1-O-Methylemodin

ID: ALA453316

Chembl Id: CHEMBL453316

Cas Number: 3775-08-4

PubChem CID: 10469084

Max Phase: Preclinical

Molecular Formula: C16H12O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 1-O-Methylemodin | 1-O-Methylemodin|3775-08-4|1,3-Dihydroxy-8-methoxy-6-methylanthracene-9,10-dione|1-METHYL EMODIN|6,8-Dihydroxy-1-methoxy-3-methylanthraquinone|O-methylemodin|CHEMBL453316|SCHEMBL16225819|1,3-dihydroxy-8-methoxy-6-methyl-anthracene-9,10-dione|9,10-Anthracenedione, 1,3-dihydroxy-8-methoxy-6-methyl-|DTXSID30440475|CHEBI:216784|HY-N9755|CS-0203763|D85146

Canonical SMILES:  COc1cc(C)cc2c1C(=O)c1c(O)cc(O)cc1C2=O

Standard InChI:  InChI=1S/C16H12O5/c1-7-3-9-14(12(4-7)21-2)16(20)13-10(15(9)19)5-8(17)6-11(13)18/h3-6,17-18H,1-2H3

Standard InChI Key:  IKIAXVIGUJMLHC-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Jurkat (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-937 (7138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW-620 (52400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Phellinus tremulae (4 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 284.27Molecular Weight (Monoisotopic): 284.0685AlogP: 2.19#Rotatable Bonds: 1
Polar Surface Area: 83.83Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 7.33CX Basic pKa: CX LogP: 3.32CX LogD: 2.98
Aromatic Rings: 2Heavy Atoms: 21QED Weighted: 0.72Np Likeness Score: 1.31

References

1. Koyama J, Nisino Y, Morita I, Kobayashi N, Osakai T, Tokuda H..  (2008)  Correlation between reduction potentials and inhibitions of Epstein-Barr virus activation by anthraquinone derivatives.,  18  (14): [PMID:18556196] [10.1016/j.bmcl.2008.05.109]
2. Ayer WA, Trifonov LS.  (1994)  Anthraquinones and a 10-Hydroxyanthrone from Phialophora alba,  57  (2): [10.1021/np50104a021]
3. Aly AH, Debbab A, Clements C, Edrada-Ebel R, Orlikova B, Diederich M, Wray V, Lin W, Proksch P..  (2011)  NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum.,  19  (1): [PMID:21146414] [10.1016/j.bmc.2010.11.012]
4. Yang Y, Yan YM, Wei W, Luo J, Zhang LS, Zhou XJ, Wang PC, Yang YX, Cheng YX..  (2013)  Anthraquinone derivatives from Rumex plants and endophytic Aspergillus fumigatus and their effects on diabetic nephropathy.,  23  (13): [PMID:23683594] [10.1016/j.bmcl.2013.04.059]
5. Wang C, Guo L, Hao J, Wang L, Zhu W..  (2016)  α-Glucosidase Inhibitors from the Marine-Derived Fungus Aspergillus flavipes HN4-13.,  79  (11): [PMID:27933892] [10.1021/acs.jnatprod.6b00766]
6. Elbanna AH, Khalil ZG, Bernhardt PV, Capon RJ..  (2021)  Neobulgarones Revisited: Anti and Syn Bianthrones from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD22.,  84  (3.0): [PMID:33534571] [10.1021/acs.jnatprod.0c01035]

Source