Basic information
- CAS
479-20-9- Standard SMILES
COC(=O)c1c(C)cc(OC(=O)c2c(C)cc(O)c(C=O)c2O)c(C)c1O- InChIKey
YLOYKYXNDHOHHT-UHFFFAOYSA-N- Molecular formula
- C19H18O8
- Average molar mass
- 374.3 g/mol
- Monoisotopic mass
- 374.10016753
Overview
Atranorin is a carbonyl compound.
Names & identifiers
- Preferred name
- Atranorin
- IUPAC
- (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
- English name
- ATRANORIN
- Molecular formula
- C19H18O8
- Molecular weight
- 374.34
Names & synonyms
Atranorin479-20-9Atranoric acid3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoateNSC-685591450U2VJ2VGDTXSID10197319NSC-249980(3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoateRefChem:115497DTXCID70119810207-527-7
Show more names
AtrarinATRANORIN(P)Atranorin-RM
AtranorineAntranoric acidParmelinUsnarinParmelin acidUsnarin acidBSPBio_003332NSC 249980
Database identifiers
- CAS
479-20-9- PubChem CID
- 68066
- DTXSID
DTXSID10197319- ChEMBL
CHEMBL173395- ChEBI
CHEBI:144119- UNII
- 450U2VJ2VG
- EC Number
- 207-527-7
- Nikkaji
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 564
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section181.27 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 156 · 156-158°C
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Chloroform: soluble,DMSO: soluble
- form
- A crystalline solid
- color
- White to off-white
- InChI
- 1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
- InChIKey
- YLOYKYXNDHOHHT-UHFFFAOYSA-N
- SMILES
- COC(=O)c1c(C)cc(OC(=O)c2c(C)cc(O)c(C=O)c2O)c(C)c1O
- LogP
- 6.14 · 6.140 (est)
- FDA UNII
- 450 U2VJ2VG · 450U2VJ2VG
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- wgk
- WGK 3
- Toxicity
- skn-gpg 5% CODEDG 11,168,1984
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P280-P302+P352
Chemistry & industry
Applications
DescriptionAtranorin is a depside lichen metabolite that has been found in S. alpinum and has diverse biological activities. It is active against the bacteria B. cereus, B. subtilis, S. aureus, S. faecalis, P. vulgaris, L. monocytogenes, and A. hydrophila (MICs = 1.67, 0.38, 26.7, 13.4, 3.34, 9.83, and 1.67 mM, respectively), the fungi C. albicans and C. glabrata (MIC = 26.7 mM for both), as well as the mycobacterium M. aurum (MIC = 250 μg/ml). Atranorin is cytotoxic to A270, HL-60, and Jurkat cancer cells (IC50s = 197.9, 93.5, and 181.6 μM, respectively) but not HeLa, MCF-7, SK-BR-3, or HT-29 cancer cells (IC50s = >200 μM). It inhibits acetic acid-induced writhing in mice when administered orally at doses of 200 and 400 mg/kg. Atranorin (200 and 400 mg/kg, p.o.) also reduces paw licking and biting in the second, but not first, phase of the formalin test when administered 30 minutes prior to formalin in mice.
Usesantinociceptive, antiinflammatory, antibacterial
UsesComponent in extracts of oak moss used as fragrance. Atranorin is a derivative compound of Chloratranorin (C364120), which are metabolites of Evernia prunastri and functions as antioxidant, antimicrobial and potential anticancer agents.
Upstream & downstream products
Downstream products
Suppliers63 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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