Details of the Drug

General Information of Drug (ID: DMEV7FY)

Drug Name

TINGENIN B

Synonyms

Tingenin B; 22-Hydroxytingenone; 50656-68-3; (6aS,6bS,8aR,9S,11R,12aS,14aR)-3,9-dihydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione; AC1L2JCW; AC1Q6P5G; (6bs,8ar,9s,11r,12as,12bs,14ar)-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydropicene-2,10(6bh,9h)-dione; CTK4J2949; D:A-Friedo-24,30-dinoroleana-1(10),3,5,7-tetraene-2,21-dione, 3,22-dihydroxy-, (20beta,22beta)-

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

436.6

Logarithm of the Partition Coefficient (xlogp)

4.7

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C28H36O4
IUPAC Name: (6aS,6bS,8aR,9S,11R,12aS,14aR)-3,9-dihydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione
Canonical SMILES: C[C@@H]1C[C@@H]2[C@@](CC[C@]3([C@]2(CC[C@@]4(C3=CC=C5C4=CC(=O)C(=C5C)O)C)C)C)([C@@H](C1=O)O)C
InChI: InChI=1S/C28H36O4/c1-15-13-21-26(4,24(32)22(15)30)10-12-27(5)20-8-7-17-16(2)23(31)19(29)14-18(17)25(20,3)9-11-28(21,27)6/h7-8,14-15,21,24,31-32H,9-13H2,1-6H3/t15-,21-,24-,25+,26-,27-,28+/m1/s1
InChIKey: QIRUFAFQGKOTKA-ZRWKYKNNSA-N

Cross-matching ID

PubChem CID: 73147
CAS Number: 50656-68-3
TTD ID: D0BU5K

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Aldose reductase (AKR1B1)	TTFBNVI	ALDR_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[2]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[3]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Post-Translational Modifications	[3]
Endoplasmic reticulum chaperone BiP (HSPA5)	OTFUIRAO	BIP_HUMAN	Gene/Protein Processing	[3]
Keratin, type I cytoskeletal 18 (KRT18)	OTVLQFIP	K1C18_HUMAN	Protein Interaction/Cellular Processes	[3]
L-lactate dehydrogenase A chain (LDHA)	OTN7K4XB	LDHA_HUMAN	Gene/Protein Processing	[2]
Matrix metalloproteinase-9 (MMP9)	OTB2QDAV	MMP9_HUMAN	Gene/Protein Processing	[2]
Poly polymerase 1 (PARP1)	OT310QSG	PARP1_HUMAN	Protein Interaction/Cellular Processes	[3]
Serine/threonine-protein kinase/endoribonuclease IRE1 (ERN1)	OTY9R6FZ	ERN1_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Aldose reductase (AKR1B1)	DTT	AKR1B1	1.08E-20	0.94	1.58

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis. J Nat Prod. 2003 Sep;66(9):1191-6.
2	22-hydroxytingenone reduces proliferation and invasion of human melanoma cells. Toxicol In Vitro. 2020 Aug;66:104879. doi: 10.1016/j.tiv.2020.104879. Epub 2020 Apr 29.
3	The plant-derived triterpenoid tingenin B is a potent anticancer agent due to its cytotoxic activity on cancer stem cells of breast cancer in?vitro. Chem Biol Interact. 2016 Dec 25;260:248-255. doi: 10.1016/j.cbi.2016.10.001. Epub 2016 Oct 5.