Natural Product: NPC302235

Natural Product ID:  NPC302235
Common Name:   Dehydrobis(Methylthio)Gliotoxin
IUPAC Name:   (3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-10H-pyrazino[1,2-a]indole-1,4-dione
Synonyms:   Dehydrobis(Methylthio)Gliotoxin
Molecular Formula:   C15H18N2O4S2
Standard InCHIKey:  BUSZSWVUELPPBM-HUUCEWRRSA-N
Standard InCHI:  InChI=1S/C15H18N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,18-19H,7-8H2,1-3H3/t14-,15-/m1/s1
Canonical SMILES:  CS[C@]12Cc3c(N2C(=O)[C@](N(C1=O)C)(SC)CO)c(O)ccc3
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
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota isolated from sediment At >33 m depth in Vanuatu 2003 PMID[20303767]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota PMID[22148349]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens IC50 = 58000 nM 12542343
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 8500 nM 25993619
NPT2 Others Unspecified IC50 > 50000 nM 15787444
NPT2 Others Unspecified Ratio IC50 = 16.6 nM 20439609
NPT168 Cell Line P388 Mus musculus IC50 = 110 nM 19128055
NPT2 Others Unspecified IC50 = 19500 nM 9917297
NPT2 Others Unspecified IC50 = 16900 nM 23570615
NPT15 Cell Line Jurkat Homo sapiens IC50 = 141000 nM Open TG-GATES in vivo data: Hematology

  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 NPC302235 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
0.9458 High Similarity NPC166169
0.8402 Intermediate Similarity NPC475609
0.7598 Intermediate Similarity NPC33507
0.75 Intermediate Similarity NPC470301
0.743 Intermediate Similarity NPC328270
0.7306 Intermediate Similarity NPC470485
0.7273 Intermediate Similarity NPC1464
0.7202 Intermediate Similarity NPC470483
0.7173 Intermediate Similarity NPC262725
0.7158 Intermediate Similarity NPC472114
0.7158 Intermediate Similarity NPC472115
0.7157 Intermediate Similarity NPC265642
0.7157 Intermediate Similarity NPC132874
0.7157 Intermediate Similarity NPC138615
0.7157 Intermediate Similarity NPC218733
0.709 Intermediate Similarity NPC39822
0.6989 Remote Similarity NPC146370
0.6978 Remote Similarity NPC301163
0.6957 Remote Similarity NPC470481
0.6957 Remote Similarity NPC470482
0.6927 Remote Similarity NPC470491
0.6919 Remote Similarity NPC471124
0.6914 Remote Similarity NPC471680
0.6912 Remote Similarity NPC246140
0.6912 Remote Similarity NPC195787
0.6904 Remote Similarity NPC204970
0.6901 Remote Similarity NPC478141
0.69 Remote Similarity NPC112937
0.6884 Remote Similarity NPC170333
0.6881 Remote Similarity NPC469732
0.685 Remote Similarity NPC316282
0.685 Remote Similarity NPC161804
0.6842 Remote Similarity NPC129624
0.6837 Remote Similarity NPC477394
0.6836 Remote Similarity NPC470824
0.68 Remote Similarity NPC251439
0.6793 Remote Similarity NPC471122
0.678 Remote Similarity NPC470484
0.6774 Remote Similarity NPC204867
0.6768 Remote Similarity NPC302169
0.6759 Remote Similarity NPC122886
0.6749 Remote Similarity NPC138830
0.6734 Remote Similarity NPC473004
0.6725 Remote Similarity NPC257390
0.6724 Remote Similarity NPC313694
0.6724 Remote Similarity NPC242159
0.6722 Remote Similarity NPC473491
0.672 Remote Similarity NPC133470
0.672 Remote Similarity NPC289776
0.672 Remote Similarity NPC191863
0.6704 Remote Similarity NPC189908
0.6701 Remote Similarity NPC270301
0.6701 Remote Similarity NPC197335
0.6701 Remote Similarity NPC116096
0.6698 Remote Similarity NPC234772
0.6697 Remote Similarity NPC470480
0.6682 Remote Similarity NPC222046
0.6682 Remote Similarity NPC288110
0.6667 Remote Similarity NPC476268
0.6667 Remote Similarity NPC314659
0.6667 Remote Similarity NPC148124
0.6667 Remote Similarity NPC315388
0.6651 Remote Similarity NPC266994
0.665 Remote Similarity NPC476098
0.665 Remote Similarity NPC477179
0.6648 Remote Similarity NPC16188
0.6648 Remote Similarity NPC262166
0.6648 Remote Similarity NPC125852
0.6635 Remote Similarity NPC270918
0.6635 Remote Similarity NPC478075
0.6635 Remote Similarity NPC212123
0.6633 Remote Similarity NPC5630
0.6633 Remote Similarity NPC174629
0.6631 Remote Similarity NPC472117
0.6621 Remote Similarity NPC471513
0.662 Remote Similarity NPC99724
0.6618 Remote Similarity NPC133156
0.6618 Remote Similarity NPC477178
0.6618 Remote Similarity NPC477181
0.6618 Remote Similarity NPC254850
0.6618 Remote Similarity NPC477180
0.6616 Remote Similarity NPC21425
0.6603 Remote Similarity NPC330683
0.6603 Remote Similarity NPC329567
0.6591 Remote Similarity NPC74216
0.6587 Remote Similarity NPC477173
0.6587 Remote Similarity NPC470490
0.6587 Remote Similarity NPC477174
0.6585 Remote Similarity NPC67904
0.6577 Remote Similarity NPC477516
0.6571 Remote Similarity NPC109580
0.6571 Remote Similarity NPC477160
0.6569 Remote Similarity NPC100863
0.6566 Remote Similarity NPC150308
0.6562 Remote Similarity NPC137627
0.6555 Remote Similarity NPC470488
0.6555 Remote Similarity NPC53344
0.6545 Remote Similarity NPC475123
0.6545 Remote Similarity NPC248903
0.6545 Remote Similarity NPC469915
0.6545 Remote Similarity NPC475204
0.6544 Remote Similarity NPC46259
0.6528 Remote Similarity NPC219397
0.6528 Remote Similarity NPC470548
0.6524 Remote Similarity NPC475259
0.6524 Remote Similarity NPC471945
0.6524 Remote Similarity NPC471950
0.6522 Remote Similarity NPC68967
0.6517 Remote Similarity NPC203628
0.6517 Remote Similarity NPC92803
0.6515 Remote Similarity NPC473007
0.6514 Remote Similarity NPC71539
0.6514 Remote Similarity NPC250960
0.651 Remote Similarity NPC89831
0.6505 Remote Similarity NPC29285
0.6504 Remote Similarity NPC470784
0.6504 Remote Similarity NPC474183
0.6503 Remote Similarity NPC144691
0.6503 Remote Similarity NPC233702
0.6502 Remote Similarity NPC230313
0.65 Remote Similarity NPC18890
0.65 Remote Similarity NPC284706
0.65 Remote Similarity NPC26928
0.6498 Remote Similarity NPC478007
0.6495 Remote Similarity NPC476441
0.6493 Remote Similarity NPC471946
0.6493 Remote Similarity NPC471951
0.6489 Remote Similarity NPC309531
0.6489 Remote Similarity NPC472102
0.6486 Remote Similarity NPC244509
0.6486 Remote Similarity NPC477397
0.6484 Remote Similarity NPC315829
0.6482 Remote Similarity NPC87391
0.6471 Remote Similarity NPC244336
0.6471 Remote Similarity NPC473458
0.6468 Remote Similarity NPC45389
0.6468 Remote Similarity NPC474059
0.6468 Remote Similarity NPC473008
0.6467 Remote Similarity NPC202198
0.6462 Remote Similarity NPC475359
0.6462 Remote Similarity NPC191817
0.6459 Remote Similarity NPC470489
0.6455 Remote Similarity NPC476231
0.6455 Remote Similarity NPC472120
0.6455 Remote Similarity NPC472101
0.6452 Remote Similarity NPC37957
0.6452 Remote Similarity NPC315804
0.6452 Remote Similarity NPC313804
0.645 Remote Similarity NPC329731
0.6443 Remote Similarity NPC279871
0.6443 Remote Similarity NPC136797
0.6443 Remote Similarity NPC476227
0.6442 Remote Similarity NPC471436
0.6438 Remote Similarity NPC478008
0.6429 Remote Similarity NPC474815
0.6429 Remote Similarity NPC287152
0.6425 Remote Similarity NPC127178
0.6422 Remote Similarity NPC318525
0.6422 Remote Similarity NPC10653
0.6422 Remote Similarity NPC243626
0.6421 Remote Similarity NPC313757
0.6419 Remote Similarity NPC477395
0.6417 Remote Similarity NPC323336
0.6417 Remote Similarity NPC326349
0.6414 Remote Similarity NPC477159
0.6413 Remote Similarity NPC470821
0.6413 Remote Similarity NPC241392
0.6402 Remote Similarity NPC305542
0.6402 Remote Similarity NPC10732
0.6402 Remote Similarity NPC127996
0.6402 Remote Similarity NPC159815
0.6402 Remote Similarity NPC474058
0.6396 Remote Similarity NPC298320
0.6394 Remote Similarity NPC232600
0.639 Remote Similarity NPC303214
0.6388 Remote Similarity NPC184680
0.6387 Remote Similarity NPC472106
0.6386 Remote Similarity NPC473569
0.6386 Remote Similarity NPC22689
0.6386 Remote Similarity NPC105055
0.6384 Remote Similarity NPC14288
0.6383 Remote Similarity NPC211525
0.6383 Remote Similarity NPC153694
0.6383 Remote Similarity NPC113946
0.6381 Remote Similarity NPC14339
0.6381 Remote Similarity NPC163829
0.6381 Remote Similarity NPC473422
0.6381 Remote Similarity NPC268077
0.6378 Remote Similarity NPC261934
0.6378 Remote Similarity NPC5194
0.6373 Remote Similarity NPC254957
0.6372 Remote Similarity NPC151781
0.6372 Remote Similarity NPC74562
0.6372 Remote Similarity NPC316181
0.6372 Remote Similarity NPC30749
0.6369 Remote Similarity NPC476989
0.6369 Remote Similarity NPC204156
0.636 Remote Similarity NPC470785
0.6359 Remote Similarity NPC26108
0.6358 Remote Similarity NPC469666

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC302235 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
0.6968 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6865 Remote Similarity NPD2098 Approved
0.6862 Remote Similarity NPD5137 Approved
0.6859 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4652 Approved
0.6793 Remote Similarity NPD5294 Clinical (unspecified phase)
0.678 Remote Similarity NPD4465 Phase 2
0.678 Remote Similarity NPD4467 Phase 2
0.6776 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7071 Clinical (unspecified phase)
0.6757 Remote Similarity NPD2097 Approved
0.6754 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6734 Remote Similarity NPD3479 Discontinued
0.6716 Remote Similarity NPD6321 Discontinued
0.6715 Remote Similarity NPD6518 Discontinued
0.6702 Remote Similarity NPD5823 Approved
0.6702 Remote Similarity NPD7324 Discontinued
0.6701 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6699 Remote Similarity NPD5860 Discontinued
0.6667 Remote Similarity NPD2889 Approved
0.6667 Remote Similarity NPD2888 Approved
0.6667 Remote Similarity NPD2017 Approved
0.6667 Remote Similarity NPD2890 Approved
0.6667 Remote Similarity NPD1544 Phase 1
0.6635 Remote Similarity NPD4492 Approved
0.6635 Remote Similarity NPD4494 Approved
0.6632 Remote Similarity NPD3449 Discontinued
0.6611 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6603 Remote Similarity NPD4082 Approved
0.6603 Remote Similarity NPD2906 Approved
0.6603 Remote Similarity NPD2907 Approved
0.66 Remote Similarity NPD2327 Clinical (unspecified phase)
0.6589 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7603 Discontinued
0.6564 Remote Similarity NPD6879 Phase 2
0.6564 Remote Similarity NPD6878 Phase 2
0.655 Remote Similarity NPD5112 Approved
0.655 Remote Similarity NPD5113 Approved
0.655 Remote Similarity NPD5114 Approved
0.6524 Remote Similarity NPD4022 Approved
0.6524 Remote Similarity NPD3472 Approved
0.6522 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3141 Discontinued
0.6517 Remote Similarity NPD5994 Discontinued
0.6507 Remote Similarity NPD6260 Discontinued
0.65 Remote Similarity NPD5620 Clinical (unspecified phase)
0.65 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6488 Remote Similarity NPD5194 Approved
0.6488 Remote Similarity NPD5196 Approved
0.6488 Remote Similarity NPD5197 Approved
0.6486 Remote Similarity NPD5639 Clinical (unspecified phase)
0.648 Remote Similarity NPD5445 Approved
0.648 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6479 Remote Similarity NPD3888 Discontinued
0.6471 Remote Similarity NPD1769 Discontinued
0.6462 Remote Similarity NPD3372 Discontinued
0.6459 Remote Similarity NPD4456 Clinical (unspecified phase)
0.6459 Remote Similarity NPD6644 Discontinued
0.645 Remote Similarity NPD4515 Suspended
0.6449 Remote Similarity NPD4455 Discontinued
0.6448 Remote Similarity NPD4432 Discontinued
0.6445 Remote Similarity NPD6376 Discontinued
0.6444 Remote Similarity NPD4127 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5077 Approved
0.6436 Remote Similarity NPD5076 Approved
0.6432 Remote Similarity NPD4493 Discontinued
0.642 Remote Similarity NPD2791 Discontinued
0.6417 Remote Similarity NPD6395 Phase 2
0.6417 Remote Similarity NPD6396 Clinical (unspecified phase)
0.6398 Remote Similarity NPD4596 Phase 1
0.6396 Remote Similarity NPD6297 Approved
0.6394 Remote Similarity NPD6238 Discontinued
0.6385 Remote Similarity NPD3893 Discontinued
0.6385 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6381 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6369 Remote Similarity NPD3391 Approved
0.6368 Remote Similarity NPD3351 Approved
0.6368 Remote Similarity NPD6891 Phase 2
0.6364 Remote Similarity NPD3684 Discontinued
0.6359 Remote Similarity NPD5938 Phase 3
0.6359 Remote Similarity NPD5942 Approved
0.6359 Remote Similarity NPD5941 Approved
0.6355 Remote Similarity NPD1945 Phase 1
0.6355 Remote Similarity NPD6659 Phase 2
0.6354 Remote Similarity NPD5024 Approved
0.6354 Remote Similarity NPD2162 Clinical (unspecified phase)
0.635 Remote Similarity NPD6851 Approved
0.635 Remote Similarity NPD6853 Approved
0.6349 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6347 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6805 Discontinued
0.6343 Remote Similarity NPD4897 Phase 2
0.6335 Remote Similarity NPD7820 Phase 3
0.6333 Remote Similarity NPD3802 Phase 3
0.6332 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6329 Remote Similarity NPD5071 Phase 2
0.6327 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6321 Remote Similarity NPD3350 Approved
0.6321 Remote Similarity NPD7126 Discontinued
0.6316 Remote Similarity NPD6982 Phase 2
0.6316 Remote Similarity NPD8157 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6255 Approved
0.6316 Remote Similarity NPD6256 Approved
0.6316 Remote Similarity NPD6254 Approved
0.6313 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6313 Remote Similarity NPD5025 Approved
0.6306 Remote Similarity NPD7821 Clinical (unspecified phase)
0.6305 Remote Similarity NPD7617 Discontinued
0.6305 Remote Similarity NPD7628 Phase 3
0.6305 Remote Similarity NPD7629 Clinical (unspecified phase)
0.6305 Remote Similarity NPD7630 Phase 3
0.63 Remote Similarity NPD7281 Phase 3
0.63 Remote Similarity NPD7280 Phase 3
0.6296 Remote Similarity NPD7735 Clinical (unspecified phase)
0.6294 Remote Similarity NPD3793 Phase 3
0.6294 Remote Similarity NPD6020 Phase 2
0.6289 Remote Similarity NPD5186 Approved
0.6289 Remote Similarity NPD5183 Approved
0.6289 Remote Similarity NPD5847 Phase 1
0.6283 Remote Similarity NPD7664 Discontinued
0.6278 Remote Similarity NPD7186 Phase 3
0.6275 Remote Similarity NPD4370 Phase 3
0.6274 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6269 Remote Similarity NPD6557 Phase 2
0.6268 Remote Similarity NPD6253 Approved
0.6264 Remote Similarity NPD5265 Approved
0.6264 Remote Similarity NPD5264 Approved
0.6264 Remote Similarity NPD4430 Phase 2
0.6263 Remote Similarity NPD4514 Approved
0.6263 Remote Similarity NPD6283 Phase 2
0.6257 Remote Similarity NPD4126 Approved
0.6256 Remote Similarity NPD3975 Discontinued
0.6256 Remote Similarity NPD7205 Discontinued
0.625 Remote Similarity NPD7178 Clinical (unspecified phase)
0.625 Remote Similarity NPD4668 Phase 2
0.625 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7167 Discontinued
0.6238 Remote Similarity NPD3416 Discontinued
0.6237 Remote Similarity NPD7303 Discontinued
0.623 Remote Similarity NPD5967 Approved
0.623 Remote Similarity NPD7600 Phase 2
0.6226 Remote Similarity NPD1294 Discontinued
0.6225 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6225 Remote Similarity NPD4428 Discontinued
0.6216 Remote Similarity NPD8356 Approved
0.6216 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6215 Remote Similarity NPD2916 Discontinued
0.6214 Remote Similarity NPD5610 Approved
0.6212 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6205 Remote Similarity NPD7224 Discontinued
0.6205 Remote Similarity NPD1293 Approved
0.6205 Remote Similarity NPD7223 Discontinued
0.6202 Remote Similarity NPD5195 Discontinued
0.62 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6199 Discontinued
0.6193 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7133 Discontinued
0.6184 Remote Similarity NPD6493 Phase 3
0.6182 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6182 Remote Similarity NPD7692 Discontinued
0.6181 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6181 Remote Similarity NPD5485 Approved
0.6181 Remote Similarity NPD5484 Approved
0.6179 Remote Similarity NPD6478 Clinical (unspecified phase)
0.6178 Remote Similarity NPD7599 Phase 2
0.6178 Remote Similarity NPD8430 Approved
0.6176 Remote Similarity NPD5188 Clinical (unspecified phase)
0.6176 Remote Similarity NPD8025 Phase 2
0.6171 Remote Similarity NPD7805 Phase 3
0.6171 Remote Similarity NPD5506 Approved
0.6171 Remote Similarity NPD5507 Approved
0.6169 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5143 Clinical (unspecified phase)
0.6165 Remote Similarity NPD6665 Discontinued
0.6164 Remote Similarity NPD7432 Phase 2
0.6162 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6161 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6158 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6157 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6457 Approved
0.6154 Remote Similarity NPD2680 Approved
0.6154 Remote Similarity NPD2681 Approved
0.6154 Remote Similarity NPD5582 Discontinued
0.6154 Remote Similarity NPD2899 Discontinued
0.615 Remote Similarity NPD5055 Clinical (unspecified phase)
0.6143 Remote Similarity NPD6874 Approved
0.6142 Remote Similarity NPD6607 Clinical (unspecified phase)
0.614 Remote Similarity NPD8027 Approved
0.614 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6138 Remote Similarity NPD3229 Phase 2
0.6136 Remote Similarity NPD5263 Approved
0.6132 Remote Similarity NPD956 Clinical (unspecified phase)
0.6131 Remote Similarity NPD5600 Discontinued
0.6131 Remote Similarity NPD5313 Approved
0.6131 Remote Similarity NPD5312 Approved
0.6129 Remote Similarity NPD5613 Approved
0.6129 Remote Similarity NPD5614 Approved
0.6127 Remote Similarity NPD2383 Phase 1
0.6127 Remote Similarity NPD1755 Approved

Structure

External Identifiers

PubChem CID   13989139
ChEMBL   CHEMBL1088849
ZINC  

Physicochemical Properties

Molecular Weight:  354.07
ALogP:  -0.5881
MLogP:  2.23
XLogP:  0.49
# Rotatable Bonds:  8
Polar Surface Area:  131.68
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  23

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs