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Chemistry

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Also known as: Bl-8040, 4f-benzoyl-tn14003, Motixafortide [usan], Tf14016, Bkt140, Bkt 140

Molecular Formula

C₉₇H₁₄₄FN₃₃O₁₉S₂

Molecular Weight

2159.5 g/mol

InChI Key

JJVZSYKFCOBILL-MKMRYRNGSA-N

FDA UNII

DA9G065962

Motixafortide is an orally bioavailable inhibitor of CXC Chemokine Receptor 4 (CXCR4) with potential antineoplastic activity. CXCR4 antagonist BL-8040 selectively binds to the chemokine receptor CXCR4, preventing the binding of stromal derived factor 1 (SDF-1 or CXCL12) to the CXCR4 receptor and subsequent receptor activation, which may result in decreased tumor cell proliferation and migration. In addition, inhibition of CXCR4 may induce mobilization of hematopoietic cells from the bone marrow into blood. The G protein-coupled receptor CXCR4 plays an important role in chemotaxis and angiogenesis and is upregulated in several tumor cell types; SDF-1/CXCR4 interaction induces retention of hematopoietic cells in the bone marrow.

1 2D Structure

Motixafortide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,6S,9S,12S,15R,20R,23S,26S,29S,32S)-3,6-bis(4-aminobutyl)-N-[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]-15-[[(2S)-2-[[(2S)-5-carbamimidamido-2-[[(2S)-5-carbamimidamido-2-[(4-fluorobenzoyl)amino]pentanoyl]amino]pentanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]-26-(3-carbamimidamidopropyl)-9,23-bis[3-(carbamoylamino)propyl]-12,29-bis[(4-hydroxyphenyl)methyl]-2,5,8,11,14,22,25,28,31-nonaoxo-17,18-dithia-1,4,7,10,13,21,24,27,30-nonazabicyclo[30.3.0]pentatriacontane-20-carboxamide

2.1.2 InChI

InChI=1S/C97H144FN33O19S2/c98-60-33-31-58(32-34-60)78(135)119-65(19-8-42-113-93(104)105)79(136)121-68(21-10-44-115-95(108)109)83(140)126-73(51-56-25-30-57-14-1-2-15-59(57)48-56)87(144)130-75-53-152-151-52-74(88(145)118-63(77(101)134)18-7-41-112-92(102)103)129-84(141)69(23-12-46-117-97(111)150)122-81(138)66(20-9-43-114-94(106)107)124-86(143)72(50-55-28-37-62(133)38-29-55)128-90(147)76-24-13-47-131(76)91(148)70(17-4-6-40-100)125-82(139)64(16-3-5-39-99)120-80(137)67(22-11-45-116-96(110)149)123-85(142)71(127-89(75)146)49-54-26-35-61(132)36-27-54/h1-2,14-15,25-38,48,63-76,132-133H,3-13,16-24,39-47,49-53,99-100H2,(H2,101,134)(H,118,145)(H,119,135)(H,120,137)(H,121,136)(H,122,138)(H,123,142)(H,124,143)(H,125,139)(H,126,140)(H,127,146)(H,128,147)(H,129,141)(H,130,144)(H4,102,103,112)(H4,104,105,113)(H4,106,107,114)(H4,108,109,115)(H3,110,116,149)(H3,111,117,150)/t63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-/m0/s1

2.1.3 InChI Key

JJVZSYKFCOBILL-MKMRYRNGSA-N

2.1.4 Canonical SMILES

C1CC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2C1)CCCCN)CCCCN)CCCNC(=O)N)CC3=CC=C(C=C3)O)NC(=O)C(CC4=CC5=CC=CC=C5C=C4)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C6=CC=C(C=C6)F)C(=O)NC(CCCNC(=N)N)C(=O)N)CCCNC(=O)N)CCCNC(=N)N)CC7=CC=C(C=C7)O

2.1.5 Isomeric SMILES

C1C[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2C1)CCCCN)CCCCN)CCCNC(=O)N)CC3=CC=C(C=C3)O)NC(=O)[C@H](CC4=CC5=CC=CC=C5C=C4)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)C6=CC=C(C=C6)F)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)CCCNC(=O)N)CCCNC(=N)N)CC7=CC=C(C=C7)O

2.2 Other Identifiers

2.2.1 UNII

DA9G065962

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Bl-8040

2. 4f-benzoyl-tn14003

3. Motixafortide [usan]

4. Tf14016

5. Bkt140

6. Bkt 140

7. Bkt-140

8. 664334-36-5

9. Da9g065962

10. Tf 14016

11. Tf-14016

12. Motixafortida

13. Motixafortidum

14. Motixafortide [inn]

15. Motixafortide [who-dd]

16. Unii-da9g065962

17. Gtpl10679

18. Chebi:145536

19. 4f-benzoyl-tn-14003

20. Bl8040

21. Who 10935

22. Bl 8040

23. Db14939

24. Q27276305

25. L-argininamide, N2-(4-fluorobenzoyl)-l-arginyl-l-arginyl-3-(2-naphthalenyl)-l-alanyl-l-cysteinyl-l-tyrosyl-n5-(aminocarbonyl)-l-ornithyl-l-lysyl-d-lysyl-l-prolyl-l-tyrosyl-l-arginyl-n5-(aminocarbonyl)-l-ornithyl-l-cysteinyl-, Cyclic (4->13)-disulfide

26. N-(4-fluoro-benzoyl)-l-arginyl-l-arginyl-(l-3-(naphthyl)alanyl)-l-cysteinyl-l-tyrosyl-l-citrullinyl-l-lysyl-d-lysyl-l-prolyl-l-tyrosyl-l-arginyl-l-citrullinyl-l-cysteinyl-l-arginine Amide,cyclic (4-13)-disulfide

27. S3.4,s3.13-cyclo(n.alpha.-(4-fluorobenzoyl)-l-arginyl-l-arginyl-3-(naphthalen-2-yl)-l-alanyl-l-cysteinyl-l-tyrosyl-n5-carbamoyl-l-ornithyl-l-lysyl-d-lysyl-l-prolyl-l-tyrosyl-larginyl-n5-carbamoyl-l-ornithyl-l-cysteinyl-l-argininamide)

2.4 Create Date

2015-09-16

3 Chemical and Physical Properties

Molecular Formula	C₉₇H₁₄₄FN₃₃O₁₉S₂
Molecular Weight	2159.5 g/mol
XLogP3	-2.9
Hydrogen Bond Donor Count	34
Hydrogen Bond Acceptor Count	28
Rotatable Bond Count	53
Exact Mass	2159.0775248 g/mol
Monoisotopic Mass	2158.0741700 g/mol
Topological Polar Surface Area	943 Å²
Heavy Atom Count	152
Formal Charge	0
Complexity	4500
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1