6-(1S-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one

ID: ALA572366

Chembl Id: CHEMBL572366

PubChem CID: 45484187

Max Phase: Preclinical

Molecular Formula: C15H18O4

Molecular Weight: 262.31

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc2oc(=O)ccc2cc1[C@@H](O)CC(C)C

Standard InChI:  InChI=1S/C15H18O4/c1-9(2)6-12(16)11-7-10-4-5-15(17)19-13(10)8-14(11)18-3/h4-5,7-9,12,16H,6H2,1-3H3/t12-/m0/s1

Standard InChI Key:  ZRXJDVGAMZQYJX-LBPRGKRZSA-N

Associated Targets(Human)

CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA3 Tclin Carbonic anhydrase III (753 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA4 Tclin Carbonic anhydrase IV (2163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5A Tclin Carbonic anhydrase VA (1168 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5B Tclin Carbonic anhydrase VB (957 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA6 Tclin Carbonic anhydrase VI (993 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA7 Tclin Carbonic anhydrase VII (2318 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA12 Tclin Carbonic anhydrase XII (6231 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA13 Tclin Carbonic anhydrase XIII (905 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA14 Tclin Carbonic anhydrase XIV (1305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Ca15 Carbonic anhydrase 15 (173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ca13 Carbonic anhydrase XIII (322 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NtBBF1.1 Zn finger protein (22 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: 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: 262.31Molecular Weight (Monoisotopic): 262.1205AlogP: 2.88#Rotatable Bonds: 4
Polar Surface Area: 59.67Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 2.53CX LogD: 2.53
Aromatic Rings: 2Heavy Atoms: 19QED Weighted: 0.86Np Likeness Score: 0.68

References

1. Temperini C, Innocenti A, Scozzafava A, Parkkila S, Supuran CT..  (2010)  The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors.,  53  (2): [PMID:20028100] [10.1021/jm901524f]
2. Maresca A, Temperini C, Pochet L, Masereel B, Scozzafava A, Supuran CT..  (2010)  Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins.,  53  (1): [PMID:19911821] [10.1021/jm901287j]
3. Maresca A, Supuran CT..  (2010)  Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II.,  20  (15): [PMID:20580555] [10.1016/j.bmcl.2010.06.040]
4. Maresca A, Scozzafava A, Supuran CT..  (2010)  7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range.,  20  (24): [PMID:21067924] [10.1016/j.bmcl.2010.10.094]
5. Tars K, Vullo D, Kazaks A, Leitans J, Lends A, Grandane A, Zalubovskis R, Scozzafava A, Supuran CT..  (2013)  Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases.,  56  (1): [PMID:23241068] [10.1021/jm301625s]

Source