Details of the Drug

General Information of Drug (ID: DM1EK5D)

Drug Name

Ortataxel

Synonyms

UNII-8H61Y4E29N; 186348-23-2; 8H61Y4E29N; IDN-5109; IDN 5109; Ortataxel [INN]; Bay-59-8862; SB-T-101131; SB-T 101131; idn5109; SCHEMBL9932772; CHEMBL382300; BAY-59; IND-5109; DB11669; Z-3102; Hexanoic acid, 3-(((1,1-dimethylethoxy)carbonyl)amino)-2-hydroxy-5-methyl-,; Hexanoic acid; IND5109; 13-(N-tert-butoxycarbonyl-beta-isobutyisoserinyl)-14-hydroxy-baccatin-1,14-carbonate; 13-(N-tert-butoxycarbonyl-beta-isobutyisoserinyl)-14-hydroxybaccatin-1,14-carbonate; Genz29155

Indication

Disease Entry	ICD 11	Status	REF
Solid tumour/cancer	2A00-2F9Z	Phase 2	[1]
Heart transplant rejection	NE84	Preclinical	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

871.9

Logarithm of the Partition Coefficient (xlogp)

3.7

Rotatable Bond Count (rotbonds)

16

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

17

Chemical Identifiers

Formula: C44H57NO17
IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15R,16S)-4,12-diacetyloxy-9-hydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]oxy-10,14,20,20-tetramethyl-11,18-dioxo-6,17,19-trioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-2-yl] benzoate
Canonical SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@]5(C2(C)C)[C@H]([C@@H]1OC(=O)[C@@H]([C@H](CC(C)C)NC(=O)OC(C)(C)C)O)OC(=O)O5)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)OC(=O)C
InChI: InChI=1S/C44H57NO17/c1-20(2)17-25(45-38(53)61-40(6,7)8)29(49)37(52)57-30-21(3)28-31(56-22(4)46)33(50)42(11)26(48)18-27-43(19-55-27,60-23(5)47)32(42)35(58-36(51)24-15-13-12-14-16-24)44(41(28,9)10)34(30)59-39(54)62-44/h12-16,20,25-27,29-32,34-35,48-49H,17-19H2,1-11H3,(H,45,53)/t25-,26-,27+,29+,30+,31+,32-,34-,35-,42+,43-,44+/m0/s1
InChIKey: BWKDAMBGCPRVPI-ZQRPHVBESA-N

Cross-matching ID

PubChem CID: 6918412
CAS Number: 186348-23-2
UNII: 8H61Y4E29N
DrugBank ID: DB11669
TTD ID: D0YX7E
VARIDT ID: DR01287

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Multidrug resistance protein (MDR)	TT0JLSD	NOUNIPROTAC	Modulator	[3]
Tumor necrosis factor (TNF)	TTF8CQI	TNFA_HUMAN	Inhibitor	[2]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[5]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[5]
Bcl-2-like protein 1 (BCL2L1)	OTRC5K9O	B2CL1_HUMAN	Gene/Protein Processing	[5]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Protein Interaction/Cellular Processes	[5]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Protein Interaction/Cellular Processes	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Solid tumour/cancer

ICD Disease Classification

2A00-2F9Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Tumor necrosis factor (TNF)	DTT	TNF	8.51E-01	0.05	0.27
Breast cancer resistance protein (ABCG2)	DTP	BCRP	2.86E-02	-9.76E-01	-8.53E-01
Breast cancer resistance protein (ABCG2)	DTP	BCRP	1.12E-01	7.91E-02	1.09E+00

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Broad-spectrum modulation of ATP-binding cassette transport proteins by the taxane derivatives ortataxel (IDN-5109, BAY 59-8862) and tRA96023. Cancer Chemother Pharmacol. 2004 May;53(5):363-9.
2	New developments in immunosuppressive therapy for heart transplantation. Expert Opin Emerg Drugs. 2009 Mar;14(1):1-21.
3	Clinical pipeline report, company report or official report of Spectrum Phamaceuticals (2009).
4	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
5	Antitumor effects of IDN5109 on head and neck squamous cell carcinoma. Oncol Rep. 2006 Feb;15(2):329-34.