Structure

Physi-Chem Properties

Molecular Weight:  289.17
Volume:  303.74
LogP:  1.881
LogD:  0.86
LogS:  -2.16
# Rotatable Bonds:  5
TPSA:  49.77
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.861
Synthetic Accessibility Score:  4.071
Fsp3:  0.588
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:  -4.924
MDCK Permeability:  6.368821050273255e-05
Pgp-inhibitor:  0.011
Pgp-substrate:  0.713
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.221
Plasma Protein Binding (PPB):  42.333736419677734%
Volume Distribution (VD):  2.405
Pgp-substrate:  66.20044708251953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.032
CYP1A2-substrate:  0.091
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.91
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.292
CYP2D6-inhibitor:  0.605
CYP2D6-substrate:  0.836
CYP3A4-inhibitor:  0.189
CYP3A4-substrate:  0.767

ADMET: Excretion

Clearance (CL):  5.557
Half-life (T1/2):  0.14

ADMET: Toxicity

hERG Blockers:  0.235
Human Hepatotoxicity (H-HT):  0.972
Drug-inuced Liver Injury (DILI):  0.622
AMES Toxicity:  0.101
Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.989
Skin Sensitization:  0.913
Carcinogencity:  0.194
Eye Corrosion:  0.004
Eye Irritation:  0.019
Respiratory Toxicity:  0.912

Download Data

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

  Natural Product: NPC213126

Natural Product ID:  NPC213126
Common Name*:   Hyoscyamine
IUPAC Name:   n.a.
Synonyms:   Hyoscyamine
Standard InCHIKey:  RKUNBYITZUJHSG-FXUDXRNXSA-N
Standard InCHI:  InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
SMILES:  OC[C@H](c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1331216
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000492] Tropane alkaloids

*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
NPO16999 Paeonia emodi Species Paeoniaceae Eukaryota n.a. root n.a. PMID[12612406]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[15387648]
NPO9587 Saussurea laniceps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15921425]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. PMID[20121165]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota leaves n.a. n.a. PMID[20666364]
NPO21393 Datura inoxia Species Solanaceae Eukaryota n.a. leaf n.a. PMID[21280589]
NPO21393 Datura inoxia Species Solanaceae Eukaryota n.a. flower n.a. PMID[21280589]
NPO7191 Mimosa pudica Species Fabaceae Eukaryota n.a. root n.a. PMID[26661932]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[32468815]
NPO10071 Ipomopsis aggregata Species Polemoniaceae Eukaryota n.a. n.a. n.a. PMID[6736973]
NPO11089 Sanicula europaea Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[9392884]
NPO1865 Penicillium raistrickii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9748377]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16999 Paeonia emodi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1854 Cardiospermum hirsutum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7191 Mimosa pudica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10384 Scopolia carniolica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10384 Scopolia carniolica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16464 Podocarpus philippinensis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7191 Mimosa pudica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21393 Datura inoxia Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11086 Maesa chisia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9587 Saussurea laniceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1854 Cardiospermum hirsutum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13850 Bazzania trilobata Species Lepidoziaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5201 Peucedanum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16999 Paeonia emodi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11086 Maesa chisia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16464 Podocarpus philippinensis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15163 Euphorbia stepposa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10384 Scopolia carniolica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14957 Byssomerulius corium Species Irpicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26585 Botrylloides leachii Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16333 Chenopodium album Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24530 Ulva reticulata Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12260 Penicillium aragonense Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12621 Celastrus rosthornianus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16843 Euonymus revolutus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11361 Pelargonium quercifolium Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8906 Baptisia versicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16999 Paeonia emodi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10384 Scopolia carniolica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13850 Bazzania trilobata Species Lepidoziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11089 Sanicula europaea Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7191 Mimosa pudica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10071 Ipomopsis aggregata Species Polemoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11377 Vespa orientalis Species Vespidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8657 Mikania batatifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2527 Physochlaina orientalis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12629 Potentilla argentea Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15163 Euphorbia stepposa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14552 Stevia tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4787 Capuronianthus mahafalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10047 Psychotria correae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14263 Cipadessa baccifera Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9587 Saussurea laniceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10848 Ligularia speciosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10756 Callitris drummondii Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14410 Doris odhneri Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14011 Sargassum yezoense Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11086 Maesa chisia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7940 Leiothrix curvifolia Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13602 Lavandula multifida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5201 Peucedanum officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21393 Datura inoxia Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16464 Podocarpus philippinensis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27933 Sarcostemma clausum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5830 Ilex canariensis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7015 Fagara chalybea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16093 Achillea atrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1854 Cardiospermum hirsutum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9779 Streptomyces endus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7945 Tecomella undulata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10096 Streptomyces flaveolus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17581 Streptomyces fulvoviridis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1865 Penicillium raistrickii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17634 Lycopodium carinatum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25348 Metapochonia suchlasporia Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11703 Terpios hoshinota Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7152 Centaurea hyrcanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8002 Solanum olgae Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9411 Alternaria radicina Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13345 Dendrobium farmerii 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
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 8912.5 nM PMID[525865]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 1031.8 nM PMID[525865]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 183.6 nM PMID[525865]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 15.53 % PMID[525866]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2936.2 nM PMID[525865]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 6513.1 nM PMID[525865]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[525865]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 3.5 % PMID[525866]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 97.76 % PMID[525867]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 102.17 % PMID[525867]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens Potency n.a. 29934.9 nM PMID[525865]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 1000000.0 nM PMID[525868]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.2122 n.a. PMID[525869]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.25 % PMID[525870]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.0469 n.a. PMID[525871]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 28.35 % PMID[525872]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.15 % PMID[525873]

☑ 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 NPC213126 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 NPC317474
1.0 High Similarity NPC291027
1.0 High Similarity NPC84281
1.0 High Similarity NPC169485
0.9421 High Similarity NPC69496
0.9194 High Similarity NPC245836
0.9194 High Similarity NPC233910
0.878 High Similarity NPC474847
0.871 High Similarity NPC65310
0.822 Intermediate Similarity NPC158854
0.8195 Intermediate Similarity NPC281104
0.8095 Intermediate Similarity NPC26285
0.7829 Intermediate Similarity NPC285394
0.7795 Intermediate Similarity NPC80150
0.768 Intermediate Similarity NPC188010
0.7647 Intermediate Similarity NPC19136
0.763 Intermediate Similarity NPC313663
0.7623 Intermediate Similarity NPC65855
0.7623 Intermediate Similarity NPC292758
0.7519 Intermediate Similarity NPC478016
0.7519 Intermediate Similarity NPC190663
0.7519 Intermediate Similarity NPC478014
0.7519 Intermediate Similarity NPC478015
0.7518 Intermediate Similarity NPC260045
0.7518 Intermediate Similarity NPC475318
0.7518 Intermediate Similarity NPC49577
0.7518 Intermediate Similarity NPC474855
0.7518 Intermediate Similarity NPC476102
0.7518 Intermediate Similarity NPC76785
0.7518 Intermediate Similarity NPC151706
0.7518 Intermediate Similarity NPC79465
0.7518 Intermediate Similarity NPC273907
0.7518 Intermediate Similarity NPC475598
0.7518 Intermediate Similarity NPC474787
0.7518 Intermediate Similarity NPC293377
0.7518 Intermediate Similarity NPC118099
0.7518 Intermediate Similarity NPC90194
0.7518 Intermediate Similarity NPC474811
0.7518 Intermediate Similarity NPC9687
0.75 Intermediate Similarity NPC310467
0.7448 Intermediate Similarity NPC162104
0.7422 Intermediate Similarity NPC169328
0.7413 Intermediate Similarity NPC145113
0.7405 Intermediate Similarity NPC160493
0.7376 Intermediate Similarity NPC57976
0.7376 Intermediate Similarity NPC161069
0.7368 Intermediate Similarity NPC47667
0.7347 Intermediate Similarity NPC68967
0.7333 Intermediate Similarity NPC103605
0.7333 Intermediate Similarity NPC81092
0.7324 Intermediate Similarity NPC471516
0.7324 Intermediate Similarity NPC476978
0.7305 Intermediate Similarity NPC263493
0.7305 Intermediate Similarity NPC269398
0.7292 Intermediate Similarity NPC225648
0.7292 Intermediate Similarity NPC329761
0.7252 Intermediate Similarity NPC45777
0.7252 Intermediate Similarity NPC477061
0.7236 Intermediate Similarity NPC474111
0.7236 Intermediate Similarity NPC329705
0.7227 Intermediate Similarity NPC322598
0.7227 Intermediate Similarity NPC271475
0.7172 Intermediate Similarity NPC138775
0.7154 Intermediate Similarity NPC476198
0.7153 Intermediate Similarity NPC209509
0.7153 Intermediate Similarity NPC5620
0.7143 Intermediate Similarity NPC477767
0.7113 Intermediate Similarity NPC163392
0.7113 Intermediate Similarity NPC239762
0.7105 Intermediate Similarity NPC322387
0.7092 Intermediate Similarity NPC478140
0.7092 Intermediate Similarity NPC471265
0.7092 Intermediate Similarity NPC471264
0.709 Intermediate Similarity NPC35996
0.7069 Intermediate Similarity NPC86670
0.7069 Intermediate Similarity NPC274455
0.7069 Intermediate Similarity NPC70940
0.7044 Intermediate Similarity NPC476441
0.7042 Intermediate Similarity NPC92784
0.7042 Intermediate Similarity NPC476133
0.7042 Intermediate Similarity NPC178662
0.7042 Intermediate Similarity NPC470884
0.7042 Intermediate Similarity NPC98424
0.7025 Intermediate Similarity NPC12730
0.7016 Intermediate Similarity NPC67043
0.7016 Intermediate Similarity NPC167336
0.7016 Intermediate Similarity NPC321670
0.7014 Intermediate Similarity NPC251439
0.7009 Intermediate Similarity NPC141607
0.7009 Intermediate Similarity NPC187725
0.7007 Intermediate Similarity NPC105114
0.7007 Intermediate Similarity NPC71933
0.7007 Intermediate Similarity NPC89923
0.7007 Intermediate Similarity NPC239990
0.7007 Intermediate Similarity NPC152850
0.6993 Remote Similarity NPC46098
0.6993 Remote Similarity NPC268841
0.6993 Remote Similarity NPC307357
0.6985 Remote Similarity NPC317163
0.6983 Remote Similarity NPC9822
0.6974 Remote Similarity NPC29285
0.6972 Remote Similarity NPC127741
0.697 Remote Similarity NPC237420
0.697 Remote Similarity NPC314992
0.6967 Remote Similarity NPC214200
0.6967 Remote Similarity NPC228400
0.6963 Remote Similarity NPC175726
0.6963 Remote Similarity NPC474082
0.6963 Remote Similarity NPC108286
0.6963 Remote Similarity NPC6975
0.6959 Remote Similarity NPC94602
0.6959 Remote Similarity NPC129666
0.6959 Remote Similarity NPC2501
0.6957 Remote Similarity NPC213969
0.6957 Remote Similarity NPC116057
0.6957 Remote Similarity NPC165726
0.695 Remote Similarity NPC248283
0.6934 Remote Similarity NPC136453
0.6933 Remote Similarity NPC122590
0.693 Remote Similarity NPC294134
0.6929 Remote Similarity NPC246913
0.6928 Remote Similarity NPC153694
0.6928 Remote Similarity NPC211525
0.6923 Remote Similarity NPC84288
0.6911 Remote Similarity NPC474820
0.6911 Remote Similarity NPC475978
0.6905 Remote Similarity NPC20485
0.6897 Remote Similarity NPC139326
0.6889 Remote Similarity NPC252878
0.6884 Remote Similarity NPC305717
0.6884 Remote Similarity NPC319766
0.6883 Remote Similarity NPC133817
0.6883 Remote Similarity NPC263709
0.6883 Remote Similarity NPC310403
0.6883 Remote Similarity NPC97380
0.6883 Remote Similarity NPC63210
0.6883 Remote Similarity NPC243673
0.6883 Remote Similarity NPC148468
0.6883 Remote Similarity NPC476443
0.6879 Remote Similarity NPC287401
0.6871 Remote Similarity NPC314358
0.6864 Remote Similarity NPC317645
0.6863 Remote Similarity NPC297145
0.6863 Remote Similarity NPC197743
0.6861 Remote Similarity NPC4974
0.6861 Remote Similarity NPC477249
0.6861 Remote Similarity NPC477248
0.686 Remote Similarity NPC293628
0.686 Remote Similarity NPC122493
0.686 Remote Similarity NPC10781
0.686 Remote Similarity NPC324569
0.6857 Remote Similarity NPC157311
0.6855 Remote Similarity NPC160382
0.6846 Remote Similarity NPC172525
0.6838 Remote Similarity NPC46427
0.6838 Remote Similarity NPC231591
0.6835 Remote Similarity NPC469666
0.6835 Remote Similarity NPC472413
0.6833 Remote Similarity NPC206764
0.6831 Remote Similarity NPC477680
0.6829 Remote Similarity NPC94487
0.6828 Remote Similarity NPC150712
0.6825 Remote Similarity NPC475905
0.6825 Remote Similarity NPC94751
0.6825 Remote Similarity NPC142326
0.6825 Remote Similarity NPC193640
0.6825 Remote Similarity NPC25385
0.6824 Remote Similarity NPC135121
0.6822 Remote Similarity NPC269340
0.6818 Remote Similarity NPC2265
0.6815 Remote Similarity NPC52059
0.6815 Remote Similarity NPC202521
0.6815 Remote Similarity NPC472106
0.6815 Remote Similarity NPC470069
0.6813 Remote Similarity NPC476425
0.6809 Remote Similarity NPC8761
0.6809 Remote Similarity NPC44805
0.6803 Remote Similarity NPC313867
0.6803 Remote Similarity NPC316008
0.6795 Remote Similarity NPC476750
0.6794 Remote Similarity NPC33742
0.6788 Remote Similarity NPC138798
0.6788 Remote Similarity NPC236981
0.6788 Remote Similarity NPC307020
0.6781 Remote Similarity NPC176226
0.6779 Remote Similarity NPC240848
0.6774 Remote Similarity NPC474112
0.6769 Remote Similarity NPC273814
0.6769 Remote Similarity NPC474584
0.6759 Remote Similarity NPC476259
0.6757 Remote Similarity NPC297322
0.6757 Remote Similarity NPC262077
0.6754 Remote Similarity NPC288903
0.6754 Remote Similarity NPC270507
0.6754 Remote Similarity NPC285773
0.6754 Remote Similarity NPC44830
0.6752 Remote Similarity NPC329064
0.6748 Remote Similarity NPC476042
0.6746 Remote Similarity NPC474307
0.6744 Remote Similarity NPC319579

  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 NPC213126 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
1.0 High Similarity NPD2609 Approved
1.0 High Similarity NPD4216 Approved
1.0 High Similarity NPD3131 Approved
1.0 High Similarity NPD2612 Approved
1.0 High Similarity NPD2608 Approved
1.0 High Similarity NPD3132 Approved
1.0 High Similarity NPD4218 Approved
1.0 High Similarity NPD2610 Approved
1.0 High Similarity NPD2611 Approved
1.0 High Similarity NPD4215 Approved
1.0 High Similarity NPD4217 Approved
0.9421 High Similarity NPD2613 Approved
0.9194 High Similarity NPD3090 Approved
0.9194 High Similarity NPD3616 Approved
0.9194 High Similarity NPD4745 Approved
0.9194 High Similarity NPD2570 Approved
0.9194 High Similarity NPD3087 Approved
0.9194 High Similarity NPD3614 Approved
0.9194 High Similarity NPD3089 Approved
0.9194 High Similarity NPD3615 Approved
0.9194 High Similarity NPD4746 Phase 3
0.9194 High Similarity NPD2566 Approved
0.9194 High Similarity NPD2574 Discontinued
0.9194 High Similarity NPD2571 Approved
0.9194 High Similarity NPD2572 Clinical (unspecified phase)
0.9194 High Similarity NPD2573 Approved
0.9194 High Similarity NPD3088 Approved
0.9048 High Similarity NPD4684 Phase 3
0.9048 High Similarity NPD4685 Phase 3
0.9048 High Similarity NPD4686 Approved
0.871 High Similarity NPD2160 Approved
0.871 High Similarity NPD2628 Approved
0.871 High Similarity NPD2626 Approved
0.871 High Similarity NPD2625 Approved
0.871 High Similarity NPD2159 Approved
0.871 High Similarity NPD2627 Approved
0.8403 Intermediate Similarity NPD2652 Approved
0.8403 Intermediate Similarity NPD2650 Approved
0.837 Intermediate Similarity NPD2575 Approved
0.8347 Intermediate Similarity NPD4574 Approved
0.8347 Intermediate Similarity NPD4576 Approved
0.8244 Intermediate Similarity NPD6310 Approved
0.8244 Intermediate Similarity NPD6311 Approved
0.8244 Intermediate Similarity NPD6309 Approved
0.822 Intermediate Similarity NPD1756 Approved
0.822 Intermediate Similarity NPD1752 Approved
0.8195 Intermediate Similarity NPD2569 Approved
0.8195 Intermediate Similarity NPD2567 Approved
0.8167 Intermediate Similarity NPD2607 Approved
0.813 Intermediate Similarity NPD2117 Pre-registration
0.813 Intermediate Similarity NPD2116 Approved
0.813 Intermediate Similarity NPD2115 Approved
0.8099 Intermediate Similarity NPD1371 Approved
0.8099 Intermediate Similarity NPD1373 Approved
0.8099 Intermediate Similarity NPD1370 Approved
0.8099 Intermediate Similarity NPD1374 Approved
0.8065 Intermediate Similarity NPD2994 Approved
0.8 Intermediate Similarity NPD3032 Approved
0.8 Intermediate Similarity NPD5204 Approved
0.8 Intermediate Similarity NPD3661 Approved
0.8 Intermediate Similarity NPD3031 Approved
0.8 Intermediate Similarity NPD3664 Approved
0.8 Intermediate Similarity NPD3663 Approved
0.8 Intermediate Similarity NPD3648 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3030 Approved
0.8 Intermediate Similarity NPD3662 Phase 3
0.7955 Intermediate Similarity NPD4621 Approved
0.7955 Intermediate Similarity NPD4619 Approved
0.7939 Intermediate Similarity NPD5202 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD2946 Phase 2
0.7829 Intermediate Similarity NPD5159 Phase 2
0.7829 Intermediate Similarity NPD5157 Phase 1
0.7829 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD5704 Approved
0.7815 Intermediate Similarity NPD5705 Approved
0.7815 Intermediate Similarity NPD5706 Approved
0.7803 Intermediate Similarity NPD5203 Approved
0.7803 Intermediate Similarity NPD4617 Approved
0.7803 Intermediate Similarity NPD5201 Approved
0.7803 Intermediate Similarity NPD4620 Approved
0.7769 Intermediate Similarity NPD3646 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD5667 Approved
0.7742 Intermediate Similarity NPD4766 Approved
0.7705 Intermediate Similarity NPD2201 Approved
0.7704 Intermediate Similarity NPD5121 Approved
0.7704 Intermediate Similarity NPD5119 Approved
0.7704 Intermediate Similarity NPD5120 Approved
0.7661 Intermediate Similarity NPD3598 Phase 3
0.7656 Intermediate Similarity NPD5306 Approved
0.7656 Intermediate Similarity NPD5305 Approved
0.763 Intermediate Similarity NPD7715 Approved
0.763 Intermediate Similarity NPD7714 Approved
0.7623 Intermediate Similarity NPD4233 Approved
0.7623 Intermediate Similarity NPD4234 Approved
0.76 Intermediate Similarity NPD1711 Phase 2
0.7576 Intermediate Similarity NPD6564 Approved
0.7576 Intermediate Similarity NPD6563 Approved
0.7576 Intermediate Similarity NPD6565 Approved
0.7538 Intermediate Similarity NPD7437 Approved
0.7538 Intermediate Similarity NPD4806 Approved
0.7538 Intermediate Similarity NPD7436 Approved
0.7538 Intermediate Similarity NPD4807 Approved
0.75 Intermediate Similarity NPD4571 Approved
0.75 Intermediate Similarity NPD4573 Approved
0.75 Intermediate Similarity NPD4572 Approved
0.7479 Intermediate Similarity NPD4719 Phase 2
0.7462 Intermediate Similarity NPD4136 Approved
0.7462 Intermediate Similarity NPD4106 Approved
0.7462 Intermediate Similarity NPD4135 Approved
0.7442 Intermediate Similarity NPD6993 Approved
0.7442 Intermediate Similarity NPD6994 Approved
0.7422 Intermediate Similarity NPD6065 Approved
0.7379 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7702 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6792 Phase 3
0.7353 Intermediate Similarity NPD4738 Phase 2
0.7348 Intermediate Similarity NPD2584 Suspended
0.7343 Intermediate Similarity NPD7488 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD5237 Approved
0.7339 Intermediate Similarity NPD5239 Approved
0.7339 Intermediate Similarity NPD5240 Approved
0.7339 Intermediate Similarity NPD5236 Approved
0.7339 Intermediate Similarity NPD5235 Approved
0.7338 Intermediate Similarity NPD8172 Phase 2
0.7338 Intermediate Similarity NPD8173 Phase 2
0.7308 Intermediate Similarity NPD4102 Approved
0.7308 Intermediate Similarity NPD5981 Approved
0.7308 Intermediate Similarity NPD4105 Approved
0.728 Intermediate Similarity NPD3644 Approved
0.728 Intermediate Similarity NPD3643 Approved
0.728 Intermediate Similarity NPD5927 Discontinued
0.728 Intermediate Similarity NPD3642 Approved
0.7273 Intermediate Similarity NPD3681 Approved
0.7273 Intermediate Similarity NPD3683 Approved
0.7273 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3680 Approved
0.7273 Intermediate Similarity NPD3682 Approved
0.7246 Intermediate Similarity NPD7086 Phase 2
0.7231 Intermediate Similarity NPD6343 Approved
0.7231 Intermediate Similarity NPD4479 Discontinued
0.7231 Intermediate Similarity NPD6345 Approved
0.7214 Intermediate Similarity NPD1654 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4175 Approved
0.7206 Intermediate Similarity NPD4177 Approved
0.719 Intermediate Similarity NPD6024 Approved
0.719 Intermediate Similarity NPD6027 Approved
0.7188 Intermediate Similarity NPD747 Discontinued
0.7183 Intermediate Similarity NPD7511 Approved
0.7183 Intermediate Similarity NPD7512 Approved
0.7177 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD6852 Discontinued
0.7154 Intermediate Similarity NPD5991 Approved
0.7154 Intermediate Similarity NPD7522 Discontinued
0.7154 Intermediate Similarity NPD5990 Approved
0.7143 Intermediate Similarity NPD3529 Phase 2
0.7133 Intermediate Similarity NPD4152 Approved
0.7131 Intermediate Similarity NPD4229 Approved
0.7131 Intermediate Similarity NPD4231 Approved
0.7119 Intermediate Similarity NPD1693 Approved
0.7111 Intermediate Similarity NPD2198 Approved
0.7111 Intermediate Similarity NPD2199 Approved
0.7097 Intermediate Similarity NPD3524 Approved
0.7097 Intermediate Similarity NPD3526 Approved
0.7092 Intermediate Similarity NPD6073 Approved
0.708 Intermediate Similarity NPD5759 Approved
0.7077 Intermediate Similarity NPD5162 Approved
0.7071 Intermediate Similarity NPD5185 Approved
0.7071 Intermediate Similarity NPD5184 Approved
0.7071 Intermediate Similarity NPD8416 Discontinued
0.7071 Intermediate Similarity NPD5182 Approved
0.7071 Intermediate Similarity NPD4153 Approved
0.7069 Intermediate Similarity NPD1090 Approved
0.7069 Intermediate Similarity NPD1086 Approved
0.7069 Intermediate Similarity NPD1089 Approved
0.7067 Intermediate Similarity NPD6591 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1989 Approved
0.7049 Intermediate Similarity NPD854 Approved
0.7049 Intermediate Similarity NPD855 Approved
0.7049 Intermediate Similarity NPD4817 Approved
0.7049 Intermediate Similarity NPD4818 Approved
0.704 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4677 Discontinued
0.7025 Intermediate Similarity NPD2066 Phase 3
0.7015 Intermediate Similarity NPD5618 Discontinued
0.7008 Intermediate Similarity NPD4025 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7713 Phase 3
0.7 Intermediate Similarity NPD4655 Approved
0.7 Intermediate Similarity NPD4657 Approved
0.6986 Remote Similarity NPD6676 Phase 2
0.6984 Remote Similarity NPD4720 Approved
0.6984 Remote Similarity NPD4717 Approved
0.6984 Remote Similarity NPD4718 Approved
0.6983 Remote Similarity NPD800 Approved
0.6978 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6039 Approved
0.6974 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6972 Remote Similarity NPD7510 Approved
0.6972 Remote Similarity NPD5725 Approved
0.697 Remote Similarity NPD2217 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