Structure

Physi-Chem Properties

Molecular Weight:  400.22
Volume:  408.363
LogP:  3.276
LogD:  3.317
LogS:  -4.349
# Rotatable Bonds:  1
TPSA:  83.2
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.707
Synthetic Accessibility Score:  5.195
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:  -4.942
MDCK Permeability:  1.4417239981412422e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.932
30% Bioavailability (F30%):  0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.194
Plasma Protein Binding (PPB):  91.48296356201172%
Volume Distribution (VD):  1.961
Pgp-substrate:  6.523805618286133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.067
CYP1A2-substrate:  0.727
CYP2C19-inhibitor:  0.076
CYP2C19-substrate:  0.592
CYP2C9-inhibitor:  0.181
CYP2C9-substrate:  0.047
CYP2D6-inhibitor:  0.048
CYP2D6-substrate:  0.448
CYP3A4-inhibitor:  0.585
CYP3A4-substrate:  0.228

ADMET: Excretion

Clearance (CL):  12.94
Half-life (T1/2):  0.292

ADMET: Toxicity

hERG Blockers:  0.854
Human Hepatotoxicity (H-HT):  0.799
Drug-inuced Liver Injury (DILI):  0.419
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.9
Maximum Recommended Daily Dose:  0.891
Skin Sensitization:  0.518
Carcinogencity:  0.461
Eye Corrosion:  0.027
Eye Irritation:  0.062
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC185287

Natural Product ID:  NPC185287
Common Name*:   Desacetylcinobufagin
IUPAC Name:   n.a.
Synonyms:   Desacetylcinobufagin
Standard InCHIKey:  IXZHDDUFQVXHIL-UOAIQHMYSA-N
Standard InCHI:  InChI=1S/C24H32O5/c1-22-9-7-15(25)11-14(22)4-5-17-16(22)8-10-23(2)19(13-3-6-18(26)28-12-13)20(27)21-24(17,23)29-21/h3,6,12,14-17,19-21,25,27H,4-5,7-11H2,1-2H3/t14-,15+,16+,17-,19+,20-,21-,22+,23-,24-/m1/s1
SMILES:  C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)[C@H]([C@@H]3[C@]12O3)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465893
PubChem CID:   11877495
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]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
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]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae 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]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae 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]
NPO12735 Halimeda macroloba Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9398 Cortinarius rubellus Species Cortinariaceae 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]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11981 Bufo gargarizans Species Bufonidae 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 = 0.44 ug.mL-1 PMID[458508]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1.0 ug.mL-1 PMID[458508]
NPT1366 Cell Line MH60 Mus musculus IC50 > 25.0 ug.mL-1 PMID[458508]
NPT2 Others Unspecified IC50 = 0.52 ug.mL-1 PMID[458507]
NPT2 Others Unspecified IC50 = 4.8 ug.mL-1 PMID[458507]
NPT587 Tissue Liver microsome Rattus norvegicus Retention_time = 6.95 min PMID[458509]

☑ 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 NPC185287 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
0.9817 High Similarity NPC278681
0.9815 High Similarity NPC157380
0.9727 High Similarity NPC112936
0.9725 High Similarity NPC16701
0.9636 High Similarity NPC213761
0.9636 High Similarity NPC35171
0.9346 High Similarity NPC75389
0.9292 High Similarity NPC312481
0.9266 High Similarity NPC44537
0.9252 High Similarity NPC275060
0.9182 High Similarity NPC171126
0.9159 High Similarity NPC79298
0.9159 High Similarity NPC43063
0.9138 High Similarity NPC159499
0.913 High Similarity NPC6193
0.9083 High Similarity NPC103491
0.8909 High Similarity NPC12795
0.8899 High Similarity NPC137462
0.8899 High Similarity NPC304276
0.8889 High Similarity NPC295843
0.8879 High Similarity NPC171014
0.8839 High Similarity NPC241977
0.8624 High Similarity NPC165969
0.8509 High Similarity NPC154815
0.8496 Intermediate Similarity NPC183603
0.8496 Intermediate Similarity NPC470076
0.8421 Intermediate Similarity NPC247760
0.8407 Intermediate Similarity NPC16270
0.839 Intermediate Similarity NPC41123
0.839 Intermediate Similarity NPC474370
0.839 Intermediate Similarity NPC114939
0.839 Intermediate Similarity NPC257610
0.839 Intermediate Similarity NPC145074
0.8378 Intermediate Similarity NPC119855
0.8378 Intermediate Similarity NPC220217
0.8362 Intermediate Similarity NPC113425
0.8362 Intermediate Similarity NPC232564
0.8319 Intermediate Similarity NPC233500
0.8318 Intermediate Similarity NPC299654
0.8305 Intermediate Similarity NPC268326
0.8305 Intermediate Similarity NPC219656
0.8305 Intermediate Similarity NPC153085
0.8305 Intermediate Similarity NPC264954
0.8291 Intermediate Similarity NPC290693
0.8288 Intermediate Similarity NPC472822
0.8276 Intermediate Similarity NPC216665
0.8264 Intermediate Similarity NPC8374
0.825 Intermediate Similarity NPC115349
0.825 Intermediate Similarity NPC153700
0.825 Intermediate Similarity NPC196130
0.825 Intermediate Similarity NPC88326
0.8235 Intermediate Similarity NPC79579
0.822 Intermediate Similarity NPC709
0.822 Intermediate Similarity NPC50774
0.822 Intermediate Similarity NPC146786
0.8214 Intermediate Similarity NPC265502
0.8214 Intermediate Similarity NPC186668
0.8214 Intermediate Similarity NPC29389
0.8214 Intermediate Similarity NPC469960
0.8214 Intermediate Similarity NPC93026
0.8205 Intermediate Similarity NPC470075
0.8198 Intermediate Similarity NPC472821
0.8198 Intermediate Similarity NPC297617
0.8197 Intermediate Similarity NPC179261
0.819 Intermediate Similarity NPC73050
0.8182 Intermediate Similarity NPC219804
0.8174 Intermediate Similarity NPC71680
0.8167 Intermediate Similarity NPC67569
0.8151 Intermediate Similarity NPC305260
0.8151 Intermediate Similarity NPC29639
0.8151 Intermediate Similarity NPC304260
0.8151 Intermediate Similarity NPC270850
0.8151 Intermediate Similarity NPC44899
0.8151 Intermediate Similarity NPC5883
0.8145 Intermediate Similarity NPC221414
0.8142 Intermediate Similarity NPC472263
0.8142 Intermediate Similarity NPC472820
0.8142 Intermediate Similarity NPC469959
0.8142 Intermediate Similarity NPC108682
0.8142 Intermediate Similarity NPC469957
0.8136 Intermediate Similarity NPC167606
0.8136 Intermediate Similarity NPC470492
0.8136 Intermediate Similarity NPC286528
0.8136 Intermediate Similarity NPC20302
0.8136 Intermediate Similarity NPC140055
0.812 Intermediate Similarity NPC31354
0.812 Intermediate Similarity NPC84949
0.812 Intermediate Similarity NPC471633
0.812 Intermediate Similarity NPC43213
0.812 Intermediate Similarity NPC69576
0.8108 Intermediate Similarity NPC470972
0.8099 Intermediate Similarity NPC23786
0.8099 Intermediate Similarity NPC470265
0.8099 Intermediate Similarity NPC471082
0.8091 Intermediate Similarity NPC473510
0.8087 Intermediate Similarity NPC15551
0.8083 Intermediate Similarity NPC184555
0.8073 Intermediate Similarity NPC210337
0.8073 Intermediate Similarity NPC231751
0.8067 Intermediate Similarity NPC153440
0.8062 Intermediate Similarity NPC75616
0.8053 Intermediate Similarity NPC266570
0.8053 Intermediate Similarity NPC472818
0.8053 Intermediate Similarity NPC470980
0.8053 Intermediate Similarity NPC189863
0.8051 Intermediate Similarity NPC310341
0.8051 Intermediate Similarity NPC99620
0.8051 Intermediate Similarity NPC193382
0.8051 Intermediate Similarity NPC199428
0.8051 Intermediate Similarity NPC298278
0.8051 Intermediate Similarity NPC5311
0.8036 Intermediate Similarity NPC10232
0.8036 Intermediate Similarity NPC187302
0.8036 Intermediate Similarity NPC189588
0.8036 Intermediate Similarity NPC196471
0.8036 Intermediate Similarity NPC97487
0.8036 Intermediate Similarity NPC160583
0.8033 Intermediate Similarity NPC55602
0.8033 Intermediate Similarity NPC469789
0.8018 Intermediate Similarity NPC222875
0.8018 Intermediate Similarity NPC295110
0.8018 Intermediate Similarity NPC268829
0.8018 Intermediate Similarity NPC475617
0.8018 Intermediate Similarity NPC247701
0.8018 Intermediate Similarity NPC25177
0.8017 Intermediate Similarity NPC475219
0.8017 Intermediate Similarity NPC255401
0.8017 Intermediate Similarity NPC231518
0.8017 Intermediate Similarity NPC284162
0.8 Intermediate Similarity NPC5292
0.8 Intermediate Similarity NPC278673
0.8 Intermediate Similarity NPC181147
0.7983 Intermediate Similarity NPC99728
0.7983 Intermediate Similarity NPC50305
0.7983 Intermediate Similarity NPC244402
0.7983 Intermediate Similarity NPC312824
0.7983 Intermediate Similarity NPC471355
0.7983 Intermediate Similarity NPC34390
0.7983 Intermediate Similarity NPC158344
0.7983 Intermediate Similarity NPC474418
0.7983 Intermediate Similarity NPC77319
0.7983 Intermediate Similarity NPC27507
0.7983 Intermediate Similarity NPC470493
0.7983 Intermediate Similarity NPC471354
0.7983 Intermediate Similarity NPC473852
0.7983 Intermediate Similarity NPC196429
0.7983 Intermediate Similarity NPC471351
0.7983 Intermediate Similarity NPC142066
0.7983 Intermediate Similarity NPC183580
0.7983 Intermediate Similarity NPC152615
0.7983 Intermediate Similarity NPC203862
0.7983 Intermediate Similarity NPC84987
0.7983 Intermediate Similarity NPC471353
0.7983 Intermediate Similarity NPC87250
0.7983 Intermediate Similarity NPC309034
0.7983 Intermediate Similarity NPC243196
0.7983 Intermediate Similarity NPC93883
0.7983 Intermediate Similarity NPC157376
0.7982 Intermediate Similarity NPC16967
0.7982 Intermediate Similarity NPC88009
0.7969 Intermediate Similarity NPC158350
0.7966 Intermediate Similarity NPC265290
0.7966 Intermediate Similarity NPC305044
0.7965 Intermediate Similarity NPC472819
0.7965 Intermediate Similarity NPC200861
0.7951 Intermediate Similarity NPC107493
0.7951 Intermediate Similarity NPC193893
0.7949 Intermediate Similarity NPC241477
0.7949 Intermediate Similarity NPC150228
0.7949 Intermediate Similarity NPC214005
0.7934 Intermediate Similarity NPC474585
0.7931 Intermediate Similarity NPC238850
0.7931 Intermediate Similarity NPC177047
0.7928 Intermediate Similarity NPC230546
0.7928 Intermediate Similarity NPC38855
0.7928 Intermediate Similarity NPC79631
0.7917 Intermediate Similarity NPC186525
0.7917 Intermediate Similarity NPC83287
0.7917 Intermediate Similarity NPC472080
0.7913 Intermediate Similarity NPC50124
0.7913 Intermediate Similarity NPC472825
0.7907 Intermediate Similarity NPC62172
0.7907 Intermediate Similarity NPC289700
0.7903 Intermediate Similarity NPC293112
0.7899 Intermediate Similarity NPC190286
0.7895 Intermediate Similarity NPC471206
0.7895 Intermediate Similarity NPC88349
0.7886 Intermediate Similarity NPC11895
0.7886 Intermediate Similarity NPC473979
0.7881 Intermediate Similarity NPC101965
0.7881 Intermediate Similarity NPC122056
0.7881 Intermediate Similarity NPC101400
0.7876 Intermediate Similarity NPC474124
0.7874 Intermediate Similarity NPC155529
0.7869 Intermediate Similarity NPC40749
0.7869 Intermediate Similarity NPC470878
0.7869 Intermediate Similarity NPC46570
0.7869 Intermediate Similarity NPC473256
0.7863 Intermediate Similarity NPC471484
0.7863 Intermediate Similarity NPC262083

  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 NPC185287 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
0.8475 Intermediate Similarity NPD7503 Approved
0.8136 Intermediate Similarity NPD7115 Discovery
0.8017 Intermediate Similarity NPD8033 Approved
0.7917 Intermediate Similarity NPD7327 Approved
0.7917 Intermediate Similarity NPD7328 Approved
0.7851 Intermediate Similarity NPD7516 Approved
0.7787 Intermediate Similarity NPD8294 Approved
0.7787 Intermediate Similarity NPD8377 Approved
0.7724 Intermediate Similarity NPD8380 Approved
0.7724 Intermediate Similarity NPD8335 Approved
0.7724 Intermediate Similarity NPD8379 Approved
0.7724 Intermediate Similarity NPD8296 Approved
0.7724 Intermediate Similarity NPD8378 Approved
0.7679 Intermediate Similarity NPD7638 Approved
0.7611 Intermediate Similarity NPD7640 Approved
0.7611 Intermediate Similarity NPD7639 Approved
0.748 Intermediate Similarity NPD7507 Approved
0.7391 Intermediate Similarity NPD5344 Discontinued
0.7368 Intermediate Similarity NPD4225 Approved
0.7355 Intermediate Similarity NPD8297 Approved
0.7311 Intermediate Similarity NPD6899 Approved
0.7311 Intermediate Similarity NPD6881 Approved
0.7308 Intermediate Similarity NPD7319 Approved
0.7304 Intermediate Similarity NPD6648 Approved
0.7227 Intermediate Similarity NPD5697 Approved
0.7222 Intermediate Similarity NPD6319 Approved
0.7213 Intermediate Similarity NPD6053 Discontinued
0.719 Intermediate Similarity NPD6883 Approved
0.719 Intermediate Similarity NPD7102 Approved
0.719 Intermediate Similarity NPD7290 Approved
0.7154 Intermediate Similarity NPD4632 Approved
0.7143 Intermediate Similarity NPD7128 Approved
0.7143 Intermediate Similarity NPD6402 Approved
0.7143 Intermediate Similarity NPD5739 Approved
0.7143 Intermediate Similarity NPD6675 Approved
0.7131 Intermediate Similarity NPD6869 Approved
0.7131 Intermediate Similarity NPD6649 Approved
0.7131 Intermediate Similarity NPD6847 Approved
0.7131 Intermediate Similarity NPD8130 Phase 1
0.7131 Intermediate Similarity NPD6650 Approved
0.7131 Intermediate Similarity NPD6617 Approved
0.7107 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6013 Approved
0.7107 Intermediate Similarity NPD6012 Approved
0.7107 Intermediate Similarity NPD6014 Approved
0.7099 Intermediate Similarity NPD7736 Approved
0.7073 Intermediate Similarity NPD6882 Approved
0.7054 Intermediate Similarity NPD7838 Discovery
0.7034 Intermediate Similarity NPD7632 Discontinued
0.7025 Intermediate Similarity NPD7320 Approved
0.7025 Intermediate Similarity NPD6011 Approved
0.7 Intermediate Similarity NPD7492 Approved
0.6967 Remote Similarity NPD6372 Approved
0.6967 Remote Similarity NPD6373 Approved
0.6964 Remote Similarity NPD6051 Approved
0.6953 Remote Similarity NPD6054 Approved
0.6949 Remote Similarity NPD4159 Approved
0.6947 Remote Similarity NPD6616 Approved
0.6942 Remote Similarity NPD5701 Approved
0.6937 Remote Similarity NPD7524 Approved
0.6923 Remote Similarity NPD7604 Phase 2
0.6916 Remote Similarity NPD7525 Registered
0.6911 Remote Similarity NPD4634 Approved
0.6894 Remote Similarity NPD7078 Approved
0.6891 Remote Similarity NPD5211 Phase 2
0.6885 Remote Similarity NPD6686 Approved
0.6864 Remote Similarity NPD5285 Approved
0.6864 Remote Similarity NPD5286 Approved
0.6864 Remote Similarity NPD4696 Approved
0.686 Remote Similarity NPD6008 Approved
0.685 Remote Similarity NPD6009 Approved
0.6846 Remote Similarity NPD6370 Approved
0.6842 Remote Similarity NPD7637 Suspended
0.6838 Remote Similarity NPD6084 Phase 2
0.6838 Remote Similarity NPD6083 Phase 2
0.6818 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6803 Remote Similarity NPD6412 Phase 2
0.6777 Remote Similarity NPD5141 Approved
0.6774 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6769 Remote Similarity NPD5983 Phase 2
0.6769 Remote Similarity NPD6015 Approved
0.6769 Remote Similarity NPD6016 Approved
0.675 Remote Similarity NPD5224 Approved
0.675 Remote Similarity NPD5226 Approved
0.675 Remote Similarity NPD4633 Approved
0.675 Remote Similarity NPD5225 Approved
0.6746 Remote Similarity NPD8133 Approved
0.6744 Remote Similarity NPD7101 Approved
0.6744 Remote Similarity NPD7100 Approved
0.6727 Remote Similarity NPD6695 Phase 3
0.672 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6718 Remote Similarity NPD5988 Approved
0.6695 Remote Similarity NPD4755 Approved
0.6694 Remote Similarity NPD5174 Approved
0.6694 Remote Similarity NPD5175 Approved
0.6692 Remote Similarity NPD6336 Discontinued
0.6692 Remote Similarity NPD6059 Approved
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6642 Remote Similarity NPD8293 Discontinued
0.6641 Remote Similarity NPD6274 Approved
0.664 Remote Similarity NPD6371 Approved
0.6638 Remote Similarity NPD6399 Phase 3
0.6638 Remote Similarity NPD4202 Approved
0.6589 Remote Similarity NPD6317 Approved
0.6583 Remote Similarity NPD4700 Approved
0.6581 Remote Similarity NPD7748 Approved
0.6579 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7902 Approved
0.6552 Remote Similarity NPD7515 Phase 2
0.6552 Remote Similarity NPD8035 Phase 2
0.6552 Remote Similarity NPD8034 Phase 2
0.6552 Remote Similarity NPD6079 Approved
0.6552 Remote Similarity NPD5281 Approved
0.6552 Remote Similarity NPD5284 Approved
0.6542 Remote Similarity NPD6933 Approved
0.6538 Remote Similarity NPD6314 Approved
0.6538 Remote Similarity NPD6313 Approved
0.6532 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6531 Remote Similarity NPD7236 Approved
0.6525 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5695 Phase 3
0.6514 Remote Similarity NPD4195 Approved
0.65 Remote Similarity NPD5696 Approved
0.6491 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6491 Remote Similarity NPD7750 Discontinued
0.648 Remote Similarity NPD4729 Approved
0.648 Remote Similarity NPD4730 Approved
0.6466 Remote Similarity NPD6698 Approved
0.6466 Remote Similarity NPD46 Approved
0.646 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6455 Remote Similarity NPD7514 Phase 3
0.6455 Remote Similarity NPD6931 Approved
0.6455 Remote Similarity NPD6930 Phase 2
0.641 Remote Similarity NPD5693 Phase 1
0.6404 Remote Similarity NPD7521 Approved
0.6404 Remote Similarity NPD7334 Approved
0.6404 Remote Similarity NPD6684 Approved
0.6404 Remote Similarity NPD7146 Approved
0.6404 Remote Similarity NPD6409 Approved
0.6404 Remote Similarity NPD5330 Approved
0.6396 Remote Similarity NPD6902 Approved
0.6395 Remote Similarity NPD7625 Phase 1
0.6391 Remote Similarity NPD8513 Phase 3
0.6391 Remote Similarity NPD6909 Approved
0.6391 Remote Similarity NPD6908 Approved
0.6391 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6389 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6387 Remote Similarity NPD4629 Approved
0.6387 Remote Similarity NPD5210 Approved
0.6379 Remote Similarity NPD4753 Phase 2
0.6379 Remote Similarity NPD5328 Approved
0.6378 Remote Similarity NPD5250 Approved
0.6378 Remote Similarity NPD5248 Approved
0.6378 Remote Similarity NPD5249 Phase 3
0.6378 Remote Similarity NPD5247 Approved
0.6378 Remote Similarity NPD5251 Approved
0.6364 Remote Similarity NPD6929 Approved
0.6364 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7645 Phase 2
0.6355 Remote Similarity NPD6926 Approved
0.6355 Remote Similarity NPD6924 Approved
0.6349 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6349 Remote Similarity NPD5128 Approved
0.6348 Remote Similarity NPD4250 Approved
0.6348 Remote Similarity NPD4251 Approved
0.6333 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6333 Remote Similarity NPD5222 Approved
0.6333 Remote Similarity NPD5221 Approved
0.6331 Remote Similarity NPD7260 Phase 2
0.633 Remote Similarity NPD6932 Approved
0.6328 Remote Similarity NPD5216 Approved
0.6328 Remote Similarity NPD5215 Approved
0.6328 Remote Similarity NPD5217 Approved
0.6325 Remote Similarity NPD5785 Approved
0.632 Remote Similarity NPD4767 Approved
0.632 Remote Similarity NPD4768 Approved
0.6316 Remote Similarity NPD7239 Suspended
0.6306 Remote Similarity NPD7332 Phase 2
0.6306 Remote Similarity NPD4820 Approved
0.6306 Remote Similarity NPD4819 Approved
0.6306 Remote Similarity NPD4821 Approved
0.6306 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6306 Remote Similarity NPD4822 Approved
0.6303 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7900 Approved
0.6296 Remote Similarity NPD7339 Approved
0.6296 Remote Similarity NPD6942 Approved
0.6293 Remote Similarity NPD6903 Approved
0.629 Remote Similarity NPD4754 Approved
0.6283 Remote Similarity NPD4788 Approved
0.6281 Remote Similarity NPD5173 Approved
0.6273 Remote Similarity NPD7145 Approved
0.6271 Remote Similarity NPD5694 Approved
0.6271 Remote Similarity NPD7087 Discontinued
0.6271 Remote Similarity NPD6050 Approved
0.627 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6269 Remote Similarity NPD8515 Approved
0.6269 Remote Similarity NPD8517 Approved
0.6269 Remote Similarity NPD8516 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