ID: ALA559673

Max Phase: Preclinical

Molecular Formula: C17H14O3

Molecular Weight: 266.30

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  O=C(/C=C/c1ccccc1O)/C=C/c1ccccc1O

Standard InChI:  InChI=1S/C17H14O3/c18-15(11-9-13-5-1-3-7-16(13)19)12-10-14-6-2-4-8-17(14)20/h1-12,19-20H/b11-9+,12-10+

Standard InChI Key:  YNVAHBUBGBLIEY-WGDLNXRISA-N

Associated Targets(Human)

Tyrosinase 717 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Nuclear factor NF-kappa-B p105 subunit 1459 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Proto-oncogene c-JUN 434 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Nuclear factor erythroid 2-related factor 2 95332 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MDA-MB-231 73002 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

RPMI-7951 420 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HUVEC 11049 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HeLa 62764 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Ca-Ski 420 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

RAW264.7 28094 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Luciferin 4-monooxygenase 66902 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SVR 53 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

Properties

Molecular Weight: 266.30Molecular Weight (Monoisotopic): 266.0943AlogP: 3.39#Rotatable Bonds: 4
Polar Surface Area: 57.53Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: 0HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 8.56CX Basic pKa: CX LogP: 4.22CX LogD: 4.19
Aromatic Rings: 2Heavy Atoms: 20QED Weighted: 0.83Np Likeness Score: 0.36

References

1. Lee KH, Ab Aziz FH, Syahida A, Abas F, Shaari K, Israf DA, Lajis NH..  (2009)  Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.,  44  (8): [PMID:19359068] [10.1016/j.ejmech.2009.03.020]
2.  (2015)  Therapeutic curcumin derivatives, 
3. Jackson PA, Widen JC, Harki DA, Brummond KM..  (2017)  Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.,  60  (3): [PMID:27996267] [10.1021/acs.jmedchem.6b00788]
4. Deck LM, Hunsaker LA, Vander Jagt TA, Whalen LJ, Royer RE, Vander Jagt DL..  (2018)  Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.,  143  [PMID:29223100] [10.1016/j.ejmech.2017.11.048]
5. Moreira J, Saraiva L, Pinto MM, Cidade H..  (2020)  Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies.,  192  [PMID:32172081] [10.1016/j.ejmech.2020.112177]