Natural Product: NPC199259

Natural Product ID:  NPC199259
Common Name:   Penitrem F
IUPAC Name:  
Synonyms:  
Molecular Formula:   C37H44ClNO5
Standard InCHIKey:  YWORPEZTBDVGCS-JCMMWUKFSA-N
Standard InCHI:  InChI=1S/C37H44ClNO5/c1-15(2)29-28(40)32-37(44-32)23(42-29)9-10-34(6)35(7)19(8-11-36(34,37)41)30-27-26-22(39-31(27)35)14-21(38)18-12-16(3)17-13-20(24(17)25(18)26)33(4,5)43-30/h14,17,19-20,23-24,28-30,32,39-41H,1,3,8-13H2,2,4-7H3/t17-,19+,20+,23+,24+,28+,29-,30+,32-,34-,35-,36+,37+/m1/s1
Canonical SMILES:  CC(=C)[C@H]1O[C@H]2CC[C@]3([C@@]([C@]42[C@@H]([C@H]1O)O4)(O)CC[C@@H]1[C@]3(C)c2[nH]c3c4c2[C@H]1OC(C)(C)[C@@H]1[C@H]2c4c(c(c3)Cl)CC(=C)[C@H]2C1)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   BGC0001375 ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO13779 Penicillium crustosum Species Aspergillaceae Eukaryota PMID[12670149]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2212 Organism Oncopeltus fasciatus Oncopeltus fasciatus Survival = 9.5 % 23398362
NPT6649 Organism Ceratitis capitata Ceratitis capitata Activity = 100 % 22705001
NPT6649 Organism Ceratitis capitata Ceratitis capitata Activity = 0 % 22705001
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 35000 nM 22088956
NPT83 Cell Line MCF7 Homo sapiens IC50 = 15000 nM 10.6019/CHEMBL1201861
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 13800 nM 15217273
NPT6649 Organism Ceratitis capitata Ceratitis capitata Activity = 100 % 17958396

  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 NPC199259 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
0.9954 High Similarity NPC473389
0.9541 High Similarity NPC188239
0.9128 High Similarity NPC249342
0.8784 High Similarity NPC470873
0.8682 High Similarity NPC470874
0.7298 Intermediate Similarity NPC470843
0.7298 Intermediate Similarity NPC94541
0.7289 Intermediate Similarity NPC231342
0.7197 Intermediate Similarity NPC61813
0.7071 Intermediate Similarity NPC96131
0.7069 Intermediate Similarity NPC477135
0.7033 Intermediate Similarity NPC473806
0.7033 Intermediate Similarity NPC471634
0.7021 Intermediate Similarity NPC61637
0.6987 Remote Similarity NPC473650
0.6987 Remote Similarity NPC160527
0.698 Remote Similarity NPC79107
0.698 Remote Similarity NPC475424
0.6978 Remote Similarity NPC119700
0.6947 Remote Similarity NPC34271
0.6942 Remote Similarity NPC475476
0.6942 Remote Similarity NPC242446
0.6935 Remote Similarity NPC282033
0.6917 Remote Similarity NPC471284
0.6904 Remote Similarity NPC235900
0.6897 Remote Similarity NPC32200
0.6891 Remote Similarity NPC475165
0.6862 Remote Similarity NPC250129
0.6844 Remote Similarity NPC165201
0.6805 Remote Similarity NPC473547
0.6795 Remote Similarity NPC475151
0.6793 Remote Similarity NPC187456
0.6777 Remote Similarity NPC97388
0.6767 Remote Similarity NPC205403
0.6756 Remote Similarity NPC302191
0.6681 Remote Similarity NPC476175
0.6653 Remote Similarity NPC18661
0.6653 Remote Similarity NPC204303
0.6641 Remote Similarity NPC473565
0.664 Remote Similarity NPC112547
0.6638 Remote Similarity NPC473747
0.6637 Remote Similarity NPC198339
0.6597 Remote Similarity NPC123019
0.6586 Remote Similarity NPC41318
0.6586 Remote Similarity NPC469312
0.6548 Remote Similarity NPC183426
0.652 Remote Similarity NPC6093
0.6518 Remote Similarity NPC314552
0.6502 Remote Similarity NPC154293
0.6489 Remote Similarity NPC97525
0.6454 Remote Similarity NPC472842
0.6435 Remote Similarity NPC19679
0.6434 Remote Similarity NPC284102
0.6421 Remote Similarity NPC1203
0.6406 Remote Similarity NPC477531
0.6392 Remote Similarity NPC252251
0.6379 Remote Similarity NPC476319
0.6379 Remote Similarity NPC476106
0.6367 Remote Similarity NPC209174
0.6364 Remote Similarity NPC472444
0.6343 Remote Similarity NPC131273
0.6343 Remote Similarity NPC473441
0.634 Remote Similarity NPC206967
0.629 Remote Similarity NPC48353
0.6289 Remote Similarity NPC57690
0.6286 Remote Similarity NPC193777
0.6285 Remote Similarity NPC477532
0.6281 Remote Similarity NPC267423
0.6281 Remote Similarity NPC476044
0.6274 Remote Similarity NPC37473
0.6269 Remote Similarity NPC277351
0.6265 Remote Similarity NPC475602
0.6265 Remote Similarity NPC478074
0.626 Remote Similarity NPC278540
0.6255 Remote Similarity NPC249428
0.625 Remote Similarity NPC192270
0.6239 Remote Similarity NPC473189
0.6236 Remote Similarity NPC471583
0.6236 Remote Similarity NPC471782
0.6235 Remote Similarity NPC201697
0.6235 Remote Similarity NPC473667
0.6234 Remote Similarity NPC85066
0.6234 Remote Similarity NPC270009
0.6234 Remote Similarity NPC181502
0.6234 Remote Similarity NPC472443
0.6229 Remote Similarity NPC46413
0.6226 Remote Similarity NPC476492
0.6217 Remote Similarity NPC107836
0.6216 Remote Similarity NPC290529
0.6211 Remote Similarity NPC475137
0.6211 Remote Similarity NPC473850
0.6211 Remote Similarity NPC141428
0.6211 Remote Similarity NPC475498
0.621 Remote Similarity NPC234999
0.6203 Remote Similarity NPC284141
0.6203 Remote Similarity NPC311451
0.6202 Remote Similarity NPC475644
0.6202 Remote Similarity NPC471190
0.6202 Remote Similarity NPC470486
0.6202 Remote Similarity NPC475362
0.6202 Remote Similarity NPC471977
0.6192 Remote Similarity NPC79293
0.6192 Remote Similarity NPC30456
0.6192 Remote Similarity NPC279401
0.6187 Remote Similarity NPC267926
0.6183 Remote Similarity NPC153042
0.6174 Remote Similarity NPC472586
0.6172 Remote Similarity NPC76565
0.6172 Remote Similarity NPC266192
0.6172 Remote Similarity NPC57797
0.6172 Remote Similarity NPC250807
0.6169 Remote Similarity NPC70155
0.6169 Remote Similarity NPC237702
0.6166 Remote Similarity NPC62367
0.6163 Remote Similarity NPC228377
0.6163 Remote Similarity NPC87152
0.6163 Remote Similarity NPC122968
0.6163 Remote Similarity NPC146824
0.6163 Remote Similarity NPC477787
0.6163 Remote Similarity NPC475631
0.6163 Remote Similarity NPC475600
0.6163 Remote Similarity NPC476110
0.6163 Remote Similarity NPC328186
0.6163 Remote Similarity NPC110151
0.616 Remote Similarity NPC177056
0.616 Remote Similarity NPC472553
0.616 Remote Similarity NPC246700
0.616 Remote Similarity NPC475778
0.6154 Remote Similarity NPC316841
0.6154 Remote Similarity NPC475303
0.6154 Remote Similarity NPC473689
0.6154 Remote Similarity NPC292416
0.6154 Remote Similarity NPC475596
0.6151 Remote Similarity NPC477907
0.6151 Remote Similarity NPC477909
0.6151 Remote Similarity NPC42678
0.6151 Remote Similarity NPC204491
0.6148 Remote Similarity NPC98371
0.6148 Remote Similarity NPC313884
0.6145 Remote Similarity NPC475406
0.6142 Remote Similarity NPC216428
0.6134 Remote Similarity NPC106833
0.6134 Remote Similarity NPC469497
0.6134 Remote Similarity NPC95783
0.6134 Remote Similarity NPC471564
0.6133 Remote Similarity NPC106593
0.613 Remote Similarity NPC319880
0.613 Remote Similarity NPC244839
0.613 Remote Similarity NPC320324
0.6124 Remote Similarity NPC200888
0.6124 Remote Similarity NPC473506
0.6122 Remote Similarity NPC475085
0.6122 Remote Similarity NPC475112
0.6122 Remote Similarity NPC38959
0.6122 Remote Similarity NPC327904
0.6122 Remote Similarity NPC291535
0.6121 Remote Similarity NPC293472
0.6116 Remote Similarity NPC243834
0.6116 Remote Similarity NPC70956
0.6107 Remote Similarity NPC473182
0.6104 Remote Similarity NPC472550
0.6104 Remote Similarity NPC48042
0.6104 Remote Similarity NPC304179
0.6102 Remote Similarity NPC469594
0.6102 Remote Similarity NPC144779
0.6102 Remote Similarity NPC294579
0.6098 Remote Similarity NPC162484
0.6095 Remote Similarity NPC476514
0.6095 Remote Similarity NPC472843
0.6094 Remote Similarity NPC477912
0.6092 Remote Similarity NPC128751
0.6091 Remote Similarity NPC72211
0.609 Remote Similarity NPC217554
0.609 Remote Similarity NPC475844
0.6087 Remote Similarity NPC30570
0.6087 Remote Similarity NPC477910
0.6085 Remote Similarity NPC139291
0.6085 Remote Similarity NPC235885
0.6085 Remote Similarity NPC477902
0.6085 Remote Similarity NPC472108
0.6084 Remote Similarity NPC327769
0.6084 Remote Similarity NPC170751
0.608 Remote Similarity NPC475422
0.6078 Remote Similarity NPC472555
0.6078 Remote Similarity NPC223590
0.6076 Remote Similarity NPC99428
0.6075 Remote Similarity NPC11408
0.607 Remote Similarity NPC122463
0.6066 Remote Similarity NPC476493
0.6064 Remote Similarity NPC63041
0.6063 Remote Similarity NPC206343
0.6063 Remote Similarity NPC477908
0.6063 Remote Similarity NPC162812
0.6063 Remote Similarity NPC475408
0.6063 Remote Similarity NPC471014
0.6063 Remote Similarity NPC6981
0.6062 Remote Similarity NPC148860
0.6062 Remote Similarity NPC202503
0.6061 Remote Similarity NPC34508
0.6055 Remote Similarity NPC477533

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC199259 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
0.6578 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5164 Discontinued
0.635 Remote Similarity NPD6773 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7169 Suspended
0.6296 Remote Similarity NPD8244 Phase 2
0.6292 Remote Similarity NPD2727 Phase 2
0.6245 Remote Similarity NPD4305 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6978 Phase 2
0.6226 Remote Similarity NPD6977 Clinical (unspecified phase)
0.6196 Remote Similarity NPD7221 Approved
0.6196 Remote Similarity NPD7219 Approved
0.6183 Remote Similarity NPD5003 Discontinued
0.6176 Remote Similarity NPD5913 Phase 3
0.6176 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6148 Remote Similarity NPD7931 Approved
0.6148 Remote Similarity NPD6976 Clinical (unspecified phase)
0.6148 Remote Similarity NPD7932 Clinical (unspecified phase)
0.6148 Remote Similarity NPD7933 Approved
0.6148 Remote Similarity NPD7934 Discovery
0.6142 Remote Similarity NPD6455 Phase 3
0.6118 Remote Similarity NPD6717 Clinical (unspecified phase)
0.6106 Remote Similarity NPD972 Clinical (unspecified phase)
0.6091 Remote Similarity NPD3230 Clinical (unspecified phase)
0.6071 Remote Similarity NPD8364 Approved
0.6071 Remote Similarity NPD8363 Approved
0.6056 Remote Similarity NPD5936 Approved
0.6056 Remote Similarity NPD8427 Approved
0.6056 Remote Similarity NPD5939 Approved
0.6056 Remote Similarity NPD8429 Approved
0.6056 Remote Similarity NPD8428 Approved
0.6055 Remote Similarity NPD3280 Approved
0.604 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6033 Remote Similarity NPD3791 Clinical (unspecified phase)
0.6032 Remote Similarity NPD2920 Discontinued
0.603 Remote Similarity NPD7576 Discontinued
0.6028 Remote Similarity NPD8426 Approved
0.6028 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6028 Remote Similarity NPD8425 Approved
0.6024 Remote Similarity NPD7218 Clinical (unspecified phase)
0.6008 Remote Similarity NPD6736 Discontinued
0.6008 Remote Similarity NPD1322 Clinical (unspecified phase)
0.6008 Remote Similarity NPD6995 Phase 1
0.6 Remote Similarity NPD8465 Approved
0.6 Remote Similarity NPD8467 Approved
0.6 Remote Similarity NPD2565 Phase 2
0.6 Remote Similarity NPD2564 Approved
0.6 Remote Similarity NPD8466 Approved
0.5991 Remote Similarity NPD4112 Clinical (unspecified phase)
0.5985 Remote Similarity NPD7558 Phase 2
0.5985 Remote Similarity NPD6494 Phase 2
0.5985 Remote Similarity NPD7548 Discontinued
0.5984 Remote Similarity NPD3003 Approved
0.5984 Remote Similarity NPD5902 Approved
0.5984 Remote Similarity NPD7073 Clinical (unspecified phase)
0.5984 Remote Similarity NPD5903 Approved
0.5978 Remote Similarity NPD7772 Phase 3
0.5974 Remote Similarity NPD1325 Approved
0.5974 Remote Similarity NPD1326 Approved
0.5974 Remote Similarity NPD7474 Suspended
0.5963 Remote Similarity NPD4350 Approved
0.5963 Remote Similarity NPD4349 Approved
0.5961 Remote Similarity NPD6803 Clinical (unspecified phase)
0.5958 Remote Similarity NPD1534 Approved
0.5957 Remote Similarity NPD7956 Approved
0.5957 Remote Similarity NPD7955 Approved
0.5957 Remote Similarity NPD1503 Clinical (unspecified phase)
0.5949 Remote Similarity NPD5596 Phase 2
0.5948 Remote Similarity NPD4876 Phase 3
0.5948 Remote Similarity NPD4875 Phase 3
0.5947 Remote Similarity NPD1554 Clinical (unspecified phase)
0.5929 Remote Similarity NPD4502 Phase 2
0.5923 Remote Similarity NPD7418 Discontinued
0.5917 Remote Similarity NPD8460 Approved
0.5917 Remote Similarity NPD8459 Approved
0.5914 Remote Similarity NPD8109 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4699 Discontinued
0.5894 Remote Similarity NPD7889 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8468 Phase 2
0.5878 Remote Similarity NPD7708 Approved
0.5863 Remote Similarity NPD5669 Clinical (unspecified phase)
0.5857 Remote Similarity NPD2715 Clinical (unspecified phase)
0.5857 Remote Similarity NPD3932 Clinical (unspecified phase)
0.5851 Remote Similarity NPD7803 Approved
0.5847 Remote Similarity NPD4600 Approved
0.5847 Remote Similarity NPD4601 Approved
0.5833 Remote Similarity NPD3930 Clinical (unspecified phase)
0.5833 Remote Similarity NPD6290 Phase 2
0.583 Remote Similarity NPD7673 Phase 3
0.5821 Remote Similarity NPD4454 Phase 2
0.5817 Remote Similarity NPD2721 Clinical (unspecified phase)
0.5816 Remote Similarity NPD7252 Clinical (unspecified phase)
0.581 Remote Similarity NPD8399 Phase 1
0.581 Remote Similarity NPD5658 Approved
0.581 Remote Similarity NPD8423 Phase 2
0.5806 Remote Similarity NPD4118 Clinical (unspecified phase)
0.5806 Remote Similarity NPD1768 Approved
0.5806 Remote Similarity NPD2176 Approved
0.5806 Remote Similarity NPD2177 Approved
0.5806 Remote Similarity NPD2175 Phase 3
0.5804 Remote Similarity NPD6220 Phase 3
0.5803 Remote Similarity NPD8358 Approved
0.58 Remote Similarity NPD3931 Approved
0.58 Remote Similarity NPD3928 Approved
0.5792 Remote Similarity NPD6985 Discontinued
0.5789 Remote Similarity NPD1229 Phase 2
0.5789 Remote Similarity NPD7688 Phase 1
0.5776 Remote Similarity NPD5744 Clinical (unspecified phase)
0.5772 Remote Similarity NPD6491 Clinical (unspecified phase)
0.5769 Remote Similarity NPD7194 Discontinued
0.5766 Remote Similarity NPD5807 Phase 2
0.5766 Remote Similarity NPD7946 Pre-registration
0.5763 Remote Similarity NPD6160 Clinical (unspecified phase)
0.576 Remote Similarity NPD6456 Discontinued
0.5759 Remote Similarity NPD2615 Phase 3
0.5759 Remote Similarity NPD2616 Phase 3
0.5749 Remote Similarity NPD5411 Discontinued
0.5748 Remote Similarity NPD7671 Approved
0.5748 Remote Similarity NPD7672 Approved
0.5738 Remote Similarity NPD6281 Approved
0.5737 Remote Similarity NPD5721 Clinical (unspecified phase)
0.5736 Remote Similarity NPD4328 Approved
0.5731 Remote Similarity NPD5530 Phase 1
0.573 Remote Similarity NPD7921 Approved
0.5725 Remote Similarity NPD4506 Discontinued
0.572 Remote Similarity NPD4951 Discontinued
0.5714 Remote Similarity NPD6642 Approved
0.5714 Remote Similarity NPD8160 Phase 2
0.5714 Remote Similarity NPD5612 Discontinued
0.5714 Remote Similarity NPD6630 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6641 Approved
0.57 Remote Similarity NPD8489 Phase 1
0.5698 Remote Similarity NPD7571 Clinical (unspecified phase)
0.5697 Remote Similarity NPD4511 Phase 1
0.569 Remote Similarity NPD3920 Phase 2
0.5687 Remote Similarity NPD5930 Phase 3
0.5686 Remote Similarity NPD7947 Clinical (unspecified phase)
0.5685 Remote Similarity NPD5522 Clinical (unspecified phase)
0.568 Remote Similarity NPD8396 Approved
0.568 Remote Similarity NPD8395 Approved
0.5679 Remote Similarity NPD8442 Discontinued
0.5676 Remote Similarity NPD7707 Approved
0.5672 Remote Similarity NPD2380 Approved
0.5672 Remote Similarity NPD2381 Approved
0.5672 Remote Similarity NPD2382 Approved
0.5669 Remote Similarity NPD7958 Clinical (unspecified phase)
0.5669 Remote Similarity NPD7957 Phase 1
0.5669 Remote Similarity NPD4901 Clinical (unspecified phase)
0.5664 Remote Similarity NPD5835 Phase 3
0.5664 Remote Similarity NPD5834 Phase 3
0.5661 Remote Similarity NPD5083 Clinical (unspecified phase)
0.5659 Remote Similarity NPD6657 Clinical (unspecified phase)
0.5657 Remote Similarity NPD5497 Clinical (unspecified phase)
0.5656 Remote Similarity NPD8431 Approved
0.5649 Remote Similarity NPD3258 Approved
0.5647 Remote Similarity NPD7769 Phase 3
0.5647 Remote Similarity NPD1392 Approved
0.5642 Remote Similarity NPD648 Clinical (unspecified phase)
0.5631 Remote Similarity NPD7181 Phase 3
0.5625 Remote Similarity NPD8386 Phase 2
0.5625 Remote Similarity NPD4079 Approved
0.5625 Remote Similarity NPD4076 Approved
0.5625 Remote Similarity NPD2739 Clinical (unspecified phase)
0.562 Remote Similarity NPD5066 Phase 2
0.562 Remote Similarity NPD5067 Phase 2
0.5607 Remote Similarity NPD7859 Phase 2
0.5607 Remote Similarity NPD6375 Clinical (unspecified phase)
0.5606 Remote Similarity NPD6615 Clinical (unspecified phase)
0.5605 Remote Similarity NPD4526 Approved
0.5605 Remote Similarity NPD4528 Approved
0.5605 Remote Similarity NPD4529 Approved
0.5604 Remote Similarity NPD3849 Clinical (unspecified phase)
0.5602 Remote Similarity NPD8464 Clinical (unspecified phase)
0.56 Remote Similarity NPD7770 Phase 3
0.56 Remote Similarity NPD6517 Phase 3

Structure

External Identifiers

PubChem CID   3086086
ChEMBL   CHEMBL2272678
ZINC  

Physicochemical Properties

Molecular Weight:  617.29
ALogP:  0.7699
MLogP:  4.76
XLogP:  3.394
# Rotatable Bonds:  9
Polar Surface Area:  83.48
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  10
# Heavy Atoms:  44

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs