed citation	Europe PMC
14705145	PubMed citation	Europe PMC
14978018	PubMed citation	Europe PMC
15194426	PubMed citation	Europe PMC
15318809	PubMed citation	Europe PMC
15327395	PubMed citation	Europe PMC
15359008	PubMed citation	Europe PMC
15376324	PubMed citation	Europe PMC
15476854	PubMed citation	Europe PMC
15537748	PubMed citation	Europe PMC
15539337	PubMed citation	Europe PMC
15675886	PubMed citation	Europe PMC
15839997	PubMed citation	Europe PMC
16569247	PubMed citation	Europe PMC
16685080	PubMed citation	Europe PMC
16688769	PubMed citation	Europe PMC
16720557	PubMed citation	Europe PMC
16819260	PubMed citation	Europe PMC
16847436	PubMed citation	Europe PMC
16920920	PubMed citation	Europe PMC
17073551	PubMed citation	Europe PMC
17166212	PubMed citation	Europe PMC
17204142	PubMed citation	Europe PMC
17447762	PubMed citation	Europe PMC
18052213	PubMed citation	Europe PMC
18085670	PubMed citation	Europe PMC
18162363	PubMed citation	Europe PMC
18183617	PubMed citation	Europe PMC
18318655	PubMed citation	Europe PMC
18322276	PubMed citation	Europe PMC
18400206	PubMed citation	Europe PMC
18404486	PubMed citation	Europe PMC
18440196	PubMed citation	Europe PMC
18678272	PubMed citation	Europe PMC
18800767	PubMed citation	Europe PMC
18819820	PubMed citation	Europe PMC
18977311	PubMed citation	Europe PMC
19018099	PubMed citation	Europe PMC
19112091	PubMed citation	Europe PMC
19144697	PubMed citation	Europe PMC
19427305	PubMed citation	Europe PMC
19587328	PubMed citation	Europe PMC
19597529	PubMed citation	Europe PMC
19814868	PubMed citation	Europe PMC
19841174	PubMed citation	Europe PMC
21898109	PubMed citation	Europe PMC
21924320	PubMed citation	Europe PMC
21993673	PubMed citation	Europe PMC
22134377	PubMed citation	Europe PMC
22177959	PubMed citation	Europe PMC
22180426	PubMed citation	Europe PMC
22244299	PubMed citation	Europe PMC
22261335	PubMed citation	Europe PMC
22428994	PubMed citation	Europe PMC
22514600	PubMed citation	Europe PMC
22532966	PubMed citation	Europe PMC
22534100	PubMed citation	Europe PMC
22538278	PubMed citation	Europe PMC
22741806	PubMed citation	Europe PMC
27759097	PubMed citation	Europe PMC
29492455	PubMed citation	Europe PMC
33662750	PubMed citation	Europe PMC
33820492	PubMed citation	Europe PMC
34050114	PubMed citation	Europe PMC
34050360	PubMed citation	Europe PMC
34091189	PubMed citation	Europe PMC
7501014	PubMed citation	Europe PMC
7704533	PubMed citation	Europe PMC
7961949	PubMed citation	Europe PMC

Last Modified

13 October 2023

CHEBI:15367 - all-trans-retinoic acid

ChEBI is part of the ELIXIR infrastructure