UMBELLIFERONE (PD002087, ORHBXUUXSCNDEV-UHFFFAOYSA-N)

General

Preferred name

UMBELLIFERONE

Synonyms

Hydrangin

hydrangine

NSC 19790

skimmetine

7-Hydroxycoumarin

7-hydroxycoumarin, hydrangine, skimmetine, beta-umbelliferone

NSC-019790

P&D ID

PD002087

CAS

93-35-6

142044-47-1

Tags

available

covalent binder

drug candidate

Drug indication

Discovery agent

Structure

PD002087

UMBELLIFERONE

RO5

162.03

HBA

HBD

LOGP

1.5

226

Structure formats

SMILES

O=c1ccc2ccc(O)cc2o1

InChI

InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H

InChIkey

ORHBXUUXSCNDEV-UHFFFAOYSA-N

MOL

UMBELLIFERONE RDKit 2D 12 13 0 0 0 0 0 0 0 0999 V2000 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 2 1 0 11 5 1 0 M END > <ID> PD002087 > <Name> UMBELLIFERONE

Protein targets

6.32

CA9 Carbonic anhydrase 9

BIOCHEM 1.6x

6.12

CA12 Carbonic anhydrase 12

6.12

NTBBF1.1 Dof zinc finger protein

5.05

MCL1 Induced myeloid leukemia cell differentiation protein Mcl-1

4.92

ERAP1 Endoplasmic reticulum aminopeptidase 1

4.85

KDM4E Lysine-specific demethylase 4E

4.8

CASP7 Caspase-7

4.7

CASP1 Caspase-1

4.64

AKR1B1 Aldo-keto reductase family 1 member B1

4.6

HSD17B10 3-hydroxyacyl-CoA dehydrogenase type-2

4.55

ALDH1A1 Aldehyde dehydrogenase 1A1

4.55

HPGD 15-hydroxyprostaglandin dehydrogenase [NAD(+)]

4.5

GAA Lysosomal alpha-glucosidase

4.45

GLA Alpha-galactosidase A

4.4

Cruzipain

4.4

KMT2A,MEN1 Menin/Histone-lysine N-methyltransferase MLL

4.37

LOX1.1 Seed linoleate 13S-lipoxygenase-1

4.23

CA1 Carbonic anhydrase 1

Chymotrypsinogen A inhibitor

Target pathways

Activation of caspases through apoptosome-mediated cleavage

R-HSA-111459

CASP7

Antigen Presentation: Folding, assembly and peptide loading of class I MHC

R-HSA-983170

ERAP1

Apoptotic cleavage of cellular proteins

R-HSA-111465

CASP7

Biosynthesis of D-series resolvins

R-HSA-9018676

HPGD

Biosynthesis of E-series 18(S)-resolvins

R-HSA-9018896

HPGD

Biosynthesis of Lipoxins (LX)

R-HSA-2142700

HPGD

Branched-chain amino acid catabolism

R-HSA-70895

HSD17B10

Caspase-mediated cleavage of cytoskeletal proteins

R-HSA-264870

CASP7

Erythrocytes take up carbon dioxide and release oxygen

R-HSA-1237044

CA1

Erythrocytes take up oxygen and release carbon dioxide

R-HSA-1247673

CA1

Ethanol oxidation

R-HSA-71384

ALDH1A1

Fructose biosynthesis

R-HSA-5652227

AKR1B1

Fructose catabolism

R-HSA-70350

ALDH1A1

Gene and protein expression by JAK-STAT signaling after Interleukin-12 stimulation

R-HSA-8950505

CA1

Glycogen breakdown (glycogenolysis)

R-HSA-70221

GAA

Glycogen storage disease type II (GAA)

R-HSA-5357609

GAA

Glycosphingolipid catabolism

R-HSA-9840310

GLA

Interleukin-1 processing

R-HSA-448706

CASP1

Interleukin-37 signaling

R-HSA-9008059

CASP1

Interleukin-4 and Interleukin-13 signaling

R-HSA-6785807

MCL1

Mitochondrial protein degradation

R-HSA-9837999

HSD17B10

Neutrophil degranulation

R-HSA-6798695

GLA

GAA

NOD1/2 Signaling Pathway

R-HSA-168638

CASP1

Pregnenolone biosynthesis

R-HSA-196108

AKR1B1

Purinergic signaling in leishmaniasis infection

R-HSA-9660826

CASP1

Pyroptosis

R-HSA-5620971

CASP1

RA biosynthesis pathway

R-HSA-5365859

ALDH1A1

Regulation of gene expression by Hypoxia-inducible Factor

R-HSA-1234158

CA9

Reversible hydration of carbon dioxide

R-HSA-1475029

CA1

CA12

CA9

rRNA processing in the mitochondrion

R-HSA-8868766

HSD17B10

SARS-CoV-1 activates/modulates innate immune responses

R-HSA-9692916

CASP1

Signaling by ALK fusions and activated point mutants

R-HSA-9725370

MCL1

SMAC (DIABLO) binds to IAPs

R-HSA-111463

CASP7

SMAC(DIABLO)-mediated dissociation of IAP:caspase complexes

R-HSA-111464

CASP7

SMAC, XIAP-regulated apoptotic response

R-HSA-111469

CASP7

Synthesis of Prostaglandins (PG) and Thromboxanes (TX)

R-HSA-2162123

HPGD

The AIM2 inflammasome

R-HSA-844615

CASP1

The IPAF inflammasome

R-HSA-844623

CASP1

The NLRP3 inflammasome

R-HSA-844456

CASP1

TP53 Regulates Transcription of Caspase Activators and Caspases

R-HSA-6803207

CASP1

tRNA modification in the mitochondrion

R-HSA-6787450

HSD17B10

tRNA processing in the mitochondrion

R-HSA-6785470

HSD17B10

Zygotic genome activation (ZGA)

R-HSA-9819196

KDM4E

References

2023 Synthesis of Artesunic Acid-Coumarin Hybrids as Potential Antimelanoma Agents.

Zippilli C, Filippi S et al. ACS Med Chem Lett

2021 Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment.

Xia YL,Wang JJ et al. Bioorg Med Chem

2020 Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors.

Ashooriha M, Khoshneviszadeh M et al. Eur J Med Chem

2018 Inhibitory effects and structural insights for a novel series of coumarin-based compounds that selectively target human CA IX and CA XII carbonic anhydrases.

De Luca L, Mancuso F et al. Eur J Med Chem

2018 Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.

Chibli LA, Schmidt TJ et al. Eur J Med Chem

2017 Synthesis of novel hybrids of pyrazole and coumarin as dual inhibitors of COX-2 and 5-LOX.

Shen FQ, Wang ZC et al. Bioorg Med Chem Lett

2017 Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.

Hasan M, Genovese S et al. J Nat Prod

2016 Thioxocoumarins Show an Alternative Carbonic Anhydrase Inhibition Mechanism Compared to Coumarins.

Ferraroni M, Carta F et al. J. Med. Chem.

2013 New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire.

Ben Salem S, Jabrane A et al. Bioorg. Med. Chem. Lett.

2013 Design, synthesis and evaluation of novel tacrine-coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease.

Xie SS, Wang XB et al. Eur. J. Med. Chem.

2012 Structure-activity relationships for naturally occurring coumarins as -secretase inhibitor.

Marumoto S, Miyazawa M. Bioorg. Med. Chem.

2011 Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors.

Touisni N, Maresca A et al. J. Med. Chem.

2011 New halogenated phenylcoumarins as tyrosinase inhibitors.

Matos MJ; Santana L et al.

2011 Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.

Bruyere C, Genovese S et al. Bioorg. Med. Chem. Lett.

2010 6,7-Dihydroxy-4-phenylcoumarin as inhibitor of aldose reductase 2.

Kato A, Kobayashi K et al. Bioorg. Med. Chem. Lett.

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.

Maresca A, Scozzafava A et al. Bioorg. Med. Chem. Lett.

2009 Antiamoebic coumarins from the root bark of Adina cordifolia and their new thiosemicarbazone derivatives.

Iqbal PF, Bhat AR et al. Eur. J. Med. Chem.

2009 Discovery of novel Trypanosoma cruzi glyceraldehyde-3-phosphate dehydrogenase inhibitors.

Freitas RF, Prokopczyk IM et al. Bioorg. Med. Chem.

2007 Relationship between quantum-chemical descriptors of proton dissociation and experimental acidity constants of various hydroxylated coumarins. Identification of the biologically active species for xanthine oxidase inhibition.

Ferrari AM; Sgobba M et al.

2005 Synthesis and antiinflammatory activity of coumarin derivatives.

Kontogiorgis CA, Hadjipavlou-Litina DJ. J. Med. Chem.

2004 Structure-activity relationships of novel inhibitors of glyceraldehyde-3-phosphate dehydrogenase.

Leitao A, Andricopulo AD et al. Bioorg. Med. Chem. Lett.

2001 Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships.

Kang SY, Lee KY et al. J. Nat. Prod.

1996 Identification and structure-activity relationship studies of osthol, a cytotoxic principle from Cnidium monnieri

Hitotsuyanagi Y, Kojima H et al. Bioorg. Med. Chem. Lett.

PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease: Purified N370S Glucocerebrosidase. (Class of assay: confirmatory) [Related pubchem assays: 2101 ] AID 2597

CovBinderInPDB (dataset)