Structure

Physi-Chem Properties

Molecular Weight:  400.22
Volume:  408.363
LogP:  2.9
LogD:  2.755
LogS:  -4.119
# Rotatable Bonds:  2
TPSA:  83.2
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.745
Synthetic Accessibility Score:  5.284
Fsp3:  0.792
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.993
MDCK Permeability:  2.6740839530248195e-05
Pgp-inhibitor:  0.032
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.288
Plasma Protein Binding (PPB):  92.3582992553711%
Volume Distribution (VD):  1.312
Pgp-substrate:  5.382038116455078%

ADMET: Metabolism

CYP1A2-inhibitor:  0.064
CYP1A2-substrate:  0.408
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.601
CYP2C9-inhibitor:  0.179
CYP2C9-substrate:  0.036
CYP2D6-inhibitor:  0.02
CYP2D6-substrate:  0.478
CYP3A4-inhibitor:  0.773
CYP3A4-substrate:  0.273

ADMET: Excretion

Clearance (CL):  11.817
Half-life (T1/2):  0.39

ADMET: Toxicity

hERG Blockers:  0.645
Human Hepatotoxicity (H-HT):  0.909
Drug-inuced Liver Injury (DILI):  0.325
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.936
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.589
Carcinogencity:  0.531
Eye Corrosion:  0.144
Eye Irritation:  0.486
Respiratory Toxicity:  0.972

Download Data

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

  Natural Product: NPC103491

Natural Product ID:  NPC103491
Common Name*:   XTGMXQCGCNTMEI-RLKKFORUSA-N
IUPAC Name:   n.a.
Synonyms:   19-Hydroxyresibufogenin
Standard InCHIKey:  XTGMXQCGCNTMEI-RLKKFORUSA-N
Standard InCHI:  InChI=1S/C24H32O5/c1-22-8-7-17-18(4-3-15-10-16(26)6-9-23(15,17)13-25)24(22)20(29-24)11-19(22)14-2-5-21(27)28-12-14/h2,5,12,15-20,25-26H,3-4,6-11,13H2,1H3/t15-,16+,17+,18-,19-,20-,22-,23-,24-/m1/s1
SMILES:  C[C@@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](CC[C@]34CO)O)[C@]32[C@@H](C[C@@H]1c1ccc(=O)oc1)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL515346
PubChem CID:   12314891
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001557] Bufanolides and derivatives

*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
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)99818-1]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota roots n.a. n.a. PMID[10346940]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11421725]
NPO33241 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[11575946]
NPO33241 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[12141860]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15165135]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[15635246]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15730237]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[17504571]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[21185919]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. leaf n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. twig n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[22708620]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota venom n.a. n.a. PMID[24050254]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[26722868]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[28256122]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[32223924]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8733 Duttaphrynus melanostictus Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11515 Streptomyces plumbeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26231 Vicia villosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6887 Lytanthus salicinus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12735 Halimeda macroloba Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8733 Duttaphrynus melanostictus Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2498 Kochia trichophylla Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9398 Cortinarius rubellus Species Cortinariaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 1.2 ug.mL-1 PMID[490145]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 0.48 ug.mL-1 PMID[490145]
NPT1366 Cell Line MH60 Mus musculus IC50 > 25.0 ug.mL-1 PMID[490145]
NPT1081 Cell Line BXPC-3 Homo sapiens IC50 = 0.63 ug.mL-1 PMID[490145]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 0.33 ug.mL-1 PMID[490145]
NPT395 Cell Line SF-268 Homo sapiens IC50 = 0.25 ug.mL-1 PMID[490145]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 0.44 ug.mL-1 PMID[490145]
NPT575 Cell Line KM-20L2 Homo sapiens IC50 = 0.45 ug.mL-1 PMID[490145]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 0.38 ug.mL-1 PMID[490145]
NPT2 Others Unspecified IC50 = 0.61 ug.mL-1 PMID[490144]
NPT2 Others Unspecified IC50 = 8.2 ug.mL-1 PMID[490144]

☑ 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 NPC103491 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
0.9712 High Similarity NPC171126
0.9703 High Similarity NPC79298
0.9703 High Similarity NPC43063
0.9417 High Similarity NPC137462
0.9417 High Similarity NPC304276
0.9406 High Similarity NPC171014
0.9352 High Similarity NPC16701
0.9266 High Similarity NPC213761
0.9266 High Similarity NPC35171
0.9266 High Similarity NPC278681
0.9259 High Similarity NPC157380
0.9245 High Similarity NPC44537
0.9238 High Similarity NPC12795
0.9223 High Similarity NPC295843
0.9182 High Similarity NPC112936
0.9151 High Similarity NPC183603
0.9143 High Similarity NPC75389
0.9126 High Similarity NPC165969
0.9083 High Similarity NPC185287
0.9048 High Similarity NPC275060
0.8981 High Similarity NPC154815
0.8889 High Similarity NPC247760
0.8879 High Similarity NPC16270
0.8839 High Similarity NPC41123
0.8839 High Similarity NPC257610
0.8839 High Similarity NPC145074
0.8839 High Similarity NPC114939
0.8835 High Similarity NPC268829
0.8835 High Similarity NPC25177
0.8835 High Similarity NPC295110
0.8835 High Similarity NPC247701
0.8835 High Similarity NPC222875
0.8761 High Similarity NPC312481
0.8667 High Similarity NPC189588
0.8667 High Similarity NPC10232
0.8667 High Similarity NPC160583
0.8667 High Similarity NPC187302
0.8667 High Similarity NPC97487
0.8667 High Similarity NPC196471
0.8661 High Similarity NPC146786
0.8636 High Similarity NPC73050
0.8636 High Similarity NPC241977
0.8609 High Similarity NPC55602
0.8609 High Similarity NPC6193
0.8509 High Similarity NPC184555
0.8505 High Similarity NPC189863
0.8505 High Similarity NPC119855
0.8505 High Similarity NPC186668
0.8505 High Similarity NPC220217
0.8491 Intermediate Similarity NPC472821
0.8482 Intermediate Similarity NPC113425
0.8482 Intermediate Similarity NPC232564
0.844 Intermediate Similarity NPC475030
0.8411 Intermediate Similarity NPC200861
0.8381 Intermediate Similarity NPC251680
0.8333 Intermediate Similarity NPC266570
0.8318 Intermediate Similarity NPC297617
0.8305 Intermediate Similarity NPC159499
0.8288 Intermediate Similarity NPC262083
0.8288 Intermediate Similarity NPC255401
0.8288 Intermediate Similarity NPC470076
0.8288 Intermediate Similarity NPC471484
0.8288 Intermediate Similarity NPC284162
0.8286 Intermediate Similarity NPC278673
0.8286 Intermediate Similarity NPC218107
0.8252 Intermediate Similarity NPC201725
0.825 Intermediate Similarity NPC221414
0.8246 Intermediate Similarity NPC290693
0.8241 Intermediate Similarity NPC472822
0.819 Intermediate Similarity NPC51499
0.819 Intermediate Similarity NPC99726
0.819 Intermediate Similarity NPC231751
0.8151 Intermediate Similarity NPC179261
0.8148 Intermediate Similarity NPC45897
0.8148 Intermediate Similarity NPC85742
0.8113 Intermediate Similarity NPC325229
0.8113 Intermediate Similarity NPC181147
0.8113 Intermediate Similarity NPC92275
0.8113 Intermediate Similarity NPC275086
0.8103 Intermediate Similarity NPC153085
0.8103 Intermediate Similarity NPC268326
0.8095 Intermediate Similarity NPC16967
0.8095 Intermediate Similarity NPC299654
0.8095 Intermediate Similarity NPC304899
0.8095 Intermediate Similarity NPC253115
0.8077 Intermediate Similarity NPC105490
0.807 Intermediate Similarity NPC69576
0.807 Intermediate Similarity NPC31354
0.807 Intermediate Similarity NPC84949
0.807 Intermediate Similarity NPC471633
0.807 Intermediate Similarity NPC216665
0.8067 Intermediate Similarity NPC233041
0.8058 Intermediate Similarity NPC234335
0.8056 Intermediate Similarity NPC475038
0.8056 Intermediate Similarity NPC109195
0.8053 Intermediate Similarity NPC150228
0.8053 Intermediate Similarity NPC214005
0.8036 Intermediate Similarity NPC238850
0.8 Intermediate Similarity NPC470075
0.8 Intermediate Similarity NPC193382
0.8 Intermediate Similarity NPC472818
0.8 Intermediate Similarity NPC310341
0.8 Intermediate Similarity NPC99620
0.8 Intermediate Similarity NPC5311
0.8 Intermediate Similarity NPC281134
0.8 Intermediate Similarity NPC199428
0.8 Intermediate Similarity NPC471206
0.7984 Intermediate Similarity NPC248703
0.7983 Intermediate Similarity NPC204812
0.7982 Intermediate Similarity NPC122056
0.7982 Intermediate Similarity NPC112009
0.7981 Intermediate Similarity NPC476304
0.7981 Intermediate Similarity NPC7349
0.7966 Intermediate Similarity NPC233500
0.7966 Intermediate Similarity NPC67569
0.7965 Intermediate Similarity NPC71680
0.7963 Intermediate Similarity NPC168319
0.7963 Intermediate Similarity NPC194028
0.7961 Intermediate Similarity NPC302280
0.7949 Intermediate Similarity NPC219656
0.7949 Intermediate Similarity NPC264954
0.7944 Intermediate Similarity NPC57079
0.7944 Intermediate Similarity NPC108368
0.7941 Intermediate Similarity NPC106332
0.7931 Intermediate Similarity NPC27507
0.7931 Intermediate Similarity NPC77319
0.7931 Intermediate Similarity NPC309034
0.7931 Intermediate Similarity NPC84987
0.7931 Intermediate Similarity NPC152615
0.7931 Intermediate Similarity NPC244402
0.7931 Intermediate Similarity NPC93883
0.7931 Intermediate Similarity NPC157376
0.7931 Intermediate Similarity NPC87250
0.7931 Intermediate Similarity NPC99728
0.7931 Intermediate Similarity NPC50305
0.7931 Intermediate Similarity NPC471353
0.7931 Intermediate Similarity NPC34390
0.7931 Intermediate Similarity NPC158344
0.7931 Intermediate Similarity NPC471355
0.7931 Intermediate Similarity NPC471354
0.7931 Intermediate Similarity NPC243196
0.7931 Intermediate Similarity NPC471351
0.7931 Intermediate Similarity NPC142066
0.7931 Intermediate Similarity NPC473852
0.7931 Intermediate Similarity NPC196429
0.7931 Intermediate Similarity NPC474418
0.7928 Intermediate Similarity NPC472820
0.7928 Intermediate Similarity NPC475074
0.7925 Intermediate Similarity NPC190713
0.7925 Intermediate Similarity NPC276103
0.7925 Intermediate Similarity NPC54248
0.7917 Intermediate Similarity NPC32868
0.7917 Intermediate Similarity NPC8374
0.7917 Intermediate Similarity NPC241456
0.7913 Intermediate Similarity NPC43213
0.7909 Intermediate Similarity NPC472819
0.7905 Intermediate Similarity NPC476186
0.7905 Intermediate Similarity NPC191521
0.7905 Intermediate Similarity NPC119562
0.7905 Intermediate Similarity NPC279410
0.7899 Intermediate Similarity NPC196130
0.7899 Intermediate Similarity NPC470265
0.7899 Intermediate Similarity NPC23786
0.7899 Intermediate Similarity NPC115349
0.789 Intermediate Similarity NPC470972
0.7885 Intermediate Similarity NPC130840
0.7885 Intermediate Similarity NPC110923
0.7885 Intermediate Similarity NPC74296
0.7881 Intermediate Similarity NPC474370
0.7881 Intermediate Similarity NPC476962
0.7876 Intermediate Similarity NPC179642
0.7876 Intermediate Similarity NPC181298
0.7876 Intermediate Similarity NPC15551
0.787 Intermediate Similarity NPC208358
0.787 Intermediate Similarity NPC472826
0.787 Intermediate Similarity NPC201406
0.7864 Intermediate Similarity NPC74258
0.7864 Intermediate Similarity NPC170633
0.7863 Intermediate Similarity NPC83287
0.7857 Intermediate Similarity NPC62172
0.7857 Intermediate Similarity NPC289700
0.7857 Intermediate Similarity NPC88701
0.7857 Intermediate Similarity NPC472825
0.785 Intermediate Similarity NPC141401
0.7845 Intermediate Similarity NPC190286
0.7845 Intermediate Similarity NPC72772
0.7845 Intermediate Similarity NPC196931
0.7845 Intermediate Similarity NPC469794
0.7838 Intermediate Similarity NPC34768
0.7838 Intermediate Similarity NPC218158
0.7833 Intermediate Similarity NPC11895
0.7833 Intermediate Similarity NPC469789
0.7833 Intermediate Similarity NPC219804
0.783 Intermediate Similarity NPC276110
0.7823 Intermediate Similarity NPC155529
0.7818 Intermediate Similarity NPC473523
0.7818 Intermediate Similarity NPC180204
0.781 Intermediate Similarity NPC152778
0.781 Intermediate Similarity NPC205034
0.781 Intermediate Similarity NPC38232

  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 NPC103491 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
0.8462 Intermediate Similarity NPD7638 Approved
0.8435 Intermediate Similarity NPD7503 Approved
0.8381 Intermediate Similarity NPD7640 Approved
0.8381 Intermediate Similarity NPD7639 Approved
0.7863 Intermediate Similarity NPD7327 Approved
0.7863 Intermediate Similarity NPD7328 Approved
0.7797 Intermediate Similarity NPD7516 Approved
0.7778 Intermediate Similarity NPD7115 Discovery
0.7731 Intermediate Similarity NPD8294 Approved
0.7731 Intermediate Similarity NPD8377 Approved
0.7727 Intermediate Similarity NPD7632 Discontinued
0.7667 Intermediate Similarity NPD8380 Approved
0.7667 Intermediate Similarity NPD8335 Approved
0.7667 Intermediate Similarity NPD8379 Approved
0.7667 Intermediate Similarity NPD8378 Approved
0.7667 Intermediate Similarity NPD8296 Approved
0.7667 Intermediate Similarity NPD8033 Approved
0.7419 Intermediate Similarity NPD7507 Approved
0.7391 Intermediate Similarity NPD6899 Approved
0.7391 Intermediate Similarity NPD6881 Approved
0.7358 Intermediate Similarity NPD6051 Approved
0.7304 Intermediate Similarity NPD5697 Approved
0.7288 Intermediate Similarity NPD6053 Discontinued
0.7265 Intermediate Similarity NPD6883 Approved
0.7265 Intermediate Similarity NPD7290 Approved
0.7265 Intermediate Similarity NPD7102 Approved
0.7244 Intermediate Similarity NPD7319 Approved
0.7241 Intermediate Similarity NPD6011 Approved
0.7232 Intermediate Similarity NPD6648 Approved
0.7227 Intermediate Similarity NPD4632 Approved
0.7217 Intermediate Similarity NPD7128 Approved
0.7217 Intermediate Similarity NPD5739 Approved
0.7217 Intermediate Similarity NPD6675 Approved
0.7217 Intermediate Similarity NPD6008 Approved
0.7217 Intermediate Similarity NPD6402 Approved
0.7203 Intermediate Similarity NPD8130 Phase 1
0.7203 Intermediate Similarity NPD6649 Approved
0.7203 Intermediate Similarity NPD6847 Approved
0.7203 Intermediate Similarity NPD6617 Approved
0.7203 Intermediate Similarity NPD6650 Approved
0.7203 Intermediate Similarity NPD6869 Approved
0.7179 Intermediate Similarity NPD6014 Approved
0.7179 Intermediate Similarity NPD6012 Approved
0.7179 Intermediate Similarity NPD6013 Approved
0.7168 Intermediate Similarity NPD5344 Discontinued
0.7157 Intermediate Similarity NPD7525 Registered
0.7143 Intermediate Similarity NPD8297 Approved
0.7143 Intermediate Similarity NPD6882 Approved
0.712 Intermediate Similarity NPD7604 Phase 2
0.7094 Intermediate Similarity NPD7320 Approved
0.7064 Intermediate Similarity NPD7637 Suspended
0.7054 Intermediate Similarity NPD6084 Phase 2
0.7054 Intermediate Similarity NPD6083 Phase 2
0.7049 Intermediate Similarity NPD6009 Approved
0.7034 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD6372 Approved
0.7034 Intermediate Similarity NPD6373 Approved
0.7031 Intermediate Similarity NPD7736 Approved
0.7016 Intermediate Similarity NPD6319 Approved
0.7009 Intermediate Similarity NPD5701 Approved
0.6991 Remote Similarity NPD4225 Approved
0.696 Remote Similarity NPD5983 Phase 2
0.6957 Remote Similarity NPD5211 Phase 2
0.6952 Remote Similarity NPD6695 Phase 3
0.6944 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7748 Approved
0.693 Remote Similarity NPD5286 Approved
0.693 Remote Similarity NPD5285 Approved
0.693 Remote Similarity NPD4696 Approved
0.6929 Remote Similarity NPD7492 Approved
0.6917 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6079 Approved
0.6909 Remote Similarity NPD7515 Phase 2
0.6893 Remote Similarity NPD4195 Approved
0.6887 Remote Similarity NPD7338 Clinical (unspecified phase)
0.688 Remote Similarity NPD6054 Approved
0.6875 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6616 Approved
0.6875 Remote Similarity NPD6336 Discontinued
0.687 Remote Similarity NPD5223 Approved
0.6855 Remote Similarity NPD6335 Approved
0.6852 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6847 Remote Similarity NPD4202 Approved
0.6838 Remote Similarity NPD5141 Approved
0.6833 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7078 Approved
0.6822 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7838 Discovery
0.681 Remote Similarity NPD5225 Approved
0.681 Remote Similarity NPD4633 Approved
0.681 Remote Similarity NPD5226 Approved
0.681 Remote Similarity NPD5224 Approved
0.6807 Remote Similarity NPD6686 Approved
0.68 Remote Similarity NPD7101 Approved
0.68 Remote Similarity NPD7100 Approved
0.6774 Remote Similarity NPD6317 Approved
0.6772 Remote Similarity NPD6370 Approved
0.6759 Remote Similarity NPD7521 Approved
0.6759 Remote Similarity NPD7146 Approved
0.6759 Remote Similarity NPD7334 Approved
0.6759 Remote Similarity NPD6409 Approved
0.6759 Remote Similarity NPD6684 Approved
0.6759 Remote Similarity NPD5330 Approved
0.6757 Remote Similarity NPD5281 Approved
0.6757 Remote Similarity NPD5284 Approved
0.6757 Remote Similarity NPD8035 Phase 2
0.6757 Remote Similarity NPD8034 Phase 2
0.6757 Remote Similarity NPD5693 Phase 1
0.6754 Remote Similarity NPD7902 Approved
0.6754 Remote Similarity NPD4755 Approved
0.6752 Remote Similarity NPD5174 Approved
0.6752 Remote Similarity NPD5175 Approved
0.6727 Remote Similarity NPD5328 Approved
0.6726 Remote Similarity NPD5695 Phase 3
0.6723 Remote Similarity NPD6412 Phase 2
0.672 Remote Similarity NPD6313 Approved
0.672 Remote Similarity NPD6314 Approved
0.6697 Remote Similarity NPD7524 Approved
0.6697 Remote Similarity NPD7750 Discontinued
0.6696 Remote Similarity NPD5696 Approved
0.6696 Remote Similarity NPD6399 Phase 3
0.6694 Remote Similarity NPD4634 Approved
0.6694 Remote Similarity NPD6274 Approved
0.6693 Remote Similarity NPD6015 Approved
0.6693 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD6930 Phase 2
0.6667 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5221 Approved
0.6667 Remote Similarity NPD7514 Phase 3
0.6667 Remote Similarity NPD8133 Approved
0.6667 Remote Similarity NPD6931 Approved
0.6667 Remote Similarity NPD5222 Approved
0.6641 Remote Similarity NPD5988 Approved
0.6638 Remote Similarity NPD4700 Approved
0.6636 Remote Similarity NPD6903 Approved
0.6636 Remote Similarity NPD4788 Approved
0.6614 Remote Similarity NPD6059 Approved
0.6609 Remote Similarity NPD5173 Approved
0.6607 Remote Similarity NPD5694 Approved
0.6607 Remote Similarity NPD6050 Approved
0.6606 Remote Similarity NPD3618 Phase 1
0.6604 Remote Similarity NPD6902 Approved
0.6602 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6583 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4159 Approved
0.6579 Remote Similarity NPD5210 Approved
0.6579 Remote Similarity NPD4629 Approved
0.6577 Remote Similarity NPD6904 Approved
0.6577 Remote Similarity NPD6673 Approved
0.6577 Remote Similarity NPD6080 Approved
0.6577 Remote Similarity NPD4753 Phase 2
0.6574 Remote Similarity NPD3666 Approved
0.6574 Remote Similarity NPD3133 Approved
0.6574 Remote Similarity NPD3665 Phase 1
0.6571 Remote Similarity NPD6929 Approved
0.6571 Remote Similarity NPD7645 Phase 2
0.6569 Remote Similarity NPD6924 Approved
0.6569 Remote Similarity NPD6926 Approved
0.6565 Remote Similarity NPD8293 Discontinued
0.6562 Remote Similarity NPD6291 Clinical (unspecified phase)
0.656 Remote Similarity NPD6868 Approved
0.6542 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6932 Approved
0.6529 Remote Similarity NPD4730 Approved
0.6529 Remote Similarity NPD4729 Approved
0.6518 Remote Similarity NPD5207 Approved
0.6518 Remote Similarity NPD5785 Approved
0.6518 Remote Similarity NPD5692 Phase 3
0.6509 Remote Similarity NPD7332 Phase 2
0.6505 Remote Similarity NPD6942 Approved
0.6505 Remote Similarity NPD7339 Approved
0.6491 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6001 Approved
0.6491 Remote Similarity NPD7900 Approved
0.6486 Remote Similarity NPD6672 Approved
0.6486 Remote Similarity NPD5737 Approved
0.6476 Remote Similarity NPD7145 Approved
0.6471 Remote Similarity NPD4754 Approved
0.646 Remote Similarity NPD7087 Discontinued
0.6458 Remote Similarity NPD7236 Approved
0.6442 Remote Similarity NPD6933 Approved
0.6434 Remote Similarity NPD6909 Approved
0.6434 Remote Similarity NPD6908 Approved
0.6434 Remote Similarity NPD7625 Phase 1
0.6423 Remote Similarity NPD5250 Approved
0.6423 Remote Similarity NPD5249 Phase 3
0.6423 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6423 Remote Similarity NPD5247 Approved
0.6423 Remote Similarity NPD6371 Approved
0.6423 Remote Similarity NPD5135 Approved
0.6423 Remote Similarity NPD5169 Approved
0.6423 Remote Similarity NPD5248 Approved
0.6423 Remote Similarity NPD5251 Approved
0.6422 Remote Similarity NPD4786 Approved
0.641 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6408 Remote Similarity NPD4785 Approved
0.6408 Remote Similarity NPD4784 Approved
0.6396 Remote Similarity NPD4250 Approved
0.6396 Remote Similarity NPD4251 Approved
0.6396 Remote Similarity NPD3573 Approved

  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