Natural Product: NPC291799

Natural Product ID:  NPC291799
Common Name:   Dehydro-Alpha-Lapachone
IUPAC Name:   2,2-dimethylbenzo[g]chromene-5,10-dione
Synonyms:   Dehydro-Alpha-Lapachone
Molecular Formula:   C15H12O3
Standard InCHIKey:  OWFHAMHRUCUSRM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3
Canonical SMILES:  O=C1C2=C(C=CC(O2)(C)C)C(=O)c2c1cccc2
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
NPO3751 Orthantha lutea NA NA NA UNPD*
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota UNPD*
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota TCMSP*
NPO12083 Hydnellum zonatum Species Thelephoraceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens IC50 = 214 nM 18318466
NPT941 Cell Line HaCaT Homo sapiens IC50 > 10000 nM 10479319

  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 NPC291799 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
0.9423 High Similarity NPC192577
0.9327 High Similarity NPC470391
0.9065 High Similarity NPC137315
0.8981 High Similarity NPC212415
0.8932 High Similarity NPC112552
0.8909 High Similarity NPC470764
0.8667 High Similarity NPC244427
0.8667 High Similarity NPC222390
0.8649 High Similarity NPC196075
0.8585 High Similarity NPC274443
0.8559 High Similarity NPC13784
0.8547 High Similarity NPC65627
0.8482 Intermediate Similarity NPC241851
0.8482 Intermediate Similarity NPC326664
0.844 Intermediate Similarity NPC203732
0.8426 Intermediate Similarity NPC209632
0.8426 Intermediate Similarity NPC172483
0.8407 Intermediate Similarity NPC474408
0.8407 Intermediate Similarity NPC228936
0.8362 Intermediate Similarity NPC204784
0.8333 Intermediate Similarity NPC114594
0.8333 Intermediate Similarity NPC135730
0.8319 Intermediate Similarity NPC477411
0.8291 Intermediate Similarity NPC232958
0.8286 Intermediate Similarity NPC156021
0.8198 Intermediate Similarity NPC269023
0.8198 Intermediate Similarity NPC99846
0.8182 Intermediate Similarity NPC236405
0.8174 Intermediate Similarity NPC226093
0.8158 Intermediate Similarity NPC67377
0.8142 Intermediate Similarity NPC292834
0.8136 Intermediate Similarity NPC476225
0.8136 Intermediate Similarity NPC105709
0.8099 Intermediate Similarity NPC295664
0.8087 Intermediate Similarity NPC474095
0.8067 Intermediate Similarity NPC144547
0.8053 Intermediate Similarity NPC474157
0.8053 Intermediate Similarity NPC210089
0.8019 Intermediate Similarity NPC12695
0.8018 Intermediate Similarity NPC30594
0.8018 Intermediate Similarity NPC37622
0.8017 Intermediate Similarity NPC62138
0.7983 Intermediate Similarity NPC289432
0.7983 Intermediate Similarity NPC988
0.7981 Intermediate Similarity NPC476484
0.7967 Intermediate Similarity NPC81135
0.7941 Intermediate Similarity NPC43945
0.7928 Intermediate Similarity NPC134120
0.7913 Intermediate Similarity NPC143768
0.7913 Intermediate Similarity NPC272524
0.7909 Intermediate Similarity NPC60679
0.7864 Intermediate Similarity NPC157778
0.7846 Intermediate Similarity NPC284184
0.7846 Intermediate Similarity NPC301341
0.7845 Intermediate Similarity NPC308744
0.7833 Intermediate Similarity NPC77000
0.7833 Intermediate Similarity NPC238861
0.7812 Intermediate Similarity NPC171968
0.7778 Intermediate Similarity NPC471832
0.7778 Intermediate Similarity NPC474685
0.7778 Intermediate Similarity NPC103048
0.7778 Intermediate Similarity NPC210092
0.7739 Intermediate Similarity NPC243355
0.7739 Intermediate Similarity NPC474057
0.7724 Intermediate Similarity NPC51079
0.7714 Intermediate Similarity NPC173413
0.7706 Intermediate Similarity NPC145052
0.7699 Intermediate Similarity NPC100767
0.7699 Intermediate Similarity NPC119271
0.7679 Intermediate Similarity NPC31786
0.7672 Intermediate Similarity NPC186128
0.7672 Intermediate Similarity NPC79496
0.7667 Intermediate Similarity NPC318173
0.7658 Intermediate Similarity NPC45613
0.7647 Intermediate Similarity NPC469843
0.7642 Intermediate Similarity NPC284475
0.7636 Intermediate Similarity NPC325497
0.7632 Intermediate Similarity NPC56493
0.7607 Intermediate Similarity NPC161611
0.7593 Intermediate Similarity NPC5472
0.7589 Intermediate Similarity NPC247976
0.7586 Intermediate Similarity NPC167504
0.7583 Intermediate Similarity NPC323440
0.7583 Intermediate Similarity NPC222968
0.7583 Intermediate Similarity NPC80605
0.7581 Intermediate Similarity NPC328107
0.7581 Intermediate Similarity NPC182646
0.7581 Intermediate Similarity NPC318067
0.7578 Intermediate Similarity NPC27659
0.757 Intermediate Similarity NPC188844
0.757 Intermediate Similarity NPC1682
0.757 Intermediate Similarity NPC155232
0.7565 Intermediate Similarity NPC83628
0.7565 Intermediate Similarity NPC17417
0.7565 Intermediate Similarity NPC265407
0.7565 Intermediate Similarity NPC10251
0.7563 Intermediate Similarity NPC149691
0.7563 Intermediate Similarity NPC260886
0.7559 Intermediate Similarity NPC237225
0.7549 Intermediate Similarity NPC215008
0.7547 Intermediate Similarity NPC110420
0.7547 Intermediate Similarity NPC67585
0.7547 Intermediate Similarity NPC303967
0.7547 Intermediate Similarity NPC19256
0.7542 Intermediate Similarity NPC196673
0.754 Intermediate Similarity NPC177925
0.754 Intermediate Similarity NPC51292
0.7522 Intermediate Similarity NPC329282
0.7519 Intermediate Similarity NPC173980
0.7519 Intermediate Similarity NPC205360
0.75 Intermediate Similarity NPC214067
0.75 Intermediate Similarity NPC320891
0.75 Intermediate Similarity NPC238219
0.75 Intermediate Similarity NPC232996
0.75 Intermediate Similarity NPC174099
0.75 Intermediate Similarity NPC93084
0.75 Intermediate Similarity NPC251854
0.75 Intermediate Similarity NPC164947
0.75 Intermediate Similarity NPC289883
0.75 Intermediate Similarity NPC196246
0.7479 Intermediate Similarity NPC93181
0.7477 Intermediate Similarity NPC133461
0.7455 Intermediate Similarity NPC249912
0.7455 Intermediate Similarity NPC276775
0.7455 Intermediate Similarity NPC92754
0.744 Intermediate Similarity NPC135062
0.7438 Intermediate Similarity NPC268930
0.7438 Intermediate Similarity NPC228318
0.7436 Intermediate Similarity NPC305912
0.7436 Intermediate Similarity NPC260818
0.7436 Intermediate Similarity NPC1082
0.7434 Intermediate Similarity NPC474365
0.7434 Intermediate Similarity NPC301943
0.7434 Intermediate Similarity NPC89886
0.7431 Intermediate Similarity NPC130398
0.7431 Intermediate Similarity NPC260233
0.7424 Intermediate Similarity NPC217914
0.7414 Intermediate Similarity NPC40178
0.7414 Intermediate Similarity NPC85493
0.7411 Intermediate Similarity NPC42211
0.7411 Intermediate Similarity NPC70624
0.7407 Intermediate Similarity NPC153885
0.7407 Intermediate Similarity NPC59677
0.7402 Intermediate Similarity NPC51037
0.7398 Intermediate Similarity NPC473243
0.7387 Intermediate Similarity NPC49994
0.7387 Intermediate Similarity NPC75724
0.7387 Intermediate Similarity NPC134882
0.7387 Intermediate Similarity NPC78701
0.7387 Intermediate Similarity NPC35448
0.7387 Intermediate Similarity NPC229242
0.7387 Intermediate Similarity NPC225060
0.7381 Intermediate Similarity NPC310540
0.7373 Intermediate Similarity NPC270699
0.7373 Intermediate Similarity NPC321852
0.7373 Intermediate Similarity NPC82899
0.7373 Intermediate Similarity NPC23332
0.7358 Intermediate Similarity NPC267262
0.7355 Intermediate Similarity NPC158157
0.735 Intermediate Similarity NPC273837
0.7344 Intermediate Similarity NPC45537
0.7344 Intermediate Similarity NPC428300
0.7344 Intermediate Similarity NPC478162
0.7344 Intermediate Similarity NPC478165
0.7339 Intermediate Similarity NPC472981
0.7339 Intermediate Similarity NPC34243
0.7333 Intermediate Similarity NPC306740
0.7333 Intermediate Similarity NPC160339
0.7333 Intermediate Similarity NPC307
0.7328 Intermediate Similarity NPC470007
0.7328 Intermediate Similarity NPC47536
0.7323 Intermediate Similarity NPC476599
0.7321 Intermediate Similarity NPC203925
0.7321 Intermediate Similarity NPC146351
0.7321 Intermediate Similarity NPC118343
0.7315 Intermediate Similarity NPC110704
0.7313 Intermediate Similarity NPC186647
0.7311 Intermediate Similarity NPC128368
0.7308 Intermediate Similarity NPC198305
0.7302 Intermediate Similarity NPC325740
0.7297 Intermediate Similarity NPC265220
0.7297 Intermediate Similarity NPC239185
0.7295 Intermediate Similarity NPC61651
0.7293 Intermediate Similarity NPC309056
0.7293 Intermediate Similarity NPC22644
0.729 Intermediate Similarity NPC418308
0.7288 Intermediate Similarity NPC183648
0.7287 Intermediate Similarity NPC165257
0.7273 Intermediate Similarity NPC100353
0.7273 Intermediate Similarity NPC471616
0.7266 Intermediate Similarity NPC231774
0.7265 Intermediate Similarity NPC474364
0.7264 Intermediate Similarity NPC96625
0.7259 Intermediate Similarity NPC265181
0.7258 Intermediate Similarity NPC206778
0.7258 Intermediate Similarity NPC285829
0.7257 Intermediate Similarity NPC109514
0.7257 Intermediate Similarity NPC476993
0.725 Intermediate Similarity NPC471721
0.725 Intermediate Similarity NPC153053

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC291799 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
0.8981 High Similarity NPD1609 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD650 Approved
0.7833 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD164 Approved
0.7642 Intermediate Similarity NPD7609 Phase 3
0.7627 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD7631 Approved
0.7565 Intermediate Similarity NPD2182 Approved
0.7436 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5909 Discontinued
0.7339 Intermediate Similarity NPD4879 Approved
0.7339 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1238 Approved
0.7297 Intermediate Similarity NPD3495 Discontinued
0.7259 Intermediate Similarity NPD1471 Phase 3
0.725 Intermediate Similarity NPD1241 Discontinued
0.7217 Intermediate Similarity NPD1237 Approved
0.7203 Intermediate Similarity NPD2067 Discontinued
0.7143 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD1930 Approved
0.713 Intermediate Similarity NPD1929 Approved
0.7109 Intermediate Similarity NPD1876 Approved
0.7087 Intermediate Similarity NPD3972 Approved
0.7049 Intermediate Similarity NPD5951 Approved
0.7027 Intermediate Similarity NPD1202 Approved
0.7018 Intermediate Similarity NPD2066 Phase 3
0.7009 Intermediate Similarity NPD9257 Approved
0.7009 Intermediate Similarity NPD9259 Approved
0.6975 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6953 Remote Similarity NPD4878 Approved
0.695 Remote Similarity NPD3950 Discontinued
0.6937 Remote Similarity NPD1508 Approved
0.6935 Remote Similarity NPD405 Clinical (unspecified phase)
0.6897 Remote Similarity NPD1932 Approved
0.6879 Remote Similarity NPD7236 Approved
0.6875 Remote Similarity NPD1547 Clinical (unspecified phase)
0.687 Remote Similarity NPD2798 Approved
0.6857 Remote Similarity NPD942 Approved
0.685 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6794 Remote Similarity NPD1470 Approved
0.6789 Remote Similarity NPD1087 Approved
0.6789 Remote Similarity NPD1282 Approved
0.6772 Remote Similarity NPD1651 Approved
0.6763 Remote Similarity NPD2346 Discontinued
0.6757 Remote Similarity NPD9256 Approved
0.6757 Remote Similarity NPD9258 Approved
0.6754 Remote Similarity NPD1989 Approved
0.6754 Remote Similarity NPD1843 Approved
0.6744 Remote Similarity NPD6287 Discontinued
0.6744 Remote Similarity NPD1201 Approved
0.6742 Remote Similarity NPD2788 Approved
0.6739 Remote Similarity NPD3748 Approved
0.6726 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7008 Discontinued
0.6694 Remote Similarity NPD2329 Discontinued
0.6693 Remote Similarity NPD7009 Phase 2
0.6693 Remote Similarity NPD9545 Approved
0.6691 Remote Similarity NPD4307 Phase 2
0.6667 Remote Similarity NPD9490 Approved
0.6667 Remote Similarity NPD2313 Discontinued
0.6667 Remote Similarity NPD3764 Approved
0.6667 Remote Similarity NPD1693 Approved
0.6667 Remote Similarity NPD3266 Approved
0.6667 Remote Similarity NPD688 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3267 Approved
0.6644 Remote Similarity NPD7239 Suspended
0.6643 Remote Similarity NPD2353 Approved
0.6643 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6618 Remote Similarity NPD7961 Discontinued
0.6615 Remote Similarity NPD518 Clinical (unspecified phase)
0.6615 Remote Similarity NPD1281 Approved
0.6614 Remote Similarity NPD7610 Discontinued
0.6613 Remote Similarity NPD7094 Approved
0.6613 Remote Similarity NPD6858 Approved
0.6607 Remote Similarity NPD1089 Approved
0.6607 Remote Similarity NPD1090 Approved
0.6607 Remote Similarity NPD1086 Approved
0.6579 Remote Similarity NPD1563 Approved
0.6574 Remote Similarity NPD9491 Approved
0.6565 Remote Similarity NPD6637 Approved
0.6549 Remote Similarity NPD1239 Approved
0.6535 Remote Similarity NPD9493 Approved
0.6522 Remote Similarity NPD9260 Approved
0.6518 Remote Similarity NPD800 Approved
0.6512 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6503 Remote Similarity NPD3750 Approved
0.65 Remote Similarity NPD4308 Phase 3
0.6496 Remote Similarity NPD9495 Approved
0.6496 Remote Similarity NPD7713 Phase 3
0.6491 Remote Similarity NPD1088 Approved
0.6486 Remote Similarity NPD506 Clinical (unspecified phase)
0.6486 Remote Similarity NPD3226 Approved
0.6466 Remote Similarity NPD5667 Approved
0.6466 Remote Similarity NPD1283 Approved
0.6462 Remote Similarity NPD2932 Approved
0.6462 Remote Similarity NPD17 Approved
0.6458 Remote Similarity NPD3887 Approved
0.6458 Remote Similarity NPD2354 Approved
0.6457 Remote Similarity NPD4198 Discontinued
0.6457 Remote Similarity NPD3317 Approved
0.6454 Remote Similarity NPD2796 Approved
0.6449 Remote Similarity NPD3140 Approved
0.6449 Remote Similarity NPD3142 Approved
0.6449 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6439 Remote Similarity NPD9717 Approved
0.6429 Remote Similarity NPD6010 Discontinued
0.6423 Remote Similarity NPD3268 Approved
0.6418 Remote Similarity NPD2797 Approved
0.6417 Remote Similarity NPD6647 Phase 2
0.6417 Remote Similarity NPD9261 Approved
0.6415 Remote Similarity NPD227 Approved
0.6415 Remote Similarity NPD225 Approved
0.641 Remote Similarity NPD1565 Approved
0.641 Remote Similarity NPD1566 Phase 3
0.641 Remote Similarity NPD1564 Approved
0.6408 Remote Similarity NPD2344 Approved
0.6408 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6397 Remote Similarity NPD6832 Phase 2
0.6397 Remote Similarity NPD7055 Discontinued
0.6389 Remote Similarity NPD7003 Approved
0.6385 Remote Similarity NPD3025 Approved
0.6385 Remote Similarity NPD3024 Approved
0.6383 Remote Similarity NPD2799 Discontinued
0.6383 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6378 Remote Similarity NPD2629 Approved
0.6377 Remote Similarity NPD8032 Phase 2
0.6371 Remote Similarity NPD1317 Discontinued
0.637 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6357 Remote Similarity NPD1607 Approved
0.635 Remote Similarity NPD6039 Approved
0.6341 Remote Similarity NPD9265 Clinical (unspecified phase)
0.634 Remote Similarity NPD7057 Phase 3
0.634 Remote Similarity NPD7058 Phase 2
0.6336 Remote Similarity NPD3019 Approved
0.6331 Remote Similarity NPD1240 Approved
0.6327 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6319 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3672 Approved
0.6316 Remote Similarity NPD3673 Approved
0.6316 Remote Similarity NPD1608 Approved
0.6311 Remote Similarity NPD9697 Approved
0.6301 Remote Similarity NPD3300 Phase 2
0.6296 Remote Similarity NPD1203 Approved
0.6288 Remote Similarity NPD3023 Approved
0.6288 Remote Similarity NPD3026 Approved
0.6284 Remote Similarity NPD6273 Approved
0.6284 Remote Similarity NPD5049 Phase 3
0.6269 Remote Similarity NPD182 Clinical (unspecified phase)
0.6268 Remote Similarity NPD1510 Phase 2
0.626 Remote Similarity NPD4102 Approved
0.626 Remote Similarity NPD4105 Approved
0.626 Remote Similarity NPD5691 Approved
0.6259 Remote Similarity NPD6799 Approved
0.625 Remote Similarity NPD4980 Approved
0.625 Remote Similarity NPD970 Clinical (unspecified phase)
0.625 Remote Similarity NPD1019 Discontinued
0.6239 Remote Similarity NPD226 Approved
0.6233 Remote Similarity NPD2309 Approved
0.6233 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6231 Remote Similarity NPD2347 Approved
0.6225 Remote Similarity NPD6599 Discontinued
0.6222 Remote Similarity NPD2198 Approved
0.6222 Remote Similarity NPD2199 Approved
0.6216 Remote Similarity NPD5401 Approved
0.6214 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6214 Remote Similarity NPD2979 Phase 3
0.6212 Remote Similarity NPD5305 Approved
0.6212 Remote Similarity NPD5306 Approved
0.6212 Remote Similarity NPD2345 Approved
0.621 Remote Similarity NPD9267 Approved
0.621 Remote Similarity NPD9263 Approved
0.621 Remote Similarity NPD9264 Approved
0.6207 Remote Similarity NPD1243 Approved
0.6181 Remote Similarity NPD7611 Approved
0.6181 Remote Similarity NPD7702 Clinical (unspecified phase)
0.617 Remote Similarity NPD1933 Approved
0.6165 Remote Similarity NPD4106 Approved
0.6165 Remote Similarity NPD4135 Approved
0.6165 Remote Similarity NPD4136 Approved
0.6164 Remote Similarity NPD8166 Discontinued
0.6164 Remote Similarity NPD4628 Phase 3
0.616 Remote Similarity NPD74 Approved
0.616 Remote Similarity NPD9266 Approved
0.6154 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6148 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6148 Remote Similarity NPD5159 Phase 2
0.6148 Remote Similarity NPD5157 Phase 1
0.6144 Remote Similarity NPD6801 Discontinued
0.6142 Remote Similarity NPD9508 Approved
0.6138 Remote Similarity NPD1549 Phase 2
0.6138 Remote Similarity NPD2897 Discontinued
0.6136 Remote Similarity NPD1245 Approved
0.6133 Remote Similarity NPD5403 Approved
0.6129 Remote Similarity NPD3134 Approved
0.6126 Remote Similarity NPD3971 Phase 1
0.6124 Remote Similarity NPD1246 Approved
0.6119 Remote Similarity NPD4807 Approved

Structure

External Identifiers

PubChem CID   72734
ChEMBL   CHEMBL272253
ZINC  

Physicochemical Properties

Molecular Weight:  240.08
ALogP:  0.2056
MLogP:  2.78
XLogP:  3.044
# Rotatable Bonds:  2
Polar Surface Area:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  18

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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