Details of the Drug

General Information of Drug (ID: DMXT7WG)

Drug Name
Deguelin
Synonyms
522-17-8; (-)-Deguelin; (-)-cis-deguelin; DEGUELIN(-); UNII-K5Z93K66IE; CHEBI:4357; K5Z93K66IE; MFCD01740600; C23H22O6; (7as,13as)-13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3h-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7ah)-one; (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one; (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one.; SR-01000597503; CCRIS 8104; Deguelin/; (-)-Deguelin, Mundulea sericea; Spectrum_001044; Tocris-1770; Spectrum2_000298; Spectrum3_001122; Spectrum4_001965; Spectrum5_001852; SCHEMBL73183; BSPBio_002583; KBioGR_002434; KBioSS_001524; SPECTRUM201138; MLS006010295; SPBio_000236; CHEMBL393417; KBio2_001524; KBio2_004092; KBio2_006660; KBio3_002083; DTXSID10200231; HMS1923A05; HMS3268E12; 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-; EX-A4158; ZINC3978987; 1702AH; ABP000411; BDBM50505204; CCG-39856; LMPK12060019; s8132; AKOS024456769; ACN-053693; BCP9000596; CS-1802; SDCCGMLS-0066380.P001; NCGC00025288-01; NCGC00025288-02; NCGC00025288-03; (-)-Deguelin, >98% (HPLC), powder; AS-56004; HY-13425; SMR004701363; C10417; Q5251862; SR-01000597503-1; SR-01000597503-3; SR-01000597503-4; BRD-K61401890-001-02-0; BRD-K61401890-001-03-8; BRD-K61401890-001-04-6; (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one; (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H,7aH-pyrano[2,3-c;6,5-f']dichromen-7-one; 13,13aS-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aS)-one; 3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-; 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
Indication
Disease Entry ICD 11 Status REF
Esophageal squamous cell carcinoma 2E60.1 Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 394.4
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C23H22O6
IUPAC Name
(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
Canonical SMILES
CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C
InChI
InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
InChIKey
ORDAZKGHSNRHTD-UXHICEINSA-N
Cross-matching ID
PubChem CID
107935
ChEBI ID
CHEMBL393417
CAS Number
522-17-8
TTD ID
D14NDZ
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aurora kinase B (AURKB) TT5LS6T AURKB_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
(3R)-3-hydroxyacyl-CoA dehydrogenase (HSD17B8) OTX1DWEF DHB8_HUMAN Gene/Protein Processing [3]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3 (PLCB3) OT0OMDEM PLCB3_HUMAN Gene/Protein Processing [3]
10 kDa heat shock protein, mitochondrial (HSPE1) OT7JSZLB CH10_HUMAN Gene/Protein Processing [3]
14-3-3 protein beta/alpha OTGBS3RF 1433B_HUMAN Gene/Protein Processing [3]
2-aminoethanethiol dioxygenase (ADO) OTRLGQ7V AEDO_HUMAN Gene/Protein Processing [3]
5'-3' exoribonuclease 2 OT7PNO08 XRN2_HUMAN Gene/Protein Processing [3]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4 (PFKFB4) OTQYEXL2 F264_HUMAN Gene/Protein Processing [3]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [3]
A-kinase anchor protein 8-like (AKAP8L) OTM3ZHGU AKP8L_HUMAN Gene/Protein Processing [3]
Achaete-scute homolog 1 (ASCL1) OTI4X44G ASCL1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Esophageal squamous cell carcinoma
ICD Disease Classification 2E60.1
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Aurora kinase B (AURKB) DTT AURKB 3.52E-36 -0.82 -1.62
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Deguelin, an Aurora B Kinase Inhibitor, Exhibits Potent Anti-Tumor Effect in Human Esophageal Squamous Cell Carcinoma. EBioMedicine. 2017 Dec;26:100-111.
2 An Electrophilic Deguelin Analogue Inhibits STAT3 Signaling in H- Ras-Transformed Human Mammary Epithelial Cells: The Cysteine 259 Residue as a Potential Target. Biomedicines. 2020 Oct 12;8(10):407.
3 Neurotoxicity and underlying cellular changes of 21 mitochondrial respiratory chain inhibitors. Arch Toxicol. 2021 Feb;95(2):591-615. doi: 10.1007/s00204-020-02970-5. Epub 2021 Jan 29.