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]
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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: CHEBI:4357
CAS Number: 522-17-8
TTD ID: D14NDZ

Combinatorial Drugs (CBD)

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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]

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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]
2-aminomuconic semialdehyde dehydrogenase (ALDH8A1)	OTINY3MW	AL8A1_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]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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.
4	Deguelin inhibits the migration and invasion of lung cancer A549 and H460 cells via regulating actin cytoskeleton rearrangement. Int J Clin Exp Pathol. 2015 Dec 1;8(12):15582-90. eCollection 2015.