Natural Product: NPC65627

Natural Product ID:  NPC65627
Common Name:   4-Hydroxy-Alpha-Lapachone
IUPAC Name:   (4S)-4-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:  
Molecular Formula:   C15H14O4
Standard InCHIKey:  KHDNNHZLJJJVFO-JTQLQIEISA-N
Standard InCHI:  InChI=1S/C15H14O4/c1-15(2)7-10(16)11-12(17)8-5-3-4-6-9(8)13(18)14(11)19-15/h3-6,10,16H,7H2,1-2H3/t10-/m0/s1
Canonical SMILES:  O[C@H]1CC(C)(C)OC2=C1C(=O)c1c(C2=O)cccc1
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
NPO9835 Catalpa ovata Species Bignoniaceae Eukaryota PMID[9599262]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 86.7 % 18249473
NPT2 Others Unspecified Activity = 11.2 % 20452225
NPT2 Others Unspecified Activity = 27.9 % 12398540
NPT2 Others Unspecified Activity = 56.3 % 2045817
NPT80 Cell Line Raji Homo sapiens Activity = 60 % 26126961

  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 NPC65627 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
0.9339 High Similarity NPC81135
0.8943 High Similarity NPC236405
0.8779 High Similarity NPC173980
0.876 High Similarity NPC105709
0.8696 High Similarity NPC192577
0.8547 High Similarity NPC291799
0.8547 High Similarity NPC137315
0.8417 Intermediate Similarity NPC470764
0.8397 Intermediate Similarity NPC171968
0.8347 Intermediate Similarity NPC62138
0.8333 Intermediate Similarity NPC241851
0.8291 Intermediate Similarity NPC470391
0.8261 Intermediate Similarity NPC274443
0.8231 Intermediate Similarity NPC262819
0.8226 Intermediate Similarity NPC204784
0.8211 Intermediate Similarity NPC471553
0.8195 Intermediate Similarity NPC23894
0.8174 Intermediate Similarity NPC222390
0.8174 Intermediate Similarity NPC244427
0.8167 Intermediate Similarity NPC292834
0.8145 Intermediate Similarity NPC318173
0.812 Intermediate Similarity NPC172483
0.8095 Intermediate Similarity NPC472981
0.8087 Intermediate Similarity NPC112552
0.8065 Intermediate Similarity NPC323440
0.8065 Intermediate Similarity NPC222968
0.8065 Intermediate Similarity NPC80605
0.8033 Intermediate Similarity NPC196673
0.8017 Intermediate Similarity NPC212415
0.8015 Intermediate Similarity NPC237225
0.7984 Intermediate Similarity NPC295664
0.7983 Intermediate Similarity NPC203732
0.7969 Intermediate Similarity NPC223351
0.7941 Intermediate Similarity NPC38158
0.7939 Intermediate Similarity NPC478162
0.7939 Intermediate Similarity NPC478165
0.7926 Intermediate Similarity NPC474659
0.7923 Intermediate Similarity NPC294050
0.7923 Intermediate Similarity NPC328997
0.7907 Intermediate Similarity NPC325740
0.7907 Intermediate Similarity NPC318067
0.7907 Intermediate Similarity NPC328107
0.7903 Intermediate Similarity NPC471616
0.7899 Intermediate Similarity NPC103337
0.7899 Intermediate Similarity NPC477408
0.7899 Intermediate Similarity NPC114620
0.7895 Intermediate Similarity NPC27659
0.7895 Intermediate Similarity NPC198305
0.7887 Intermediate Similarity NPC136878
0.7886 Intermediate Similarity NPC477411
0.7886 Intermediate Similarity NPC196075
0.7886 Intermediate Similarity NPC326664
0.7863 Intermediate Similarity NPC51037
0.7829 Intermediate Similarity NPC164947
0.7826 Intermediate Similarity NPC156021
0.7823 Intermediate Similarity NPC474408
0.782 Intermediate Similarity NPC471832
0.7817 Intermediate Similarity NPC474630
0.7815 Intermediate Similarity NPC134120
0.7805 Intermediate Similarity NPC13784
0.7805 Intermediate Similarity NPC272524
0.7805 Intermediate Similarity NPC143768
0.7803 Intermediate Similarity NPC51448
0.7803 Intermediate Similarity NPC316553
0.7803 Intermediate Similarity NPC115797
0.7787 Intermediate Similarity NPC474057
0.7778 Intermediate Similarity NPC309430
0.7778 Intermediate Similarity NPC144257
0.7769 Intermediate Similarity NPC135062
0.776 Intermediate Similarity NPC135730
0.776 Intermediate Similarity NPC226093
0.7754 Intermediate Similarity NPC301341
0.7754 Intermediate Similarity NPC284184
0.775 Intermediate Similarity NPC100767
0.7746 Intermediate Similarity NPC29932
0.7744 Intermediate Similarity NPC165257
0.7742 Intermediate Similarity NPC67377
0.7737 Intermediate Similarity NPC309056
0.7731 Intermediate Similarity NPC249067
0.7727 Intermediate Similarity NPC231774
0.7727 Intermediate Similarity NPC146239
0.7721 Intermediate Similarity NPC254603
0.771 Intermediate Similarity NPC310540
0.7698 Intermediate Similarity NPC61590
0.7698 Intermediate Similarity NPC469843
0.7692 Intermediate Similarity NPC478160
0.7687 Intermediate Similarity NPC49272
0.7686 Intermediate Similarity NPC211439
0.7681 Intermediate Similarity NPC315275
0.768 Intermediate Similarity NPC228936
0.7664 Intermediate Similarity NPC212207
0.766 Intermediate Similarity NPC283292
0.7656 Intermediate Similarity NPC476645
0.7647 Intermediate Similarity NPC477406
0.7643 Intermediate Similarity NPC295339
0.7638 Intermediate Similarity NPC61651
0.7634 Intermediate Similarity NPC85511
0.7634 Intermediate Similarity NPC228739
0.763 Intermediate Similarity NPC31799
0.7626 Intermediate Similarity NPC264022
0.7619 Intermediate Similarity NPC260886
0.7619 Intermediate Similarity NPC149691
0.7612 Intermediate Similarity NPC469930
0.7603 Intermediate Similarity NPC120171
0.7597 Intermediate Similarity NPC474223
0.7597 Intermediate Similarity NPC476225
0.7597 Intermediate Similarity NPC475827
0.7591 Intermediate Similarity NPC310662
0.7589 Intermediate Similarity NPC156872
0.7581 Intermediate Similarity NPC218855
0.7581 Intermediate Similarity NPC186128
0.7576 Intermediate Similarity NPC474766
0.7574 Intermediate Similarity NPC205360
0.7559 Intermediate Similarity NPC158157
0.7554 Intermediate Similarity NPC232996
0.7552 Intermediate Similarity NPC478164
0.7541 Intermediate Similarity NPC20485
0.754 Intermediate Similarity NPC474095
0.754 Intermediate Similarity NPC215419
0.754 Intermediate Similarity NPC474685
0.754 Intermediate Similarity NPC217111
0.7538 Intermediate Similarity NPC144547
0.7534 Intermediate Similarity NPC306799
0.7534 Intermediate Similarity NPC101043
0.7534 Intermediate Similarity NPC94781
0.752 Intermediate Similarity NPC470253
0.7519 Intermediate Similarity NPC472708
0.7518 Intermediate Similarity NPC242358
0.7518 Intermediate Similarity NPC88864
0.7518 Intermediate Similarity NPC246693
0.7518 Intermediate Similarity NPC477407
0.7518 Intermediate Similarity NPC110609
0.75 Intermediate Similarity NPC91809
0.75 Intermediate Similarity NPC477409
0.75 Intermediate Similarity NPC469385
0.75 Intermediate Similarity NPC247976
0.75 Intermediate Similarity NPC199253
0.75 Intermediate Similarity NPC136588
0.75 Intermediate Similarity NPC140118
0.75 Intermediate Similarity NPC103910
0.75 Intermediate Similarity NPC268930
0.75 Intermediate Similarity NPC12881
0.75 Intermediate Similarity NPC474157
0.75 Intermediate Similarity NPC265513
0.75 Intermediate Similarity NPC79627
0.7483 Intermediate Similarity NPC84142
0.7483 Intermediate Similarity NPC44378
0.7483 Intermediate Similarity NPC308572
0.7483 Intermediate Similarity NPC472889
0.7483 Intermediate Similarity NPC280753
0.7481 Intermediate Similarity NPC269923
0.7481 Intermediate Similarity NPC167323
0.748 Intermediate Similarity NPC475282
0.748 Intermediate Similarity NPC40178
0.7466 Intermediate Similarity NPC476821
0.7466 Intermediate Similarity NPC469425
0.7464 Intermediate Similarity NPC52407
0.7463 Intermediate Similarity NPC15837
0.7463 Intermediate Similarity NPC3224
0.7463 Intermediate Similarity NPC474106
0.7462 Intermediate Similarity NPC206778
0.7462 Intermediate Similarity NPC285829
0.7462 Intermediate Similarity NPC133302
0.7462 Intermediate Similarity NPC232958
0.7462 Intermediate Similarity NPC988
0.7462 Intermediate Similarity NPC289432
0.746 Intermediate Similarity NPC234637
0.746 Intermediate Similarity NPC130591
0.746 Intermediate Similarity NPC11824
0.7458 Intermediate Similarity NPC145052
0.7458 Intermediate Similarity NPC317280
0.7458 Intermediate Similarity NPC329387
0.7448 Intermediate Similarity NPC478019
0.7445 Intermediate Similarity NPC93015
0.7444 Intermediate Similarity NPC74507
0.7444 Intermediate Similarity NPC234890
0.744 Intermediate Similarity NPC477250
0.7438 Intermediate Similarity NPC329282
0.7432 Intermediate Similarity NPC164762
0.7431 Intermediate Similarity NPC21873
0.7431 Intermediate Similarity NPC143898
0.7429 Intermediate Similarity NPC475549
0.7424 Intermediate Similarity NPC474254
0.7424 Intermediate Similarity NPC307174
0.7424 Intermediate Similarity NPC474159
0.7424 Intermediate Similarity NPC91478
0.7424 Intermediate Similarity NPC139171
0.7422 Intermediate Similarity NPC325646
0.7422 Intermediate Similarity NPC108532
0.7422 Intermediate Similarity NPC28951
0.7415 Intermediate Similarity NPC112816
0.7413 Intermediate Similarity NPC257003
0.7413 Intermediate Similarity NPC110810
0.7407 Intermediate Similarity NPC472707
0.7402 Intermediate Similarity NPC93181
0.7402 Intermediate Similarity NPC306740
0.7402 Intermediate Similarity NPC274839
0.7398 Intermediate Similarity NPC47536
0.7391 Intermediate Similarity NPC70622
0.7391 Intermediate Similarity NPC15850

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC65627 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
0.8017 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7787 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7731 Intermediate Similarity NPD1237 Approved
0.7431 Intermediate Similarity NPD7236 Approved
0.7328 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD1470 Approved
0.7181 Intermediate Similarity NPD7239 Suspended
0.7154 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4879 Approved
0.7132 Intermediate Similarity NPD5951 Approved
0.709 Intermediate Similarity NPD1201 Approved
0.7083 Intermediate Similarity NPD1471 Phase 3
0.708 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1929 Approved
0.7073 Intermediate Similarity NPD1930 Approved
0.7073 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6010 Discontinued
0.705 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD650 Approved
0.7021 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2629 Approved
0.696 Remote Similarity NPD5048 Discontinued
0.6953 Remote Similarity NPD2181 Clinical (unspecified phase)
0.695 Remote Similarity NPD7961 Discontinued
0.6949 Remote Similarity NPD7609 Phase 3
0.6944 Remote Similarity NPD1510 Phase 2
0.694 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6647 Phase 2
0.6929 Remote Similarity NPD2182 Approved
0.6929 Remote Similarity NPD7008 Discontinued
0.6912 Remote Similarity NPD4878 Approved
0.6891 Remote Similarity NPD7631 Approved
0.6889 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6885 Remote Similarity NPD9495 Approved
0.688 Remote Similarity NPD164 Approved
0.688 Remote Similarity NPD5909 Discontinued
0.6875 Remote Similarity NPD2067 Discontinued
0.6867 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6859 Remote Similarity NPD7058 Phase 2
0.6859 Remote Similarity NPD7057 Phase 3
0.6855 Remote Similarity NPD1932 Approved
0.6849 Remote Similarity NPD2346 Discontinued
0.6829 Remote Similarity NPD2066 Phase 3
0.6818 Remote Similarity NPD3317 Approved
0.6803 Remote Similarity NPD1549 Phase 2
0.68 Remote Similarity NPD3950 Discontinued
0.6774 Remote Similarity NPD6801 Discontinued
0.6761 Remote Similarity NPD2313 Discontinued
0.6753 Remote Similarity NPD4380 Phase 2
0.6735 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6735 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6733 Remote Similarity NPD3300 Phase 2
0.6731 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6715 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6714 Remote Similarity NPD2798 Approved
0.6711 Remote Similarity NPD4628 Phase 3
0.6709 Remote Similarity NPD7075 Discontinued
0.6694 Remote Similarity NPD5122 Clinical (unspecified phase)
0.669 Remote Similarity NPD1607 Approved
0.6689 Remote Similarity NPD970 Clinical (unspecified phase)
0.6688 Remote Similarity NPD3226 Approved
0.6687 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD1240 Approved
0.6667 Remote Similarity NPD2329 Discontinued
0.6667 Remote Similarity NPD7009 Phase 2
0.6667 Remote Similarity NPD2796 Approved
0.6667 Remote Similarity NPD3495 Discontinued
0.6667 Remote Similarity NPD9545 Approved
0.6645 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6643 Remote Similarity NPD3764 Approved
0.6642 Remote Similarity NPD9493 Approved
0.6639 Remote Similarity NPD688 Clinical (unspecified phase)
0.6627 Remote Similarity NPD8434 Phase 2
0.6624 Remote Similarity NPD7819 Suspended
0.6622 Remote Similarity NPD2344 Approved
0.6619 Remote Similarity NPD5157 Phase 1
0.6619 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6619 Remote Similarity NPD5159 Phase 2
0.6618 Remote Similarity NPD4196 Clinical (unspecified phase)
0.66 Remote Similarity NPD3750 Approved
0.66 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6599 Remote Similarity NPD4308 Phase 3
0.6599 Remote Similarity NPD651 Clinical (unspecified phase)
0.6593 Remote Similarity NPD7610 Discontinued
0.6591 Remote Similarity NPD7094 Approved
0.6591 Remote Similarity NPD6858 Approved
0.6583 Remote Similarity NPD9258 Approved
0.6583 Remote Similarity NPD9256 Approved
0.6581 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6571 Remote Similarity NPD1876 Approved
0.657 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6569 Remote Similarity NPD2932 Approved
0.6567 Remote Similarity NPD4198 Discontinued
0.656 Remote Similarity NPD1238 Approved
0.6558 Remote Similarity NPD5403 Approved
0.6554 Remote Similarity NPD5405 Approved
0.6554 Remote Similarity NPD5408 Approved
0.6554 Remote Similarity NPD5404 Approved
0.6554 Remote Similarity NPD5406 Approved
0.6547 Remote Similarity NPD9717 Approved
0.6547 Remote Similarity NPD3972 Approved
0.6541 Remote Similarity NPD1241 Discontinued
0.6538 Remote Similarity NPD6599 Discontinued
0.6536 Remote Similarity NPD5401 Approved
0.6533 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6529 Remote Similarity NPD8150 Discontinued
0.6527 Remote Similarity NPD8368 Discontinued
0.6525 Remote Similarity NPD1164 Approved
0.6504 Remote Similarity NPD1693 Approved
0.65 Remote Similarity NPD182 Clinical (unspecified phase)
0.6494 Remote Similarity NPD6273 Approved
0.6489 Remote Similarity NPD1317 Discontinued
0.6486 Remote Similarity NPD7033 Discontinued
0.6486 Remote Similarity NPD2799 Discontinued
0.6486 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6485 Remote Similarity NPD3751 Discontinued
0.6478 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7390 Discontinued
0.6471 Remote Similarity NPD6799 Approved
0.6462 Remote Similarity NPD9267 Approved
0.6462 Remote Similarity NPD9264 Approved
0.6462 Remote Similarity NPD9263 Approved
0.6452 Remote Similarity NPD1989 Approved
0.6449 Remote Similarity NPD3019 Approved
0.6449 Remote Similarity NPD5306 Approved
0.6449 Remote Similarity NPD5305 Approved
0.6447 Remote Similarity NPD2309 Approved
0.6446 Remote Similarity NPD1086 Approved
0.6446 Remote Similarity NPD1090 Approved
0.6446 Remote Similarity NPD1089 Approved
0.6446 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6443 Remote Similarity NPD2935 Discontinued
0.6438 Remote Similarity NPD943 Approved
0.6429 Remote Similarity NPD2533 Approved
0.6429 Remote Similarity NPD2532 Approved
0.6429 Remote Similarity NPD2534 Approved
0.6423 Remote Similarity NPD1202 Approved
0.6418 Remote Similarity NPD2650 Approved
0.6418 Remote Similarity NPD2652 Approved
0.6415 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6414 Remote Similarity NPD3268 Approved
0.6412 Remote Similarity NPD8407 Phase 2
0.6412 Remote Similarity NPD74 Approved
0.6412 Remote Similarity NPD9266 Approved
0.6408 Remote Similarity NPD1203 Approved
0.6406 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6403 Remote Similarity NPD4136 Approved
0.6403 Remote Similarity NPD4106 Approved
0.6403 Remote Similarity NPD4135 Approved
0.64 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6398 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6393 Remote Similarity NPD1239 Approved
0.6392 Remote Similarity NPD7411 Suspended
0.6387 Remote Similarity NPD1512 Approved
0.6382 Remote Similarity NPD7003 Approved
0.6382 Remote Similarity NPD8166 Discontinued
0.638 Remote Similarity NPD6959 Discontinued
0.6376 Remote Similarity NPD7305 Phase 1
0.6376 Remote Similarity NPD3748 Approved
0.6375 Remote Similarity NPD5402 Approved
0.637 Remote Similarity NPD6663 Approved
0.6369 Remote Similarity NPD7458 Discontinued
0.6369 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6364 Remote Similarity NPD800 Approved
0.6364 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6085 Phase 2
0.6357 Remote Similarity NPD6287 Discontinued
0.6357 Remote Similarity NPD4806 Approved
0.6357 Remote Similarity NPD4807 Approved
0.6352 Remote Similarity NPD1934 Approved
0.6341 Remote Similarity NPD1508 Approved
0.6341 Remote Similarity NPD1088 Approved
0.634 Remote Similarity NPD6190 Approved
0.634 Remote Similarity NPD3887 Approved
0.634 Remote Similarity NPD2354 Approved
0.6338 Remote Similarity NPD1283 Approved
0.6336 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6335 Remote Similarity NPD3882 Suspended
0.6333 Remote Similarity NPD1551 Phase 2
0.6333 Remote Similarity NPD1282 Approved
0.6331 Remote Similarity NPD5030 Phase 2
0.6327 Remote Similarity NPD4307 Phase 2
0.6319 Remote Similarity NPD5736 Approved
0.6316 Remote Similarity NPD2800 Approved
0.6312 Remote Similarity NPD5760 Phase 2
0.6312 Remote Similarity NPD5761 Phase 2
0.6312 Remote Similarity NPD6637 Approved
0.6307 Remote Similarity NPD6535 Approved
0.6307 Remote Similarity NPD6534 Approved
0.6304 Remote Similarity NPD7741 Discontinued
0.6301 Remote Similarity NPD411 Approved
0.6296 Remote Similarity NPD3749 Approved
0.6296 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6294 Remote Similarity NPD2797 Approved
0.6294 Remote Similarity NPD5028 Approved
0.6294 Remote Similarity NPD5026 Approved
0.6294 Remote Similarity NPD5034 Approved

Structure

External Identifiers

PubChem CID   10061048
ChEMBL   CHEMBL471807
ZINC  

Physicochemical Properties

Molecular Weight:  258.09
ALogP:  -0.5173
MLogP:  2.67
XLogP:  2.472
# Rotatable Bonds:  3
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  19

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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