Structure

Physi-Chem Properties

Molecular Weight:  416.22
Volume:  417.153
LogP:  1.753
LogD:  1.514
LogS:  -3.608
# Rotatable Bonds:  1
TPSA:  103.43
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.607
Synthetic Accessibility Score:  5.378
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:  -5.306
MDCK Permeability:  1.903299562400207e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.09
20% Bioavailability (F20%):  0.952
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.482
Plasma Protein Binding (PPB):  78.73831939697266%
Volume Distribution (VD):  0.861
Pgp-substrate:  17.445398330688477%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.937
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.673
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.03
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.81
CYP3A4-substrate:  0.216

ADMET: Excretion

Clearance (CL):  10.632
Half-life (T1/2):  0.33

ADMET: Toxicity

hERG Blockers:  0.304
Human Hepatotoxicity (H-HT):  0.721
Drug-inuced Liver Injury (DILI):  0.061
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.903
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.191
Carcinogencity:  0.869
Eye Corrosion:  0.007
Eye Irritation:  0.037
Respiratory Toxicity:  0.979

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

  Natural Product: NPC112936

Natural Product ID:  NPC112936
Common Name*:   Desacetylcinobufotalin
IUPAC Name:   n.a.
Synonyms:   Desacetylcinobufotalin
Standard InCHIKey:  FRYICJTUIXEEGK-NNWVIVGYSA-N
Standard InCHI:  InChI=1S/C24H32O6/c1-21-8-5-14(25)11-23(21,28)10-7-16-15(21)6-9-22(2)18(13-3-4-17(26)29-12-13)19(27)20-24(16,22)30-20/h3-4,12,14-16,18-20,25,27-28H,5-11H2,1-2H3/t14-,15-,16+,18-,19+,20+,21+,22+,23-,24+/m0/s1
SMILES:  O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]31O[C@@H]3[C@@H]([C@@H]2c1ccc(=O)oc1)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465444
PubChem CID:   15513544
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. twig n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. leaf n.a. 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]
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]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
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]
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]
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]
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]
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]
NPO8733 Duttaphrynus melanostictus Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26231 Vicia villosa Species Fabaceae 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]

☑ 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 = 10.0 ug.mL-1 PMID[524006]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 4.3 ug.mL-1 PMID[524006]
NPT1366 Cell Line MH60 Mus musculus IC50 > 25.0 ug.mL-1 PMID[524006]
NPT2 Others Unspecified IC50 = 0.67 ug.mL-1 PMID[524005]
NPT2 Others Unspecified IC50 = 0.64 ug.mL-1 PMID[524005]

☑ 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 NPC112936 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
0.9909 High Similarity NPC213761
0.9909 High Similarity NPC35171
0.9909 High Similarity NPC278681
0.9818 High Similarity NPC16701
0.9727 High Similarity NPC157380
0.9727 High Similarity NPC185287
0.9455 High Similarity NPC171126
0.9364 High Similarity NPC44537
0.9217 High Similarity NPC312481
0.9182 High Similarity NPC103491
0.9091 High Similarity NPC75389
0.906 High Similarity NPC6193
0.9009 High Similarity NPC12795
0.9 High Similarity NPC304276
0.9 High Similarity NPC137462
0.9 High Similarity NPC275060
0.8909 High Similarity NPC43063
0.8909 High Similarity NPC79298
0.8908 High Similarity NPC159499
0.8649 High Similarity NPC295843
0.8644 High Similarity NPC114939
0.8644 High Similarity NPC257610
0.8644 High Similarity NPC41123
0.8644 High Similarity NPC145074
0.8636 High Similarity NPC171014
0.8609 High Similarity NPC154815
0.8609 High Similarity NPC241977
0.8596 High Similarity NPC470076
0.8571 High Similarity NPC233500
0.8522 High Similarity NPC247760
0.85 High Similarity NPC196130
0.8482 Intermediate Similarity NPC119855
0.8482 Intermediate Similarity NPC220217
0.8462 Intermediate Similarity NPC113425
0.8462 Intermediate Similarity NPC232564
0.8435 Intermediate Similarity NPC183603
0.8403 Intermediate Similarity NPC268326
0.8403 Intermediate Similarity NPC219656
0.8403 Intermediate Similarity NPC153085
0.8393 Intermediate Similarity NPC165969
0.839 Intermediate Similarity NPC290693
0.8376 Intermediate Similarity NPC216665
0.8347 Intermediate Similarity NPC471082
0.8347 Intermediate Similarity NPC115349
0.8333 Intermediate Similarity NPC79579
0.8319 Intermediate Similarity NPC469960
0.8319 Intermediate Similarity NPC93026
0.8319 Intermediate Similarity NPC186668
0.8319 Intermediate Similarity NPC29389
0.8319 Intermediate Similarity NPC146786
0.8319 Intermediate Similarity NPC265502
0.8305 Intermediate Similarity NPC470075
0.8304 Intermediate Similarity NPC189588
0.8304 Intermediate Similarity NPC10232
0.8304 Intermediate Similarity NPC196471
0.8304 Intermediate Similarity NPC97487
0.8304 Intermediate Similarity NPC472821
0.8304 Intermediate Similarity NPC187302
0.8295 Intermediate Similarity NPC75616
0.8293 Intermediate Similarity NPC179261
0.8279 Intermediate Similarity NPC55602
0.8279 Intermediate Similarity NPC219804
0.8276 Intermediate Similarity NPC71680
0.8264 Intermediate Similarity NPC67569
0.825 Intermediate Similarity NPC305260
0.825 Intermediate Similarity NPC5883
0.825 Intermediate Similarity NPC270850
0.825 Intermediate Similarity NPC29639
0.825 Intermediate Similarity NPC44899
0.825 Intermediate Similarity NPC304260
0.8246 Intermediate Similarity NPC469957
0.8246 Intermediate Similarity NPC108682
0.8246 Intermediate Similarity NPC472263
0.8246 Intermediate Similarity NPC469959
0.824 Intermediate Similarity NPC221414
0.8235 Intermediate Similarity NPC471351
0.8235 Intermediate Similarity NPC309034
0.8235 Intermediate Similarity NPC34390
0.8235 Intermediate Similarity NPC87250
0.8235 Intermediate Similarity NPC142066
0.8235 Intermediate Similarity NPC158344
0.8235 Intermediate Similarity NPC196429
0.8235 Intermediate Similarity NPC77319
0.8235 Intermediate Similarity NPC157376
0.8235 Intermediate Similarity NPC474418
0.8235 Intermediate Similarity NPC84987
0.8235 Intermediate Similarity NPC243196
0.8235 Intermediate Similarity NPC99728
0.8235 Intermediate Similarity NPC50305
0.8235 Intermediate Similarity NPC473852
0.8235 Intermediate Similarity NPC471355
0.8235 Intermediate Similarity NPC471354
0.8235 Intermediate Similarity NPC244402
0.8235 Intermediate Similarity NPC471353
0.8235 Intermediate Similarity NPC27507
0.823 Intermediate Similarity NPC472822
0.822 Intermediate Similarity NPC69576
0.822 Intermediate Similarity NPC31354
0.822 Intermediate Similarity NPC84949
0.822 Intermediate Similarity NPC43213
0.822 Intermediate Similarity NPC471633
0.8214 Intermediate Similarity NPC470972
0.8211 Intermediate Similarity NPC8374
0.8197 Intermediate Similarity NPC470265
0.8197 Intermediate Similarity NPC23786
0.819 Intermediate Similarity NPC177047
0.819 Intermediate Similarity NPC15551
0.819 Intermediate Similarity NPC16270
0.8182 Intermediate Similarity NPC184555
0.8182 Intermediate Similarity NPC474370
0.8174 Intermediate Similarity NPC50124
0.8167 Intermediate Similarity NPC83287
0.8167 Intermediate Similarity NPC153440
0.8158 Intermediate Similarity NPC470980
0.8158 Intermediate Similarity NPC471206
0.8151 Intermediate Similarity NPC193382
0.8151 Intermediate Similarity NPC99620
0.8151 Intermediate Similarity NPC5311
0.8151 Intermediate Similarity NPC310341
0.8151 Intermediate Similarity NPC199428
0.8145 Intermediate Similarity NPC293112
0.8142 Intermediate Similarity NPC160583
0.814 Intermediate Similarity NPC289700
0.814 Intermediate Similarity NPC62172
0.813 Intermediate Similarity NPC469789
0.813 Intermediate Similarity NPC11895
0.8125 Intermediate Similarity NPC25177
0.8125 Intermediate Similarity NPC295110
0.8125 Intermediate Similarity NPC475617
0.8125 Intermediate Similarity NPC247701
0.8125 Intermediate Similarity NPC268829
0.8125 Intermediate Similarity NPC222875
0.8115 Intermediate Similarity NPC475219
0.8115 Intermediate Similarity NPC231518
0.8108 Intermediate Similarity NPC278673
0.8103 Intermediate Similarity NPC475030
0.8099 Intermediate Similarity NPC5292
0.8099 Intermediate Similarity NPC264954
0.8091 Intermediate Similarity NPC299654
0.8087 Intermediate Similarity NPC472820
0.8083 Intermediate Similarity NPC152615
0.8083 Intermediate Similarity NPC203862
0.8083 Intermediate Similarity NPC93883
0.807 Intermediate Similarity NPC200861
0.8067 Intermediate Similarity NPC265290
0.8067 Intermediate Similarity NPC305044
0.8065 Intermediate Similarity NPC81736
0.8065 Intermediate Similarity NPC172154
0.8062 Intermediate Similarity NPC158350
0.8053 Intermediate Similarity NPC11956
0.8051 Intermediate Similarity NPC150228
0.8051 Intermediate Similarity NPC214005
0.8051 Intermediate Similarity NPC241477
0.8049 Intermediate Similarity NPC170538
0.8049 Intermediate Similarity NPC153700
0.8049 Intermediate Similarity NPC193893
0.8049 Intermediate Similarity NPC107493
0.8049 Intermediate Similarity NPC88326
0.8036 Intermediate Similarity NPC38855
0.8036 Intermediate Similarity NPC79631
0.8033 Intermediate Similarity NPC475556
0.8033 Intermediate Similarity NPC475629
0.8033 Intermediate Similarity NPC475136
0.8033 Intermediate Similarity NPC474585
0.8033 Intermediate Similarity NPC474466
0.8017 Intermediate Similarity NPC50774
0.8017 Intermediate Similarity NPC709
0.8017 Intermediate Similarity NPC472080
0.8 Intermediate Similarity NPC190286
0.8 Intermediate Similarity NPC298278
0.8 Intermediate Similarity NPC473635
0.8 Intermediate Similarity NPC472818
0.7984 Intermediate Similarity NPC473979
0.7983 Intermediate Similarity NPC73050
0.7983 Intermediate Similarity NPC101965
0.7983 Intermediate Similarity NPC101400
0.7982 Intermediate Similarity NPC474124
0.7982 Intermediate Similarity NPC45897
0.7982 Intermediate Similarity NPC297617
0.7982 Intermediate Similarity NPC23584
0.7969 Intermediate Similarity NPC155529
0.7967 Intermediate Similarity NPC46570
0.7967 Intermediate Similarity NPC173555
0.7967 Intermediate Similarity NPC40749
0.7967 Intermediate Similarity NPC314535
0.7966 Intermediate Similarity NPC255401
0.7966 Intermediate Similarity NPC262083
0.7966 Intermediate Similarity NPC471484
0.7966 Intermediate Similarity NPC284162
0.7965 Intermediate Similarity NPC155974
0.7953 Intermediate Similarity NPC231529
0.7951 Intermediate Similarity NPC291820
0.7951 Intermediate Similarity NPC32177
0.7951 Intermediate Similarity NPC469756
0.7951 Intermediate Similarity NPC329905
0.7951 Intermediate Similarity NPC236973
0.7951 Intermediate Similarity NPC55532
0.7951 Intermediate Similarity NPC292467
0.7951 Intermediate Similarity NPC81222
0.7951 Intermediate Similarity NPC475041

  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 NPC112936 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
0.8571 High Similarity NPD7503 Approved
0.8167 Intermediate Similarity NPD7327 Approved
0.8167 Intermediate Similarity NPD7328 Approved
0.8115 Intermediate Similarity NPD8033 Approved
0.8099 Intermediate Similarity NPD7516 Approved
0.7967 Intermediate Similarity NPD8380 Approved
0.7967 Intermediate Similarity NPD8379 Approved
0.7967 Intermediate Similarity NPD8296 Approved
0.7967 Intermediate Similarity NPD8378 Approved
0.7967 Intermediate Similarity NPD8335 Approved
0.7934 Intermediate Similarity NPD7115 Discovery
0.7886 Intermediate Similarity NPD8294 Approved
0.7886 Intermediate Similarity NPD8377 Approved
0.7788 Intermediate Similarity NPD7638 Approved
0.7719 Intermediate Similarity NPD7640 Approved
0.7719 Intermediate Similarity NPD7639 Approved
0.7652 Intermediate Similarity NPD5344 Discontinued
0.7578 Intermediate Similarity NPD7507 Approved
0.7565 Intermediate Similarity NPD6648 Approved
0.7538 Intermediate Similarity NPD7319 Approved
0.7355 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD6319 Approved
0.7317 Intermediate Similarity NPD6053 Discontinued
0.7258 Intermediate Similarity NPD4632 Approved
0.7197 Intermediate Similarity NPD7736 Approved
0.7179 Intermediate Similarity NPD4225 Approved
0.7177 Intermediate Similarity NPD8297 Approved
0.7168 Intermediate Similarity NPD7838 Discovery
0.7143 Intermediate Similarity NPD7632 Discontinued
0.7131 Intermediate Similarity NPD6899 Approved
0.7131 Intermediate Similarity NPD6881 Approved
0.7099 Intermediate Similarity NPD7492 Approved
0.7054 Intermediate Similarity NPD6054 Approved
0.7054 Intermediate Similarity NPD7524 Approved
0.7049 Intermediate Similarity NPD5697 Approved
0.7045 Intermediate Similarity NPD6616 Approved
0.7023 Intermediate Similarity NPD7604 Phase 2
0.7016 Intermediate Similarity NPD7290 Approved
0.7016 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7102 Approved
0.7016 Intermediate Similarity NPD6883 Approved
0.6992 Remote Similarity NPD6686 Approved
0.6992 Remote Similarity NPD7078 Approved
0.6967 Remote Similarity NPD5739 Approved
0.6967 Remote Similarity NPD6008 Approved
0.6967 Remote Similarity NPD7128 Approved
0.6967 Remote Similarity NPD6675 Approved
0.6967 Remote Similarity NPD6402 Approved
0.696 Remote Similarity NPD8130 Phase 1
0.696 Remote Similarity NPD6869 Approved
0.696 Remote Similarity NPD6847 Approved
0.696 Remote Similarity NPD6617 Approved
0.696 Remote Similarity NPD6650 Approved
0.696 Remote Similarity NPD6649 Approved
0.6957 Remote Similarity NPD7637 Suspended
0.6953 Remote Similarity NPD6009 Approved
0.6947 Remote Similarity NPD6370 Approved
0.6937 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6012 Approved
0.6935 Remote Similarity NPD6014 Approved
0.6935 Remote Similarity NPD6013 Approved
0.6917 Remote Similarity NPD4159 Approved
0.6911 Remote Similarity NPD6412 Phase 2
0.6905 Remote Similarity NPD6882 Approved
0.688 Remote Similarity NPD4634 Approved
0.687 Remote Similarity NPD6015 Approved
0.687 Remote Similarity NPD5983 Phase 2
0.687 Remote Similarity NPD6016 Approved
0.6855 Remote Similarity NPD6011 Approved
0.6855 Remote Similarity NPD7320 Approved
0.685 Remote Similarity NPD8133 Approved
0.6847 Remote Similarity NPD6695 Phase 3
0.6818 Remote Similarity NPD5988 Approved
0.68 Remote Similarity NPD6373 Approved
0.68 Remote Similarity NPD6372 Approved
0.6794 Remote Similarity NPD6059 Approved
0.6791 Remote Similarity NPD6336 Discontinued
0.6783 Remote Similarity NPD6051 Approved
0.6774 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5701 Approved
0.6746 Remote Similarity NPD6371 Approved
0.6741 Remote Similarity NPD8293 Discontinued
0.6727 Remote Similarity NPD7525 Registered
0.6721 Remote Similarity NPD5211 Phase 2
0.6694 Remote Similarity NPD5286 Approved
0.6694 Remote Similarity NPD5285 Approved
0.6694 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD6084 Phase 2
0.6613 Remote Similarity NPD5141 Approved
0.6609 Remote Similarity NPD7750 Discontinued
0.6591 Remote Similarity NPD7100 Approved
0.6591 Remote Similarity NPD7101 Approved
0.6587 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5224 Approved
0.6585 Remote Similarity NPD5226 Approved
0.6585 Remote Similarity NPD4633 Approved
0.6585 Remote Similarity NPD5225 Approved
0.6581 Remote Similarity NPD6698 Approved
0.6581 Remote Similarity NPD46 Approved
0.6577 Remote Similarity NPD6930 Phase 2
0.6577 Remote Similarity NPD7514 Phase 3
0.6577 Remote Similarity NPD6931 Approved
0.6562 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6532 Remote Similarity NPD5174 Approved
0.6532 Remote Similarity NPD5175 Approved
0.6529 Remote Similarity NPD4755 Approved
0.6518 Remote Similarity NPD6902 Approved
0.6515 Remote Similarity NPD6335 Approved
0.6504 Remote Similarity NPD5223 Approved
0.6493 Remote Similarity NPD8513 Phase 3
0.6489 Remote Similarity NPD6274 Approved
0.6486 Remote Similarity NPD7625 Phase 1
0.6486 Remote Similarity NPD6929 Approved
0.6475 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4202 Approved
0.6471 Remote Similarity NPD6399 Phase 3
0.6466 Remote Similarity NPD4251 Approved
0.6466 Remote Similarity NPD4250 Approved
0.6466 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6932 Approved
0.6439 Remote Similarity NPD6317 Approved
0.6429 Remote Similarity NPD7260 Phase 2
0.6429 Remote Similarity NPD7332 Phase 2
0.6423 Remote Similarity NPD4700 Approved
0.6417 Remote Similarity NPD7748 Approved
0.641 Remote Similarity NPD7513 Clinical (unspecified phase)
0.64 Remote Similarity NPD7236 Approved
0.6396 Remote Similarity NPD7145 Approved
0.6393 Remote Similarity NPD7902 Approved
0.6391 Remote Similarity NPD6313 Approved
0.6391 Remote Similarity NPD6314 Approved
0.6387 Remote Similarity NPD5284 Approved
0.6387 Remote Similarity NPD7087 Discontinued
0.6387 Remote Similarity NPD7515 Phase 2
0.6387 Remote Similarity NPD5281 Approved
0.6387 Remote Similarity NPD8035 Phase 2
0.6387 Remote Similarity NPD6079 Approved
0.6387 Remote Similarity NPD8034 Phase 2
0.6379 Remote Similarity NPD4249 Approved
0.6378 Remote Similarity NPD7899 Clinical (unspecified phase)
0.637 Remote Similarity NPD8515 Approved
0.637 Remote Similarity NPD8517 Approved
0.637 Remote Similarity NPD8516 Approved
0.6364 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5695 Phase 3
0.6341 Remote Similarity NPD5696 Approved
0.6339 Remote Similarity NPD4195 Approved
0.6331 Remote Similarity NPD6033 Approved
0.6328 Remote Similarity NPD4730 Approved
0.6328 Remote Similarity NPD4729 Approved
0.6306 Remote Similarity NPD6925 Approved
0.6306 Remote Similarity NPD5776 Phase 2
0.6293 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6893 Approved
0.6277 Remote Similarity NPD8328 Phase 3
0.6277 Remote Similarity NPD6067 Discontinued
0.625 Remote Similarity NPD5693 Phase 1
0.625 Remote Similarity NPD6909 Approved
0.625 Remote Similarity NPD6908 Approved
0.625 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6684 Approved
0.6239 Remote Similarity NPD7521 Approved
0.6239 Remote Similarity NPD6409 Approved
0.6239 Remote Similarity NPD7334 Approved
0.6239 Remote Similarity NPD5330 Approved
0.6239 Remote Similarity NPD7146 Approved
0.6231 Remote Similarity NPD5250 Approved
0.6231 Remote Similarity NPD5249 Phase 3
0.6231 Remote Similarity NPD5247 Approved
0.6231 Remote Similarity NPD5251 Approved
0.6231 Remote Similarity NPD5248 Approved
0.623 Remote Similarity NPD4629 Approved
0.623 Remote Similarity NPD5210 Approved
0.6218 Remote Similarity NPD4753 Phase 2
0.6218 Remote Similarity NPD5328 Approved
0.6216 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6202 Remote Similarity NPD5128 Approved
0.6195 Remote Similarity NPD7645 Phase 2
0.6195 Remote Similarity NPD6683 Phase 2
0.6194 Remote Similarity NPD7239 Suspended
0.6183 Remote Similarity NPD5215 Approved
0.6183 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6183 Remote Similarity NPD5217 Approved
0.6183 Remote Similarity NPD5216 Approved
0.6182 Remote Similarity NPD6924 Approved
0.6182 Remote Similarity NPD7799 Discontinued
0.6182 Remote Similarity NPD6926 Approved
0.6179 Remote Similarity NPD5221 Approved
0.6179 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6179 Remote Similarity NPD5222 Approved
0.6176 Remote Similarity NPD7741 Discontinued
0.6172 Remote Similarity NPD6640 Phase 3
0.6172 Remote Similarity NPD4767 Approved
0.6172 Remote Similarity NPD4768 Approved
0.6167 Remote Similarity NPD5785 Approved
0.6154 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6148 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6148 Remote Similarity NPD7900 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