3,6,9-Trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione

ID: ALA362672

Chembl Id: CHEMBL362672

Cas Number: 5090-87-9

PubChem CID: 94303

Max Phase: Preclinical

Molecular Formula: C15H14O3

Molecular Weight: 242.27

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Mansonone E | Mansonone E|5090-87-9|3,6,9-Trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione|2,3-Dihydro-3,6,9-trimethylnaphtho[1,8-bc]pyran-7,8-dione|Naphtho(1,8-bc)pyran-7,8-dione, 2,3-dihydro-3,6,9-trimethyl-|Naphtho[1,8-bc]pyran-7,8-dione, 2,3-dihydro-3,6,9-trimethyl-|4,8,12-trimethyl-2-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8-tetraene-10,11-dione|CHEMBL362672|SCHEMBL7755715|DTXSID40965144|SYWTYRLIJCHSLJ-UHFFFAOYSA-N|BDBM50493328|3,6,9-Trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione #|Show More

Canonical SMILES:  CC1=C2OCC(C)c3ccc(C)c(c32)C(=O)C1=O

Standard InChI:  InChI=1S/C15H14O3/c1-7-4-5-10-8(2)6-18-15-9(3)13(16)14(17)11(7)12(10)15/h4-5,8H,6H2,1-3H3

Standard InChI Key:  SYWTYRLIJCHSLJ-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA362672

    MANSONONE E

Associated Targets(Human)

MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780 (11979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-8 (3484 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BGC-823 (3035 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bel-7402 (4577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leptomonas seymouri (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Crithidia fasciculata (29 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (8692 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Coxsackievirus (559 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus mutans (2687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus sobrinus (228 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cutibacterium acnes (887 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Salmonella typhi (4293 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: 242.27Molecular Weight (Monoisotopic): 242.0943AlogP: 2.63#Rotatable Bonds:
Polar Surface Area: 43.37Molecular Species: NEUTRALHBA: 3HBD:
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 2.88CX LogD: 2.88
Aromatic Rings: 1Heavy Atoms: 18QED Weighted: 0.66Np Likeness Score: 1.98

References

1. Shin DY, Kim SN, Chae JH, Hyun SS, Seo SY, Lee YS, Lee KO, Kim SH, Lee YS, Jeong JM, Choi NS, Suh YG..  (2004)  Syntheses and anti-MRSA activities of the C3 analogs of mansonone F, a potent anti-bacterial sesquiterpenoid: insights into its structural requirements for anti-MRSA activity.,  14  (17): [PMID:15357984] [10.1016/j.bmcl.2004.06.039]
2. Boonsri S, Karalai C, Ponglimanont C, Chantrapromma S, Kanjana-Opas A..  (2008)  Cytotoxic and antibacterial sesquiterpenes from Thespesia populnea.,  71  (7): [PMID:18553924] [10.1021/np800055q]
3. Paulino M, Alvareda EM, Denis PA, Barreiro EJ, Sperandio da Silva GM, Dubin M, Gastellú C, Aguilera S, Tapia O..  (2008)  Studies of trypanocidal (inhibitory) power of naphthoquinones: evaluation of quantum chemical molecular descriptors for structure-activity relationships.,  43  (10): [PMID:18276039] [10.1016/j.ejmech.2007.12.023]
4. Zhang Y, Liu YB, Li Y, Ma SG, Li L, Qu J, Zhang D, Chen XG, Jiang JD, Yu SS..  (2013)  Sesquiterpenes and alkaloids from the roots of Alangium chinense.,  76  (6): [PMID:23734721] [10.1021/np4000747]
5. Huang ZH, Zhuo ST, Li CY, Xie HT, Li D, Tan JH, Ou TM, Huang ZS, Gu LQ, Huang SL..  (2013)  Design, synthesis and biological evaluation of novel mansonone E derivatives prepared via CuAAC click chemistry as topoisomerase II inhibitors.,  68  [PMID:23968711] [10.1016/j.ejmech.2013.07.011]
6. Hairani R, Mongkol R, Chavasiri W..  (2016)  Allyl and prenyl ethers of mansonone G, new potential semisynthetic antibacterial agents.,  26  (21): [PMID:27680587] [10.1016/j.bmcl.2016.09.044]

Source