Structure

Physi-Chem Properties

Molecular Weight:  346.18
Volume:  371.416
LogP:  4.675
LogD:  3.983
LogS:  -3.492
# Rotatable Bonds:  11
TPSA:  87.74
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.445
Synthetic Accessibility Score:  3.212
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.478
MDCK Permeability:  3.2308686058968306e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.411
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.064
Plasma Protein Binding (PPB):  95.46570587158203%
Volume Distribution (VD):  0.782
Pgp-substrate:  3.8834280967712402%

ADMET: Metabolism

CYP1A2-inhibitor:  0.326
CYP1A2-substrate:  0.06
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.795
CYP2C9-substrate:  0.342
CYP2D6-inhibitor:  0.439
CYP2D6-substrate:  0.182
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.057

ADMET: Excretion

Clearance (CL):  1.772
Half-life (T1/2):  0.906

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.907
Drug-inuced Liver Injury (DILI):  0.021
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.711
Maximum Recommended Daily Dose:  0.532
Skin Sensitization:  0.946
Carcinogencity:  0.803
Eye Corrosion:  0.022
Eye Irritation:  0.902
Respiratory Toxicity:  0.963

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

  Natural Product: NPC1811

Natural Product ID:  NPC1811
Common Name*:   (E,6E)-6-[3-(Furan-3-Yl)Propylidene]-2-(4-Methylpent-3-Enyl)Hept-2-Enedioic Acid
IUPAC Name:   (E,6E)-6-[3-(furan-3-yl)propylidene]-2-(4-methylpent-3-enyl)hept-2-enedioic acid
Synonyms:   6,10-(E,E)-Thymifodioic Acid
Standard InCHIKey:  QZDPUYWKZQBXTJ-SCNFBCNRSA-N
Standard InCHI:  InChI=1S/C20H26O5/c1-15(2)6-3-8-17(19(21)22)10-5-11-18(20(23)24)9-4-7-16-12-13-25-14-16/h6,9-10,12-14H,3-5,7-8,11H2,1-2H3,(H,21,22)(H,23,24)/b17-10+,18-9+
SMILES:  CC(=CCC/C(=CCC/C(=CCCc1cocc1)/C(=O)O)/C(=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL256290
PubChem CID:   5469523
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12372 Baccharis thymifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18232640]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[18582112]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. aerial part n.a. PMID[18582112]
NPO15946 Laurenciella marilzae Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[26967625]
NPO15946 Laurenciella marilzae Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29102 Stemodia foliosa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25514 Oxytropis trichophysa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29228 Streptomyces sviceus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29069 Aplophyllum buxbaumii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29382 Bladhia japonica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12372 Baccharis thymifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6308 Protobothrops flavoviridis Species Viperidae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 11694.99 nM PMID[450060]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 92257.14 nM PMID[450060]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[450060]
NPT454 Organism Tenebrio molitor Tenebrio molitor Activity = 10.7 day PMID[450059]
NPT454 Organism Tenebrio molitor Tenebrio molitor Inhibition = 33.6 % PMID[450059]

☑ 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 NPC1811 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC26157
0.9615 High Similarity NPC471521
0.9615 High Similarity NPC473356
0.9524 High Similarity NPC177331
0.9279 High Similarity NPC21831
0.9279 High Similarity NPC187547
0.9189 High Similarity NPC208906
0.9189 High Similarity NPC144745
0.9167 High Similarity NPC105249
0.9115 High Similarity NPC474817
0.9035 High Similarity NPC474136
0.8957 High Similarity NPC289911
0.8957 High Similarity NPC283284
0.8879 High Similarity NPC475818
0.8879 High Similarity NPC476351
0.885 High Similarity NPC131801
0.8803 High Similarity NPC243269
0.8729 High Similarity NPC71274
0.8729 High Similarity NPC75557
0.8729 High Similarity NPC471559
0.8729 High Similarity NPC474829
0.8696 High Similarity NPC4898
0.8696 High Similarity NPC473969
0.8667 High Similarity NPC474438
0.8667 High Similarity NPC474279
0.8655 High Similarity NPC474260
0.8655 High Similarity NPC329922
0.8655 High Similarity NPC81912
0.8655 High Similarity NPC329694
0.8583 High Similarity NPC471501
0.8583 High Similarity NPC476016
0.8583 High Similarity NPC473355
0.8583 High Similarity NPC471573
0.8583 High Similarity NPC471554
0.8583 High Similarity NPC474830
0.8547 High Similarity NPC1848
0.8512 High Similarity NPC207294
0.8512 High Similarity NPC112706
0.85 High Similarity NPC46536
0.85 High Similarity NPC138139
0.8475 Intermediate Similarity NPC263870
0.8475 Intermediate Similarity NPC471549
0.8475 Intermediate Similarity NPC473379
0.843 Intermediate Similarity NPC83178
0.8387 Intermediate Similarity NPC45358
0.8387 Intermediate Similarity NPC97740
0.8348 Intermediate Similarity NPC28054
0.8333 Intermediate Similarity NPC118853
0.8319 Intermediate Similarity NPC477967
0.8306 Intermediate Similarity NPC17681
0.8306 Intermediate Similarity NPC89133
0.8264 Intermediate Similarity NPC179354
0.825 Intermediate Similarity NPC16922
0.8197 Intermediate Similarity NPC23086
0.8175 Intermediate Similarity NPC474425
0.8175 Intermediate Similarity NPC474407
0.8175 Intermediate Similarity NPC474426
0.8167 Intermediate Similarity NPC174915
0.8167 Intermediate Similarity NPC270807
0.8136 Intermediate Similarity NPC243704
0.813 Intermediate Similarity NPC137570
0.811 Intermediate Similarity NPC288209
0.8103 Intermediate Similarity NPC292036
0.8083 Intermediate Similarity NPC79557
0.8051 Intermediate Similarity NPC217180
0.8051 Intermediate Similarity NPC227660
0.8051 Intermediate Similarity NPC312525
0.8049 Intermediate Similarity NPC74612
0.8047 Intermediate Similarity NPC14650
0.8034 Intermediate Similarity NPC150895
0.8034 Intermediate Similarity NPC205523
0.8033 Intermediate Similarity NPC188377
0.8033 Intermediate Similarity NPC477965
0.8033 Intermediate Similarity NPC477038
0.8033 Intermediate Similarity NPC65735
0.8017 Intermediate Similarity NPC317217
0.7983 Intermediate Similarity NPC291619
0.7983 Intermediate Similarity NPC254958
0.7966 Intermediate Similarity NPC45536
0.7965 Intermediate Similarity NPC140688
0.7939 Intermediate Similarity NPC90953
0.7923 Intermediate Similarity NPC170604
0.7923 Intermediate Similarity NPC186626
0.7923 Intermediate Similarity NPC215109
0.7917 Intermediate Similarity NPC244862
0.7917 Intermediate Similarity NPC67345
0.7886 Intermediate Similarity NPC130275
0.784 Intermediate Similarity NPC319140
0.784 Intermediate Similarity NPC95567
0.7823 Intermediate Similarity NPC221798
0.7815 Intermediate Similarity NPC476031
0.7815 Intermediate Similarity NPC476014
0.7812 Intermediate Similarity NPC471544
0.7812 Intermediate Similarity NPC473344
0.7812 Intermediate Similarity NPC471817
0.7812 Intermediate Similarity NPC471545
0.7778 Intermediate Similarity NPC477040
0.7778 Intermediate Similarity NPC477966
0.7778 Intermediate Similarity NPC477123
0.7778 Intermediate Similarity NPC477039
0.7769 Intermediate Similarity NPC159786
0.7752 Intermediate Similarity NPC470740
0.7748 Intermediate Similarity NPC156768
0.7734 Intermediate Similarity NPC298190
0.7734 Intermediate Similarity NPC61788
0.7731 Intermediate Similarity NPC11821
0.7717 Intermediate Similarity NPC223063
0.7717 Intermediate Similarity NPC120836
0.771 Intermediate Similarity NPC303217
0.7692 Intermediate Similarity NPC106247
0.7674 Intermediate Similarity NPC473982
0.7669 Intermediate Similarity NPC202260
0.7667 Intermediate Similarity NPC76844
0.7667 Intermediate Similarity NPC474987
0.7661 Intermediate Similarity NPC69403
0.7661 Intermediate Similarity NPC291189
0.7656 Intermediate Similarity NPC21460
0.7656 Intermediate Similarity NPC238309
0.7656 Intermediate Similarity NPC476925
0.7652 Intermediate Similarity NPC473268
0.7647 Intermediate Similarity NPC476944
0.7638 Intermediate Similarity NPC327527
0.7638 Intermediate Similarity NPC476917
0.7634 Intermediate Similarity NPC92941
0.763 Intermediate Similarity NPC121158
0.7627 Intermediate Similarity NPC22678
0.7623 Intermediate Similarity NPC137710
0.7615 Intermediate Similarity NPC218838
0.7597 Intermediate Similarity NPC475092
0.7597 Intermediate Similarity NPC477645
0.7581 Intermediate Similarity NPC272487
0.7581 Intermediate Similarity NPC36255
0.7576 Intermediate Similarity NPC146872
0.7574 Intermediate Similarity NPC267632
0.7565 Intermediate Similarity NPC42471
0.7559 Intermediate Similarity NPC475236
0.7559 Intermediate Similarity NPC474476
0.7559 Intermediate Similarity NPC290955
0.7541 Intermediate Similarity NPC293424
0.754 Intermediate Similarity NPC230979
0.7537 Intermediate Similarity NPC107571
0.7536 Intermediate Similarity NPC346
0.752 Intermediate Similarity NPC311219
0.752 Intermediate Similarity NPC272899
0.7519 Intermediate Similarity NPC310830
0.7519 Intermediate Similarity NPC278832
0.7519 Intermediate Similarity NPC42400
0.7519 Intermediate Similarity NPC64157
0.7519 Intermediate Similarity NPC470742
0.7518 Intermediate Similarity NPC251865
0.7518 Intermediate Similarity NPC261733
0.7518 Intermediate Similarity NPC137295
0.7518 Intermediate Similarity NPC307346
0.7518 Intermediate Similarity NPC218712
0.7518 Intermediate Similarity NPC267004
0.75 Intermediate Similarity NPC252004
0.75 Intermediate Similarity NPC279877
0.75 Intermediate Similarity NPC158525
0.75 Intermediate Similarity NPC476947
0.75 Intermediate Similarity NPC26532
0.75 Intermediate Similarity NPC265793
0.75 Intermediate Similarity NPC329707
0.7482 Intermediate Similarity NPC308799
0.7482 Intermediate Similarity NPC250228
0.7481 Intermediate Similarity NPC148374
0.748 Intermediate Similarity NPC216810
0.7463 Intermediate Similarity NPC220094
0.7463 Intermediate Similarity NPC236532
0.7463 Intermediate Similarity NPC476943
0.7463 Intermediate Similarity NPC130976
0.7462 Intermediate Similarity NPC136340
0.746 Intermediate Similarity NPC83115
0.7459 Intermediate Similarity NPC240664
0.7444 Intermediate Similarity NPC46896
0.7442 Intermediate Similarity NPC208389
0.7442 Intermediate Similarity NPC2596
0.7429 Intermediate Similarity NPC113428
0.7429 Intermediate Similarity NPC61284
0.7424 Intermediate Similarity NPC471998
0.7422 Intermediate Similarity NPC246392
0.7419 Intermediate Similarity NPC193193
0.7419 Intermediate Similarity NPC31314
0.7417 Intermediate Similarity NPC311987
0.7402 Intermediate Similarity NPC300098
0.7402 Intermediate Similarity NPC473885
0.7402 Intermediate Similarity NPC303010
0.7402 Intermediate Similarity NPC471074
0.7398 Intermediate Similarity NPC206007
0.7388 Intermediate Similarity NPC307401
0.7387 Intermediate Similarity NPC146316
0.7357 Intermediate Similarity NPC476937
0.7357 Intermediate Similarity NPC216755
0.7357 Intermediate Similarity NPC471174
0.7357 Intermediate Similarity NPC476938
0.7357 Intermediate Similarity NPC255414
0.7353 Intermediate Similarity NPC56197
0.7353 Intermediate Similarity NPC67003
0.7353 Intermediate Similarity NPC90296
0.735 Intermediate Similarity NPC151530
0.735 Intermediate Similarity NPC157473

  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 NPC1811 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
0.752 Intermediate Similarity NPD9717 Approved
0.7407 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD1203 Approved
0.7177 Intermediate Similarity NPD9092 Discovery
0.7176 Intermediate Similarity NPD6832 Phase 2
0.712 Intermediate Similarity NPD9545 Approved
0.7119 Intermediate Similarity NPD3134 Approved
0.708 Intermediate Similarity NPD1551 Phase 2
0.7059 Intermediate Similarity NPD1358 Approved
0.705 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD1019 Discontinued
0.7 Intermediate Similarity NPD4628 Phase 3
0.6992 Remote Similarity NPD1241 Discontinued
0.696 Remote Similarity NPD9493 Approved
0.6953 Remote Similarity NPD3496 Discontinued
0.6947 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6947 Remote Similarity NPD2797 Approved
0.694 Remote Similarity NPD411 Approved
0.6912 Remote Similarity NPD447 Suspended
0.6894 Remote Similarity NPD5647 Approved
0.6884 Remote Similarity NPD2799 Discontinued
0.6884 Remote Similarity NPD4308 Phase 3
0.6875 Remote Similarity NPD1778 Approved
0.685 Remote Similarity NPD1894 Discontinued
0.6842 Remote Similarity NPD9494 Approved
0.6815 Remote Similarity NPD2313 Discontinued
0.6815 Remote Similarity NPD3268 Approved
0.6788 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6786 Remote Similarity NPD2344 Approved
0.6783 Remote Similarity NPD7440 Discontinued
0.6779 Remote Similarity NPD5761 Phase 2
0.6779 Remote Similarity NPD5760 Phase 2
0.6748 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6742 Remote Similarity NPD3225 Approved
0.6721 Remote Similarity NPD2182 Approved
0.6718 Remote Similarity NPD1481 Phase 2
0.6714 Remote Similarity NPD2935 Discontinued
0.6692 Remote Similarity NPD6362 Approved
0.6691 Remote Similarity NPD6798 Discontinued
0.6691 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD5585 Approved
0.6667 Remote Similarity NPD1933 Approved
0.6644 Remote Similarity NPD6273 Approved
0.6643 Remote Similarity NPD7033 Discontinued
0.6642 Remote Similarity NPD6233 Phase 2
0.6642 Remote Similarity NPD4062 Phase 3
0.6641 Remote Similarity NPD1535 Discovery
0.6641 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6621 Remote Similarity NPD6799 Approved
0.6619 Remote Similarity NPD6653 Approved
0.6612 Remote Similarity NPD9697 Approved
0.661 Remote Similarity NPD1238 Approved
0.6599 Remote Similarity NPD920 Approved
0.6597 Remote Similarity NPD2309 Approved
0.6594 Remote Similarity NPD4307 Phase 2
0.6591 Remote Similarity NPD1608 Approved
0.6569 Remote Similarity NPD3764 Approved
0.6565 Remote Similarity NPD3847 Discontinued
0.6552 Remote Similarity NPD643 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6004 Phase 3
0.6549 Remote Similarity NPD6005 Phase 3
0.6549 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6002 Phase 3
0.6549 Remote Similarity NPD2346 Discontinued
0.6533 Remote Similarity NPD7411 Suspended
0.6528 Remote Similarity NPD3750 Approved
0.6528 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6519 Remote Similarity NPD2798 Approved
0.651 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6508 Remote Similarity NPD5535 Approved
0.6486 Remote Similarity NPD5403 Approved
0.6483 Remote Similarity NPD2354 Approved
0.6483 Remote Similarity NPD3887 Approved
0.6475 Remote Similarity NPD3140 Approved
0.6475 Remote Similarity NPD3142 Approved
0.6471 Remote Similarity NPD454 Approved
0.6466 Remote Similarity NPD3972 Approved
0.6463 Remote Similarity NPD642 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2684 Approved
0.6447 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3266 Approved
0.6444 Remote Similarity NPD3267 Approved
0.6423 Remote Similarity NPD2614 Approved
0.6423 Remote Similarity NPD968 Approved
0.6418 Remote Similarity NPD4359 Approved
0.6418 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6414 Remote Similarity NPD7003 Approved
0.6406 Remote Similarity NPD690 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6393 Remote Similarity NPD164 Approved
0.6391 Remote Similarity NPD422 Phase 1
0.6389 Remote Similarity NPD1549 Phase 2
0.6378 Remote Similarity NPD7843 Approved
0.6377 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6371 Remote Similarity NPD9264 Approved
0.6371 Remote Similarity NPD9267 Approved
0.6371 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6371 Remote Similarity NPD290 Approved
0.6371 Remote Similarity NPD9263 Approved
0.637 Remote Similarity NPD1876 Approved
0.6364 Remote Similarity NPD4477 Approved
0.6364 Remote Similarity NPD4476 Approved
0.6364 Remote Similarity NPD17 Approved
0.6364 Remote Similarity NPD7768 Phase 2
0.6364 Remote Similarity NPD4626 Approved
0.6358 Remote Similarity NPD6559 Discontinued
0.6358 Remote Similarity NPD6599 Discontinued
0.6351 Remote Similarity NPD5401 Approved
0.6348 Remote Similarity NPD9258 Approved
0.6348 Remote Similarity NPD9256 Approved
0.6345 Remote Similarity NPD1243 Approved
0.6345 Remote Similarity NPD2976 Clinical (unspecified phase)
0.634 Remote Similarity NPD7096 Clinical (unspecified phase)
0.634 Remote Similarity NPD7819 Suspended
0.6323 Remote Similarity NPD3749 Approved
0.6323 Remote Similarity NPD7075 Discontinued
0.632 Remote Similarity NPD9266 Approved
0.632 Remote Similarity NPD6831 Clinical (unspecified phase)
0.632 Remote Similarity NPD74 Approved
0.6319 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6319 Remote Similarity NPD6800 Clinical (unspecified phase)
0.6319 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6319 Remote Similarity NPD2353 Approved
0.6319 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6319 Remote Similarity NPD1471 Phase 3
0.6312 Remote Similarity NPD230 Phase 1
0.6309 Remote Similarity NPD5049 Phase 3
0.6309 Remote Similarity NPD2186 Approved
0.6301 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6301 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6301 Remote Similarity NPD4110 Phase 3
0.6294 Remote Similarity NPD3748 Approved
0.6291 Remote Similarity NPD7458 Discontinued
0.6291 Remote Similarity NPD3226 Approved
0.6288 Remote Similarity NPD5691 Approved
0.6282 Remote Similarity NPD919 Approved
0.6277 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6276 Remote Similarity NPD970 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6801 Discontinued
0.6267 Remote Similarity NPD1670 Discontinued
0.6265 Remote Similarity NPD8434 Phase 2
0.626 Remote Similarity NPD5536 Phase 2
0.6259 Remote Similarity NPD7095 Approved
0.6259 Remote Similarity NPD5163 Phase 2
0.6258 Remote Similarity NPD3882 Suspended
0.6258 Remote Similarity NPD6765 Approved
0.6258 Remote Similarity NPD6764 Approved
0.625 Remote Similarity NPD2240 Approved
0.625 Remote Similarity NPD2796 Approved
0.625 Remote Similarity NPD2239 Approved
0.625 Remote Similarity NPD1283 Approved
0.625 Remote Similarity NPD821 Approved
0.6242 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6242 Remote Similarity NPD2534 Approved
0.6242 Remote Similarity NPD2532 Approved
0.6242 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6242 Remote Similarity NPD2533 Approved
0.6241 Remote Similarity NPD1240 Approved
0.6241 Remote Similarity NPD4060 Phase 1
0.6231 Remote Similarity NPD7157 Approved
0.6224 Remote Similarity NPD7097 Phase 1
0.6218 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6214 Remote Similarity NPD1048 Approved
0.6197 Remote Similarity NPD4618 Approved
0.6197 Remote Similarity NPD4340 Discontinued
0.6197 Remote Similarity NPD4622 Approved
0.6194 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6194 Remote Similarity NPD5402 Approved
0.6181 Remote Similarity NPD1510 Phase 2
0.6179 Remote Similarity NPD6647 Phase 2
0.6164 Remote Similarity NPD4534 Discontinued
0.6164 Remote Similarity NPD6808 Phase 2
0.6164 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6164 Remote Similarity NPD5958 Discontinued
0.6159 Remote Similarity NPD3873 Phase 3
0.6159 Remote Similarity NPD3869 Phase 3
0.6154 Remote Similarity NPD1607 Approved
0.6154 Remote Similarity NPD9281 Approved
0.6154 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6142 Remote Similarity NPD2067 Discontinued
0.6138 Remote Similarity NPD2862 Discontinued
0.6138 Remote Similarity NPD6032 Approved
0.6133 Remote Similarity NPD4662 Approved
0.6133 Remote Similarity NPD4661 Approved
0.6133 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6127 Remote Similarity NPD2979 Phase 3
0.6127 Remote Similarity NPD4140 Approved
0.6111 Remote Similarity NPD5688 Approved
0.6111 Remote Similarity NPD5689 Approved
0.6108 Remote Similarity NPD6785 Approved
0.6108 Remote Similarity NPD6784 Approved
0.6107 Remote Similarity NPD6671 Approved
0.6104 Remote Similarity NPD958 Approved
0.6101 Remote Similarity NPD5262 Discontinued
0.609 Remote Similarity NPD3817 Phase 2
0.609 Remote Similarity NPD2296 Approved
0.6087 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4575 Clinical (unspecified phase)

  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