Details of the Drug

General Information of Drug (ID: DM678IB)

Drug Name

Rapamycin Immunosuppressant Drug

Synonyms

mTOR Inhibitor, Rapamycin

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): 3

Molecular Weight (mw)

914.2

Logarithm of the Partition Coefficient (xlogp)

6

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

13

Chemical Identifiers

Formula: C51H79NO13
IUPAC Name: (1R,9S,12S,15R,16E,18R,19R,21R,23S,24Z,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
Canonical SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C\\[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
InChI: InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12-,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
InChIKey: QFJCIRLUMZQUOT-KADBNGAOSA-N

Cross-matching ID

PubChem CID: 21944094
TTD ID: D0Q5YP

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
FK506-binding protein 1A (FKBP1A)	TTMW94E	FKB1A_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
26S proteasome non-ATPase regulatory subunit 11 (PSMD11)	OT8KO67V	PSD11_HUMAN	Gene/Protein Processing	[2]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[3]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]
Alpha-1-antitrypsin (SERPINA1)	OTACYW9J	A1AT_HUMAN	Protein Interaction/Cellular Processes	[5]
Amyloid-beta precursor protein (APP)	OTKFD7R4	A4_HUMAN	Gene/Protein Processing	[6]
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[7]
Apolipoprotein D (APOD)	OTT77XW8	APOD_HUMAN	Protein Interaction/Cellular Processes	[8]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[2]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[9]
ATP-binding cassette sub-family D member 3 (ABCD3)	OT2PITLX	ABCD3_HUMAN	Gene/Protein Processing	[10]

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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
FK506-binding protein 1A (FKBP1A)	DTT	FKBP1A	9.70E-01	-0.04	-0.09

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
2	Rapamycin induces apoptosis of JN-DSRCT-1 cells by increasing the Bax : Bcl-xL ratio through concurrent mechanisms dependent and independent of its mTOR inhibitory activity. Oncogene. 2005 May 5;24(20):3348-57. doi: 10.1038/sj.onc.1208471.
3	Compared effect of immunosuppressive drugs cyclosporine A and rapamycin on cholesterol homeostasis key enzymes CYP27A1 and HMG-CoA reductase. Basic Clin Pharmacol Toxicol. 2007 Jun;100(6):392-7.
4	Inhibition of ATF4-mediated elevation of both autophagy and AKT/mTOR was involved in antitumorigenic activity of curcumin. Food Chem Toxicol. 2023 Mar;173:113609. doi: 10.1016/j.fct.2023.113609. Epub 2023 Jan 12.
5	Rapamycin reduces intrahepatic alpha-1-antitrypsin mutant Z protein polymers and liver injury in a mouse model. Exp Biol Med (Maywood). 2010 Jun;235(6):700-9. doi: 10.1258/ebm.2010.009297.
6	Rapamycin promotes beta-amyloid production via ADAM-10 inhibition. Biochem Biophys Res Commun. 2010 Jul 30;398(3):337-41. doi: 10.1016/j.bbrc.2010.06.017. Epub 2010 Jun 11.
7	Regulation of androgen receptor transcriptional activity by rapamycin in prostate cancer cell proliferation and survival. Oncogene. 2008 Nov 27;27(56):7106-17. doi: 10.1038/onc.2008.318. Epub 2008 Sep 8.
8	Protecting cells by protecting their vulnerable lysosomes: Identification of a new mechanism for preserving lysosomal functional integrity upon oxidative stress. PLoS Genet. 2017 Feb 9;13(2):e1006603. doi: 10.1371/journal.pgen.1006603. eCollection 2017 Feb.
9	Synergistic antiproliferative effect of mTOR inhibitors in combination with 5-fluorouracil in scirrhous gastric cancer. Cancer Sci. 2009 Dec;100(12):2402-10.
10	Activation of autophagy triggers mitochondrial loss and changes acetylation profile relevant for mechanotransduction in bladder cancer cells. Arch Toxicol. 2023 Jan;97(1):217-233. doi: 10.1007/s00204-022-03375-2. Epub 2022 Oct 10.