Structure

Physi-Chem Properties

Molecular Weight:  446.12
Volume:  421.653
LogP:  1.907
LogD:  1.477
LogS:  -4.687
# Rotatable Bonds:  4
TPSA:  162.98
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.358
Synthetic Accessibility Score:  3.855
Fsp3:  0.364
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.021
MDCK Permeability:  1.6272557331831194e-05
Pgp-inhibitor:  0.699
Pgp-substrate:  0.825
Human Intestinal Absorption (HIA):  0.817
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.076
Plasma Protein Binding (PPB):  85.72343444824219%
Volume Distribution (VD):  0.671
Pgp-substrate:  4.610515117645264%

ADMET: Metabolism

CYP1A2-inhibitor:  0.351
CYP1A2-substrate:  0.172
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.071
CYP2C9-inhibitor:  0.05
CYP2C9-substrate:  0.121
CYP2D6-inhibitor:  0.144
CYP2D6-substrate:  0.174
CYP3A4-inhibitor:  0.191
CYP3A4-substrate:  0.092

ADMET: Excretion

Clearance (CL):  7.165
Half-life (T1/2):  0.26

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.063
Drug-inuced Liver Injury (DILI):  0.922
AMES Toxicity:  0.895
Rat Oral Acute Toxicity:  0.033
Maximum Recommended Daily Dose:  0.037
Skin Sensitization:  0.082
Carcinogencity:  0.383
Eye Corrosion:  0.003
Eye Irritation:  0.512
Respiratory Toxicity:  0.033

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC30432

Natural Product ID:  NPC30432
Common Name*:   Physcion 8-O-Glucoside
IUPAC Name:   1-hydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Synonyms:   Physcion 8-O-Glucoside
Standard InCHIKey:  WLXGUTUUWXVZNM-DQMLXFRHSA-N
Standard InCHI:  InChI=1S/C22H22O10/c1-8-3-10-16(19(27)15-11(17(10)25)5-9(30-2)6-12(15)24)13(4-8)31-22-21(29)20(28)18(26)14(7-23)32-22/h3-6,14,18,20-24,26,28-29H,7H2,1-2H3/t14-,18-,20+,21-,22-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2cc(C)cc3c2C(=O)c2c(C3=O)cc(cc2O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL457944
PubChem CID:   5319323
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO12079 Dysoxylum cumingianum Species Meliaceae Eukaryota n.a. leaf n.a. DOI[10.1021/jo00051a050]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO14520 Bassia muricata Species Chenopodiaceae Eukaryota n.a. aerial part n.a. PMID[11454355]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota Roots Gorkha district, Nepal 1996-OCT PMID[12932135]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. root n.a. PMID[16564530]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[19719093]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[22512738]
NPO13237 Teucrium yemense Species n.a. n.a. Aerial Parts n.a. n.a. PMID[28581290]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[29359942]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[31944695]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots; Tubers n.a. n.a. PMID[7714535]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30021 Rheum emodi Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15297 Aconitum seravschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18339 Rheum wittrocki Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14217 Adansonia grandidieri Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO986 Rattus rattus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14412 Aphyllocladus denticulatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8386 Enceliopsis argophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13403 Gadus morhua callarias Species Gadidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16590 Cytophaga hutchinsoni Species Cytophagaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7819.1 Epichloe festucae var. lolii Varieties Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2631 Aster sedifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9448 Dictyopteris australis Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12252 Psychotria stachyoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12079 Dysoxylum cumingianum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13237 Teucrium yemense Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12477 Dodonaea viscosa Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10688 Flacourtia jangomas Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14520 Bassia muricata Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13421 Sphaerella laricina n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15297 Aconitum seravschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13716 Aconitum tasiromontanum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14014 Eriocheir sinensis Species Varunidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1501 Senecio subdentatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4345 Caulocystis cephalornithos Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9752 Miliusa velutina Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22526 Justicia secunda Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2198 Rivularia firma Species Rivulariaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO624 Isaria fumosorosea Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13523 Neobalanocarpus heimii Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11580 Onobrychis arenaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14104 Dendriopoterium menendezii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3214 Lavandula vera Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11749 Eria mollis Species Orchidaceae 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
NPT1 Others Radical scavenging activity IC50 > 100.0 ug.mL-1 PMID[551600]

☑ 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 NPC30432 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 NPC271385
1.0 High Similarity NPC111536
1.0 High Similarity NPC5029
1.0 High Similarity NPC76128
0.9877 High Similarity NPC68381
0.9816 High Similarity NPC46958
0.9816 High Similarity NPC475246
0.9816 High Similarity NPC475233
0.9755 High Similarity NPC3718
0.9752 High Similarity NPC222455
0.9697 High Similarity NPC114257
0.9697 High Similarity NPC277710
0.9697 High Similarity NPC299149
0.9697 High Similarity NPC212290
0.9697 High Similarity NPC153578
0.9693 High Similarity NPC98776
0.9691 High Similarity NPC298778
0.9639 High Similarity NPC477860
0.9639 High Similarity NPC475161
0.9634 High Similarity NPC146803
0.963 High Similarity NPC259905
0.9627 High Similarity NPC178851
0.9573 High Similarity NPC472054
0.9515 High Similarity NPC474345
0.9467 High Similarity NPC87583
0.9455 High Similarity NPC213052
0.9455 High Similarity NPC85368
0.9455 High Similarity NPC199357
0.9441 High Similarity NPC278329
0.9441 High Similarity NPC146837
0.9441 High Similarity NPC212099
0.9441 High Similarity NPC101116
0.9412 High Similarity NPC105591
0.9405 High Similarity NPC315221
0.9398 High Similarity NPC470454
0.9398 High Similarity NPC199533
0.9349 High Similarity NPC313452
0.9325 High Similarity NPC178281
0.9321 High Similarity NPC216752
0.9281 High Similarity NPC63105
0.9273 High Similarity NPC473202
0.9235 High Similarity NPC473717
0.9235 High Similarity NPC475662
0.9235 High Similarity NPC293227
0.9235 High Similarity NPC473631
0.9231 High Similarity NPC245059
0.9231 High Similarity NPC84494
0.9222 High Similarity NPC203751
0.9207 High Similarity NPC478022
0.9207 High Similarity NPC478020
0.9198 High Similarity NPC472320
0.9193 High Similarity NPC23817
0.9176 High Similarity NPC470448
0.9176 High Similarity NPC164047
0.9176 High Similarity NPC470453
0.9176 High Similarity NPC470452
0.9136 High Similarity NPC73511
0.913 High Similarity NPC261866
0.9128 High Similarity NPC473686
0.9128 High Similarity NPC475220
0.9128 High Similarity NPC221140
0.9128 High Similarity NPC229817
0.9128 High Similarity NPC475352
0.9112 High Similarity NPC289876
0.9112 High Similarity NPC102053
0.9096 High Similarity NPC63470
0.9096 High Similarity NPC477502
0.9096 High Similarity NPC249977
0.9091 High Similarity NPC7752
0.9085 High Similarity NPC131745
0.9085 High Similarity NPC44947
0.9085 High Similarity NPC259834
0.908 High Similarity NPC271479
0.908 High Similarity NPC314672
0.908 High Similarity NPC470810
0.9074 High Similarity NPC313163
0.9074 High Similarity NPC161749
0.9074 High Similarity NPC197896
0.9074 High Similarity NPC258035
0.9074 High Similarity NPC156457
0.9068 High Similarity NPC470603
0.9068 High Similarity NPC470604
0.9068 High Similarity NPC470605
0.9068 High Similarity NPC99233
0.9064 High Similarity NPC208069
0.9062 High Similarity NPC40356
0.9062 High Similarity NPC154683
0.9042 High Similarity NPC229687
0.903 High Similarity NPC66087
0.903 High Similarity NPC257566
0.903 High Similarity NPC183672
0.903 High Similarity NPC179198
0.903 High Similarity NPC124155
0.903 High Similarity NPC278419
0.9024 High Similarity NPC303913
0.9024 High Similarity NPC47923
0.9018 High Similarity NPC308265
0.9012 High Similarity NPC208152
0.9012 High Similarity NPC78492
0.9012 High Similarity NPC170475
0.9012 High Similarity NPC206378
0.9012 High Similarity NPC45165
0.9006 High Similarity NPC106625
0.9006 High Similarity NPC268950
0.9006 High Similarity NPC211158
0.9006 High Similarity NPC108706
0.9006 High Similarity NPC78021
0.9006 High Similarity NPC87304
0.9006 High Similarity NPC58538
0.9 High Similarity NPC470569
0.8988 High Similarity NPC241874
0.8988 High Similarity NPC44558
0.8988 High Similarity NPC105511
0.8988 High Similarity NPC478021
0.8988 High Similarity NPC76047
0.8988 High Similarity NPC78734
0.8988 High Similarity NPC150767
0.8988 High Similarity NPC224462
0.8982 High Similarity NPC229729
0.8982 High Similarity NPC45400
0.8982 High Similarity NPC474024
0.8977 High Similarity NPC314459
0.8977 High Similarity NPC470199
0.8976 High Similarity NPC165720
0.897 High Similarity NPC190450
0.897 High Similarity NPC473043
0.897 High Similarity NPC127782
0.897 High Similarity NPC300537
0.8963 High Similarity NPC328093
0.8963 High Similarity NPC470358
0.8957 High Similarity NPC177742
0.8957 High Similarity NPC6985
0.8957 High Similarity NPC470606
0.8957 High Similarity NPC43638
0.8953 High Similarity NPC85316
0.8953 High Similarity NPC197357
0.8951 High Similarity NPC95090
0.8951 High Similarity NPC169248
0.8951 High Similarity NPC27408
0.8951 High Similarity NPC72649
0.8951 High Similarity NPC97052
0.8951 High Similarity NPC39351
0.8951 High Similarity NPC26195
0.8944 High Similarity NPC259767
0.8944 High Similarity NPC259182
0.8944 High Similarity NPC88484
0.8944 High Similarity NPC121001
0.8941 High Similarity NPC108202
0.8941 High Similarity NPC470667
0.8941 High Similarity NPC186800
0.8938 High Similarity NPC147735
0.8938 High Similarity NPC202595
0.8938 High Similarity NPC470568
0.8935 High Similarity NPC260263
0.8935 High Similarity NPC48773
0.8935 High Similarity NPC205076
0.8935 High Similarity NPC256760
0.8935 High Similarity NPC294501
0.8935 High Similarity NPC307518
0.8929 High Similarity NPC470206
0.8929 High Similarity NPC470207
0.8929 High Similarity NPC246274
0.8929 High Similarity NPC472383
0.8929 High Similarity NPC472381
0.8929 High Similarity NPC191653
0.8929 High Similarity NPC183036
0.8922 High Similarity NPC236934
0.8922 High Similarity NPC5778
0.8922 High Similarity NPC70441
0.8922 High Similarity NPC178173
0.892 High Similarity NPC264302
0.8916 High Similarity NPC284960
0.8916 High Similarity NPC168822
0.8916 High Similarity NPC243930
0.8916 High Similarity NPC29830
0.8916 High Similarity NPC19709
0.8916 High Similarity NPC309025
0.8916 High Similarity NPC88023
0.8916 High Similarity NPC222936
0.8916 High Similarity NPC88043
0.8914 High Similarity NPC205721
0.8908 High Similarity NPC241847
0.8902 High Similarity NPC43761
0.8902 High Similarity NPC324736
0.8902 High Similarity NPC470607
0.8902 High Similarity NPC85121
0.8896 High Similarity NPC127406
0.8889 High Similarity NPC83283
0.8889 High Similarity NPC143851
0.8889 High Similarity NPC312630
0.8889 High Similarity NPC469405
0.8889 High Similarity NPC324220
0.8889 High Similarity NPC29763
0.8889 High Similarity NPC39360
0.8889 High Similarity NPC210003
0.8882 High Similarity NPC172033
0.8882 High Similarity NPC175230
0.8882 High Similarity NPC168789
0.8882 High Similarity NPC25724
0.8882 High Similarity NPC154986

  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 NPC30432 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
0.9074 High Similarity NPD4381 Clinical (unspecified phase)
0.8882 High Similarity NPD6559 Discontinued
0.8857 High Similarity NPD7879 Clinical (unspecified phase)
0.8817 High Similarity NPD7804 Clinical (unspecified phase)
0.8795 High Similarity NPD6959 Discontinued
0.8765 High Similarity NPD7074 Phase 3
0.8757 High Similarity NPD3818 Discontinued
0.8706 High Similarity NPD7054 Approved
0.8704 High Similarity NPD4380 Phase 2
0.8671 High Similarity NPD8312 Approved
0.8671 High Similarity NPD8313 Approved
0.8655 High Similarity NPD7472 Approved
0.8605 High Similarity NPD6797 Phase 2
0.8555 High Similarity NPD7251 Discontinued
0.8545 High Similarity NPD2393 Clinical (unspecified phase)
0.8545 High Similarity NPD7819 Suspended
0.8521 High Similarity NPD6232 Discontinued
0.8516 High Similarity NPD6776 Approved
0.8516 High Similarity NPD6779 Approved
0.8516 High Similarity NPD6782 Approved
0.8516 High Similarity NPD6778 Approved
0.8516 High Similarity NPD6780 Approved
0.8516 High Similarity NPD6777 Approved
0.8516 High Similarity NPD6781 Approved
0.8506 High Similarity NPD4338 Clinical (unspecified phase)
0.8506 High Similarity NPD7808 Phase 3
0.8503 High Similarity NPD7075 Discontinued
0.8488 Intermediate Similarity NPD5844 Phase 1
0.848 Intermediate Similarity NPD7473 Discontinued
0.8449 Intermediate Similarity NPD8151 Discontinued
0.8443 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD6166 Phase 2
0.8421 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD7435 Discontinued
0.8373 Intermediate Similarity NPD1934 Approved
0.8323 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7411 Suspended
0.828 Intermediate Similarity NPD7698 Approved
0.828 Intermediate Similarity NPD7696 Phase 3
0.828 Intermediate Similarity NPD7697 Approved
0.8263 Intermediate Similarity NPD6801 Discontinued
0.8242 Intermediate Similarity NPD6534 Approved
0.8242 Intermediate Similarity NPD6535 Approved
0.8235 Intermediate Similarity NPD7871 Phase 2
0.8235 Intermediate Similarity NPD7870 Phase 2
0.8218 Intermediate Similarity NPD3751 Discontinued
0.8201 Intermediate Similarity NPD7701 Phase 2
0.8193 Intermediate Similarity NPD3226 Approved
0.8187 Intermediate Similarity NPD5494 Approved
0.8171 Intermediate Similarity NPD2534 Approved
0.8171 Intermediate Similarity NPD2533 Approved
0.8171 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD2532 Approved
0.8171 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD1549 Phase 2
0.8128 Intermediate Similarity NPD6823 Phase 2
0.8122 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8115 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.8115 Intermediate Similarity NPD7874 Approved
0.8114 Intermediate Similarity NPD7228 Approved
0.8108 Intermediate Similarity NPD7700 Phase 2
0.8108 Intermediate Similarity NPD7699 Phase 2
0.8107 Intermediate Similarity NPD2801 Approved
0.8103 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8073 Intermediate Similarity NPD7801 Approved
0.8073 Intermediate Similarity NPD7783 Phase 2
0.8073 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD5402 Approved
0.8047 Intermediate Similarity NPD37 Approved
0.8036 Intermediate Similarity NPD6599 Discontinued
0.8023 Intermediate Similarity NPD6234 Discontinued
0.8012 Intermediate Similarity NPD4965 Approved
0.8012 Intermediate Similarity NPD4967 Phase 2
0.8012 Intermediate Similarity NPD4966 Approved
0.8012 Intermediate Similarity NPD3882 Suspended
0.8 Intermediate Similarity NPD1465 Phase 2
0.7989 Intermediate Similarity NPD6213 Phase 3
0.7989 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD6212 Phase 3
0.7989 Intermediate Similarity NPD3787 Discontinued
0.7965 Intermediate Similarity NPD3749 Approved
0.7953 Intermediate Similarity NPD3817 Phase 2
0.7947 Intermediate Similarity NPD8320 Phase 1
0.7947 Intermediate Similarity NPD8319 Approved
0.7907 Intermediate Similarity NPD7768 Phase 2
0.7901 Intermediate Similarity NPD2796 Approved
0.7892 Intermediate Similarity NPD6799 Approved
0.7892 Intermediate Similarity NPD7390 Discontinued
0.7892 Intermediate Similarity NPD1511 Approved
0.7857 Intermediate Similarity NPD5403 Approved
0.7853 Intermediate Similarity NPD2346 Discontinued
0.784 Intermediate Similarity NPD1510 Phase 2
0.7829 Intermediate Similarity NPD7199 Phase 2
0.7826 Intermediate Similarity NPD1607 Approved
0.7818 Intermediate Similarity NPD4628 Phase 3
0.7818 Intermediate Similarity NPD3750 Approved
0.7814 Intermediate Similarity NPD8150 Discontinued
0.7805 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD1512 Approved
0.7791 Intermediate Similarity NPD8455 Phase 2
0.7772 Intermediate Similarity NPD7584 Approved
0.7765 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7458 Discontinued
0.776 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD5401 Approved
0.7735 Intermediate Similarity NPD7240 Approved
0.7711 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1240 Approved
0.7684 Intermediate Similarity NPD5710 Approved
0.7684 Intermediate Similarity NPD5711 Approved
0.7651 Intermediate Similarity NPD6674 Discontinued
0.7651 Intermediate Similarity NPD2800 Approved
0.7651 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD5953 Discontinued
0.7576 Intermediate Similarity NPD1551 Phase 2
0.7576 Intermediate Similarity NPD2935 Discontinued
0.7576 Intermediate Similarity NPD6099 Approved
0.7576 Intermediate Similarity NPD6100 Approved
0.7541 Intermediate Similarity NPD7685 Pre-registration
0.7529 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD8434 Phase 2
0.7524 Intermediate Similarity NPD8059 Phase 3
0.7524 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3748 Approved
0.75 Intermediate Similarity NPD1653 Approved
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD3926 Phase 2
0.7442 Intermediate Similarity NPD920 Approved
0.7427 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD2799 Discontinued
0.7377 Intermediate Similarity NPD7286 Phase 2
0.7374 Intermediate Similarity NPD7585 Approved
0.7365 Intermediate Similarity NPD5408 Approved
0.7365 Intermediate Similarity NPD5404 Approved
0.7365 Intermediate Similarity NPD5405 Approved
0.7365 Intermediate Similarity NPD5406 Approved
0.7362 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1243 Approved
0.7333 Intermediate Similarity NPD1247 Approved
0.7326 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD7583 Approved
0.7321 Intermediate Similarity NPD2344 Approved
0.732 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD8285 Discontinued
0.7318 Intermediate Similarity NPD919 Approved
0.7312 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD4625 Phase 3
0.7293 Intermediate Similarity NPD7229 Phase 3
0.7292 Intermediate Similarity NPD4360 Phase 2
0.7292 Intermediate Similarity NPD4363 Phase 3
0.7289 Intermediate Similarity NPD6651 Approved
0.7283 Intermediate Similarity NPD6273 Approved
0.7273 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD943 Approved
0.7273 Intermediate Similarity NPD1613 Approved
0.7267 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1470 Approved
0.7256 Intermediate Similarity NPD2313 Discontinued
0.7256 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7930 Approved
0.7239 Intermediate Similarity NPD4908 Phase 1
0.7235 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD230 Phase 1
0.7228 Intermediate Similarity NPD7177 Discontinued
0.7219 Intermediate Similarity NPD7266 Discontinued
0.7209 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7003 Approved
0.7172 Intermediate Similarity NPD7680 Approved
0.7151 Intermediate Similarity NPD2309 Approved
0.7151 Intermediate Similarity NPD6190 Approved
0.7126 Intermediate Similarity NPD1933 Approved
0.7117 Intermediate Similarity NPD2798 Approved
0.7115 Intermediate Similarity NPD8366 Approved
0.7101 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD5760 Phase 2
0.7095 Intermediate Similarity NPD5761 Phase 2
0.7083 Intermediate Similarity NPD4287 Approved
0.7079 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD4060 Phase 1
0.7053 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD8127 Discontinued
0.7048 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7097 Phase 1
0.7039 Intermediate Similarity NPD6844 Discontinued
0.7033 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6832 Phase 2

  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