Natural Product: NPC12270

Natural Product ID:  NPC12270
Common Name:   Marizomib
IUPAC Name:   (1S,2R,5R)-2-(2-chloroethyl)-5-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione
Synonyms:   Marizomib; NPI-0052
Molecular Formula:   C15H20ClNO4
Standard InCHIKey:  NGWSFRIPKNWYAO-SHTIJGAHSA-N
Standard InCHI:  InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1
Canonical SMILES:  ClCC[C@H]1C(=N[C@@]2([C@@]1(C)OC2=O)[C@H]([C@H]1CCCC=C1)O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO4320 Salinispora tropica Species Micromonosporaceae Bacteria PMID[15916417]
NPO15076 Salinispora arenicola Species Micromonosporaceae Bacteria PMID[15916417]
NPO4320 Salinispora tropica Species Micromonosporaceae Bacteria PMID[19133779]
NPO4320 Salinispora tropica Species Micromonosporaceae Bacteria PMID[12548698]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT389 Cell Line RPMI-8226 Homo sapiens IC50 = 8.2 nM 15916417
NPT71 Cell Line HEK293 Homo sapiens IC50 = 11 nM 15916417
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus IC50 = 2.6 nM 15916417
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus IC50 = 21 nM 15916417
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus IC50 = 430 nM 15916417
NPT2 Others Unspecified IC50 = 2.5 nM 18939815
NPT2 Others Unspecified IC50 = 26 nM 18939815
NPT2 Others Unspecified IC50 = 330 nM 18939815
NPT2 Others Unspecified IC50 = 2 nM 18939815
NPT2 Others Unspecified IC50 = 59 nM 18939815
NPT2 Others Unspecified IC50 = 2600 nM 18939815
NPT2 Others Unspecified IC50 = 3.5 nM 18939815
NPT2 Others Unspecified IC50 = 28 nM 18939815
NPT2 Others Unspecified IC50 = 430 nM 18939815
NPT2 Others Unspecified Ki = 23 nM 18939815
NPT2 Others Unspecified Ki = 97 nM 18939815
NPT2 Others Unspecified Ki > 1000 nM 18939815
NPT2 Others Unspecified Activity = 0.01 /s 18939815
NPT2 Others Unspecified Activity = 0.003 /s 18939815
NPT2 Others Unspecified Activity > 0.02 /s 18939815
NPT393 Cell Line HCT-116 Homo sapiens IC50 <= 0.002 ug/ml 19022674
NPT2 Others Unspecified GI50 < 10 nM 19022674
NPT2 Others Unspecified IC50 = 4 nM 19133779
NPT389 Cell Line RPMI-8226 Homo sapiens IC50 = 11 nM 19133779
NPT2 Others Unspecified IC50 = 34 nM 19133779
NPT2 Others Unspecified IC50 = 364 nM 19133779
NPT2 Others Unspecified IC50 = 1.9 nM 19746976
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 16 nM 19746976
NPT2 Others Unspecified IC50 = 1.3 nM 21835627
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 35 nM 21835627
NPT1185 Individual Protein Proteasome component C5 Homo sapiens IC50 = 430 nM 22978849
NPT1186 Individual Protein Proteasome Macropain subunit Homo sapiens IC50 = 28 nM 22978849
NPT1187 Individual Protein Proteasome Macropain subunit MB1 Homo sapiens IC50 = 3.5 nM 22978849
NPT2 Others Unspecified IC50 = 460 nM 23541650
NPT2 Others Unspecified IC50 = 21 nM 23541650
NPT2 Others Unspecified IC50 = 2.6 nM 23541650
NPT1188 Organism Plasmodium yoelii yoelii Plasmodium yoelii yoelii ED50 = 0.25 mg/kg/day 23587422
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 11 nM 23587422
NPT1187 Individual Protein Proteasome Macropain subunit MB1 Homo sapiens IC50 = 22 nM 24269479
NPT2 Others Unspecified IC50 = 460 nM 24534487
NPT2 Others Unspecified IC50 = 21 nM 24534487
NPT2 Others Unspecified IC50 = 2.6 nM 24534487

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC12270 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9223 High Similarity NPC14537
0.9135 High Similarity NPC473252
0.8738 High Similarity NPC234542
0.8654 High Similarity NPC473224
0.8544 High Similarity NPC123141
0.8431 Intermediate Similarity NPC226513
0.7863 Intermediate Similarity NPC201968
0.7692 Intermediate Similarity NPC50694
0.6803 Remote Similarity NPC7797
0.6694 Remote Similarity NPC474725
0.6667 Remote Similarity NPC475800
0.6639 Remote Similarity NPC46764
0.6615 Remote Similarity NPC204639
0.6614 Remote Similarity NPC323532
0.6612 Remote Similarity NPC70235
0.6587 Remote Similarity NPC216335
0.6583 Remote Similarity NPC472615
0.6569 Remote Similarity NPC230889
0.6549 Remote Similarity NPC314500
0.6538 Remote Similarity NPC16709
0.6504 Remote Similarity NPC92829
0.65 Remote Similarity NPC259476
0.65 Remote Similarity NPC472616
0.6475 Remote Similarity NPC168733
0.6471 Remote Similarity NPC78189
0.6446 Remote Similarity NPC271269
0.6429 Remote Similarity NPC475712
0.6423 Remote Similarity NPC473578
0.6417 Remote Similarity NPC215988
0.6396 Remote Similarity NPC475753
0.6372 Remote Similarity NPC118193
0.6372 Remote Similarity NPC256902
0.6364 Remote Similarity NPC74035
0.6349 Remote Similarity NPC122404
0.6341 Remote Similarity NPC307903
0.6341 Remote Similarity NPC140251
0.6341 Remote Similarity NPC475150
0.6339 Remote Similarity NPC475405
0.633 Remote Similarity NPC474312
0.6311 Remote Similarity NPC154601
0.6303 Remote Similarity NPC233932
0.6299 Remote Similarity NPC24462
0.629 Remote Similarity NPC133729
0.6288 Remote Similarity NPC280498
0.6281 Remote Similarity NPC474563
0.627 Remote Similarity NPC469865
0.626 Remote Similarity NPC251330
0.625 Remote Similarity NPC184461
0.625 Remote Similarity NPC329869
0.6228 Remote Similarity NPC159369
0.6228 Remote Similarity NPC39290
0.6195 Remote Similarity NPC86005
0.6186 Remote Similarity NPC165332
0.6186 Remote Similarity NPC180722
0.6186 Remote Similarity NPC195645
0.6182 Remote Similarity NPC47135
0.6179 Remote Similarity NPC475918
0.6172 Remote Similarity NPC471645
0.6154 Remote Similarity NPC471121
0.6154 Remote Similarity NPC471118
0.6148 Remote Similarity NPC204556
0.6134 Remote Similarity NPC475438
0.6111 Remote Similarity NPC127578
0.6111 Remote Similarity NPC113012
0.6111 Remote Similarity NPC122926
0.6106 Remote Similarity NPC258824
0.6103 Remote Similarity NPC329919
0.6103 Remote Similarity NPC477793
0.6087 Remote Similarity NPC97577
0.6077 Remote Similarity NPC471120
0.6077 Remote Similarity NPC147707
0.6077 Remote Similarity NPC471117
0.6071 Remote Similarity NPC475732
0.6068 Remote Similarity NPC472613
0.6053 Remote Similarity NPC477959
0.6048 Remote Similarity NPC166115
0.6032 Remote Similarity NPC474891
0.6032 Remote Similarity NPC329305
0.6031 Remote Similarity NPC477555
0.6031 Remote Similarity NPC9714
0.6017 Remote Similarity NPC5418
0.6016 Remote Similarity NPC261750
0.6016 Remote Similarity NPC1111
0.6015 Remote Similarity NPC469515
0.6015 Remote Similarity NPC23963
0.6 Remote Similarity NPC4834
0.6 Remote Similarity NPC193386
0.6 Remote Similarity NPC469494
0.6 Remote Similarity NPC167380
0.5984 Remote Similarity NPC474873
0.5984 Remote Similarity NPC476290
0.5983 Remote Similarity NPC36491
0.597 Remote Similarity NPC80150
0.5966 Remote Similarity NPC54905
0.5966 Remote Similarity NPC314009
0.5963 Remote Similarity NPC11796
0.5963 Remote Similarity NPC218817
0.5962 Remote Similarity NPC199557
0.5954 Remote Similarity NPC316325
0.5954 Remote Similarity NPC477553
0.594 Remote Similarity NPC476815
0.5938 Remote Similarity NPC29501
0.5935 Remote Similarity NPC469598
0.5929 Remote Similarity NPC295799
0.5926 Remote Similarity NPC469514
0.592 Remote Similarity NPC101106
0.592 Remote Similarity NPC135216
0.5917 Remote Similarity NPC475503
0.5917 Remote Similarity NPC469369
0.5917 Remote Similarity NPC469528
0.5917 Remote Similarity NPC121857
0.5909 Remote Similarity NPC113363
0.5897 Remote Similarity NPC473448
0.5897 Remote Similarity NPC313670
0.5893 Remote Similarity NPC474252
0.5891 Remote Similarity NPC35069
0.5891 Remote Similarity NPC258711
0.5891 Remote Similarity NPC268327
0.5891 Remote Similarity NPC60432
0.5891 Remote Similarity NPC295444
0.5891 Remote Similarity NPC279383
0.5891 Remote Similarity NPC476269
0.5891 Remote Similarity NPC273215
0.5887 Remote Similarity NPC76999
0.5887 Remote Similarity NPC4620
0.5882 Remote Similarity NPC473314
0.5878 Remote Similarity NPC30196
0.5873 Remote Similarity NPC199107
0.5873 Remote Similarity NPC42590
0.5873 Remote Similarity NPC232969
0.5872 Remote Similarity NPC281296
0.5868 Remote Similarity NPC245521
0.5857 Remote Similarity NPC139585
0.5856 Remote Similarity NPC103634
0.5855 Remote Similarity NPC315809
0.5855 Remote Similarity NPC314050
0.5854 Remote Similarity NPC316250
0.5852 Remote Similarity NPC273185
0.5847 Remote Similarity NPC111114
0.5847 Remote Similarity NPC300312
0.5847 Remote Similarity NPC261607
0.5845 Remote Similarity NPC75318
0.5841 Remote Similarity NPC69469
0.584 Remote Similarity NPC475676
0.584 Remote Similarity NPC220964
0.584 Remote Similarity NPC119329
0.5833 Remote Similarity NPC60718
0.5833 Remote Similarity NPC476190
0.5833 Remote Similarity NPC188010
0.5833 Remote Similarity NPC6531
0.5827 Remote Similarity NPC287572
0.5827 Remote Similarity NPC471636
0.5826 Remote Similarity NPC477993
0.5826 Remote Similarity NPC478112
0.5826 Remote Similarity NPC116575
0.5826 Remote Similarity NPC477994
0.5821 Remote Similarity NPC310467
0.582 Remote Similarity NPC474952
0.582 Remote Similarity NPC152480
0.5818 Remote Similarity NPC121200
0.5818 Remote Similarity NPC469492
0.5816 Remote Similarity NPC314361
0.5812 Remote Similarity NPC52198
0.5812 Remote Similarity NPC117405
0.5806 Remote Similarity NPC474747
0.5806 Remote Similarity NPC128501
0.5806 Remote Similarity NPC477198
0.5804 Remote Similarity NPC472430
0.5804 Remote Similarity NPC145899
0.5804 Remote Similarity NPC191711
0.5802 Remote Similarity NPC476813
0.5802 Remote Similarity NPC470540
0.5802 Remote Similarity NPC476814
0.5798 Remote Similarity NPC476049
0.5794 Remote Similarity NPC167145
0.5794 Remote Similarity NPC326024
0.5789 Remote Similarity NPC109603
0.5789 Remote Similarity NPC201889
0.5789 Remote Similarity NPC474776
0.5789 Remote Similarity NPC93688
0.5789 Remote Similarity NPC106791
0.5785 Remote Similarity NPC473859
0.5782 Remote Similarity NPC475394
0.5782 Remote Similarity NPC475584
0.5782 Remote Similarity NPC475152
0.5781 Remote Similarity NPC24389
0.5776 Remote Similarity NPC472614
0.5772 Remote Similarity NPC54705
0.5772 Remote Similarity NPC474718
0.5769 Remote Similarity NPC66108
0.5769 Remote Similarity NPC95290
0.5769 Remote Similarity NPC189338
0.5766 Remote Similarity NPC477088
0.5766 Remote Similarity NPC313333
0.5766 Remote Similarity NPC314451
0.5766 Remote Similarity NPC313342
0.5766 Remote Similarity NPC475210
0.5766 Remote Similarity NPC314512
0.5766 Remote Similarity NPC469517
0.5763 Remote Similarity NPC478003

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC12270 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD1719 Phase 1
0.6504 Remote Similarity NPD6420 Discontinued
0.6504 Remote Similarity NPD6421 Discontinued
0.6403 Remote Similarity NPD6333 Approved
0.6403 Remote Similarity NPD6334 Approved
0.6348 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6262 Remote Similarity NPD3732 Approved
0.6207 Remote Similarity NPD5778 Approved
0.6207 Remote Similarity NPD5779 Approved
0.6186 Remote Similarity NPD7839 Suspended
0.6182 Remote Similarity NPD7345 Approved
0.6091 Remote Similarity NPD5369 Approved
0.6087 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6101 Approved
0.605 Remote Similarity NPD4228 Discovery
0.6029 Remote Similarity NPD8074 Phase 3
0.5983 Remote Similarity NPD6411 Approved
0.5954 Remote Similarity NPD7500 Approved
0.592 Remote Similarity NPD4211 Phase 1
0.5906 Remote Similarity NPD6413 Approved
0.5899 Remote Similarity NPD6914 Discontinued
0.5893 Remote Similarity NPD6435 Approved
0.5847 Remote Similarity NPD7983 Approved
0.5826 Remote Similarity NPD5786 Approved
0.5822 Remote Similarity NPD8384 Approved
0.5806 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5804 Remote Similarity NPD1448 Clinical (unspecified phase)
0.5789 Remote Similarity NPD5766 Clinical (unspecified phase)
0.5766 Remote Similarity NPD8340 Approved
0.5766 Remote Similarity NPD8342 Approved
0.5766 Remote Similarity NPD8341 Approved
0.5766 Remote Similarity NPD8299 Approved
0.5752 Remote Similarity NPD4269 Approved
0.5752 Remote Similarity NPD4270 Approved
0.5725 Remote Similarity NPD1376 Discontinued
0.5725 Remote Similarity NPD8451 Approved
0.5714 Remote Similarity NPD5368 Approved
0.5714 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5702 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5702 Remote Similarity NPD7154 Phase 3
0.5692 Remote Similarity NPD2204 Approved
0.5692 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5683 Remote Similarity NPD8448 Approved
0.5674 Remote Similarity NPD8391 Approved
0.5674 Remote Similarity NPD8390 Approved
0.5674 Remote Similarity NPD8392 Approved
0.563 Remote Similarity NPD7100 Approved
0.562 Remote Similarity NPD5282 Discontinued
0.5603 Remote Similarity NPD5363 Approved

Structure

External Identifiers

PubChem CID   11347535
ChEMBL   CHEMBL371405
ZINC  

Physicochemical Properties

Molecular Weight:  313.11
ALogP:  -0.1056
MLogP:  2.45
XLogP:  2.326
# Rotatable Bonds:  8
Polar Surface Area:  79.12
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  21

Download Data

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Similar NPs/Drugs