Structure

Physi-Chem Properties

Molecular Weight:  266.13
Volume:  299.26
LogP:  3.647
LogD:  3.522
LogS:  -3.501
# Rotatable Bonds:  3
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.797
Synthetic Accessibility Score:  2.35
Fsp3:  0.111
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.972
MDCK Permeability:  1.2616732419701293e-05
Pgp-inhibitor:  0.043
Pgp-substrate:  0.015
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.072
Plasma Protein Binding (PPB):  94.73686981201172%
Volume Distribution (VD):  0.804
Pgp-substrate:  2.4160172939300537%

ADMET: Metabolism

CYP1A2-inhibitor:  0.942
CYP1A2-substrate:  0.82
CYP2C19-inhibitor:  0.94
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.713
CYP2C9-substrate:  0.959
CYP2D6-inhibitor:  0.96
CYP2D6-substrate:  0.704
CYP3A4-inhibitor:  0.834
CYP3A4-substrate:  0.294

ADMET: Excretion

Clearance (CL):  11.54
Half-life (T1/2):  0.911

ADMET: Toxicity

hERG Blockers:  0.829
Human Hepatotoxicity (H-HT):  0.797
Drug-inuced Liver Injury (DILI):  0.083
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.382
Maximum Recommended Daily Dose:  0.651
Skin Sensitization:  0.175
Carcinogencity:  0.329
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.339

Download Data

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

  Natural Product: NPC26244

Natural Product ID:  NPC26244
Common Name*:   Dienestrol
IUPAC Name:   4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
Synonyms:   Dienestrol; DV; Estraguard; Hormofemin
Standard InCHIKey:  NFDFQCUYFHCNBW-SCGPFSFSSA-N
Standard InCHI:  InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
SMILES:  C/C=C(c1ccc(cc1)O)/C(=C/C)/c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1018
PubChem CID:   667476
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

*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
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. stem n.a. PMID[18175990]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 1995.3 nM PMID[573689]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 10000.0 nM PMID[573689]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 25118.9 nM PMID[573690]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 19952.6 nM PMID[573689]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 31622.8 nM PMID[573690]
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 10000.0 nM PMID[573689]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 22387.2 nM PMID[573689]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 8912.5 nM PMID[573689]
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens Potency = 25118.9 nM PMID[573689]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens EC50 = 13241.54 nM PMID[573689]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 316.2 nM PMID[573689]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 19952.6 nM PMID[573689]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 28183.8 nM PMID[573689]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 7943.3 nM PMID[573689]
NPT226 Individual Protein Beta-2 adrenergic receptor Homo sapiens Potency n.a. 1458.1 nM PMID[573689]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 89125.1 nM PMID[573689]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 79432.8 nM PMID[573689]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens Potency n.a. 15848.9 nM PMID[573689]
NPT1861 Individual Protein Mitochondrial import inner membrane translocase subunit TIM10 Saccharomyces cerevisiae S288c IC50 = 25600.0 nM PMID[573689]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 15848.9 nM PMID[573691]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 35481.3 nM PMID[573691]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 25929.0 nM PMID[573689]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 26854.5 nM PMID[573689]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 4610.9 nM PMID[573689]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 4109.5 nM PMID[573691]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 17782.8 nM PMID[573691]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 7943.3 nM PMID[573691]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 29092.9 nM PMID[573689]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 22387.2 nM PMID[573691]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 12589.3 nM PMID[573691]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[573693]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16360.1 nM PMID[573693]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 7307.8 nM PMID[573691]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 50118.7 nM PMID[573691]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 44668.4 nM PMID[573691]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 891250.9 nM PMID[573689]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 11455.4 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 14958.9 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 33488.9 nM PubChem BioAssay data set
NPT25153 PROTEIN FAMILY Estrogen receptor Mus musculus RBA = 20.0 n.a. PMID[573686]
NPT35 Others n.a. LogP = 4.5 n.a. PMID[573687]
NPT27 Others Unspecified log Pe = -4.53 n.a. PMID[573687]
NPT1414 Organism Drosophila Drosophila Activity = 33.0 % PMID[573688]
NPT1414 Organism Drosophila Drosophila Activity = 71.3 % PMID[573688]
NPT2 Others Unspecified Potency = 29092.9 nM PMID[573689]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 25118.9 nM PMID[573689]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 31622.8 nM PMID[573690]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PMID[573689]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 580.5 nM PMID[573691]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[573691]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens Activity = 0.0 pm/min/mg PMID[573692]
NPT704 Individual Protein UDP-glucuronosyltransferase 2B15 Homo sapiens Activity = 26.0 pm/min/mg PMID[573692]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[573691]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 7079.5 nM PMID[573691]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 61.94 % PMID[573694]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 48.7 % PMID[573694]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[573693]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[573695]
NPT2 Others Unspecified Ac50 n.a. 8.913 uM PMID[573696]
NPT2 Others Unspecified AC50 n.a. 8912.5 nM PMID[573696]
NPT2 Others Unspecified Potency n.a. 44668.4 nM PMID[573691]
NPT2 Others Unspecified Ac50 n.a. 28.18 uM PMID[573696]
NPT2 Others Unspecified IC50 n.a. 40000.0 nM PMID[573696]
NPT2 Others Unspecified Ac50 n.a. 35.48 uM PMID[573696]
NPT2 Others Unspecified AC50 n.a. 28183.8 nM PMID[573696]
NPT2 Others Unspecified AC50 n.a. 35481.3 nM PMID[573696]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = -0.1001 n.a. PMID[573697]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 4.06 % PMID[573698]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.02745 n.a. PMID[573699]
NPT474 Organism Plasmodium berghei Plasmodium berghei LUCIFERASE INFECTION ASSAY - IC50 = 1.24 uM PMID[573700]
NPT474 Organism Plasmodium berghei Plasmodium berghei LUCIFERASE INFECTION ASSAY - IC90 > 12.4 uM PMID[573700]
NPT25144 CELL-LINE HepG2-CD81 Homo sapiens HEPG2TOX ASSAY - CC50 = 1.24 uM PMID[573700]
NPT25144 CELL-LINE HepG2-CD81 Homo sapiens HEPG2TOX ASSAY - CC90 = 1.24 uM PMID[573700]
NPT474 Organism Plasmodium berghei Plasmodium berghei LUCIFERASE EXPRESSION CONTROL - IC50 = 1.99 uM PMID[573700]
NPT474 Organism Plasmodium berghei Plasmodium berghei LUCIFERASE EXPRESSION CONTROL - IC90 = 1.99 uM PMID[573700]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.77 % PMID[573701]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.1 % PMID[573702]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[573703]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[573703]
NPT2 Others Unspecified Potency n.a. 14299.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29847 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 0.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3201.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2285.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 0.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33488.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 298.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12744.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9022.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15089 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 11358.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13332.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26601.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 213.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23914.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26603.2 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 NPC26244 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9889 High Similarity NPC473388
0.9888 High Similarity NPC151715
0.9663 High Similarity NPC45040
0.9462 High Similarity NPC216468
0.9462 High Similarity NPC92730
0.9462 High Similarity NPC51333
0.9462 High Similarity NPC78119
0.9462 High Similarity NPC132078
0.9457 High Similarity NPC292730
0.9457 High Similarity NPC216520
0.9457 High Similarity NPC82664
0.9457 High Similarity NPC132271
0.9451 High Similarity NPC128062
0.9438 High Similarity NPC280347
0.9438 High Similarity NPC123273
0.9438 High Similarity NPC177420
0.9438 High Similarity NPC318325
0.9438 High Similarity NPC242240
0.9362 High Similarity NPC213730
0.9355 High Similarity NPC225464
0.9348 High Similarity NPC274678
0.9333 High Similarity NPC55561
0.9326 High Similarity NPC113460
0.9326 High Similarity NPC25493
0.9263 High Similarity NPC40258
0.9263 High Similarity NPC91461
0.9263 High Similarity NPC7686
0.9239 High Similarity NPC76938
0.9222 High Similarity NPC258219
0.9213 High Similarity NPC23167
0.9175 High Similarity NPC154899
0.9175 High Similarity NPC233396
0.9175 High Similarity NPC138942
0.9167 High Similarity NPC168829
0.914 High Similarity NPC32714
0.9101 High Similarity NPC197783
0.9082 High Similarity NPC113457
0.9082 High Similarity NPC92623
0.9082 High Similarity NPC135464
0.9072 High Similarity NPC261573
0.9072 High Similarity NPC120693
0.9072 High Similarity NPC8931
0.9072 High Similarity NPC288411
0.9032 High Similarity NPC27323
0.9032 High Similarity NPC316301
0.9022 High Similarity NPC304541
0.9022 High Similarity NPC270547
0.9011 High Similarity NPC98772
0.9 High Similarity NPC184169
0.8989 High Similarity NPC248817
0.8989 High Similarity NPC175313
0.898 High Similarity NPC474839
0.8969 High Similarity NPC135784
0.8958 High Similarity NPC294741
0.8947 High Similarity NPC201967
0.8925 High Similarity NPC162314
0.8925 High Similarity NPC138117
0.8925 High Similarity NPC325292
0.8925 High Similarity NPC210497
0.8925 High Similarity NPC306884
0.8925 High Similarity NPC94139
0.8925 High Similarity NPC147284
0.8925 High Similarity NPC3358
0.8925 High Similarity NPC271440
0.8913 High Similarity NPC300017
0.8913 High Similarity NPC192
0.89 High Similarity NPC61885
0.89 High Similarity NPC63698
0.89 High Similarity NPC11554
0.8889 High Similarity NPC188677
0.8889 High Similarity NPC271274
0.8878 High Similarity NPC119860
0.8876 High Similarity NPC124436
0.8876 High Similarity NPC265146
0.8854 High Similarity NPC128723
0.8854 High Similarity NPC130193
0.8817 High Similarity NPC204210
0.8817 High Similarity NPC155908
0.8812 High Similarity NPC254833
0.8812 High Similarity NPC228343
0.8791 High Similarity NPC307235
0.8791 High Similarity NPC407
0.8788 High Similarity NPC99557
0.8788 High Similarity NPC219286
0.8763 High Similarity NPC225506
0.875 High Similarity NPC32674
0.875 High Similarity NPC77492
0.8737 High Similarity NPC8392
0.8737 High Similarity NPC313650
0.8725 High Similarity NPC296683
0.8725 High Similarity NPC63345
0.8713 High Similarity NPC75440
0.8713 High Similarity NPC262365
0.8713 High Similarity NPC201959
0.87 High Similarity NPC29989
0.87 High Similarity NPC69332
0.87 High Similarity NPC70843
0.87 High Similarity NPC95178
0.8696 High Similarity NPC104216
0.8696 High Similarity NPC27974
0.8687 High Similarity NPC323810
0.8687 High Similarity NPC30506
0.8687 High Similarity NPC471511
0.8687 High Similarity NPC241891
0.8681 High Similarity NPC155393
0.8673 High Similarity NPC51015
0.866 High Similarity NPC252821
0.866 High Similarity NPC122005
0.8641 High Similarity NPC225679
0.8641 High Similarity NPC95716
0.8641 High Similarity NPC165770
0.8641 High Similarity NPC4493
0.8641 High Similarity NPC476632
0.8632 High Similarity NPC152415
0.8627 High Similarity NPC88141
0.8627 High Similarity NPC55617
0.8627 High Similarity NPC62258
0.8627 High Similarity NPC265211
0.8627 High Similarity NPC306045
0.8617 High Similarity NPC306074
0.8602 High Similarity NPC70436
0.86 High Similarity NPC134829
0.86 High Similarity NPC239291
0.8586 High Similarity NPC68269
0.8586 High Similarity NPC196479
0.8571 High Similarity NPC129373
0.8571 High Similarity NPC248396
0.8571 High Similarity NPC48730
0.8571 High Similarity NPC286904
0.8558 High Similarity NPC46940
0.8558 High Similarity NPC166995
0.8558 High Similarity NPC43525
0.8557 High Similarity NPC152097
0.8557 High Similarity NPC260000
0.8557 High Similarity NPC474073
0.8544 High Similarity NPC475018
0.8544 High Similarity NPC79793
0.8544 High Similarity NPC147634
0.8544 High Similarity NPC44732
0.8544 High Similarity NPC252544
0.8544 High Similarity NPC120982
0.8544 High Similarity NPC321252
0.8544 High Similarity NPC174096
0.8544 High Similarity NPC226401
0.8542 High Similarity NPC144682
0.8526 High Similarity NPC55903
0.8526 High Similarity NPC181709
0.8515 High Similarity NPC302681
0.8515 High Similarity NPC39097
0.8515 High Similarity NPC248904
0.8515 High Similarity NPC39664
0.8515 High Similarity NPC118286
0.8515 High Similarity NPC477814
0.8515 High Similarity NPC109691
0.8515 High Similarity NPC54765
0.8515 High Similarity NPC470700
0.8511 High Similarity NPC300478
0.85 High Similarity NPC327811
0.85 High Similarity NPC254965
0.8485 Intermediate Similarity NPC100340
0.8485 Intermediate Similarity NPC143659
0.8485 Intermediate Similarity NPC12221
0.8485 Intermediate Similarity NPC101025
0.8485 Intermediate Similarity NPC471578
0.8485 Intermediate Similarity NPC472585
0.8476 Intermediate Similarity NPC35344
0.8476 Intermediate Similarity NPC176730
0.8476 Intermediate Similarity NPC141003
0.8476 Intermediate Similarity NPC123175
0.8476 Intermediate Similarity NPC117846
0.8469 Intermediate Similarity NPC80027
0.8469 Intermediate Similarity NPC260775
0.8469 Intermediate Similarity NPC280869
0.8469 Intermediate Similarity NPC275104
0.8462 Intermediate Similarity NPC187583
0.8462 Intermediate Similarity NPC308689
0.8462 Intermediate Similarity NPC257430
0.8462 Intermediate Similarity NPC179002
0.8462 Intermediate Similarity NPC177576
0.8447 Intermediate Similarity NPC474272
0.8447 Intermediate Similarity NPC19808
0.8447 Intermediate Similarity NPC58865
0.8447 Intermediate Similarity NPC33728
0.8438 Intermediate Similarity NPC289769
0.8431 Intermediate Similarity NPC151477
0.8431 Intermediate Similarity NPC54844
0.8431 Intermediate Similarity NPC320439
0.8416 Intermediate Similarity NPC243677
0.8416 Intermediate Similarity NPC246056
0.8416 Intermediate Similarity NPC303141
0.84 Intermediate Similarity NPC24404
0.84 Intermediate Similarity NPC302219
0.84 Intermediate Similarity NPC94351
0.84 Intermediate Similarity NPC71002
0.84 Intermediate Similarity NPC168303
0.84 Intermediate Similarity NPC53051
0.84 Intermediate Similarity NPC242342
0.84 Intermediate Similarity NPC313030
0.84 Intermediate Similarity NPC85479
0.84 Intermediate Similarity NPC62351

  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 NPC26244 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 NPD2859 Approved
1.0 High Similarity NPD2860 Approved
0.9888 High Similarity NPD2934 Approved
0.9888 High Similarity NPD2933 Approved
0.9674 High Similarity NPD3020 Approved
0.9032 High Similarity NPD1432 Clinical (unspecified phase)
0.8876 High Similarity NPD111 Approved
0.8812 High Similarity NPD3021 Approved
0.8812 High Similarity NPD3022 Approved
0.8673 High Similarity NPD846 Approved
0.8673 High Similarity NPD940 Approved
0.8571 High Similarity NPD3028 Approved
0.8542 High Similarity NPD1809 Phase 2
0.8542 High Similarity NPD844 Approved
0.8526 High Similarity NPD845 Approved
0.8384 Intermediate Similarity NPD1242 Phase 1
0.8302 Intermediate Similarity NPD2234 Approved
0.8302 Intermediate Similarity NPD2229 Approved
0.8302 Intermediate Similarity NPD2228 Approved
0.8265 Intermediate Similarity NPD288 Approved
0.82 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7635 Approved
0.7961 Intermediate Similarity NPD9608 Approved
0.7961 Intermediate Similarity NPD9610 Approved
0.7946 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7928 Intermediate Similarity NPD5303 Approved
0.7928 Intermediate Similarity NPD5304 Approved
0.7928 Intermediate Similarity NPD3091 Approved
0.7925 Intermediate Similarity NPD4750 Phase 3
0.7925 Intermediate Similarity NPD1792 Phase 2
0.7925 Intermediate Similarity NPD5451 Approved
0.7905 Intermediate Similarity NPD2342 Discontinued
0.7857 Intermediate Similarity NPD4093 Discontinued
0.783 Intermediate Similarity NPD2684 Approved
0.781 Intermediate Similarity NPD1445 Approved
0.781 Intermediate Similarity NPD1444 Approved
0.781 Intermediate Similarity NPD968 Approved
0.7788 Intermediate Similarity NPD3019 Approved
0.7788 Intermediate Similarity NPD2932 Approved
0.7788 Intermediate Similarity NPD4589 Approved
0.7788 Intermediate Similarity NPD4059 Approved
0.7778 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD5535 Approved
0.7672 Intermediate Similarity NPD6583 Phase 3
0.7672 Intermediate Similarity NPD4659 Approved
0.7672 Intermediate Similarity NPD6582 Phase 2
0.7672 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6671 Approved
0.7652 Intermediate Similarity NPD3092 Approved
0.764 Intermediate Similarity NPD9087 Approved
0.7636 Intermediate Similarity NPD5283 Phase 1
0.7636 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD2286 Discontinued
0.7615 Intermediate Similarity NPD228 Approved
0.7593 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD2561 Approved
0.7586 Intermediate Similarity NPD2562 Approved
0.7568 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD3847 Discontinued
0.7565 Intermediate Similarity NPD3421 Phase 3
0.7545 Intermediate Similarity NPD7843 Approved
0.7542 Intermediate Similarity NPD4103 Phase 2
0.7542 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD256 Approved
0.75 Intermediate Similarity NPD9088 Approved
0.75 Intermediate Similarity NPD255 Approved
0.7479 Intermediate Similarity NPD6584 Phase 3
0.7478 Intermediate Similarity NPD2667 Approved
0.7478 Intermediate Similarity NPD2668 Approved
0.7478 Intermediate Similarity NPD1751 Approved
0.7478 Intermediate Similarity NPD3095 Discontinued
0.7476 Intermediate Similarity NPD9273 Approved
0.7456 Intermediate Similarity NPD1548 Phase 1
0.7456 Intermediate Similarity NPD7330 Discontinued
0.7434 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD3053 Approved
0.7395 Intermediate Similarity NPD3094 Phase 2
0.7395 Intermediate Similarity NPD3055 Approved
0.7391 Intermediate Similarity NPD9294 Approved
0.7387 Intermediate Similarity NPD821 Approved
0.7387 Intermediate Similarity NPD9379 Approved
0.7387 Intermediate Similarity NPD9377 Approved
0.7368 Intermediate Similarity NPD16 Approved
0.7368 Intermediate Similarity NPD856 Approved
0.7358 Intermediate Similarity NPD9500 Approved
0.7358 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD4908 Phase 1
0.735 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD1610 Phase 2
0.7345 Intermediate Similarity NPD7157 Approved
0.7333 Intermediate Similarity NPD7451 Discontinued
0.7328 Intermediate Similarity NPD6516 Phase 2
0.7328 Intermediate Similarity NPD5846 Approved
0.7311 Intermediate Similarity NPD5310 Approved
0.7311 Intermediate Similarity NPD5311 Approved
0.7304 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD3027 Phase 3
0.7281 Intermediate Similarity NPD3596 Phase 2
0.7273 Intermediate Similarity NPD5736 Approved
0.7273 Intermediate Similarity NPD2861 Phase 2
0.7264 Intermediate Similarity NPD4817 Approved
0.7264 Intermediate Similarity NPD4818 Approved
0.7257 Intermediate Similarity NPD1791 Approved
0.7257 Intermediate Similarity NPD475 Phase 2
0.7257 Intermediate Similarity NPD1793 Approved
0.7248 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD318 Approved
0.7217 Intermediate Similarity NPD317 Approved
0.7203 Intermediate Similarity NPD1535 Discovery
0.7196 Intermediate Similarity NPD4656 Approved
0.7196 Intermediate Similarity NPD4658 Approved
0.719 Intermediate Similarity NPD2195 Approved
0.719 Intermediate Similarity NPD2194 Approved
0.7188 Intermediate Similarity NPD9089 Approved
0.7179 Intermediate Similarity NPD4626 Approved
0.717 Intermediate Similarity NPD1616 Discontinued
0.7156 Intermediate Similarity NPD3134 Approved
0.7155 Intermediate Similarity NPD6581 Approved
0.7155 Intermediate Similarity NPD6580 Approved
0.7155 Intermediate Similarity NPD1894 Discontinued
0.7154 Intermediate Similarity NPD5156 Approved
0.7154 Intermediate Similarity NPD5155 Approved
0.7143 Intermediate Similarity NPD2232 Approved
0.7143 Intermediate Similarity NPD2230 Approved
0.7143 Intermediate Similarity NPD1481 Phase 2
0.7143 Intermediate Similarity NPD2233 Approved
0.7131 Intermediate Similarity NPD3637 Approved
0.7131 Intermediate Similarity NPD3636 Approved
0.7131 Intermediate Similarity NPD3635 Approved
0.713 Intermediate Similarity NPD9568 Approved
0.712 Intermediate Similarity NPD4060 Phase 1
0.7119 Intermediate Similarity NPD3023 Approved
0.7119 Intermediate Similarity NPD3143 Discontinued
0.7119 Intermediate Similarity NPD3026 Approved
0.7107 Intermediate Similarity NPD1164 Approved
0.7107 Intermediate Similarity NPD2797 Approved
0.7105 Intermediate Similarity NPD497 Approved
0.7105 Intermediate Similarity NPD9618 Approved
0.7105 Intermediate Similarity NPD9614 Approved
0.7097 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD3025 Approved
0.7094 Intermediate Similarity NPD3024 Approved
0.7094 Intermediate Similarity NPD1651 Approved
0.7094 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD290 Approved
0.7083 Intermediate Similarity NPD1669 Approved
0.7083 Intermediate Similarity NPD9093 Approved
0.7073 Intermediate Similarity NPD2605 Approved
0.7073 Intermediate Similarity NPD2606 Approved
0.7059 Intermediate Similarity NPD1201 Approved
0.7059 Intermediate Similarity NPD422 Phase 1
0.7054 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD4624 Approved
0.7043 Intermediate Similarity NPD6387 Discontinued
0.7043 Intermediate Similarity NPD709 Approved
0.7043 Intermediate Similarity NPD2557 Approved
0.704 Intermediate Similarity NPD6405 Approved
0.704 Intermediate Similarity NPD6407 Approved
0.704 Intermediate Similarity NPD6663 Approved
0.7037 Intermediate Similarity NPD4231 Approved
0.7037 Intermediate Similarity NPD3680 Approved
0.7037 Intermediate Similarity NPD3682 Approved
0.7037 Intermediate Similarity NPD4229 Approved
0.703 Intermediate Similarity NPD9295 Approved
0.7025 Intermediate Similarity NPD1283 Approved
0.7018 Intermediate Similarity NPD496 Approved
0.7018 Intermediate Similarity NPD498 Approved
0.7018 Intermediate Similarity NPD495 Approved
0.7016 Intermediate Similarity NPD7095 Approved
0.7016 Intermediate Similarity NPD4625 Phase 3
0.7009 Intermediate Similarity NPD9545 Approved
0.7 Intermediate Similarity NPD3972 Approved
0.7 Intermediate Similarity NPD3070 Discontinued
0.7 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7636 Approved
0.6975 Remote Similarity NPD2688 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1980 Approved
0.6975 Remote Similarity NPD1981 Approved
0.6975 Remote Similarity NPD1983 Approved
0.6972 Remote Similarity NPD1237 Approved
0.6967 Remote Similarity NPD1135 Approved
0.6967 Remote Similarity NPD1133 Approved
0.6967 Remote Similarity NPD1134 Approved
0.6967 Remote Similarity NPD1129 Approved
0.6967 Remote Similarity NPD1131 Approved
0.696 Remote Similarity NPD3764 Approved
0.696 Remote Similarity NPD6798 Discontinued
0.6953 Remote Similarity NPD3555 Approved
0.6953 Remote Similarity NPD3553 Approved
0.6953 Remote Similarity NPD3554 Approved
0.6953 Remote Similarity NPD3552 Approved
0.6942 Remote Similarity NPD1755 Approved
0.6942 Remote Similarity NPD4749 Approved
0.6942 Remote Similarity NPD3685 Discontinued

  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