Structure

Physi-Chem Properties

Molecular Weight:  328.13
Volume:  325.167
LogP:  2.617
LogD:  2.349
LogS:  -4.409
# Rotatable Bonds:  1
TPSA:  65.74
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.584
Synthetic Accessibility Score:  6.238
Fsp3:  0.579
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.008
MDCK Permeability:  5.795235119876452e-05
Pgp-inhibitor:  0.031
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.494

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.371
Plasma Protein Binding (PPB):  80.15428161621094%
Volume Distribution (VD):  3.167
Pgp-substrate:  10.742661476135254%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.58
CYP2C19-inhibitor:  0.791
CYP2C19-substrate:  0.37
CYP2C9-inhibitor:  0.309
CYP2C9-substrate:  0.202
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.556
CYP3A4-inhibitor:  0.797
CYP3A4-substrate:  0.448

ADMET: Excretion

Clearance (CL):  11.839
Half-life (T1/2):  0.071

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.825
Drug-inuced Liver Injury (DILI):  0.304
AMES Toxicity:  0.83
Rat Oral Acute Toxicity:  0.979
Maximum Recommended Daily Dose:  0.924
Skin Sensitization:  0.132
Carcinogencity:  0.947
Eye Corrosion:  0.199
Eye Irritation:  0.221
Respiratory Toxicity:  0.97

Download Data

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

  Natural Product: NPC20500

Natural Product ID:  NPC20500
Common Name*:   UNKJMPBJRRFBEL-UJYOZEIHSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UNKJMPBJRRFBEL-UJYOZEIHSA-N
Standard InCHI:  InChI=1S/C19H20O5/c1-11-4-6-18-8-13(23-16(18)20)2-3-15(18)19(11)9-14(24-17(19)21)12-5-7-22-10-12/h5,7,10,13-15H,1-4,6,8-9H2/t13-,14+,15+,18-,19-/m1/s1
SMILES:  C=C1CC[C@]23[C@@H]([C@]41C[C@H](OC4=O)c1cocc1)CC[C@H](C2)OC3=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2374350
PubChem CID:   90662094
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO17554 Schizosaccharomyces pombe Species Schizosaccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.3390/metabo3041118]
NPO23670 Lactuca indica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12762795]
NPO22221 Ibicella lutea Species Martyniaceae Eukaryota n.a. El Volcan, Dpto. La Capital, Province of San Luis, Argentina 2001-MAR PMID[14695802]
NPO24055 Thapsia villosa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1708405]
NPO17554 Schizosaccharomyces pombe Species Schizosaccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24828577]
NPO23425 Siphonodictyon coralliphagum Species Phloeodictyidae Eukaryota n.a. n.a. n.a. PMID[7673944]
NPO23670 Lactuca indica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23247 Desmodium tiliaefolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24011 Gentiana pedicellata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24182 Syringa afghanica Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23042 Rhizocarpon geographicum Species Rhizocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23247 Desmodium tiliaefolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23670 Lactuca indica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23670 Lactuca indica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23228 Cladobotryum rubrobrunnescens Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23846 Pseudocedrela chevalieri Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24055 Thapsia villosa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22221 Ibicella lutea Species Martyniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23670 Lactuca indica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24182 Syringa afghanica Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23247 Desmodium tiliaefolium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22862 Stereum frustulosum Species Stereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23042 Rhizocarpon geographicum Species Rhizocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22933 Plectranthus rugosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23425 Siphonodictyon coralliphagum Species Phloeodictyidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21446 Burchellia bubalina Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22986 Perezia hebeclada Species Pereziidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24458 Sindora sumatrana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24011 Gentiana pedicellata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20639 Lupinus palmeri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17554 Schizosaccharomyces pombe Species Schizosaccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 62950.62 nM PMID[479933]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[479933]

☑ 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 NPC20500 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
0.942 High Similarity NPC223415
0.9296 High Similarity NPC195325
0.9155 High Similarity NPC221809
0.9143 High Similarity NPC470741
0.9124 High Similarity NPC470742
0.9097 High Similarity NPC476936
0.9007 High Similarity NPC267632
0.8978 High Similarity NPC92941
0.8921 High Similarity NPC476943
0.8904 High Similarity NPC18135
0.8867 High Similarity NPC191828
0.8849 High Similarity NPC310830
0.8844 High Similarity NPC75906
0.8836 High Similarity NPC196864
0.8836 High Similarity NPC469335
0.8836 High Similarity NPC477404
0.8836 High Similarity NPC159927
0.8819 High Similarity NPC262198
0.8811 High Similarity NPC251865
0.8811 High Similarity NPC476944
0.8767 High Similarity NPC472654
0.8759 High Similarity NPC250228
0.875 High Similarity NPC419
0.8707 High Similarity NPC156189
0.8707 High Similarity NPC476122
0.869 High Similarity NPC346
0.8686 High Similarity NPC298190
0.8681 High Similarity NPC142113
0.8667 High Similarity NPC319140
0.8667 High Similarity NPC95567
0.8658 High Similarity NPC178932
0.8658 High Similarity NPC57998
0.8657 High Similarity NPC179354
0.8652 High Similarity NPC220094
0.8652 High Similarity NPC236532
0.8643 High Similarity NPC146872
0.8639 High Similarity NPC470791
0.8639 High Similarity NPC470790
0.863 High Similarity NPC476938
0.863 High Similarity NPC476937
0.863 High Similarity NPC470941
0.8613 High Similarity NPC21460
0.8609 High Similarity NPC299038
0.86 High Similarity NPC214541
0.86 High Similarity NPC44675
0.86 High Similarity NPC469336
0.86 High Similarity NPC469850
0.8592 High Similarity NPC90953
0.8591 High Similarity NPC476201
0.8591 High Similarity NPC476940
0.8591 High Similarity NPC322546
0.8591 High Similarity NPC476939
0.8591 High Similarity NPC308205
0.8591 High Similarity NPC469503
0.8582 High Similarity NPC42400
0.8581 High Similarity NPC5180
0.8571 High Similarity NPC476942
0.8571 High Similarity NPC476941
0.8562 High Similarity NPC62799
0.8553 High Similarity NPC475226
0.8553 High Similarity NPC475967
0.8552 High Similarity NPC84479
0.8543 High Similarity NPC204663
0.8542 High Similarity NPC121158
0.8533 High Similarity NPC282445
0.8533 High Similarity NPC30222
0.8523 High Similarity NPC291150
0.8523 High Similarity NPC116717
0.8516 High Similarity NPC472141
0.8514 High Similarity NPC471001
0.8507 High Similarity NPC16922
0.8503 High Similarity NPC10088
0.8497 Intermediate Similarity NPC305016
0.8487 Intermediate Similarity NPC261597
0.8487 Intermediate Similarity NPC472772
0.8487 Intermediate Similarity NPC472777
0.8487 Intermediate Similarity NPC472776
0.8487 Intermediate Similarity NPC167142
0.8487 Intermediate Similarity NPC195131
0.8487 Intermediate Similarity NPC469847
0.8487 Intermediate Similarity NPC472778
0.8487 Intermediate Similarity NPC472283
0.8483 Intermediate Similarity NPC205071
0.8477 Intermediate Similarity NPC476262
0.8477 Intermediate Similarity NPC35000
0.8467 Intermediate Similarity NPC182427
0.8467 Intermediate Similarity NPC268905
0.8467 Intermediate Similarity NPC29695
0.8456 Intermediate Similarity NPC74612
0.8451 Intermediate Similarity NPC186626
0.8446 Intermediate Similarity NPC19747
0.8435 Intermediate Similarity NPC471292
0.8435 Intermediate Similarity NPC276676
0.8425 Intermediate Similarity NPC199044
0.8425 Intermediate Similarity NPC238843
0.8421 Intermediate Similarity NPC104736
0.8421 Intermediate Similarity NPC107646
0.8421 Intermediate Similarity NPC126723
0.8421 Intermediate Similarity NPC263265
0.8421 Intermediate Similarity NPC209364
0.8421 Intermediate Similarity NPC60973
0.8417 Intermediate Similarity NPC89133
0.8414 Intermediate Similarity NPC473152
0.8403 Intermediate Similarity NPC156077
0.8403 Intermediate Similarity NPC56197
0.84 Intermediate Similarity NPC240214
0.8389 Intermediate Similarity NPC329180
0.8389 Intermediate Similarity NPC211625
0.8387 Intermediate Similarity NPC663
0.8387 Intermediate Similarity NPC471168
0.8387 Intermediate Similarity NPC224394
0.8387 Intermediate Similarity NPC469846
0.8378 Intermediate Similarity NPC255414
0.8369 Intermediate Similarity NPC471998
0.8367 Intermediate Similarity NPC41182
0.8366 Intermediate Similarity NPC304692
0.8366 Intermediate Similarity NPC286722
0.8366 Intermediate Similarity NPC214495
0.8366 Intermediate Similarity NPC249021
0.8366 Intermediate Similarity NPC187149
0.8366 Intermediate Similarity NPC470119
0.8366 Intermediate Similarity NPC36655
0.8357 Intermediate Similarity NPC471817
0.8356 Intermediate Similarity NPC476946
0.8355 Intermediate Similarity NPC264943
0.8345 Intermediate Similarity NPC205765
0.8344 Intermediate Similarity NPC476850
0.8344 Intermediate Similarity NPC471002
0.8344 Intermediate Similarity NPC476861
0.8333 Intermediate Similarity NPC123088
0.8333 Intermediate Similarity NPC46551
0.8323 Intermediate Similarity NPC472771
0.8323 Intermediate Similarity NPC470939
0.8323 Intermediate Similarity NPC472767
0.8323 Intermediate Similarity NPC197596
0.8323 Intermediate Similarity NPC6326
0.8323 Intermediate Similarity NPC69028
0.8323 Intermediate Similarity NPC329938
0.8322 Intermediate Similarity NPC243165
0.8322 Intermediate Similarity NPC310043
0.8321 Intermediate Similarity NPC46536
0.8321 Intermediate Similarity NPC138139
0.8312 Intermediate Similarity NPC474611
0.8312 Intermediate Similarity NPC475295
0.8312 Intermediate Similarity NPC237155
0.8312 Intermediate Similarity NPC473473
0.8312 Intermediate Similarity NPC307383
0.8311 Intermediate Similarity NPC470999
0.8299 Intermediate Similarity NPC86935
0.8289 Intermediate Similarity NPC98206
0.8289 Intermediate Similarity NPC237259
0.8289 Intermediate Similarity NPC34421
0.8278 Intermediate Similarity NPC272590
0.8276 Intermediate Similarity NPC67003
0.8273 Intermediate Similarity NPC198904
0.8269 Intermediate Similarity NPC292389
0.8269 Intermediate Similarity NPC476197
0.8269 Intermediate Similarity NPC477405
0.8269 Intermediate Similarity NPC165218
0.8269 Intermediate Similarity NPC472773
0.8269 Intermediate Similarity NPC469338
0.8269 Intermediate Similarity NPC472139
0.8267 Intermediate Similarity NPC125182
0.8267 Intermediate Similarity NPC69647
0.8258 Intermediate Similarity NPC335761
0.8258 Intermediate Similarity NPC475381
0.8258 Intermediate Similarity NPC25255
0.8258 Intermediate Similarity NPC472653
0.8255 Intermediate Similarity NPC471174
0.8255 Intermediate Similarity NPC216755
0.8252 Intermediate Similarity NPC46896
0.8252 Intermediate Similarity NPC214572
0.8247 Intermediate Similarity NPC470118
0.8247 Intermediate Similarity NPC475066
0.8247 Intermediate Similarity NPC197137
0.8243 Intermediate Similarity NPC56731
0.8235 Intermediate Similarity NPC155939
0.8235 Intermediate Similarity NPC75310
0.8235 Intermediate Similarity NPC141538
0.8235 Intermediate Similarity NPC296807
0.8235 Intermediate Similarity NPC92979
0.8231 Intermediate Similarity NPC243577
0.8228 Intermediate Similarity NPC472651
0.8217 Intermediate Similarity NPC470940
0.8217 Intermediate Similarity NPC476857
0.8217 Intermediate Similarity NPC469849
0.8217 Intermediate Similarity NPC476856
0.8217 Intermediate Similarity NPC276551
0.8217 Intermediate Similarity NPC476858
0.8217 Intermediate Similarity NPC276735
0.8217 Intermediate Similarity NPC472664
0.8217 Intermediate Similarity NPC476860
0.8212 Intermediate Similarity NPC470997
0.8207 Intermediate Similarity NPC474722
0.8205 Intermediate Similarity NPC470792
0.8205 Intermediate Similarity NPC471167
0.8205 Intermediate Similarity NPC5079
0.8205 Intermediate Similarity NPC200782
0.8205 Intermediate Similarity NPC472668
0.8205 Intermediate Similarity NPC193798

  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 NPC20500 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
0.8235 Intermediate Similarity NPD5761 Phase 2
0.8235 Intermediate Similarity NPD5760 Phase 2
0.7688 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD920 Approved
0.7485 Intermediate Similarity NPD8434 Phase 2
0.7484 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD6765 Approved
0.7294 Intermediate Similarity NPD6764 Approved
0.7255 Intermediate Similarity NPD1471 Phase 3
0.7226 Intermediate Similarity NPD4628 Phase 3
0.7162 Intermediate Similarity NPD6832 Phase 2
0.7126 Intermediate Similarity NPD6785 Approved
0.7126 Intermediate Similarity NPD6784 Approved
0.7124 Intermediate Similarity NPD2799 Discontinued
0.7117 Intermediate Similarity NPD7819 Suspended
0.7108 Intermediate Similarity NPD5494 Approved
0.7107 Intermediate Similarity NPD6273 Approved
0.7078 Intermediate Similarity NPD2796 Approved
0.7051 Intermediate Similarity NPD1243 Approved
0.7048 Intermediate Similarity NPD919 Approved
0.7039 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6599 Discontinued
0.7013 Intermediate Similarity NPD3748 Approved
0.6988 Remote Similarity NPD3749 Approved
0.6975 Remote Similarity NPD3226 Approved
0.6968 Remote Similarity NPD1551 Phase 2
0.6968 Remote Similarity NPD2935 Discontinued
0.6964 Remote Similarity NPD1247 Approved
0.6959 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2313 Discontinued
0.6943 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6937 Remote Similarity NPD2532 Approved
0.6937 Remote Similarity NPD2534 Approved
0.6937 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6937 Remote Similarity NPD2533 Approved
0.6923 Remote Similarity NPD2346 Discontinued
0.6923 Remote Similarity NPD6808 Phase 2
0.6909 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6559 Discontinued
0.6897 Remote Similarity NPD17 Approved
0.689 Remote Similarity NPD7411 Suspended
0.6875 Remote Similarity NPD6799 Approved
0.6871 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6846 Remote Similarity NPD3266 Approved
0.6846 Remote Similarity NPD3267 Approved
0.6828 Remote Similarity NPD5585 Approved
0.6815 Remote Similarity NPD2344 Approved
0.6803 Remote Similarity NPD1547 Clinical (unspecified phase)
0.68 Remote Similarity NPD1019 Discontinued
0.6797 Remote Similarity NPD8032 Phase 2
0.6792 Remote Similarity NPD3750 Approved
0.6786 Remote Similarity NPD7075 Discontinued
0.6772 Remote Similarity NPD970 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1549 Phase 2
0.6766 Remote Similarity NPD5402 Approved
0.6766 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6757 Remote Similarity NPD3972 Approved
0.6757 Remote Similarity NPD1608 Approved
0.6753 Remote Similarity NPD2979 Phase 3
0.6747 Remote Similarity NPD6801 Discontinued
0.6733 Remote Similarity NPD1203 Approved
0.6732 Remote Similarity NPD3268 Approved
0.6732 Remote Similarity NPD3764 Approved
0.673 Remote Similarity NPD2800 Approved
0.6728 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7768 Phase 2
0.6726 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6709 Remote Similarity NPD6002 Phase 3
0.6709 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6709 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6709 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6709 Remote Similarity NPD6004 Phase 3
0.6709 Remote Similarity NPD6005 Phase 3
0.6709 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6689 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6686 Remote Similarity NPD3926 Phase 2
0.6667 Remote Similarity NPD3818 Discontinued
0.6667 Remote Similarity NPD1876 Approved
0.6667 Remote Similarity NPD3817 Phase 2
0.6667 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6647 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2309 Approved
0.6646 Remote Similarity NPD5403 Approved
0.6646 Remote Similarity NPD2438 Suspended
0.6645 Remote Similarity NPD4307 Phase 2
0.6644 Remote Similarity NPD9717 Approved
0.6629 Remote Similarity NPD5844 Phase 1
0.6627 Remote Similarity NPD3882 Suspended
0.6627 Remote Similarity NPD4966 Approved
0.6627 Remote Similarity NPD4380 Phase 2
0.6627 Remote Similarity NPD4967 Phase 2
0.6627 Remote Similarity NPD4965 Approved
0.6626 Remote Similarity NPD5401 Approved
0.6623 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6623 Remote Similarity NPD2797 Approved
0.6603 Remote Similarity NPD447 Suspended
0.6603 Remote Similarity NPD6355 Discontinued
0.6603 Remote Similarity NPD1933 Approved
0.66 Remote Similarity NPD4359 Approved
0.6588 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6584 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6584 Remote Similarity NPD7003 Approved
0.6584 Remote Similarity NPD4110 Phase 3
0.6582 Remote Similarity NPD7033 Discontinued
0.6582 Remote Similarity NPD1510 Phase 2
0.6579 Remote Similarity NPD2798 Approved
0.6577 Remote Similarity NPD1281 Approved
0.657 Remote Similarity NPD8127 Discontinued
0.6568 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6554 Remote Similarity NPD3412 Clinical (unspecified phase)
0.655 Remote Similarity NPD6234 Discontinued
0.6548 Remote Similarity NPD6280 Approved
0.6548 Remote Similarity NPD1934 Approved
0.6548 Remote Similarity NPD6279 Approved
0.6543 Remote Similarity NPD3887 Approved
0.6538 Remote Similarity NPD4140 Approved
0.6536 Remote Similarity NPD8312 Approved
0.6536 Remote Similarity NPD8313 Approved
0.6532 Remote Similarity NPD7229 Phase 3
0.6532 Remote Similarity NPD6232 Discontinued
0.6532 Remote Similarity NPD7315 Approved
0.6528 Remote Similarity NPD1241 Discontinued
0.6516 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6514 Remote Similarity NPD7473 Discontinued
0.6488 Remote Similarity NPD5890 Approved
0.6488 Remote Similarity NPD5889 Approved
0.6481 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6478 Remote Similarity NPD4308 Phase 3
0.6474 Remote Similarity NPD6959 Discontinued
0.6474 Remote Similarity NPD4870 Approved
0.6467 Remote Similarity NPD7458 Discontinued
0.6463 Remote Similarity NPD6143 Clinical (unspecified phase)
0.645 Remote Similarity NPD37 Approved
0.6447 Remote Similarity NPD1283 Approved
0.6447 Remote Similarity NPD3225 Approved
0.6443 Remote Similarity NPD1778 Approved
0.6438 Remote Similarity NPD2531 Phase 2
0.6437 Remote Similarity NPD5711 Approved
0.6437 Remote Similarity NPD5710 Approved
0.6433 Remote Similarity NPD1240 Approved
0.6424 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6414 Remote Similarity NPD8404 Phase 2
0.6412 Remote Similarity NPD2801 Approved
0.641 Remote Similarity NPD411 Approved
0.6408 Remote Similarity NPD2182 Approved
0.6402 Remote Similarity NPD7236 Approved
0.64 Remote Similarity NPD5242 Approved
0.6392 Remote Similarity NPD4618 Approved
0.6392 Remote Similarity NPD4622 Approved
0.6391 Remote Similarity NPD6385 Approved
0.6391 Remote Similarity NPD6386 Approved
0.6386 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6382 Remote Similarity NPD5327 Phase 3
0.6379 Remote Similarity NPD7199 Phase 2
0.6376 Remote Similarity NPD5691 Approved
0.6374 Remote Similarity NPD5353 Approved
0.6374 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6369 Remote Similarity NPD6233 Phase 2
0.6369 Remote Similarity NPD5953 Discontinued
0.6364 Remote Similarity NPD5647 Approved
0.6364 Remote Similarity NPD1511 Approved
0.6352 Remote Similarity NPD1607 Approved
0.6348 Remote Similarity NPD7286 Phase 2
0.6346 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6335 Remote Similarity NPD6099 Approved
0.6335 Remote Similarity NPD4477 Approved
0.6335 Remote Similarity NPD6100 Approved
0.6335 Remote Similarity NPD4476 Approved
0.6331 Remote Similarity NPD6585 Discontinued
0.6316 Remote Similarity NPD1465 Phase 2
0.6312 Remote Similarity NPD5689 Approved
0.6312 Remote Similarity NPD5688 Approved
0.6309 Remote Similarity NPD1894 Discontinued
0.6309 Remote Similarity NPD9545 Approved
0.6307 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6306 Remote Similarity NPD1296 Phase 2
0.6306 Remote Similarity NPD6798 Discontinued
0.6303 Remote Similarity NPD7440 Discontinued
0.6298 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6296 Remote Similarity NPD2353 Approved
0.6296 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6294 Remote Similarity NPD6873 Phase 2
0.6294 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6292 Remote Similarity NPD7228 Approved
0.6291 Remote Similarity NPD3496 Discontinued
0.629 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6289 Remote Similarity NPD230 Phase 1
0.6287 Remote Similarity NPD1512 Approved
0.6279 Remote Similarity NPD4288 Approved
0.6278 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6271 Remote Similarity NPD6166 Phase 2
0.6271 Remote Similarity NPD2403 Approved
0.6271 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6271 Remote Similarity NPD6168 Clinical (unspecified phase)

  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