Structure

Physi-Chem Properties

Molecular Weight:  390.24
Volume:  402.26
LogP:  2.986
LogD:  2.685
LogS:  -4.143
# Rotatable Bonds:  1
TPSA:  94.06
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.588
Synthetic Accessibility Score:  4.894
Fsp3:  0.826
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:  -5.426
MDCK Permeability:  4.15829299527104e-06
Pgp-inhibitor:  0.007
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.136
20% Bioavailability (F20%):  0.905
30% Bioavailability (F30%):  0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.568
Plasma Protein Binding (PPB):  92.18489837646484%
Volume Distribution (VD):  1.207
Pgp-substrate:  12.488176345825195%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.426
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.438
CYP2C9-inhibitor:  0.088
CYP2C9-substrate:  0.334
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.28
CYP3A4-inhibitor:  0.334
CYP3A4-substrate:  0.176

ADMET: Excretion

Clearance (CL):  12.057
Half-life (T1/2):  0.487

ADMET: Toxicity

hERG Blockers:  0.113
Human Hepatotoxicity (H-HT):  0.504
Drug-inuced Liver Injury (DILI):  0.025
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.843
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.65
Carcinogencity:  0.676
Eye Corrosion:  0.006
Eye Irritation:  0.019
Respiratory Toxicity:  0.958

Download Data

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

  Natural Product: NPC189588

Natural Product ID:  NPC189588
Common Name*:   Digoxigenin
IUPAC Name:   3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  SHIBSTMRCDJXLN-KCZCNTNESA-N
Standard InCHI:  InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1
SMILES:  C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2C[C@H]([C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1153
PubChem CID:   15478
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001555] Cardenolides 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
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22245 Digitalis lanata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22245 Digitalis lanata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22245 Digitalis lanata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22245 Digitalis lanata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22245 Digitalis lanata Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4443 Digitalis purpurea Species Plantaginaceae 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
NPT384 Cell Line TK-10 Homo sapiens IC50 = 317.5 nM PMID[557101]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 507.0 nM PMID[557101]
NPT398 Cell Line UACC-62 Homo sapiens IC50 = 416.1 nM PMID[557101]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 2511.9 nM PMID[557102]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 0.1 nM PMID[557103]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 3981.1 nM PMID[557102]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 1995.3 nM PMID[557103]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 631.0 nM PMID[557103]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 79432.8 nM PMID[557102]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 461.1 nM PMID[557102]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 3262.9 nM PMID[557102]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 1412.5 nM PMID[557102]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[557102]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 < 50.0 nM PMID[557102]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 1258.9 nM PMID[557102]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 n.a. 2100.0 nM PMID[557102]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 10000.0 nM PMID[557102]
NPT3812 Individual Protein Solute carrier organic anion transporter family member 4C1 Homo sapiens IC50 = 490.0 nM PMID[557105]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 920.0 nM PMID[557102]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2909.3 nM PMID[557102]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 1122.0 nM PMID[557102]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 501.2 nM PMID[557102]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[557102]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 26608.6 nM PMID[557106]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 37585.7 nM PMID[557106]
NPT1283 Individual Protein Paired box protein Pax-8 Homo sapiens AC50 = 2350.0 nM PMID[557102]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 10000.0 nM PMID[557102]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 766.7 nM PMID[557102]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 3600.0 nM PMID[557111]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 3200.0 nM PMID[557111]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 2400.0 nM PMID[557111]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 900.0 nM PMID[557111]
NPT897 Others Monoclonal antibody (mAb) IC50 ratio = 2700.0 n.a. PMID[557099]
NPT897 Others Monoclonal antibody (mAb) IC50 ratio = 4.6 n.a. PMID[557099]
NPT897 Others Monoclonal antibody (mAb) IC50 ratio = 6.2 n.a. PMID[557099]
NPT897 Others Monoclonal antibody (mAb) IC50 ratio = 2.9 n.a. PMID[557099]
NPT897 Others Monoclonal antibody (mAb) Relative Ki = 2.0 n.a. PMID[557099]
NPT897 Others Monoclonal antibody (mAb) Ki = 3100.0 nM PMID[557099]
NPT897 Others Monoclonal antibody (mAb) Ki = 1700.0 nM PMID[557099]
NPT2 Others Unspecified Ratio IC50 = 1.2 n.a. PMID[557100]
NPT2 Others Unspecified Potency = 3548.1 nM PMID[557103]
NPT2 Others Unspecified AC50 = 1157.0 nM PMID[557102]
NPT2 Others Unspecified Potency n.a. 1032.3 nM PMID[557102]
NPT2 Others Unspecified Potency n.a. 7307.8 nM PMID[557102]
NPT2 Others Unspecified IC50 = 580.0 nM PMID[557102]
NPT2 Others Unspecified IC50 = 65700.0 nM PMID[557102]
NPT2 Others Unspecified IC50 > 80000.0 nM PMID[557102]
NPT2 Others Unspecified IC50 = 1600.0 nM PMID[557102]
NPT2 Others Unspecified AC50 = 654.0 nM PMID[557102]
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Activity = 19.0 % PMID[557104]
NPT2 Others Unspecified Potency n.a. 562.3 nM PMID[557102]
NPT2 Others Unspecified Potency n.a. 819.9 nM PMID[557102]
NPT2 Others Unspecified AbsAC35 = 1.0 uM PMID[557102]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 2059.6 nM PMID[557102]
NPT2 Others Unspecified Max_Activity = 26.0 uM PMID[557102]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[557102]
NPT2 Others Unspecified AbsAC35_uM = 1.1 uM PMID[557102]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[557106]
NPT2 Others Unspecified Potency n.a. 1458.1 nM PMID[557102]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 0.373 uM PMID[557102]
NPT2 Others Unspecified Potency n.a. 354.8 nM PMID[557106]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 1.16 uM PMID[557102]
NPT2 Others Unspecified Potency n.a. 6309.6 nM PMID[557102]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.2712 n.a. PMID[557107]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 66.77 % PMID[557108]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -5.548 % PMID[557109]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.23 % PMID[557110]
NPT2 Others Unspecified Potency n.a. 1096.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 691.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2454.1 nM PubChem BioAssay data set

☑ 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 NPC189588 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
1.0 High Similarity NPC187302
1.0 High Similarity NPC196471
1.0 High Similarity NPC97487
1.0 High Similarity NPC10232
0.9789 High Similarity NPC268829
0.9789 High Similarity NPC25177
0.9789 High Similarity NPC247701
0.9789 High Similarity NPC295110
0.9789 High Similarity NPC222875
0.9592 High Similarity NPC119855
0.9592 High Similarity NPC220217
0.9588 High Similarity NPC160583
0.95 High Similarity NPC475030
0.9394 High Similarity NPC186668
0.9388 High Similarity NPC472821
0.9072 High Similarity NPC231751
0.9072 High Similarity NPC51499
0.901 High Similarity NPC472818
0.898 High Similarity NPC275086
0.898 High Similarity NPC325229
0.8962 High Similarity NPC72772
0.8962 High Similarity NPC469794
0.8922 High Similarity NPC472820
0.8911 High Similarity NPC472819
0.8889 High Similarity NPC251680
0.8879 High Similarity NPC99728
0.8879 High Similarity NPC27507
0.8879 High Similarity NPC50305
0.8879 High Similarity NPC142066
0.8879 High Similarity NPC34390
0.8879 High Similarity NPC471351
0.8879 High Similarity NPC474418
0.8879 High Similarity NPC244402
0.8879 High Similarity NPC471355
0.8879 High Similarity NPC157376
0.8879 High Similarity NPC77319
0.8879 High Similarity NPC471353
0.8879 High Similarity NPC473852
0.8879 High Similarity NPC158344
0.8879 High Similarity NPC243196
0.8879 High Similarity NPC196429
0.8879 High Similarity NPC471354
0.8879 High Similarity NPC309034
0.8879 High Similarity NPC84987
0.8879 High Similarity NPC87250
0.8868 High Similarity NPC31354
0.8868 High Similarity NPC84949
0.8868 High Similarity NPC69576
0.8868 High Similarity NPC471633
0.8866 High Similarity NPC276110
0.8835 High Similarity NPC137462
0.8835 High Similarity NPC304276
0.8812 High Similarity NPC45897
0.8812 High Similarity NPC112009
0.8796 High Similarity NPC83287
0.8785 High Similarity NPC99620
0.8785 High Similarity NPC199428
0.8785 High Similarity NPC5311
0.8785 High Similarity NPC310341
0.8785 High Similarity NPC193382
0.8774 High Similarity NPC171126
0.8763 High Similarity NPC201725
0.8763 High Similarity NPC105490
0.875 High Similarity NPC130840
0.8738 High Similarity NPC475781
0.8704 High Similarity NPC93883
0.8704 High Similarity NPC290693
0.8704 High Similarity NPC152615
0.87 High Similarity NPC472826
0.8679 High Similarity NPC44537
0.8667 High Similarity NPC103491
0.8667 High Similarity NPC12795
0.866 High Similarity NPC7349
0.8636 High Similarity NPC475136
0.8636 High Similarity NPC475629
0.8636 High Similarity NPC474466
0.8636 High Similarity NPC475556
0.8627 High Similarity NPC180204
0.8614 High Similarity NPC11974
0.8611 High Similarity NPC196931
0.86 High Similarity NPC218107
0.86 High Similarity NPC278673
0.8571 High Similarity NPC3359
0.8559 High Similarity NPC314535
0.8559 High Similarity NPC173555
0.8558 High Similarity NPC471205
0.8557 High Similarity NPC234335
0.8545 High Similarity NPC30483
0.8545 High Similarity NPC470897
0.8545 High Similarity NPC44899
0.8545 High Similarity NPC5883
0.8545 High Similarity NPC236973
0.8545 High Similarity NPC329905
0.8545 High Similarity NPC32177
0.8545 High Similarity NPC469756
0.8545 High Similarity NPC29639
0.8545 High Similarity NPC292467
0.8545 High Similarity NPC55532
0.8545 High Similarity NPC304260
0.8544 High Similarity NPC200861
0.8544 High Similarity NPC472822
0.8532 High Similarity NPC203862
0.8515 High Similarity NPC201406
0.8515 High Similarity NPC38855
0.8505 High Similarity NPC470063
0.8491 Intermediate Similarity NPC179642
0.8482 Intermediate Similarity NPC264336
0.8468 Intermediate Similarity NPC257610
0.8468 Intermediate Similarity NPC72260
0.8462 Intermediate Similarity NPC51719
0.8454 Intermediate Similarity NPC302280
0.8454 Intermediate Similarity NPC53890
0.8454 Intermediate Similarity NPC219937
0.8454 Intermediate Similarity NPC78973
0.8454 Intermediate Similarity NPC123252
0.8454 Intermediate Similarity NPC194485
0.8447 Intermediate Similarity NPC171014
0.8447 Intermediate Similarity NPC473523
0.8447 Intermediate Similarity NPC120009
0.8431 Intermediate Similarity NPC475617
0.8426 Intermediate Similarity NPC154815
0.8421 Intermediate Similarity NPC131813
0.8416 Intermediate Similarity NPC119036
0.8407 Intermediate Similarity NPC208193
0.8407 Intermediate Similarity NPC308262
0.8407 Intermediate Similarity NPC117445
0.84 Intermediate Similarity NPC304899
0.84 Intermediate Similarity NPC253115
0.8396 Intermediate Similarity NPC75389
0.8393 Intermediate Similarity NPC475590
0.8393 Intermediate Similarity NPC120390
0.8393 Intermediate Similarity NPC474908
0.8393 Intermediate Similarity NPC475419
0.8393 Intermediate Similarity NPC231518
0.8393 Intermediate Similarity NPC40749
0.8393 Intermediate Similarity NPC475219
0.8384 Intermediate Similarity NPC144202
0.8381 Intermediate Similarity NPC475074
0.8381 Intermediate Similarity NPC43063
0.8381 Intermediate Similarity NPC79298
0.8378 Intermediate Similarity NPC213761
0.8378 Intermediate Similarity NPC35171
0.8367 Intermediate Similarity NPC329842
0.8365 Intermediate Similarity NPC473543
0.835 Intermediate Similarity NPC22388
0.835 Intermediate Similarity NPC475344
0.835 Intermediate Similarity NPC109195
0.835 Intermediate Similarity NPC476081
0.835 Intermediate Similarity NPC476471
0.835 Intermediate Similarity NPC475038
0.8333 Intermediate Similarity NPC324841
0.8333 Intermediate Similarity NPC247760
0.8319 Intermediate Similarity NPC193893
0.8319 Intermediate Similarity NPC474423
0.8319 Intermediate Similarity NPC115349
0.8319 Intermediate Similarity NPC74259
0.8318 Intermediate Similarity NPC177047
0.8317 Intermediate Similarity NPC210337
0.8317 Intermediate Similarity NPC274793
0.8316 Intermediate Similarity NPC474013
0.8304 Intermediate Similarity NPC112936
0.8304 Intermediate Similarity NPC41123
0.8304 Intermediate Similarity NPC145074
0.8304 Intermediate Similarity NPC114939
0.8302 Intermediate Similarity NPC88701
0.8302 Intermediate Similarity NPC38948
0.8302 Intermediate Similarity NPC275060
0.83 Intermediate Similarity NPC329435
0.8288 Intermediate Similarity NPC218093
0.8288 Intermediate Similarity NPC16701
0.8286 Intermediate Similarity NPC295843
0.8286 Intermediate Similarity NPC471206
0.8283 Intermediate Similarity NPC26046
0.8283 Intermediate Similarity NPC27531
0.8269 Intermediate Similarity NPC474124
0.8269 Intermediate Similarity NPC36688
0.8269 Intermediate Similarity NPC120321
0.8269 Intermediate Similarity NPC297617
0.8269 Intermediate Similarity NPC281378
0.8269 Intermediate Similarity NPC222153
0.8265 Intermediate Similarity NPC10274
0.8252 Intermediate Similarity NPC472554
0.8252 Intermediate Similarity NPC49532
0.8252 Intermediate Similarity NPC471412
0.8247 Intermediate Similarity NPC160304
0.8246 Intermediate Similarity NPC27363
0.8241 Intermediate Similarity NPC470076
0.8241 Intermediate Similarity NPC183603
0.8235 Intermediate Similarity NPC181147
0.8235 Intermediate Similarity NPC300179
0.8235 Intermediate Similarity NPC102426
0.8229 Intermediate Similarity NPC201273
0.8224 Intermediate Similarity NPC206618
0.8218 Intermediate Similarity NPC194132
0.8218 Intermediate Similarity NPC276103
0.8218 Intermediate Similarity NPC471903
0.8218 Intermediate Similarity NPC54248
0.8218 Intermediate Similarity NPC88009
0.8214 Intermediate Similarity NPC291820
0.8214 Intermediate Similarity NPC153085

  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 NPC189588 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
0.898 High Similarity NPD7638 Approved
0.8889 High Similarity NPD7639 Approved
0.8889 High Similarity NPD7640 Approved
0.8796 High Similarity NPD7328 Approved
0.8796 High Similarity NPD7327 Approved
0.8716 High Similarity NPD7516 Approved
0.8559 High Similarity NPD8335 Approved
0.8559 High Similarity NPD8380 Approved
0.8559 High Similarity NPD8378 Approved
0.8559 High Similarity NPD8296 Approved
0.8559 High Similarity NPD8379 Approved
0.8468 Intermediate Similarity NPD8294 Approved
0.8468 Intermediate Similarity NPD8377 Approved
0.8393 Intermediate Similarity NPD8033 Approved
0.8173 Intermediate Similarity NPD7632 Discontinued
0.8103 Intermediate Similarity NPD7507 Approved
0.8051 Intermediate Similarity NPD7319 Approved
0.78 Intermediate Similarity NPD6051 Approved
0.7798 Intermediate Similarity NPD7320 Approved
0.7778 Intermediate Similarity NPD6675 Approved
0.7778 Intermediate Similarity NPD6402 Approved
0.7778 Intermediate Similarity NPD7128 Approved
0.7778 Intermediate Similarity NPD5739 Approved
0.7759 Intermediate Similarity NPD7503 Approved
0.7636 Intermediate Similarity NPD6881 Approved
0.7636 Intermediate Similarity NPD6899 Approved
0.7619 Intermediate Similarity NPD6083 Phase 2
0.7619 Intermediate Similarity NPD6084 Phase 2
0.7604 Intermediate Similarity NPD7525 Registered
0.7568 Intermediate Similarity NPD6372 Approved
0.7568 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD6373 Approved
0.7545 Intermediate Similarity NPD5701 Approved
0.7545 Intermediate Similarity NPD5697 Approved
0.7522 Intermediate Similarity NPD6053 Discontinued
0.75 Intermediate Similarity NPD7290 Approved
0.75 Intermediate Similarity NPD6883 Approved
0.75 Intermediate Similarity NPD7102 Approved
0.7455 Intermediate Similarity NPD6008 Approved
0.7434 Intermediate Similarity NPD6617 Approved
0.7434 Intermediate Similarity NPD6649 Approved
0.7434 Intermediate Similarity NPD6847 Approved
0.7434 Intermediate Similarity NPD6869 Approved
0.7434 Intermediate Similarity NPD8130 Phase 1
0.7434 Intermediate Similarity NPD6650 Approved
0.7414 Intermediate Similarity NPD7115 Discovery
0.7411 Intermediate Similarity NPD6013 Approved
0.7411 Intermediate Similarity NPD6014 Approved
0.7411 Intermediate Similarity NPD6012 Approved
0.7383 Intermediate Similarity NPD4225 Approved
0.7374 Intermediate Similarity NPD6695 Phase 3
0.7368 Intermediate Similarity NPD6882 Approved
0.7368 Intermediate Similarity NPD8297 Approved
0.7345 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6011 Approved
0.7321 Intermediate Similarity NPD6686 Approved
0.7308 Intermediate Similarity NPD7637 Suspended
0.7304 Intermediate Similarity NPD4632 Approved
0.73 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD4755 Approved
0.7281 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7492 Approved
0.7264 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD5695 Phase 3
0.7255 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD5344 Discontinued
0.7238 Intermediate Similarity NPD4202 Approved
0.7236 Intermediate Similarity NPD7736 Approved
0.7227 Intermediate Similarity NPD6054 Approved
0.7227 Intermediate Similarity NPD6319 Approved
0.7227 Intermediate Similarity NPD6059 Approved
0.7222 Intermediate Similarity NPD5696 Approved
0.7213 Intermediate Similarity NPD6616 Approved
0.7184 Intermediate Similarity NPD6903 Approved
0.7184 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD5211 Phase 2
0.717 Intermediate Similarity NPD7748 Approved
0.7157 Intermediate Similarity NPD7334 Approved
0.7157 Intermediate Similarity NPD7521 Approved
0.7157 Intermediate Similarity NPD6409 Approved
0.7157 Intermediate Similarity NPD7146 Approved
0.7157 Intermediate Similarity NPD6684 Approved
0.7157 Intermediate Similarity NPD5330 Approved
0.7156 Intermediate Similarity NPD5285 Approved
0.7156 Intermediate Similarity NPD4700 Approved
0.7156 Intermediate Similarity NPD5286 Approved
0.7156 Intermediate Similarity NPD4696 Approved
0.7154 Intermediate Similarity NPD7078 Approved
0.7154 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD7515 Phase 2
0.7143 Intermediate Similarity NPD5693 Phase 1
0.7119 Intermediate Similarity NPD6009 Approved
0.7115 Intermediate Similarity NPD5328 Approved
0.7115 Intermediate Similarity NPD4753 Phase 2
0.7107 Intermediate Similarity NPD6370 Approved
0.7087 Intermediate Similarity NPD7524 Approved
0.7087 Intermediate Similarity NPD7750 Discontinued
0.708 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6412 Phase 2
0.7075 Intermediate Similarity NPD6399 Phase 3
0.7071 Intermediate Similarity NPD6930 Phase 2
0.7071 Intermediate Similarity NPD6931 Approved
0.7059 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD5141 Approved
0.7049 Intermediate Similarity NPD7604 Phase 2
0.7034 Intermediate Similarity NPD6274 Approved
0.7027 Intermediate Similarity NPD5225 Approved
0.7027 Intermediate Similarity NPD5224 Approved
0.7027 Intermediate Similarity NPD4633 Approved
0.7027 Intermediate Similarity NPD5226 Approved
0.7025 Intermediate Similarity NPD6015 Approved
0.7025 Intermediate Similarity NPD6016 Approved
0.7025 Intermediate Similarity NPD5983 Phase 2
0.701 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD8133 Approved
0.7 Intermediate Similarity NPD6648 Approved
0.7 Intermediate Similarity NPD7100 Approved
0.7 Intermediate Similarity NPD7101 Approved
0.699 Remote Similarity NPD3618 Phase 1
0.6981 Remote Similarity NPD6079 Approved
0.6981 Remote Similarity NPD8035 Phase 2
0.6981 Remote Similarity NPD8034 Phase 2
0.6972 Remote Similarity NPD7902 Approved
0.697 Remote Similarity NPD6929 Approved
0.697 Remote Similarity NPD4195 Approved
0.697 Remote Similarity NPD7645 Phase 2
0.6967 Remote Similarity NPD5988 Approved
0.6964 Remote Similarity NPD5175 Approved
0.6964 Remote Similarity NPD5174 Approved
0.6961 Remote Similarity NPD3665 Phase 1
0.6961 Remote Similarity NPD3666 Approved
0.6961 Remote Similarity NPD3133 Approved
0.6952 Remote Similarity NPD6904 Approved
0.6952 Remote Similarity NPD6673 Approved
0.6952 Remote Similarity NPD6080 Approved
0.6937 Remote Similarity NPD5223 Approved
0.6935 Remote Similarity NPD6336 Discontinued
0.6931 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6335 Approved
0.6907 Remote Similarity NPD7339 Approved
0.6907 Remote Similarity NPD6942 Approved
0.69 Remote Similarity NPD7514 Phase 3
0.6897 Remote Similarity NPD4634 Approved
0.6893 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6885 Remote Similarity NPD6908 Approved
0.6885 Remote Similarity NPD6909 Approved
0.6857 Remote Similarity NPD6672 Approved
0.6857 Remote Similarity NPD5737 Approved
0.6852 Remote Similarity NPD6001 Approved
0.6842 Remote Similarity NPD4768 Approved
0.6842 Remote Similarity NPD4767 Approved
0.6838 Remote Similarity NPD7625 Phase 1
0.6833 Remote Similarity NPD6317 Approved
0.6822 Remote Similarity NPD7087 Discontinued
0.6814 Remote Similarity NPD4754 Approved
0.6796 Remote Similarity NPD4786 Approved
0.6796 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6789 Remote Similarity NPD5210 Approved
0.6789 Remote Similarity NPD4629 Approved
0.6786 Remote Similarity NPD4159 Approved
0.6777 Remote Similarity NPD6313 Approved
0.6777 Remote Similarity NPD6314 Approved
0.6771 Remote Similarity NPD4243 Approved
0.6768 Remote Similarity NPD6932 Approved
0.6768 Remote Similarity NPD6925 Approved
0.6768 Remote Similarity NPD5776 Phase 2
0.6765 Remote Similarity NPD4223 Phase 3
0.6765 Remote Similarity NPD4221 Approved
0.6748 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7332 Phase 2
0.6731 Remote Similarity NPD5329 Approved
0.6731 Remote Similarity NPD6893 Approved
0.6727 Remote Similarity NPD5221 Approved
0.6727 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5222 Approved
0.6727 Remote Similarity NPD4697 Phase 3
0.6724 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4730 Approved
0.6724 Remote Similarity NPD4729 Approved
0.6724 Remote Similarity NPD5128 Approved
0.67 Remote Similarity NPD6114 Approved
0.67 Remote Similarity NPD6115 Approved
0.67 Remote Similarity NPD6118 Approved
0.67 Remote Similarity NPD6697 Approved
0.67 Remote Similarity NPD7145 Approved
0.6699 Remote Similarity NPD4788 Approved
0.6698 Remote Similarity NPD5208 Approved
0.6697 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6697 Remote Similarity NPD7900 Approved
0.6693 Remote Similarity NPD6033 Approved
0.6667 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD5284 Approved
0.6667 Remote Similarity NPD6902 Approved
0.6667 Remote Similarity NPD6050 Approved
0.6667 Remote Similarity NPD6098 Approved
0.6667 Remote Similarity NPD5281 Approved
0.664 Remote Similarity NPD6067 Discontinued
0.6635 Remote Similarity NPD4197 Approved
0.6634 Remote Similarity NPD6683 Phase 2
0.6633 Remote Similarity NPD6926 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