Structure

Physi-Chem Properties

Molecular Weight:  270.05
Volume:  265.186
LogP:  3.155
LogD:  2.837
LogS:  -3.627
# Rotatable Bonds:  1
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.591
Synthetic Accessibility Score:  2.343
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.879
MDCK Permeability:  1.1961049494857434e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.484
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.991
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  98.56309509277344%
Volume Distribution (VD):  0.394
Pgp-substrate:  2.3992457389831543%

ADMET: Metabolism

CYP1A2-inhibitor:  0.979
CYP1A2-substrate:  0.129
CYP2C19-inhibitor:  0.381
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.6
CYP2C9-substrate:  0.847
CYP2D6-inhibitor:  0.696
CYP2D6-substrate:  0.675
CYP3A4-inhibitor:  0.439
CYP3A4-substrate:  0.122

ADMET: Excretion

Clearance (CL):  7.163
Half-life (T1/2):  0.836

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.088
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.211
Rat Oral Acute Toxicity:  0.15
Maximum Recommended Daily Dose:  0.223
Skin Sensitization:  0.949
Carcinogencity:  0.362
Eye Corrosion:  0.024
Eye Irritation:  0.951
Respiratory Toxicity:  0.226

Download Data

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

  Natural Product: NPC134969

Natural Product ID:  NPC134969
Common Name*:   Thunberginol A
IUPAC Name:   3-(3,4-dihydroxyphenyl)-8-hydroxyisochromen-1-one
Synonyms:  
Standard InCHIKey:  WHZXJVJVGGWZQI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O5/c16-10-5-4-8(6-12(10)18)13-7-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,16-18H
SMILES:  Oc1cc(ccc1O)c1cc2cccc(c2c(=O)o1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL68810
PubChem CID:   5321948
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001890] Isocoumarins and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO33513 hydrangeae dulcis folium Species n.a. n.a. n.a. n.a. n.a. PMID[11549443]
NPO9360.1 Hydrangea macrophylla var. thunbergii Varieties Hydrangeaceae Eukaryota Leaves n.a. n.a. PMID[17609121]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO33513 hydrangeae dulcis folium Species n.a. n.a. n.a. n.a. n.a. PMID[9871657]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9360.1 Hydrangea macrophylla var. thunbergii Varieties Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9360.1 Hydrangea macrophylla var. thunbergii Varieties Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19581 Marchantia polymorpha Species Marchantiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19581 Marchantia polymorpha Species Marchantiaceae 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
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 8.0 % PMID[521923]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 19.6 % PMID[521923]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 15.7 % PMID[521923]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -27.6 % PMID[521923]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 17.5 % PMID[521923]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 89125.1 nM PMID[521924]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 16353.5 nM PMID[521924]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 7304.8 nM PMID[521924]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 79432.8 nM PMID[521924]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 14354.89 nM PMID[521925]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 16069.41 nM PMID[521925]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14723.13 nM PMID[521925]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 21428.91 nM PMID[521925]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 17060.82 nM PMID[521925]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 2065.38 nM PMID[521925]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 23768.4 nM PMID[521925]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 23933.16 nM PMID[521925]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 9397.23 nM PMID[521925]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 31260.79 nM PMID[521925]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 19906.73 nM PMID[521925]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 22130.95 nM PMID[521925]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 10519.62 nM PMID[521925]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 3419.79 nM PMID[521925]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 15240.53 nM PMID[521925]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 14621.77 nM PMID[521925]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 22029.26 nM PMID[521925]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 36643.76 nM PMID[521925]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 19098.53 nM PMID[521925]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 21086.28 nM PMID[521925]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 4897.79 nM PMID[521925]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 15417.0 nM PMID[521925]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 11376.27 nM PMID[521925]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 19453.6 nM PMID[521925]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 10471.29 nM PMID[521925]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 3572.73 nM PMID[521925]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 20090.93 nM PMID[521925]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 15559.66 nM PMID[521925]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 26121.61 nM PMID[521925]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 35399.73 nM PMID[521925]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 12764.39 nM PMID[521925]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 23120.65 nM PMID[521925]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4988.84 nM PMID[521925]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 19769.7 nM PMID[521925]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 10327.61 nM PMID[521925]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 14060.48 nM PMID[521925]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 9571.94 nM PMID[521925]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 11091.75 nM PMID[521925]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 29376.5 nM PMID[521925]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 870.96 nM PMID[521925]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 13427.65 nM PMID[521925]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 24210.29 nM PMID[521925]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 6714.29 nM PMID[521925]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 6194.41 nM PMID[521925]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 27478.94 nM PMID[521925]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 21232.44 nM PMID[521925]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 22594.36 nM PMID[521925]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 19633.6 nM PMID[521925]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 997.7 nM PMID[521925]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 18879.91 nM PMID[521925]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 10543.87 nM PMID[521925]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 7307.8 nM PMID[521924]
NPT1474 Individual Protein ATP-dependent Clp protease proteolytic subunit Bacillus subtilis (strain 168) Potency n.a. 31622.8 nM PMID[521924]
NPT1852 Individual Protein Rac GTPase-activating protein 1 Homo sapiens IC50 n.a. 19650.0 nM PMID[521924]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 35481.3 nM PMID[521924]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[521924]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 16360.1 nM PMID[521924]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 3981.1 nM PMID[521924]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 31622.8 nM PMID[521924]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[521924]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 40.9 % PMID[521926]
NPT165 Cell Line HeLa Homo sapiens FC = 9.6 n.a. PMID[521926]
NPT165 Cell Line HeLa Homo sapiens FC = 1.0 n.a. PMID[521926]
NPT2 Others Unspecified Potency n.a. 32642.7 nM PMID[521924]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 19952.6 nM PMID[521924]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 9200.0 nM PMID[521924]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 70794.6 nM PMID[521924]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 44668.4 nM PMID[521924]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 35481.3 nM PMID[521924]
NPT2 Others Unspecified Potency n.a. 2818.4 nM PMID[521924]
NPT2 Others Unspecified IC50 n.a. 20720.0 nM PMID[521924]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[521924]
NPT821 Individual Protein Werner syndrome ATP-dependent helicase Homo sapiens Potency n.a. 35481.3 nM PMID[521924]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 79432.8 nM PMID[521924]
NPT35 Others n.a. Activity = 49.0 % PMID[521926]
NPT956 Individual Protein Prostaglandin E synthase Homo sapiens Inhibition = 74.0 % PMID[521926]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 68.7 % PMID[521926]
NPT2 Others Unspecified IC50 = 1400.0 nM PMID[521927]
NPT27068 PROTEIN FAMILY Prostaglandin E synthase/G/H synthase 2 Homo sapiens Inhibition = 75.0 % PMID[521926]
NPT27068 PROTEIN FAMILY Prostaglandin E synthase/G/H synthase 2 Homo sapiens Inhibition = 17.0 % PMID[521926]

☑ 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 NPC134969 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
0.9635 High Similarity NPC257025
0.9407 High Similarity NPC62907
0.9155 High Similarity NPC476463
0.8973 High Similarity NPC295646
0.8936 High Similarity NPC314271
0.8929 High Similarity NPC290664
0.8873 High Similarity NPC258307
0.8873 High Similarity NPC470130
0.8865 High Similarity NPC91546
0.8857 High Similarity NPC471819
0.8849 High Similarity NPC261292
0.8849 High Similarity NPC301915
0.8819 High Similarity NPC32058
0.8819 High Similarity NPC138978
0.8819 High Similarity NPC85734
0.8811 High Similarity NPC279121
0.8792 High Similarity NPC227062
0.8777 High Similarity NPC156307
0.8776 High Similarity NPC204350
0.8768 High Similarity NPC175943
0.875 High Similarity NPC70136
0.8741 High Similarity NPC175013
0.8732 High Similarity NPC130485
0.8723 High Similarity NPC191280
0.8723 High Similarity NPC247409
0.8722 High Similarity NPC91475
0.8722 High Similarity NPC265910
0.869 High Similarity NPC179271
0.869 High Similarity NPC20791
0.8676 High Similarity NPC94810
0.8662 High Similarity NPC155205
0.8643 High Similarity NPC223836
0.8636 High Similarity NPC198336
0.863 High Similarity NPC130230
0.863 High Similarity NPC108406
0.863 High Similarity NPC74881
0.863 High Similarity NPC239312
0.863 High Similarity NPC51443
0.863 High Similarity NPC275772
0.86 High Similarity NPC56786
0.86 High Similarity NPC20541
0.86 High Similarity NPC80534
0.8581 High Similarity NPC85131
0.8571 High Similarity NPC283514
0.8571 High Similarity NPC12367
0.8571 High Similarity NPC72918
0.8571 High Similarity NPC119059
0.8571 High Similarity NPC118726
0.8571 High Similarity NPC477689
0.8562 High Similarity NPC169749
0.8552 High Similarity NPC38065
0.8552 High Similarity NPC242893
0.8543 High Similarity NPC54928
0.8543 High Similarity NPC153512
0.8529 High Similarity NPC181715
0.8523 High Similarity NPC202157
0.8521 High Similarity NPC197666
0.8521 High Similarity NPC126739
0.8514 High Similarity NPC183950
0.8514 High Similarity NPC216318
0.8514 High Similarity NPC270465
0.8514 High Similarity NPC287101
0.8514 High Similarity NPC17286
0.8514 High Similarity NPC52005
0.8514 High Similarity NPC259713
0.8514 High Similarity NPC195351
0.8514 High Similarity NPC87125
0.8514 High Similarity NPC296197
0.8514 High Similarity NPC137062
0.8514 High Similarity NPC223579
0.8511 High Similarity NPC326847
0.8511 High Similarity NPC50455
0.8506 High Similarity NPC22324
0.8503 High Similarity NPC155910
0.8503 High Similarity NPC17042
0.8503 High Similarity NPC168803
0.85 High Similarity NPC106406
0.8493 Intermediate Similarity NPC262282
0.8487 Intermediate Similarity NPC273843
0.8477 Intermediate Similarity NPC67396
0.8477 Intermediate Similarity NPC38898
0.8472 Intermediate Similarity NPC220106
0.8472 Intermediate Similarity NPC158634
0.8467 Intermediate Similarity NPC199773
0.8462 Intermediate Similarity NPC268052
0.8462 Intermediate Similarity NPC32360
0.8456 Intermediate Similarity NPC3825
0.8456 Intermediate Similarity NPC286342
0.8456 Intermediate Similarity NPC96501
0.8456 Intermediate Similarity NPC295036
0.8456 Intermediate Similarity NPC184136
0.8456 Intermediate Similarity NPC151473
0.8456 Intermediate Similarity NPC188871
0.8456 Intermediate Similarity NPC88804
0.8456 Intermediate Similarity NPC45873
0.8456 Intermediate Similarity NPC149127
0.8456 Intermediate Similarity NPC77858
0.8446 Intermediate Similarity NPC321011
0.8446 Intermediate Similarity NPC294852
0.8446 Intermediate Similarity NPC276930
0.8446 Intermediate Similarity NPC218490
0.8446 Intermediate Similarity NPC120464
0.8446 Intermediate Similarity NPC188679
0.8431 Intermediate Similarity NPC474290
0.8431 Intermediate Similarity NPC238381
0.8431 Intermediate Similarity NPC280680
0.8429 Intermediate Similarity NPC289572
0.8429 Intermediate Similarity NPC157478
0.8429 Intermediate Similarity NPC153783
0.8429 Intermediate Similarity NPC295406
0.8429 Intermediate Similarity NPC200422
0.8421 Intermediate Similarity NPC24640
0.8421 Intermediate Similarity NPC475799
0.8421 Intermediate Similarity NPC13779
0.8417 Intermediate Similarity NPC189823
0.8417 Intermediate Similarity NPC214702
0.8417 Intermediate Similarity NPC219892
0.8417 Intermediate Similarity NPC470831
0.8414 Intermediate Similarity NPC301178
0.8414 Intermediate Similarity NPC82913
0.8414 Intermediate Similarity NPC250755
0.8414 Intermediate Similarity NPC284556
0.8414 Intermediate Similarity NPC322112
0.8414 Intermediate Similarity NPC105648
0.8411 Intermediate Similarity NPC185103
0.8411 Intermediate Similarity NPC281703
0.8411 Intermediate Similarity NPC125487
0.8411 Intermediate Similarity NPC281477
0.8411 Intermediate Similarity NPC89474
0.8403 Intermediate Similarity NPC158472
0.84 Intermediate Similarity NPC225731
0.84 Intermediate Similarity NPC125062
0.84 Intermediate Similarity NPC260895
0.84 Intermediate Similarity NPC252933
0.84 Intermediate Similarity NPC200740
0.84 Intermediate Similarity NPC54394
0.8392 Intermediate Similarity NPC257173
0.8392 Intermediate Similarity NPC233780
0.8389 Intermediate Similarity NPC1612
0.8389 Intermediate Similarity NPC48479
0.8389 Intermediate Similarity NPC177298
0.8389 Intermediate Similarity NPC183959
0.838 Intermediate Similarity NPC235115
0.838 Intermediate Similarity NPC324929
0.838 Intermediate Similarity NPC160425
0.838 Intermediate Similarity NPC291454
0.8378 Intermediate Similarity NPC125449
0.8378 Intermediate Similarity NPC188074
0.8378 Intermediate Similarity NPC95864
0.8378 Intermediate Similarity NPC12200
0.8377 Intermediate Similarity NPC130955
0.8377 Intermediate Similarity NPC139036
0.8377 Intermediate Similarity NPC200594
0.8367 Intermediate Similarity NPC32470
0.8366 Intermediate Similarity NPC143328
0.8356 Intermediate Similarity NPC183824
0.8356 Intermediate Similarity NPC287722
0.8356 Intermediate Similarity NPC471417
0.8355 Intermediate Similarity NPC82592
0.8355 Intermediate Similarity NPC16286
0.8355 Intermediate Similarity NPC16082
0.8355 Intermediate Similarity NPC199926
0.8355 Intermediate Similarity NPC471800
0.8345 Intermediate Similarity NPC233056
0.8345 Intermediate Similarity NPC26697
0.8345 Intermediate Similarity NPC244441
0.8344 Intermediate Similarity NPC301323
0.8344 Intermediate Similarity NPC156222
0.8344 Intermediate Similarity NPC39732
0.8344 Intermediate Similarity NPC162313
0.8344 Intermediate Similarity NPC120163
0.8344 Intermediate Similarity NPC131624
0.8344 Intermediate Similarity NPC222830
0.8344 Intermediate Similarity NPC198826
0.8344 Intermediate Similarity NPC275836
0.8344 Intermediate Similarity NPC289968
0.8344 Intermediate Similarity NPC63187
0.8344 Intermediate Similarity NPC212678
0.8344 Intermediate Similarity NPC279989
0.8344 Intermediate Similarity NPC293183
0.8344 Intermediate Similarity NPC241498
0.8344 Intermediate Similarity NPC256283
0.8344 Intermediate Similarity NPC25270
0.8344 Intermediate Similarity NPC27208
0.8344 Intermediate Similarity NPC184284
0.8344 Intermediate Similarity NPC82325
0.8344 Intermediate Similarity NPC275722
0.8344 Intermediate Similarity NPC239128
0.8344 Intermediate Similarity NPC157784
0.8344 Intermediate Similarity NPC71334
0.8344 Intermediate Similarity NPC187498
0.8344 Intermediate Similarity NPC57030
0.8344 Intermediate Similarity NPC60972
0.8344 Intermediate Similarity NPC167903
0.8344 Intermediate Similarity NPC100887
0.8344 Intermediate Similarity NPC37684
0.8344 Intermediate Similarity NPC76041
0.8344 Intermediate Similarity NPC188203
0.8344 Intermediate Similarity NPC55205
0.8344 Intermediate Similarity NPC115249

  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 NPC134969 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8811 High Similarity NPD1511 Approved
0.869 High Similarity NPD1512 Approved
0.8462 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8289 Intermediate Similarity NPD2801 Approved
0.8227 Intermediate Similarity NPD943 Approved
0.8224 Intermediate Similarity NPD1934 Approved
0.8219 Intermediate Similarity NPD3750 Approved
0.817 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.817 Intermediate Similarity NPD1465 Phase 2
0.8169 Intermediate Similarity NPD230 Phase 1
0.8153 Intermediate Similarity NPD6232 Discontinued
0.8125 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD3817 Phase 2
0.8085 Intermediate Similarity NPD3764 Approved
0.8069 Intermediate Similarity NPD2935 Discontinued
0.8042 Intermediate Similarity NPD447 Suspended
0.8 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD1510 Phase 2
0.7986 Intermediate Similarity NPD1203 Approved
0.7956 Intermediate Similarity NPD1201 Approved
0.7949 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD5405 Approved
0.7945 Intermediate Similarity NPD5404 Approved
0.7945 Intermediate Similarity NPD5406 Approved
0.7945 Intermediate Similarity NPD5408 Approved
0.7877 Intermediate Similarity NPD3748 Approved
0.7857 Intermediate Similarity NPD1470 Approved
0.784 Intermediate Similarity NPD3818 Discontinued
0.7834 Intermediate Similarity NPD3882 Suspended
0.7823 Intermediate Similarity NPD1551 Phase 2
0.7821 Intermediate Similarity NPD7819 Suspended
0.7818 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD3226 Approved
0.7791 Intermediate Similarity NPD7054 Approved
0.7778 Intermediate Similarity NPD9493 Approved
0.777 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD9269 Phase 2
0.777 Intermediate Similarity NPD2346 Discontinued
0.7763 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7472 Approved
0.7742 Intermediate Similarity NPD4380 Phase 2
0.773 Intermediate Similarity NPD1164 Approved
0.7724 Intermediate Similarity NPD1240 Approved
0.7718 Intermediate Similarity NPD1549 Phase 2
0.7716 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD6166 Phase 2
0.7716 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD2313 Discontinued
0.7697 Intermediate Similarity NPD6797 Phase 2
0.7692 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD6190 Approved
0.7673 Intermediate Similarity NPD3749 Approved
0.7658 Intermediate Similarity NPD5402 Approved
0.7651 Intermediate Similarity NPD7251 Discontinued
0.7647 Intermediate Similarity NPD2534 Approved
0.7647 Intermediate Similarity NPD2533 Approved
0.7647 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD2532 Approved
0.7643 Intermediate Similarity NPD9717 Approved
0.7636 Intermediate Similarity NPD7074 Phase 3
0.7635 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1607 Approved
0.7582 Intermediate Similarity NPD6799 Approved
0.7576 Intermediate Similarity NPD5844 Phase 1
0.7562 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7075 Discontinued
0.7551 Intermediate Similarity NPD1933 Approved
0.7548 Intermediate Similarity NPD5403 Approved
0.7544 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD9545 Approved
0.7532 Intermediate Similarity NPD5401 Approved
0.7518 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD2799 Discontinued
0.7516 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7808 Phase 3
0.75 Intermediate Similarity NPD7768 Phase 2
0.7484 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1613 Approved
0.7483 Intermediate Similarity NPD2797 Approved
0.7483 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD9268 Approved
0.7468 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD411 Approved
0.7444 Intermediate Similarity NPD74 Approved
0.7444 Intermediate Similarity NPD9266 Approved
0.7432 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD2798 Approved
0.7421 Intermediate Similarity NPD6801 Discontinued
0.7419 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD7266 Discontinued
0.7413 Intermediate Similarity NPD3225 Approved
0.7405 Intermediate Similarity NPD6599 Discontinued
0.74 Intermediate Similarity NPD4308 Phase 3
0.7394 Intermediate Similarity NPD1608 Approved
0.7386 Intermediate Similarity NPD8166 Discontinued
0.7386 Intermediate Similarity NPD4628 Phase 3
0.7381 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD9264 Approved
0.7368 Intermediate Similarity NPD9267 Approved
0.7368 Intermediate Similarity NPD9263 Approved
0.7358 Intermediate Similarity NPD7411 Suspended
0.7355 Intermediate Similarity NPD7390 Discontinued
0.7351 Intermediate Similarity NPD2796 Approved
0.7347 Intermediate Similarity NPD3268 Approved
0.7329 Intermediate Similarity NPD4288 Approved
0.7329 Intermediate Similarity NPD6832 Phase 2
0.7324 Intermediate Similarity NPD422 Phase 1
0.732 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6959 Discontinued
0.7312 Intermediate Similarity NPD37 Approved
0.7301 Intermediate Similarity NPD919 Approved
0.7292 Intermediate Similarity NPD1283 Approved
0.7284 Intermediate Similarity NPD4965 Approved
0.7284 Intermediate Similarity NPD4967 Phase 2
0.7284 Intermediate Similarity NPD4966 Approved
0.7278 Intermediate Similarity NPD1653 Approved
0.7273 Intermediate Similarity NPD1481 Phase 2
0.726 Intermediate Similarity NPD9494 Approved
0.7256 Intermediate Similarity NPD5494 Approved
0.7251 Intermediate Similarity NPD8312 Approved
0.7251 Intermediate Similarity NPD8313 Approved
0.7235 Intermediate Similarity NPD7685 Pre-registration
0.7235 Intermediate Similarity NPD6559 Discontinued
0.7233 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD3455 Phase 2
0.723 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD8150 Discontinued
0.7222 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7199 Phase 2
0.7208 Intermediate Similarity NPD1243 Approved
0.7203 Intermediate Similarity NPD1535 Discovery
0.7202 Intermediate Similarity NPD7228 Approved
0.719 Intermediate Similarity NPD2344 Approved
0.7186 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD17 Approved
0.7179 Intermediate Similarity NPD3300 Phase 2
0.7162 Intermediate Similarity NPD3027 Phase 3
0.7161 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7003 Approved
0.716 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD4060 Phase 1
0.7133 Intermediate Similarity NPD4307 Phase 2
0.7126 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD3266 Approved
0.7123 Intermediate Similarity NPD3267 Approved
0.7122 Intermediate Similarity NPD9281 Approved
0.7111 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD920 Approved
0.7101 Intermediate Similarity NPD3751 Discontinued
0.7097 Intermediate Similarity NPD2800 Approved
0.7089 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1281 Approved
0.7078 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD1019 Discontinued
0.707 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD9261 Approved
0.7066 Intermediate Similarity NPD5710 Approved
0.7066 Intermediate Similarity NPD5711 Approved
0.7059 Intermediate Similarity NPD7033 Discontinued
0.7042 Intermediate Similarity NPD1548 Phase 1
0.7013 Intermediate Similarity NPD9570 Approved
0.7007 Intermediate Similarity NPD3022 Approved
0.7007 Intermediate Similarity NPD3021 Approved
0.7006 Intermediate Similarity NPD1247 Approved
0.7006 Intermediate Similarity NPD2309 Approved
0.7 Intermediate Similarity NPD1296 Phase 2
0.7 Intermediate Similarity NPD6798 Discontinued
0.6974 Remote Similarity NPD6355 Discontinued
0.6966 Remote Similarity NPD1610 Phase 2
0.6964 Remote Similarity NPD3787 Discontinued
0.6954 Remote Similarity NPD6233 Phase 2
0.6954 Remote Similarity NPD520 Approved
0.6944 Remote Similarity NPD4626 Approved
0.6937 Remote Similarity NPD6273 Approved
0.6933 Remote Similarity NPD7095 Approved
0.6933 Remote Similarity NPD6386 Approved
0.6933 Remote Similarity NPD6385 Approved
0.6923 Remote Similarity NPD3926 Phase 2
0.6908 Remote Similarity NPD2979 Phase 3
0.6906 Remote Similarity NPD228 Approved
0.6903 Remote Similarity NPD6100 Approved
0.6903 Remote Similarity NPD6099 Approved
0.6848 Remote Similarity NPD8455 Phase 2
0.6846 Remote Similarity NPD258 Approved
0.6846 Remote Similarity NPD257 Approved
0.6824 Remote Similarity NPD5242 Approved
0.6824 Remote Similarity NPD1876 Approved
0.6821 Remote Similarity NPD4625 Phase 3
0.681 Remote Similarity NPD7458 Discontinued
0.6806 Remote Similarity NPD1894 Discontinued
0.6805 Remote Similarity NPD8127 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