methyl 1-hydroxy-9H-carbazole-3-carboxylate

ID: ALA235934

Chembl Id: CHEMBL235934

Cas Number: 182261-83-2

PubChem CID: 5315951

Max Phase: Preclinical

Molecular Formula: C14H11NO3

Molecular Weight: 241.25

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Clausine E | Clausine E|182261-83-2|methyl 1-hydroxy-9H-carbazole-3-carboxylate|CHEBI:69930|9H-Carbazole-3-carboxylic acid, 1-hydroxy-, methyl ester|CHEMBL235934|HY-N10340|AKOS040763681|FS-7406|CS-0380745|Q27138274

Canonical SMILES:  COC(=O)c1cc(O)c2[nH]c3ccccc3c2c1

Standard InChI:  InChI=1S/C14H11NO3/c1-18-14(17)8-6-10-9-4-2-3-5-11(9)15-13(10)12(16)7-8/h2-7,15-16H,1H3

Standard InChI Key:  ZWPODTIRGFOENJ-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA235934

    CLAUSINE E

Associated Targets(Human)

MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW48 (312 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW480 (6023 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H187 (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T98G (1524 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RHOA Tbio Transforming protein RhoA (190 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCD Tclin Protein kinase C delta (2953 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCA Tchem PKC alpha and beta-2 (4 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCI Tchem Protein kinase C iota type/zeta type (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FTO Tchem Alpha-ketoglutarate-dependent dioxygenase FTO (473 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Vero (26788 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: 241.25Molecular Weight (Monoisotopic): 241.0739AlogP: 2.81#Rotatable Bonds: 1
Polar Surface Area: 62.32Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 8.88CX Basic pKa: CX LogP: 2.79CX LogD: 2.78
Aromatic Rings: 3Heavy Atoms: 18QED Weighted: 0.64Np Likeness Score: 0.58

References

1. Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B..  (2007)  Synthesis and antiproliferative activity of clausine E, mukonine, and koenoline bioisosteres.,  15  (16): [PMID:17548198] [10.1016/j.bmc.2007.05.033]
2. Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H..  (2000)  New carbazole alkaloids from Clausena anisata with antitumor promoting activity.,  63  (1): [PMID:10650093] [10.1021/np990285x]
3. Songsiang U, Thongthoom T, Boonyarat C, Yenjai C..  (2011)  Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.,  74  (2): [PMID:21302964] [10.1021/np100654m]
4. Lin W, Wang Y, Lin S, Li C, Zhou C, Wang S, Huang H, Liu P, Ye G, Shen X..  (2012)  Induction of cell cycle arrest by the carbazole alkaloid Clauszoline-I from Clausena vestita D. D. Tao via inhibition of the PKCδ phosphorylation.,  47  [PMID:22093759] [10.1016/j.ejmech.2011.10.047]
5. Perry GS, Das M, Woon ECY..  (2021)  Inhibition of AlkB Nucleic Acid Demethylases: Promising New Epigenetic Targets.,  64  (23.0): [PMID:34792334] [10.1021/acs.jmedchem.1c01694]

Source