Structure

Physi-Chem Properties

Molecular Weight:  332.07
Volume:  329.28
LogP:  2.599
LogD:  2.336
LogS:  -5.816
# Rotatable Bonds:  0
TPSA:  81.42
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.74
Synthetic Accessibility Score:  3.664
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.827
MDCK Permeability:  2.969001798192039e-05
Pgp-inhibitor:  0.476
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  82.90351867675781%
Volume Distribution (VD):  1.37
Pgp-substrate:  8.815229415893555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.874
CYP1A2-substrate:  0.542
CYP2C19-inhibitor:  0.48
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.693
CYP2C9-substrate:  0.107
CYP2D6-inhibitor:  0.191
CYP2D6-substrate:  0.181
CYP3A4-inhibitor:  0.513
CYP3A4-substrate:  0.154

ADMET: Excretion

Clearance (CL):  1.734
Half-life (T1/2):  0.246

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.718
Drug-inuced Liver Injury (DILI):  0.735
AMES Toxicity:  0.579
Rat Oral Acute Toxicity:  0.287
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.36
Carcinogencity:  0.962
Eye Corrosion:  0.003
Eye Irritation:  0.168
Respiratory Toxicity:  0.333

Download Data

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

  Natural Product: NPC192069

Natural Product ID:  NPC192069
Common Name*:   Helenaquinone
IUPAC Name:   n.a.
Synonyms:   Halenaquinone
Standard InCHIKey:  SMGBXXZKAPMTBB-FQEVSTJZSA-N
Standard InCHI:  InChI=1S/C20H12O5/c1-20-5-4-16(23)12-8-25-19(17(12)20)18(24)11-6-9-10(7-13(11)20)15(22)3-2-14(9)21/h2-3,6-8H,4-5H2,1H3/t20-/m0/s1
SMILES:  O=C1c2cc3C(=O)C=CC(=O)c3cc2[C@]2(c3c1occ3C(=O)CC2)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL513747
PubChem CID:   370346
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32714 xestospongia Genus Petrosiidae Eukaryota n.a. n.a. n.a. PMID[10843588]
NPO32714 xestospongia Genus Petrosiidae Eukaryota n.a. South Pacific n.a. PMID[20634081]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT143 Individual Protein DNA topoisomerase I Homo sapiens MIC = 0.4 ug.mL-1 PMID[533083]
NPT137 Cell Line L1210 Mus musculus IC50 = 1.6 ug.mL-1 PMID[533083]
NPT91 Cell Line KB Homo sapiens IC50 = 3.1 ug.mL-1 PMID[533083]
NPT4422 Individual Protein Phospholipase A2 (Bee) Apis mellifera IC50 = 3700.0 nM PMID[533085]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 60000.0 nM PMID[533085]
NPT4422 Individual Protein Phospholipase A2 (Bee) Apis mellifera IC50 = 3700.0 nM PMID[533086]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 60000.0 nM PMID[533086]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 16595.87 nM PMID[533088]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 16519.62 nM PMID[533088]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 12502.59 nM PMID[533088]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 17179.08 nM PMID[533088]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 2449.06 nM PMID[533088]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 6934.26 nM PMID[533088]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 17579.24 nM PMID[533088]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 15100.8 nM PMID[533088]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 17258.38 nM PMID[533088]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[533088]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 22181.96 nM PMID[533088]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 18663.8 nM PMID[533088]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 14288.94 nM PMID[533088]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[533088]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 23713.74 nM PMID[533088]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 19998.62 nM PMID[533088]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 16330.52 nM PMID[533088]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[533088]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 15488.17 nM PMID[533088]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 30130.06 nM PMID[533088]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 31045.6 nM PMID[533088]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 19142.56 nM PMID[533088]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 6053.41 nM PMID[533088]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 9204.5 nM PMID[533088]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 24717.24 nM PMID[533088]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 14521.12 nM PMID[533088]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 18879.91 nM PMID[533088]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 92257.14 nM PMID[533088]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 64565.42 nM PMID[533088]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 18197.01 nM PMID[533088]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 8590.14 nM PMID[533088]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 23878.11 nM PMID[533088]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 71285.3 nM PMID[533088]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 86496.79 nM PMID[533088]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 45185.59 nM PMID[533088]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 20941.12 nM PMID[533088]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 15417.0 nM PMID[533088]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 17258.38 nM PMID[533088]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 18793.17 nM PMID[533088]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 23550.49 nM PMID[533088]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 17378.01 nM PMID[533088]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[533088]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 14028.14 nM PMID[533088]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 26607.25 nM PMID[533088]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 15523.87 nM PMID[533088]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 21086.28 nM PMID[533088]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 25941.79 nM PMID[533088]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 16672.47 nM PMID[533088]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 17218.69 nM PMID[533088]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 16557.7 nM PMID[533088]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 11614.49 nM PMID[533088]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 21978.6 nM PMID[533088]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 14825.18 nM PMID[533088]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 15417.0 nM PMID[533088]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 29040.23 nM PMID[533088]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 16330.52 nM PMID[533088]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 19678.86 nM PMID[533088]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 15958.79 nM PMID[533088]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 21183.61 nM PMID[533088]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 17298.16 nM PMID[533088]
NPT2 Others Unspecified IC50 = 1500.0 nM PMID[533084]
NPT2 Others Unspecified IC50 = 1570.0 nM PMID[533085]
NPT1180 Protein Complex Protein farnesyltransferase Homo sapiens IC50 = 930.0 nM PMID[533085]
NPT1225 Organism Plasmodium falciparum (isolate FcB1 / Columbia) Plasmodium falciparum FcB1/Columbia IC50 > 30000.0 nM PMID[533085]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 30000.0 nM PMID[533085]
NPT2 Others Unspecified IC50 = 1600.0 nM PMID[533086]
NPT1180 Protein Complex Protein farnesyltransferase Homo sapiens IC50 = 930.0 nM PMID[533086]
NPT1225 Organism Plasmodium falciparum (isolate FcB1 / Columbia) Plasmodium falciparum FcB1/Columbia IC50 > 30000.0 nM PMID[533086]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 30000.0 nM PMID[533086]
NPT2 Others Unspecified IC50 = 600.0 nM PMID[533089]
NPT2 Others Unspecified IC50 = 2000.0 nM PMID[533089]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC192069 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
0.9441 High Similarity NPC245522
0.9441 High Similarity NPC114513
0.9392 High Similarity NPC88958
0.9178 High Similarity NPC281398
0.911 High Similarity NPC478166
0.9103 High Similarity NPC117674
0.906 High Similarity NPC144010
0.9041 High Similarity NPC93241
0.9041 High Similarity NPC27798
0.9007 High Similarity NPC179170
0.9 High Similarity NPC145830
0.894 High Similarity NPC282793
0.8889 High Similarity NPC265181
0.8882 High Similarity NPC469966
0.8861 High Similarity NPC473945
0.8851 High Similarity NPC233763
0.8766 High Similarity NPC221992
0.8742 High Similarity NPC44602
0.869 High Similarity NPC177262
0.859 High Similarity NPC10051
0.859 High Similarity NPC299094
0.85 High Similarity NPC472784
0.8497 Intermediate Similarity NPC472298
0.8397 Intermediate Similarity NPC25351
0.8397 Intermediate Similarity NPC23559
0.8387 Intermediate Similarity NPC471613
0.8366 Intermediate Similarity NPC252208
0.8333 Intermediate Similarity NPC10429
0.8312 Intermediate Similarity NPC280025
0.8312 Intermediate Similarity NPC95526
0.8301 Intermediate Similarity NPC224418
0.8291 Intermediate Similarity NPC81405
0.8289 Intermediate Similarity NPC290038
0.828 Intermediate Similarity NPC472786
0.8258 Intermediate Similarity NPC226578
0.825 Intermediate Similarity NPC472781
0.825 Intermediate Similarity NPC472782
0.8239 Intermediate Similarity NPC140952
0.8217 Intermediate Similarity NPC24232
0.82 Intermediate Similarity NPC18904
0.8199 Intermediate Similarity NPC472780
0.8199 Intermediate Similarity NPC472783
0.8193 Intermediate Similarity NPC167340
0.8176 Intermediate Similarity NPC217914
0.8138 Intermediate Similarity NPC57552
0.8133 Intermediate Similarity NPC233707
0.8125 Intermediate Similarity NPC476404
0.8125 Intermediate Similarity NPC473282
0.8125 Intermediate Similarity NPC104380
0.8125 Intermediate Similarity NPC294300
0.8125 Intermediate Similarity NPC217602
0.8125 Intermediate Similarity NPC317900
0.8121 Intermediate Similarity NPC42400
0.8121 Intermediate Similarity NPC232996
0.8121 Intermediate Similarity NPC307401
0.8117 Intermediate Similarity NPC474261
0.8105 Intermediate Similarity NPC53016
0.8101 Intermediate Similarity NPC44606
0.8069 Intermediate Similarity NPC59502
0.8067 Intermediate Similarity NPC284184
0.8065 Intermediate Similarity NPC250331
0.8061 Intermediate Similarity NPC302392
0.805 Intermediate Similarity NPC41719
0.8049 Intermediate Similarity NPC473766
0.8049 Intermediate Similarity NPC473753
0.8037 Intermediate Similarity NPC472664
0.8037 Intermediate Similarity NPC56358
0.8013 Intermediate Similarity NPC202260
0.8013 Intermediate Similarity NPC478163
0.8012 Intermediate Similarity NPC473368
0.8 Intermediate Similarity NPC478159
0.8 Intermediate Similarity NPC3898
0.8 Intermediate Similarity NPC262198
0.8 Intermediate Similarity NPC478161
0.7988 Intermediate Similarity NPC475779
0.7987 Intermediate Similarity NPC1249
0.7987 Intermediate Similarity NPC324117
0.7975 Intermediate Similarity NPC472787
0.7974 Intermediate Similarity NPC263337
0.7974 Intermediate Similarity NPC473152
0.7963 Intermediate Similarity NPC472299
0.7963 Intermediate Similarity NPC333139
0.7963 Intermediate Similarity NPC287559
0.7962 Intermediate Similarity NPC474107
0.7949 Intermediate Similarity NPC471346
0.7947 Intermediate Similarity NPC186647
0.7947 Intermediate Similarity NPC301341
0.7939 Intermediate Similarity NPC270312
0.7937 Intermediate Similarity NPC290927
0.7937 Intermediate Similarity NPC75310
0.7931 Intermediate Similarity NPC184391
0.7911 Intermediate Similarity NPC46551
0.7901 Intermediate Similarity NPC67197
0.7901 Intermediate Similarity NPC472823
0.7901 Intermediate Similarity NPC123153
0.7898 Intermediate Similarity NPC478018
0.7892 Intermediate Similarity NPC298071
0.7885 Intermediate Similarity NPC62799
0.7879 Intermediate Similarity NPC132054
0.7875 Intermediate Similarity NPC27615
0.7875 Intermediate Similarity NPC130015
0.7875 Intermediate Similarity NPC38361
0.7871 Intermediate Similarity NPC199044
0.7871 Intermediate Similarity NPC238843
0.7871 Intermediate Similarity NPC142113
0.7867 Intermediate Similarity NPC209858
0.7866 Intermediate Similarity NPC475039
0.7866 Intermediate Similarity NPC14499
0.7866 Intermediate Similarity NPC476035
0.7862 Intermediate Similarity NPC148423
0.7862 Intermediate Similarity NPC135303
0.7857 Intermediate Similarity NPC52412
0.7852 Intermediate Similarity NPC470740
0.7849 Intermediate Similarity NPC472533
0.7848 Intermediate Similarity NPC472839
0.7847 Intermediate Similarity NPC51079
0.7847 Intermediate Similarity NPC178382
0.7844 Intermediate Similarity NPC472660
0.7843 Intermediate Similarity NPC61157
0.7843 Intermediate Similarity NPC473681
0.7843 Intermediate Similarity NPC218204
0.784 Intermediate Similarity NPC472283
0.7834 Intermediate Similarity NPC71821
0.7831 Intermediate Similarity NPC279768
0.7831 Intermediate Similarity NPC316262
0.7831 Intermediate Similarity NPC314653
0.7829 Intermediate Similarity NPC236532
0.7826 Intermediate Similarity NPC472785
0.7826 Intermediate Similarity NPC208806
0.7824 Intermediate Similarity NPC472665
0.7821 Intermediate Similarity NPC185456
0.7818 Intermediate Similarity NPC193998
0.7818 Intermediate Similarity NPC276735
0.7815 Intermediate Similarity NPC146872
0.7812 Intermediate Similarity NPC475777
0.7812 Intermediate Similarity NPC472407
0.7811 Intermediate Similarity NPC91650
0.7806 Intermediate Similarity NPC69755
0.7806 Intermediate Similarity NPC103134
0.7805 Intermediate Similarity NPC313368
0.7805 Intermediate Similarity NPC18986
0.7805 Intermediate Similarity NPC471003
0.7799 Intermediate Similarity NPC159927
0.7799 Intermediate Similarity NPC469335
0.7791 Intermediate Similarity NPC201127
0.7791 Intermediate Similarity NPC474611
0.7785 Intermediate Similarity NPC279596
0.7785 Intermediate Similarity NPC198427
0.7784 Intermediate Similarity NPC191012
0.7778 Intermediate Similarity NPC104736
0.7778 Intermediate Similarity NPC41880
0.7778 Intermediate Similarity NPC233776
0.7778 Intermediate Similarity NPC60973
0.7778 Intermediate Similarity NPC474722
0.7778 Intermediate Similarity NPC295914
0.7771 Intermediate Similarity NPC49282
0.7771 Intermediate Similarity NPC471292
0.7771 Intermediate Similarity NPC121995
0.7764 Intermediate Similarity NPC471863
0.7758 Intermediate Similarity NPC24761
0.7756 Intermediate Similarity NPC163948
0.7756 Intermediate Similarity NPC472840
0.7755 Intermediate Similarity NPC428300
0.775 Intermediate Similarity NPC472406
0.775 Intermediate Similarity NPC272590
0.7742 Intermediate Similarity NPC149780
0.7736 Intermediate Similarity NPC219560
0.7736 Intermediate Similarity NPC306788
0.7735 Intermediate Similarity NPC255861
0.7735 Intermediate Similarity NPC93574
0.7733 Intermediate Similarity NPC293253
0.773 Intermediate Similarity NPC304692
0.773 Intermediate Similarity NPC7059
0.7727 Intermediate Similarity NPC477408
0.7727 Intermediate Similarity NPC1268
0.7727 Intermediate Similarity NPC90296
0.7727 Intermediate Similarity NPC470407
0.7727 Intermediate Similarity NPC223336
0.7725 Intermediate Similarity NPC41689
0.7722 Intermediate Similarity NPC190572
0.7716 Intermediate Similarity NPC214632
0.7712 Intermediate Similarity NPC471542
0.7712 Intermediate Similarity NPC290601
0.7711 Intermediate Similarity NPC475106
0.7707 Intermediate Similarity NPC472836
0.7707 Intermediate Similarity NPC469385
0.7703 Intermediate Similarity NPC50583
0.7703 Intermediate Similarity NPC208389
0.7702 Intermediate Similarity NPC246164
0.7697 Intermediate Similarity NPC470939
0.7697 Intermediate Similarity NPC197596
0.7688 Intermediate Similarity NPC477404
0.7688 Intermediate Similarity NPC212257
0.7688 Intermediate Similarity NPC196864
0.7688 Intermediate Similarity NPC471348
0.7688 Intermediate Similarity NPC228906
0.7688 Intermediate Similarity NPC469416
0.7688 Intermediate Similarity NPC228842
0.7687 Intermediate Similarity NPC177925
0.7683 Intermediate Similarity NPC474637

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC192069 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
0.8889 High Similarity NPD1471 Phase 3
0.7963 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD3226 Approved
0.7778 Intermediate Similarity NPD2346 Discontinued
0.7662 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD2344 Approved
0.7569 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD1247 Approved
0.7543 Intermediate Similarity NPD8434 Phase 2
0.7468 Intermediate Similarity NPD2309 Approved
0.7453 Intermediate Similarity NPD920 Approved
0.7427 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD3972 Approved
0.7368 Intermediate Similarity NPD2313 Discontinued
0.7349 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD919 Approved
0.7317 Intermediate Similarity NPD6599 Discontinued
0.7315 Intermediate Similarity NPD1876 Approved
0.7308 Intermediate Similarity NPD2799 Discontinued
0.7284 Intermediate Similarity NPD6273 Approved
0.7233 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD2800 Approved
0.7229 Intermediate Similarity NPD6280 Approved
0.7229 Intermediate Similarity NPD6279 Approved
0.7222 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6808 Phase 2
0.7188 Intermediate Similarity NPD7003 Approved
0.7186 Intermediate Similarity NPD5761 Phase 2
0.7186 Intermediate Similarity NPD7819 Suspended
0.7186 Intermediate Similarity NPD5760 Phase 2
0.7176 Intermediate Similarity NPD5494 Approved
0.7169 Intermediate Similarity NPD7411 Suspended
0.716 Intermediate Similarity NPD3749 Approved
0.7159 Intermediate Similarity NPD6764 Approved
0.7159 Intermediate Similarity NPD6765 Approved
0.7152 Intermediate Similarity NPD2796 Approved
0.7151 Intermediate Similarity NPD3926 Phase 2
0.7143 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6959 Discontinued
0.7117 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3748 Approved
0.7083 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7458 Discontinued
0.7048 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1651 Approved
0.7024 Intermediate Similarity NPD6801 Discontinued
0.7019 Intermediate Similarity NPD1243 Approved
0.7013 Intermediate Similarity NPD6832 Phase 2
0.7012 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6784 Approved
0.7 Intermediate Similarity NPD6785 Approved
0.7 Intermediate Similarity NPD3882 Suspended
0.6993 Remote Similarity NPD2798 Approved
0.6987 Remote Similarity NPD8032 Phase 2
0.6975 Remote Similarity NPD4628 Phase 3
0.6968 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1241 Discontinued
0.6966 Remote Similarity NPD6559 Discontinued
0.6964 Remote Similarity NPD5889 Approved
0.6964 Remote Similarity NPD5890 Approved
0.6959 Remote Similarity NPD7075 Discontinued
0.6951 Remote Similarity NPD6799 Approved
0.6941 Remote Similarity NPD2296 Approved
0.6928 Remote Similarity NPD1470 Approved
0.6928 Remote Similarity NPD3266 Approved
0.6928 Remote Similarity NPD3267 Approved
0.6914 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2532 Approved
0.6909 Remote Similarity NPD2534 Approved
0.6909 Remote Similarity NPD2533 Approved
0.6902 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6899 Remote Similarity NPD1899 Clinical (unspecified phase)
0.689 Remote Similarity NPD7236 Approved
0.6887 Remote Similarity NPD1281 Approved
0.6875 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3750 Approved
0.6852 Remote Similarity NPD1549 Phase 2
0.6835 Remote Similarity NPD4307 Phase 2
0.6835 Remote Similarity NPD2979 Phase 3
0.6832 Remote Similarity NPD1551 Phase 2
0.6832 Remote Similarity NPD2935 Discontinued
0.6828 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6807 Remote Similarity NPD5401 Approved
0.6805 Remote Similarity NPD6585 Discontinued
0.6802 Remote Similarity NPD7768 Phase 2
0.68 Remote Similarity NPD6232 Discontinued
0.679 Remote Similarity NPD1552 Clinical (unspecified phase)
0.679 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7239 Suspended
0.6784 Remote Similarity NPD2393 Clinical (unspecified phase)
0.678 Remote Similarity NPD7473 Discontinued
0.677 Remote Similarity NPD1510 Phase 2
0.6753 Remote Similarity NPD1283 Approved
0.675 Remote Similarity NPD1607 Approved
0.6744 Remote Similarity NPD5402 Approved
0.6744 Remote Similarity NPD3817 Phase 2
0.6742 Remote Similarity NPD3751 Discontinued
0.6727 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6727 Remote Similarity NPD3887 Approved
0.6726 Remote Similarity NPD5403 Approved
0.6709 Remote Similarity NPD3268 Approved
0.6709 Remote Similarity NPD6798 Discontinued
0.6709 Remote Similarity NPD3764 Approved
0.6707 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6707 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6706 Remote Similarity NPD4380 Phase 2
0.6704 Remote Similarity NPD5844 Phase 1
0.6703 Remote Similarity NPD8312 Approved
0.6703 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6703 Remote Similarity NPD8313 Approved
0.6689 Remote Similarity NPD5691 Approved
0.6688 Remote Similarity NPD5327 Phase 3
0.6687 Remote Similarity NPD1933 Approved
0.6687 Remote Similarity NPD2353 Approved
0.6687 Remote Similarity NPD6355 Discontinued
0.6687 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8285 Discontinued
0.6667 Remote Similarity NPD4308 Phase 3
0.6667 Remote Similarity NPD1201 Approved
0.6648 Remote Similarity NPD7177 Discontinued
0.6646 Remote Similarity NPD7095 Approved
0.6646 Remote Similarity NPD7008 Discontinued
0.6629 Remote Similarity NPD6166 Phase 2
0.6629 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6629 Remote Similarity NPD2403 Approved
0.6628 Remote Similarity NPD1934 Approved
0.6628 Remote Similarity NPD6844 Discontinued
0.6626 Remote Similarity NPD5406 Approved
0.6626 Remote Similarity NPD2438 Suspended
0.6626 Remote Similarity NPD5408 Approved
0.6626 Remote Similarity NPD5404 Approved
0.6626 Remote Similarity NPD5405 Approved
0.6626 Remote Similarity NPD2531 Phase 2
0.6625 Remote Similarity NPD1240 Approved
0.6625 Remote Similarity NPD4060 Phase 1
0.6611 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6603 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6603 Remote Similarity NPD1203 Approved
0.6601 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6568 Remote Similarity NPD5049 Phase 3
0.6568 Remote Similarity NPD1512 Approved
0.6562 Remote Similarity NPD6781 Approved
0.6562 Remote Similarity NPD4107 Approved
0.6562 Remote Similarity NPD6776 Approved
0.6562 Remote Similarity NPD6778 Approved
0.6562 Remote Similarity NPD6779 Approved
0.6562 Remote Similarity NPD6780 Approved
0.6562 Remote Similarity NPD6777 Approved
0.6562 Remote Similarity NPD6782 Approved
0.6561 Remote Similarity NPD1019 Discontinued
0.6558 Remote Similarity NPD1611 Approved
0.6546 Remote Similarity NPD7435 Discontinued
0.6545 Remote Similarity NPD2897 Discontinued
0.6543 Remote Similarity NPD6651 Approved
0.6536 Remote Similarity NPD17 Approved
0.6531 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6529 Remote Similarity NPD3873 Phase 3
0.6529 Remote Similarity NPD3869 Phase 3
0.6527 Remote Similarity NPD2354 Approved
0.6524 Remote Similarity NPD4476 Approved
0.6524 Remote Similarity NPD4477 Approved
0.6522 Remote Similarity NPD4140 Approved
0.6517 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6516 Remote Similarity NPD9717 Approved
0.6514 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6505 Remote Similarity NPD8150 Discontinued
0.65 Remote Similarity NPD411 Approved
0.65 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6497 Remote Similarity NPD710 Clinical (unspecified phase)
0.6494 Remote Similarity NPD2801 Approved
0.649 Remote Similarity NPD405 Clinical (unspecified phase)
0.6485 Remote Similarity NPD8404 Phase 2
0.6477 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3025 Approved
0.6471 Remote Similarity NPD5585 Approved
0.6471 Remote Similarity NPD3024 Approved
0.6467 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6467 Remote Similarity NPD8166 Discontinued
0.6467 Remote Similarity NPD5951 Approved
0.6464 Remote Similarity NPD7799 Discontinued
0.6464 Remote Similarity NPD3818 Discontinued
0.6463 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7698 Approved
0.6462 Remote Similarity NPD7697 Approved
0.6462 Remote Similarity NPD7696 Phase 3
0.6461 Remote Similarity NPD8127 Discontinued
0.646 Remote Similarity NPD6233 Phase 2
0.646 Remote Similarity NPD7961 Discontinued
0.645 Remote Similarity NPD1511 Approved
0.645 Remote Similarity NPD7390 Discontinued
0.6446 Remote Similarity NPD970 Clinical (unspecified phase)
0.6443 Remote Similarity NPD4482 Phase 3
0.6436 Remote Similarity NPD4287 Approved
0.6433 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7871 Phase 2
0.6429 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7870 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data