pevonedistat (CHEBI:145535)

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CHEBI:145535 - pevonedistat

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ChEBI Name	pevonedistat

ChEBI ID	CHEBI:145535

Definition	A pyrrolopyrimidine that is 7H-pyrrolo[2,3-d]pyrimidine which is substituted by a (1S)-2,3-dihydro-1H-inden-1-ylnitrilo group at position 4 and by a (1S,3S,4S)-3-hydroxy-4-[(sulfamoyloxy)methyl]cyclopentyl group at position 7. It is a potent and selective NEDD8-activating enzyme inhibitor with an IC₅₀ of 4.7 nM, and currently under clinical investigation for the treatment of acute myeloid leukemia (AML) and myelodysplastic syndromes.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5512401

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

B39 - Ideal conformer

RDKit 3D

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Time for openFile(B39 - Ideal conformer

RDKit 3D

56 60 0 0 0 0 0 0 0 0999 V2000

-1.6280 0.2270 -0.2540 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.6190 -0.9340 -0.0320 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.9010 -0.5710 -0.8010 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.0820 -0.4740 0.1660 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4590 -1.4210 -1.2170 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7850 0.0400 0.4200 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0910 0.9420 2.0860 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1340 -0.4990 0.6160 C 0 0 0 0 0 0 0 0 0 0 0 0

6.4500 -2.2080 0.6880 C 0 0 0 0 0 0 0 0 0 0 0 0

6.3030 0.1880 0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0

7.3090 -0.2750 -0.5030 C 0 0 0 0 0 0 0 0 0 0 0 0

7.9730 1.9840 -0.9590 C 0 0 0 0 0 0 0 0 0 0 0 0

6.1330 1.5500 0.5080 C 0 0 0 0 0 0 0 0 0 0 0 0

7.2870 -1.7880 -0.5380 C 0 0 0 0 0 0 0 0 0 0 0 0

8.1430 0.6260 -1.1440 C 0 0 0 0 0 0 0 0 0 0 0 0

6.9650 2.4470 -0.1330 C 0 0 0 0 0 0 0 0 0 0 0 0

5.5360 -0.9830 0.9010 C 0 0 1 0 0 0 0 0 0 0 0 0

4.2690 -1.1620 0.1870 N 0 0 0 0 0 0 0 0 0 0 0 0

3.1730 0.3060 1.6740 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9250 0.8230 1.4880 N 0 0 0 0 0 0 0 0 0 0 0 0

1.9120 -0.6580 -0.0550 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1520 -1.1560 -1.3700 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2630 -0.2830 -0.3970 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.1030 0.8850 -1.5730 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.6450 0.7990 -1.4620 C 0 0 2 0 0 0 0 0 0 0 0 0

-4.1480 1.8530 -0.6390 O 0 0 0 0 0 0 0 0 0 0 0 0

-6.2860 -0.2510 -0.5720 O 0 0 0 0 0 0 0 0 0 0 0 0

-7.5310 -0.1370 0.2950 S 0 0 0 0 0 0 0 0 0 0 0 0

-8.6390 -0.1220 -0.5940 O 0 0 0 0 0 0 0 0 0 0 0 0

-7.3840 -1.0920 1.3370 O 0 0 0 0 0 0 0 0 0 0 0 0

-7.4920 1.3520 1.0180 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.6840 0.9380 0.5710 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2000 -1.8620 -0.4230 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8380 -1.0410 1.0300 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1050 -1.3220 -1.5640 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.1680 -1.4030 0.7300 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.9200 0.3550 0.8550 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0620 -2.0700 -1.8350 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1670 1.5860 2.9490 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8590 -3.0980 0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0

7.0880 -2.3720 1.5560 H 0 0 0 0 0 0 0 0 0 0 0 0

8.6250 2.6840 -1.4600 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3470 1.9120 1.1540 H 0 0 0 0 0 0 0 0 0 0 0 0

8.3000 -2.1820 -0.4580 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8160 -2.1380 -1.4570 H 0 0 0 0 0 0 0 0 0 0 0 0

8.9290 0.2660 -1.7900 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8310 3.5090 0.0130 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3530 -0.8280 1.9640 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2270 -1.7470 -0.5860 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4790 -1.5680 -2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7770 1.9240 -1.6260 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7450 0.3230 -2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1010 0.8360 -2.4520 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0130 2.7380 -1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.7540 1.9570 0.8420 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.2060 1.6200 1.6170 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0

1 23 1 0

1 24 1 0

2 3 1 0

3 4 1 0

3 25 1 0

4 27 1 0

5 21 1 0

5 22 2 0

6 20 1 0

6 21 2 0

6 23 1 0

7 19 1 0

7 20 2 0

8 18 1 0

8 19 2 0

8 21 1 0

9 14 1 0

9 17 1 0

10 11 2 0

10 13 1 0

10 17 1 0

11 14 1 0

11 15 1 0

12 15 2 0

12 16 1 0

13 16 2 0

17 18 1 0

22 23 1 0

24 25 1 0

25 26 1 0

27 28 1 0

28 29 2 0

28 30 2 0

28 31 1 0

1 32 1 1

2 33 1 0

2 34 1 0

3 35 1 6

4 36 1 0

4 37 1 0

5 38 1 0

7 39 1 0

9 40 1 0

9 41 1 0

12 42 1 0

13 43 1 0

14 44 1 0

14 45 1 0

15 46 1 0

16 47 1 0

17 48 1 1

18 49 1 0

22 50 1 0

24 51 1 0

24 52 1 0

25 53 1 6

26 54 1 0

31 55 1 0

31 56 1 0

M END): 19 ms

reading 56 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

56 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Pevonedistat (MLN4924) is a selective NEDD8 inhibitor. It is being investigated as a cancer treatment, e.g. for mantle cell lymphoma (MCL).
Read full article at Wikipedia

Formula

C21H25N5O4S

Net Charge

Average Mass

443.520

Monoisotopic Mass

443.16273

InChI

InChI=1S/C21H25N5O4S/c22-31(28,29)30-11-14-9-15(10-19(14)27)26-8-7-17-20(23-12-24-21(17)26)25-18-6-5-13-3-1-2-4-16(13)18/h1-4,7-8,12,14-15,18-19,27H,5-6,9-11H2,(H2,22,28,29)(H,23,24,25)/t14-,15+,18-,19-/m0/s1

InChIKey

MPUQHZXIXSTTDU-QXGSTGNESA-N

SMILES

C1=CC2=C(C=C1)[C@H](CC2)NC3=C4C(=NC=N3)N(C=C4)[C@@H]5C[C@H]([C@H](C5)O)COS(N)(=O)=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	pevonedistat (CHEBI:145535) has role antineoplastic agent (CHEBI:35610) pevonedistat (CHEBI:145535) has role apoptosis inducer (CHEBI:68495) pevonedistat (CHEBI:145535) is a cyclopentanols (CHEBI:23495) pevonedistat (CHEBI:145535) is a indanes (CHEBI:46940) pevonedistat (CHEBI:145535) is a pyrrolopyrimidine (CHEBI:38670) pevonedistat (CHEBI:145535) is a secondary amino compound (CHEBI:50995) pevonedistat (CHEBI:145535) is a sulfamidate (CHEBI:51872)

IUPAC Name

[(1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl]methyl sulfamate

INNs	Sources
pevonedistat	WHO MedNet
pevonedistat	WHO MedNet
pévonédistat	WHO MedNet
pevonedistatum	WHO MedNet

Synonyms	Sources
[(1S,2S,4R)-4-[4-[[(1S)-2,3-dihydro-1H-inden-1-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]-2-hydroxy-cyclopentyl]methyl sulfamate	PDBeChem
MLN 4924	ChemIDplus
MLN-4924	LINCS
MLN4924	DrugBank

Manual Xrefs	Databases
B39	PDBeChem
D10413	KEGG DRUG
DB11759	DrugBank
LSM-6263	LINCS
Pevonedistat	Wikipedia
View more database links

Registry Number	Type	Source
905579-51-3	CAS Registry Number	ChemIDplus

Citations

Last Modified

28 November 2019

CHEBI:145535 - pevonedistat

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