Structure

Physi-Chem Properties

Molecular Weight:  228.08
Volume:  235.583
LogP:  3.544
LogD:  3.304
LogS:  -5.546
# Rotatable Bonds:  0
TPSA:  43.35
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.553
Synthetic Accessibility Score:  2.516
Fsp3:  0.214
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:  -4.741
MDCK Permeability:  1.9763423551921733e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.975
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.035
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.023
Plasma Protein Binding (PPB):  84.19786071777344%
Volume Distribution (VD):  0.746
Pgp-substrate:  8.658390045166016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.966
CYP2C19-inhibitor:  0.626
CYP2C19-substrate:  0.491
CYP2C9-inhibitor:  0.261
CYP2C9-substrate:  0.737
CYP2D6-inhibitor:  0.586
CYP2D6-substrate:  0.883
CYP3A4-inhibitor:  0.486
CYP3A4-substrate:  0.277

ADMET: Excretion

Clearance (CL):  11.448
Half-life (T1/2):  0.442

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.891
Drug-inuced Liver Injury (DILI):  0.966
AMES Toxicity:  0.099
Rat Oral Acute Toxicity:  0.092
Maximum Recommended Daily Dose:  0.916
Skin Sensitization:  0.221
Carcinogencity:  0.895
Eye Corrosion:  0.006
Eye Irritation:  0.066
Respiratory Toxicity:  0.344

Download Data

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

  Natural Product: NPC262635

Natural Product ID:  NPC262635
Common Name*:   Trioxsalen
IUPAC Name:   2,5,9-trimethylfuro[3,2-g]chromen-7-one
Synonyms:   Trioxsalen; Trioxysalen; Trisoralen
Standard InCHIKey:  FMHHVULEAZTJMA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
SMILES:  Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1475
PubChem CID:   5585
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens

*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
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19778086]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf Wax n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Pt n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae 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
NPT114 Cell Line LoVo Homo sapiens EC50 = 940.0 nM PMID[485139]
NPT114 Cell Line LoVo Homo sapiens CC50 > 200000.0 nM PMID[485139]
NPT114 Cell Line LoVo Homo sapiens Ratio CC50/EC50 > 210.0 n.a. PMID[485139]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 5623.4 nM PMID[485141]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 281.8 nM PMID[485142]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 6309.6 nM PMID[485141]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 7943.3 nM PMID[485142]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3981.1 nM PMID[485141]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PMID[485143]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 1000.0 nM PMID[485141]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3981.07 nM PMID[485141]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[485143]
NPT217 Individual Protein Adenosine A2a receptor Homo sapiens IC50 = 1312.0 nM PMID[485145]
NPT217 Individual Protein Adenosine A2a receptor Homo sapiens Ki = 737.0 nM PMID[485145]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 831.0 nM PMID[485145]
NPT292 Individual Protein Serotonin 2c (5-HT2c) receptor Homo sapiens IC50 = 2356.0 nM PMID[485145]
NPT292 Individual Protein Serotonin 2c (5-HT2c) receptor Homo sapiens Ki = 1234.0 nM PMID[485145]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 90573.26 nM PMID[485146]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[485146]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 1258.9 nM PMID[485143]
NPT1043 Individual Protein Glycoprotein hormones alpha chain Homo sapiens Potency n.a. 5011.9 nM PMID[485143]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 14.28 % PMID[485147]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 21192.3 nM PMID[485143]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 11455.4 nM PubChem BioAssay data set
NPT35 Others n.a. LogP = 2.44 n.a. PMID[485139]
NPT2 Others Unspecified Activity < 0.5 uM PMID[485139]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 27.6 n.a. PMID[485140]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 3548.1 nM PMID[485142]
NPT2 Others Unspecified Potency = 1412.5 nM PMID[485142]
NPT2 Others Unspecified IC50 = 0.5 nM PMID[485144]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PMID[485143]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5858.4 nM PMID[485143]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[485143]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 2.42 % PMID[485147]
NPT27 Others Unspecified Activity = 95.2 % PMID[485148]
NPT27 Others Unspecified Activity = 92.2 % PMID[485148]
NPT27 Others Unspecified Activity = 96.7 % PMID[485148]
NPT27 Others Unspecified Activity = 106.9 % PMID[485148]
NPT2 Others Unspecified Inhibition = 40.0 % PMID[485148]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 103.1 % PMID[485149]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 86.89 % PMID[485149]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 3.3 nM PMID[485150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 47.3 nM PMID[485150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 530.5 nM PMID[485150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 13.3 nM PMID[485150]
NPT35 Others n.a. LogD7.4 n.a. 3.47 n.a. PMID[485151]
NPT2 Others Unspecified AC50 n.a. 631.0 nM PMID[485152]
NPT2 Others Unspecified Ac50 n.a. 0.631 uM PMID[485152]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 525100.0 nM PMID[485153]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.03124 n.a. PMID[485154]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -4.74 % PMID[485155]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.006457 n.a. PMID[485156]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 14.8 % PMID[485157]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.22 % PMID[485158]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[485159]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[485159]
NPT2 Others Unspecified Potency n.a. 7166.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5955.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2113.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1678.5 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 NPC262635 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
0.9852 High Similarity NPC254010
0.9779 High Similarity NPC313036
0.9493 High Similarity NPC166858
0.9493 High Similarity NPC51146
0.9433 High Similarity NPC266743
0.9366 High Similarity NPC88445
0.9362 High Similarity NPC74539
0.9362 High Similarity NPC304443
0.9357 High Similarity NPC246903
0.9338 High Similarity NPC29638
0.9301 High Similarity NPC191104
0.9236 High Similarity NPC98028
0.9203 High Similarity NPC36414
0.9197 High Similarity NPC268081
0.9149 High Similarity NPC17262
0.913 High Similarity NPC253616
0.913 High Similarity NPC103001
0.911 High Similarity NPC131725
0.9085 High Similarity NPC208584
0.9071 High Similarity NPC28337
0.9071 High Similarity NPC470856
0.9058 High Similarity NPC472516
0.9021 High Similarity NPC190572
0.9014 High Similarity NPC225884
0.9 High Similarity NPC472515
0.9 High Similarity NPC136095
0.9 High Similarity NPC473209
0.8978 High Similarity NPC247743
0.8926 High Similarity NPC269495
0.8919 High Similarity NPC250769
0.8919 High Similarity NPC278010
0.8919 High Similarity NPC295608
0.8905 High Similarity NPC229646
0.8904 High Similarity NPC155882
0.8897 High Similarity NPC272194
0.8889 High Similarity NPC210826
0.8889 High Similarity NPC300267
0.8889 High Similarity NPC51641
0.8867 High Similarity NPC33320
0.8859 High Similarity NPC19860
0.8857 High Similarity NPC332594
0.8841 High Similarity NPC292998
0.8836 High Similarity NPC37208
0.8836 High Similarity NPC221868
0.8828 High Similarity NPC12148
0.8828 High Similarity NPC198427
0.8828 High Similarity NPC130581
0.8811 High Similarity NPC53192
0.8808 High Similarity NPC169
0.8808 High Similarity NPC49009
0.8808 High Similarity NPC243509
0.88 High Similarity NPC270044
0.8776 High Similarity NPC135303
0.8776 High Similarity NPC148423
0.8767 High Similarity NPC306788
0.8767 High Similarity NPC135325
0.8759 High Similarity NPC473927
0.8759 High Similarity NPC154217
0.875 High Similarity NPC216092
0.875 High Similarity NPC14822
0.875 High Similarity NPC302181
0.8742 High Similarity NPC244750
0.8741 High Similarity NPC49852
0.8741 High Similarity NPC475496
0.8723 High Similarity NPC157855
0.8723 High Similarity NPC38153
0.8714 High Similarity NPC151113
0.8707 High Similarity NPC37226
0.8707 High Similarity NPC178202
0.8707 High Similarity NPC226644
0.8707 High Similarity NPC39929
0.8707 High Similarity NPC296030
0.8705 High Similarity NPC93756
0.8705 High Similarity NPC108113
0.8696 High Similarity NPC284424
0.869 High Similarity NPC171656
0.869 High Similarity NPC230943
0.869 High Similarity NPC1886
0.869 High Similarity NPC196137
0.8684 High Similarity NPC260296
0.8684 High Similarity NPC95472
0.8684 High Similarity NPC239270
0.8684 High Similarity NPC115432
0.8684 High Similarity NPC303210
0.8681 High Similarity NPC36181
0.8676 High Similarity NPC473907
0.8662 High Similarity NPC199458
0.8662 High Similarity NPC183639
0.8658 High Similarity NPC130015
0.8658 High Similarity NPC41326
0.8658 High Similarity NPC38361
0.8652 High Similarity NPC161196
0.8652 High Similarity NPC254741
0.8649 High Similarity NPC230713
0.8649 High Similarity NPC472406
0.8649 High Similarity NPC78335
0.8643 High Similarity NPC125920
0.8643 High Similarity NPC66705
0.8636 High Similarity NPC179464
0.8633 High Similarity NPC55147
0.863 High Similarity NPC181388
0.863 High Similarity NPC470322
0.8621 High Similarity NPC87609
0.8621 High Similarity NPC188632
0.8621 High Similarity NPC94794
0.8621 High Similarity NPC470296
0.8621 High Similarity NPC112791
0.8621 High Similarity NPC196459
0.8613 High Similarity NPC473894
0.8611 High Similarity NPC24075
0.8601 High Similarity NPC241975
0.8601 High Similarity NPC37206
0.8601 High Similarity NPC137009
0.8601 High Similarity NPC19476
0.86 High Similarity NPC41719
0.86 High Similarity NPC472462
0.8592 High Similarity NPC131782
0.8592 High Similarity NPC138047
0.8592 High Similarity NPC474624
0.8592 High Similarity NPC228661
0.8591 High Similarity NPC170169
0.8591 High Similarity NPC472407
0.8591 High Similarity NPC290671
0.8582 High Similarity NPC60667
0.8582 High Similarity NPC46869
0.8581 High Similarity NPC204088
0.8581 High Similarity NPC329215
0.8581 High Similarity NPC173149
0.8581 High Similarity NPC179015
0.8581 High Similarity NPC259007
0.8571 High Similarity NPC17816
0.8571 High Similarity NPC180477
0.8571 High Similarity NPC234536
0.8571 High Similarity NPC140120
0.8571 High Similarity NPC78612
0.8562 High Similarity NPC178627
0.8562 High Similarity NPC469935
0.8562 High Similarity NPC294365
0.8562 High Similarity NPC469953
0.8562 High Similarity NPC155144
0.8561 High Similarity NPC278556
0.8543 High Similarity NPC233776
0.8542 High Similarity NPC172986
0.8542 High Similarity NPC305355
0.8542 High Similarity NPC472409
0.8542 High Similarity NPC474037
0.8542 High Similarity NPC261227
0.8542 High Similarity NPC475680
0.8542 High Similarity NPC270883
0.8533 High Similarity NPC5871
0.8533 High Similarity NPC263676
0.8531 High Similarity NPC17848
0.8531 High Similarity NPC219584
0.8531 High Similarity NPC201395
0.8531 High Similarity NPC470083
0.8531 High Similarity NPC131130
0.8526 High Similarity NPC210460
0.8526 High Similarity NPC155264
0.8526 High Similarity NPC193881
0.8526 High Similarity NPC67450
0.8526 High Similarity NPC323137
0.8523 High Similarity NPC473466
0.8523 High Similarity NPC474660
0.8521 High Similarity NPC174999
0.8516 High Similarity NPC155640
0.8514 High Similarity NPC208303
0.8514 High Similarity NPC161864
0.8514 High Similarity NPC168085
0.8503 High Similarity NPC57470
0.85 High Similarity NPC54503
0.85 High Similarity NPC101294
0.85 High Similarity NPC182428
0.85 High Similarity NPC473655
0.8493 Intermediate Similarity NPC189650
0.8489 Intermediate Similarity NPC270369
0.8489 Intermediate Similarity NPC5515
0.8487 Intermediate Similarity NPC13879
0.8487 Intermediate Similarity NPC470625
0.8483 Intermediate Similarity NPC205006
0.8483 Intermediate Similarity NPC147688
0.8483 Intermediate Similarity NPC103362
0.8483 Intermediate Similarity NPC110969
0.8483 Intermediate Similarity NPC64908
0.8483 Intermediate Similarity NPC171870
0.8483 Intermediate Similarity NPC297985
0.8483 Intermediate Similarity NPC156590
0.8483 Intermediate Similarity NPC118840
0.8477 Intermediate Similarity NPC213608
0.8477 Intermediate Similarity NPC183874
0.8477 Intermediate Similarity NPC122365
0.8477 Intermediate Similarity NPC1477
0.8477 Intermediate Similarity NPC235333
0.8472 Intermediate Similarity NPC11566
0.8472 Intermediate Similarity NPC55018
0.8472 Intermediate Similarity NPC216978
0.8472 Intermediate Similarity NPC78913
0.8472 Intermediate Similarity NPC96565
0.8472 Intermediate Similarity NPC18260
0.8472 Intermediate Similarity NPC220062
0.8472 Intermediate Similarity NPC301217

  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 NPC262635 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 NPD1243 Approved
0.9493 High Similarity NPD643 Clinical (unspecified phase)
0.9362 High Similarity NPD920 Approved
0.9357 High Similarity NPD642 Clinical (unspecified phase)
0.8867 High Similarity NPD919 Approved
0.8652 High Similarity NPD2796 Approved
0.8431 Intermediate Similarity NPD3749 Approved
0.8322 Intermediate Similarity NPD3748 Approved
0.8311 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8298 Intermediate Similarity NPD1240 Approved
0.8269 Intermediate Similarity NPD1247 Approved
0.8243 Intermediate Similarity NPD6799 Approved
0.8235 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7819 Suspended
0.8224 Intermediate Similarity NPD7411 Suspended
0.8194 Intermediate Similarity NPD1510 Phase 2
0.8188 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1607 Approved
0.817 Intermediate Similarity NPD6801 Discontinued
0.8151 Intermediate Similarity NPD1549 Phase 2
0.8151 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD2800 Approved
0.8082 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8082 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8082 Intermediate Similarity NPD2344 Approved
0.8077 Intermediate Similarity NPD7075 Discontinued
0.8041 Intermediate Similarity NPD3750 Approved
0.8039 Intermediate Similarity NPD6599 Discontinued
0.7945 Intermediate Similarity NPD2799 Discontinued
0.7902 Intermediate Similarity NPD1296 Phase 2
0.7902 Intermediate Similarity NPD2313 Discontinued
0.7898 Intermediate Similarity NPD7768 Phase 2
0.7891 Intermediate Similarity NPD1551 Phase 2
0.7888 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD6832 Phase 2
0.7881 Intermediate Similarity NPD1511 Approved
0.7867 Intermediate Similarity NPD2309 Approved
0.7862 Intermediate Similarity NPD5494 Approved
0.7852 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD9717 Approved
0.7834 Intermediate Similarity NPD3817 Phase 2
0.7829 Intermediate Similarity NPD2533 Approved
0.7829 Intermediate Similarity NPD2532 Approved
0.7829 Intermediate Similarity NPD2534 Approved
0.7826 Intermediate Similarity NPD3926 Phase 2
0.7806 Intermediate Similarity NPD4380 Phase 2
0.7801 Intermediate Similarity NPD1203 Approved
0.7778 Intermediate Similarity NPD1512 Approved
0.7778 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD422 Phase 1
0.7722 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD1471 Phase 3
0.7712 Intermediate Similarity NPD5401 Approved
0.7711 Intermediate Similarity NPD6559 Discontinued
0.7683 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD3266 Approved
0.7676 Intermediate Similarity NPD3267 Approved
0.7673 Intermediate Similarity NPD3882 Suspended
0.7671 Intermediate Similarity NPD4307 Phase 2
0.7651 Intermediate Similarity NPD2935 Discontinued
0.7643 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD3226 Approved
0.7626 Intermediate Similarity NPD17 Approved
0.7625 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1019 Discontinued
0.7619 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD2654 Approved
0.7613 Intermediate Similarity NPD5403 Approved
0.7613 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1934 Approved
0.7547 Intermediate Similarity NPD2801 Approved
0.7545 Intermediate Similarity NPD5953 Discontinued
0.7517 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2798 Approved
0.7485 Intermediate Similarity NPD6959 Discontinued
0.7483 Intermediate Similarity NPD2346 Discontinued
0.747 Intermediate Similarity NPD3818 Discontinued
0.7467 Intermediate Similarity NPD4308 Phase 3
0.7465 Intermediate Similarity NPD1608 Approved
0.745 Intermediate Similarity NPD6651 Approved
0.7439 Intermediate Similarity NPD6232 Discontinued
0.7439 Intermediate Similarity NPD6808 Phase 2
0.7438 Intermediate Similarity NPD1465 Phase 2
0.7431 Intermediate Similarity NPD2797 Approved
0.7425 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7286 Phase 2
0.7425 Intermediate Similarity NPD5844 Phase 1
0.7415 Intermediate Similarity NPD3268 Approved
0.7415 Intermediate Similarity NPD411 Approved
0.741 Intermediate Similarity NPD7473 Discontinued
0.7399 Intermediate Similarity NPD4287 Approved
0.7391 Intermediate Similarity NPD5402 Approved
0.7383 Intermediate Similarity NPD447 Suspended
0.7383 Intermediate Similarity NPD1933 Approved
0.7375 Intermediate Similarity NPD6280 Approved
0.7375 Intermediate Similarity NPD6279 Approved
0.7372 Intermediate Similarity NPD1241 Discontinued
0.7353 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD4628 Phase 3
0.731 Intermediate Similarity NPD1164 Approved
0.7284 Intermediate Similarity NPD2296 Approved
0.7284 Intermediate Similarity NPD4288 Approved
0.7278 Intermediate Similarity NPD1729 Discontinued
0.725 Intermediate Similarity NPD6585 Discontinued
0.7241 Intermediate Similarity NPD3225 Approved
0.7237 Intermediate Similarity NPD7033 Discontinued
0.7234 Intermediate Similarity NPD9545 Approved
0.7229 Intermediate Similarity NPD5710 Approved
0.7229 Intermediate Similarity NPD5711 Approved
0.7222 Intermediate Similarity NPD3972 Approved
0.7214 Intermediate Similarity NPD9493 Approved
0.7205 Intermediate Similarity NPD5889 Approved
0.7205 Intermediate Similarity NPD5890 Approved
0.72 Intermediate Similarity NPD943 Approved
0.7164 Intermediate Similarity NPD9697 Approved
0.7153 Intermediate Similarity NPD1281 Approved
0.7152 Intermediate Similarity NPD5124 Phase 1
0.7152 Intermediate Similarity NPD230 Phase 1
0.7152 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2403 Approved
0.7143 Intermediate Similarity NPD2353 Approved
0.7143 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6166 Phase 2
0.7143 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7229 Phase 3
0.7123 Intermediate Similarity NPD1876 Approved
0.7118 Intermediate Similarity NPD7054 Approved
0.7078 Intermediate Similarity NPD6100 Approved
0.7078 Intermediate Similarity NPD6099 Approved
0.7076 Intermediate Similarity NPD7472 Approved
0.7076 Intermediate Similarity NPD7074 Phase 3
0.7067 Intermediate Similarity NPD3764 Approved
0.7052 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6797 Phase 2
0.7015 Intermediate Similarity NPD9261 Approved
0.7007 Intermediate Similarity NPD1283 Approved
0.7006 Intermediate Similarity NPD7003 Approved
0.6994 Remote Similarity NPD7251 Discontinued
0.6993 Remote Similarity NPD1548 Phase 1
0.6981 Remote Similarity NPD7390 Discontinued
0.6962 Remote Similarity NPD3887 Approved
0.6962 Remote Similarity NPD2354 Approved
0.6961 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6954 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7808 Phase 3
0.6946 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6944 Remote Similarity NPD1651 Approved
0.6937 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6936 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6929 Remote Similarity NPD5535 Approved
0.6918 Remote Similarity NPD1611 Approved
0.6918 Remote Similarity NPD1610 Phase 2
0.6908 Remote Similarity NPD8032 Phase 2
0.6906 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4361 Phase 2
0.6894 Remote Similarity NPD6273 Approved
0.6894 Remote Similarity NPD5049 Phase 3
0.6893 Remote Similarity NPD8434 Phase 2
0.689 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6871 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6871 Remote Similarity NPD7458 Discontinued
0.6864 Remote Similarity NPD7199 Phase 2
0.6863 Remote Similarity NPD3142 Approved
0.6863 Remote Similarity NPD3140 Approved
0.6859 Remote Similarity NPD5408 Approved
0.6859 Remote Similarity NPD4477 Approved
0.6859 Remote Similarity NPD5405 Approved
0.6859 Remote Similarity NPD5404 Approved
0.6859 Remote Similarity NPD5406 Approved
0.6859 Remote Similarity NPD4476 Approved
0.6842 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6835 Remote Similarity NPD1652 Phase 2
0.6828 Remote Similarity NPD5691 Approved
0.6826 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6355 Discontinued
0.6815 Remote Similarity NPD6002 Phase 3
0.6815 Remote Similarity NPD6005 Phase 3
0.6815 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6004 Phase 3
0.6815 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6812 Remote Similarity NPD9263 Approved
0.6812 Remote Similarity NPD9264 Approved
0.6812 Remote Similarity NPD9267 Approved
0.6786 Remote Similarity NPD6971 Discontinued
0.6784 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5242 Approved
0.6781 Remote Similarity NPD1778 Approved
0.6776 Remote Similarity NPD4625 Phase 3
0.677 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6766 Remote Similarity NPD5353 Approved
0.6763 Remote Similarity NPD74 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