o-orsellinic acid (CHEBI:32807)

ChEBI > Main

CHEBI:32807 - o-orsellinic acid

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	o-orsellinic acid

ChEBI ID	CHEBI:32807

ChEBI ASCII Name	o-orsellinic acid

Definition	A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group.

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

Secondary ChEBI IDs	CHEBI:7791, CHEBI:25621

Supplier Information	ChemicalBook:CB1185500, eMolecules:984090, ZINC000000901157

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__389154655500617__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__389154655500617__)

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:32807","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__389154655500617__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"389154655500617","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__389154655500617__ 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

6X7 - Ideal conformer

Mrv1927 05282121473D

starting HoverWatcher_5

Time for openFile(6X7 - Ideal conformer

Mrv1927 05282121473D

20 20 0 0 0 0 999 V2000

1.5540 1.2270 -0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4710 -2.3820 0.0030 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5790 2.5260 -0.0490 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1780 1.2230 -0.0270 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5170 0.0100 -0.0220 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9880 0.0010 -0.0380 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5850 -0.0140 -1.0970 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1950 -1.2000 -0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5790 -1.1830 0.0110 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2580 0.0270 0.0060 C 0 0 0 0 0 0 0 0 0 0 0 0

3.6150 0.0400 0.0140 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.6740 0.0090 1.1220 O 0 0 0 0 0 0 0 0 0 0 0 0

2.0890 2.1650 -0.0220 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6550 -2.7340 -0.8790 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7730 2.8510 0.9730 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0130 3.2820 -0.5640 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5260 2.3870 -0.5720 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1300 -2.1110 0.0270 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0030 0.0550 0.9000 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6400 0.0030 1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0

7 6 2 0 0 0 0

3 4 1 0 0 0 0

6 5 1 0 0 0 0

4 5 1 0 0 0 0

4 1 2 0 0 0 0

5 8 2 0 0 0 0

1 10 1 0 0 0 0

8 2 1 0 0 0 0

8 9 1 0 0 0 0

10 9 2 0 0 0 0

10 11 1 0 0 0 0

6 12 1 0 0 0 0

1 13 1 0 0 0 0

2 14 1 0 0 0 0

3 15 1 0 0 0 0

3 16 1 0 0 0 0

3 17 1 0 0 0 0

9 18 1 0 0 0 0

11 19 1 0 0 0 0

12 20 1 0 0 0 0

M END): 26 ms

reading 20 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

20 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Orsellinic acid, more specifically o-orsellinic acid, is a phenolic acid. It is of importance in the biochemistry of lichens, from which it can be extracted. It is a common subunit of depsides.
Read full article at Wikipedia

Formula

C8H8O4

Net Charge

Average Mass

168.148

Monoisotopic Mass

168.04226

InChI

InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)

InChIKey

AMKYESDOVDKZKV-UHFFFAOYSA-N

SMILES

CC1=C(C(O)=O)C(O)=CC(O)=C1

Metabolite of Species	Details
Ascomycota sp. Ind19F07 (NCBI:txid1583058)	See: PubMed
Penicillium purpurogenum (NCBI:txid28575)	Found in mycelium (BTO:0001436). Ethylacetate extract of fermentation broth and acetone extract of mycelia of strain JS03 21 See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	o-orsellinic acid (CHEBI:32807) has role fungal metabolite (CHEBI:76946) o-orsellinic acid (CHEBI:32807) has role marine metabolite (CHEBI:76507) o-orsellinic acid (CHEBI:32807) has role metabolite (CHEBI:25212) o-orsellinic acid (CHEBI:32807) is a dihydroxybenzoic acid (CHEBI:23778) o-orsellinic acid (CHEBI:32807) is a resorcinols (CHEBI:33572) o-orsellinic acid (CHEBI:32807) is conjugate acid of o-orsellinate (CHEBI:16162)

Incoming	3,5-dimethylorsellinic acid (CHEBI:132131) has functional parent o-orsellinic acid (CHEBI:32807) 3-methylorsellinic acid (CHEBI:146309) has functional parent o-orsellinic acid (CHEBI:32807) 5-methylorsellinic acid (CHEBI:146307) has functional parent o-orsellinic acid (CHEBI:32807) o-orsellinate depside (CHEBI:15871) has functional parent o-orsellinic acid (CHEBI:32807) brartemicin (CHEBI:65512) has functional parent o-orsellinic acid (CHEBI:32807) comazaphilone D (CHEBI:70013) has functional parent o-orsellinic acid (CHEBI:32807) FR191512 (CHEBI:65912) has functional parent o-orsellinic acid (CHEBI:32807) globosumone A (CHEBI:68705) has functional parent o-orsellinic acid (CHEBI:32807) globosumone B (CHEBI:68706) has functional parent o-orsellinic acid (CHEBI:32807) melleolide F (CHEBI:167712) has functional parent o-orsellinic acid (CHEBI:32807) papulacandin (CHEBI:72596) has functional parent o-orsellinic acid (CHEBI:32807) purpurquinone A (CHEBI:69469) has functional parent o-orsellinic acid (CHEBI:32807) purpurquinone C (CHEBI:69471) has functional parent o-orsellinic acid (CHEBI:32807) o-orsellinate (CHEBI:16162) is conjugate base of o-orsellinic acid (CHEBI:32807)

IUPAC Name

2,4-dihydroxy-6-methylbenzoic acid

Synonyms	Sources
2,4-Dihydroxy-6-methylbenzoic acid	KEGG COMPOUND
4,6-Dihydroxy-o-toluic acid	KEGG COMPOUND
o-Orsellinic acid	KEGG COMPOUND
orsellic acid	ChemIDplus
orsellinic acid	ChEBI
Orsellinsäure	ChEBI

Manual Xrefs	Databases
6X7	PDBeChem
C00000487	KNApSAcK
C01839	KEGG COMPOUND
CPD-47	MetaCyc
LMPK13010001	LIPID MAPS
LSM-20972	LINCS
Orsellinic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
2211027	Reaxys Registry Number	Reaxys
480-64-8	CAS Registry Number	KEGG COMPOUND
480-64-8	CAS Registry Number	ChemIDplus

Citations

Tian YQ, Lin XP, Liu J, Kaliyaperumal K, Ai W, Ju ZR, Yang B, Wang J, Yang XW, Liu Y (2015)
Ascomycotin A, a new citromycetin analogue produced by Ascomycota sp. Ind19F07 isolated from deep sea sediment.
Natural product research 29, 820-826 [PubMed:25537370]
[show Abstract]

Wang H, Wang Y, Wang W, Fu P, Liu P, Zhu W (2011)
Anti-influenza virus polyketides from the acid-tolerant fungus Penicillium purpurogenum JS03-21.
Journal of natural products 74, 2014-2018 [PubMed:21879714]
[show Abstract]

Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Nonaka T, Fujii I (2010)
Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid.
Bioorganic & medicinal chemistry letters 20, 4785-4788 [PubMed:20630753]
[show Abstract]

Sanchez JF, Chiang YM, Szewczyk E, Davidson AD, Ahuja M, Elizabeth Oakley C, Woo Bok J, Keller N, Oakley BR, Wang CC (2010)
Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans.
Molecular bioSystems 6, 587-593 [PubMed:20174687]
[show Abstract]

Schroeckh V, Scherlach K, Nützmann HW, Shelest E, Schmidt-Heck W, Schuemann J, Martin K, Hertweck C, Brakhage AA (2009)
Intimate bacterial-fungal interaction triggers biosynthesis of archetypal polyketides in Aspergillus nidulans.
Proceedings of the National Academy of Sciences of the United States of America 106, 14558-14563 [PubMed:19666480]
[show Abstract]

Mosbach K, Bävertoft I (1971)
A comparative study on the biosynthesis of palmitic and orsellinic acids in Penicillium baarnense.
Acta chemica Scandinavica 25, 1931-1936 [PubMed:4399350]

Van Eijk GW (1969)
Isolation and identification of orsellinic acid and penicillic acid produced by Penicillium fennelliae Stolk.
Antonie van Leeuwenhoek 35, 497-504 [PubMed:5311576]

BIRKINSHAW JH, GOWLLAND A (1962)
Studies in the biochemistry of micro-organisms. 110. Production and biosynthesis of orsellinic acid by Penicillium madriti G. Smith.
The Biochemical journal 84, 342-347 [PubMed:13869400]

Last Modified

06 June 2022

CHEBI:32807 - o-orsellinic acid

ChEBI is part of the ELIXIR infrastructure