Structure

Physi-Chem Properties

Molecular Weight:  277.99
Volume:  256.233
LogP:  5.014
LogD:  3.82
LogS:  -6.462
# Rotatable Bonds:  3
TPSA:  9.23
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.638
Synthetic Accessibility Score:  2.473
Fsp3:  0.077
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.395
MDCK Permeability:  5.871283065062016e-05
Pgp-inhibitor:  0.012
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.982
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.026
Plasma Protein Binding (PPB):  99.95977020263672%
Volume Distribution (VD):  1.713
Pgp-substrate:  1.2975785732269287%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.909
CYP2C19-inhibitor:  0.965
CYP2C19-substrate:  0.433
CYP2C9-inhibitor:  0.865
CYP2C9-substrate:  0.839
CYP2D6-inhibitor:  0.904
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.931
CYP3A4-substrate:  0.733

ADMET: Excretion

Clearance (CL):  2.711
Half-life (T1/2):  0.01

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.317
Drug-inuced Liver Injury (DILI):  0.927
AMES Toxicity:  0.162
Rat Oral Acute Toxicity:  0.054
Maximum Recommended Daily Dose:  0.064
Skin Sensitization:  0.114
Carcinogencity:  0.085
Eye Corrosion:  0.015
Eye Irritation:  0.663
Respiratory Toxicity:  0.315

Download Data

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

  Natural Product: NPC221877

Natural Product ID:  NPC221877
Common Name*:   3-Methoxy-2,5-Dithiophen-2-Ylthiophene
IUPAC Name:   3-methoxy-2,5-dithiophen-2-ylthiophene
Synonyms:  
Standard InCHIKey:  YBJPZZBYEHNCSU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H10OS3/c1-14-9-8-12(10-4-2-6-15-10)17-13(9)11-5-3-7-16-11/h2-8H,1H3
SMILES:  COc1cc(sc1c1cccs1)c1cccs1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1970377
PubChem CID:   373943
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002021] Bi- and oligothiophenes

*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
NPO12000 Pelteobagrus nudiceps n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12692 Roldana lobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13372 Retiboletus retipes Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11650 Renilla reniformis Species Renillidae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 81846.48 nM PMID[474405]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 53456.44 nM PMID[474405]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 15703.63 nM PMID[474405]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 24490.63 nM PMID[474405]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 38194.43 nM PMID[474405]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 14256.08 nM PMID[474405]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 73790.42 nM PMID[474405]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 29716.66 nM PMID[474405]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 38994.2 nM PMID[474405]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 13551.89 nM PMID[474405]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 63826.35 nM PMID[474405]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 32583.67 nM PMID[474405]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 43551.19 nM PMID[474405]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 97051.0 nM PMID[474405]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 22284.35 nM PMID[474405]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 12531.41 nM PMID[474405]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[474405]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 17701.09 nM PMID[474405]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 41591.06 nM PMID[474405]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 71121.35 nM PMID[474405]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 32809.53 nM PMID[474405]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 27733.2 nM PMID[474405]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 30974.19 nM PMID[474405]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 49545.02 nM PMID[474405]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 35318.32 nM PMID[474405]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 35563.13 nM PMID[474405]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 52360.04 nM PMID[474405]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 50234.26 nM PMID[474405]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 46238.1 nM PMID[474405]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 31477.48 nM PMID[474405]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 26730.06 nM PMID[474405]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 26730.06 nM PMID[474405]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 33265.96 nM PMID[474405]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 13963.68 nM PMID[474405]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4395.42 nM PMID[474405]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 28641.78 nM PMID[474405]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 53579.67 nM PMID[474405]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 6546.36 nM PMID[474405]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 30974.19 nM PMID[474405]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 44977.99 nM PMID[474405]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 29991.63 nM PMID[474405]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 26001.6 nM PMID[474405]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 40926.07 nM PMID[474405]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 25527.01 nM PMID[474405]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 23334.58 nM PMID[474405]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 39264.49 nM PMID[474405]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 39719.15 nM PMID[474405]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 36224.3 nM PMID[474405]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 8165.82 nM PMID[474405]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 29308.93 nM PMID[474405]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 20749.14 nM PMID[474405]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 43451.02 nM PMID[474405]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 34040.82 nM PMID[474405]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 21777.1 nM PMID[474405]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 13243.42 nM PMID[474405]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 1584.89 nM PMID[474405]

☑ 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 NPC221877 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
0.8692 High Similarity NPC472171
0.8611 High Similarity NPC472172
0.7857 Intermediate Similarity NPC173019
0.6981 Remote Similarity NPC195713
0.6975 Remote Similarity NPC472170
0.696 Remote Similarity NPC32356
0.6667 Remote Similarity NPC124576
0.6585 Remote Similarity NPC475086
0.6552 Remote Similarity NPC321956
0.6518 Remote Similarity NPC23837
0.6471 Remote Similarity NPC474934
0.6466 Remote Similarity NPC71853
0.6435 Remote Similarity NPC2751
0.6422 Remote Similarity NPC8981
0.6417 Remote Similarity NPC95755
0.6393 Remote Similarity NPC24122
0.6379 Remote Similarity NPC8002
0.6379 Remote Similarity NPC259134
0.6379 Remote Similarity NPC99886
0.6379 Remote Similarity NPC177844
0.6372 Remote Similarity NPC125306
0.6371 Remote Similarity NPC475269
0.6348 Remote Similarity NPC206876
0.6281 Remote Similarity NPC470161
0.626 Remote Similarity NPC300166
0.625 Remote Similarity NPC175376
0.6239 Remote Similarity NPC302546
0.623 Remote Similarity NPC100870
0.6167 Remote Similarity NPC471581
0.616 Remote Similarity NPC241224
0.6159 Remote Similarity NPC470008
0.6154 Remote Similarity NPC157213
0.6154 Remote Similarity NPC47422
0.6129 Remote Similarity NPC475115
0.608 Remote Similarity NPC12870
0.608 Remote Similarity NPC298224
0.608 Remote Similarity NPC24327
0.6063 Remote Similarity NPC113457
0.6063 Remote Similarity NPC42471
0.605 Remote Similarity NPC318429
0.6032 Remote Similarity NPC38079
0.6032 Remote Similarity NPC108875
0.6032 Remote Similarity NPC38209
0.6032 Remote Similarity NPC292792
0.6016 Remote Similarity NPC175298
0.6 Remote Similarity NPC84325
0.5984 Remote Similarity NPC470393
0.5984 Remote Similarity NPC473855
0.5969 Remote Similarity NPC75440
0.5968 Remote Similarity NPC275104
0.5968 Remote Similarity NPC471576
0.5952 Remote Similarity NPC305205
0.5938 Remote Similarity NPC326801
0.5938 Remote Similarity NPC1065
0.5938 Remote Similarity NPC473653
0.5923 Remote Similarity NPC474272
0.592 Remote Similarity NPC13755
0.5906 Remote Similarity NPC12987
0.5906 Remote Similarity NPC474603
0.5902 Remote Similarity NPC16649
0.5902 Remote Similarity NPC114325
0.5891 Remote Similarity NPC233320
0.5891 Remote Similarity NPC251306
0.5891 Remote Similarity NPC186469
0.5887 Remote Similarity NPC313918
0.5878 Remote Similarity NPC2682
0.5878 Remote Similarity NPC303521
0.5878 Remote Similarity NPC475852
0.5878 Remote Similarity NPC31279
0.5873 Remote Similarity NPC12714
0.5873 Remote Similarity NPC310905
0.5873 Remote Similarity NPC307425
0.5873 Remote Similarity NPC51633
0.5859 Remote Similarity NPC227255
0.5859 Remote Similarity NPC238115
0.5859 Remote Similarity NPC42383
0.5846 Remote Similarity NPC201959
0.5846 Remote Similarity NPC97811
0.5827 Remote Similarity NPC179686
0.5827 Remote Similarity NPC192596
0.5827 Remote Similarity NPC80241
0.5827 Remote Similarity NPC301641
0.582 Remote Similarity NPC233791
0.5816 Remote Similarity NPC475082
0.5814 Remote Similarity NPC30416
0.5804 Remote Similarity NPC158737
0.5802 Remote Similarity NPC234639
0.5802 Remote Similarity NPC127326
0.5794 Remote Similarity NPC156768
0.5794 Remote Similarity NPC107101
0.5781 Remote Similarity NPC109637
0.5781 Remote Similarity NPC2518
0.5781 Remote Similarity NPC283546
0.5778 Remote Similarity NPC296526
0.5775 Remote Similarity NPC83301
0.5772 Remote Similarity NPC321285
0.5769 Remote Similarity NPC35543
0.5769 Remote Similarity NPC194034
0.5758 Remote Similarity NPC231251
0.5758 Remote Similarity NPC473809
0.5758 Remote Similarity NPC25067
0.5758 Remote Similarity NPC137685
0.5758 Remote Similarity NPC88868
0.5746 Remote Similarity NPC35344
0.5746 Remote Similarity NPC165106
0.5746 Remote Similarity NPC141003
0.5745 Remote Similarity NPC472888
0.5736 Remote Similarity NPC288760
0.5736 Remote Similarity NPC128730
0.5736 Remote Similarity NPC8302
0.5734 Remote Similarity NPC141059
0.5725 Remote Similarity NPC245115
0.5725 Remote Similarity NPC241549
0.5725 Remote Similarity NPC291837
0.5714 Remote Similarity NPC314803
0.5714 Remote Similarity NPC132725
0.5714 Remote Similarity NPC195873
0.5714 Remote Similarity NPC23332
0.5714 Remote Similarity NPC8547
0.5714 Remote Similarity NPC21890
0.5714 Remote Similarity NPC275627
0.5714 Remote Similarity NPC257124
0.5714 Remote Similarity NPC307039
0.5714 Remote Similarity NPC156840
0.5714 Remote Similarity NPC173746
0.5704 Remote Similarity NPC18449
0.5704 Remote Similarity NPC276737
0.5704 Remote Similarity NPC121783
0.5704 Remote Similarity NPC34902
0.5704 Remote Similarity NPC22610
0.5693 Remote Similarity NPC25648
0.5692 Remote Similarity NPC326447
0.5692 Remote Similarity NPC176971
0.5688 Remote Similarity NPC105991
0.5685 Remote Similarity NPC271208
0.5685 Remote Similarity NPC233224
0.5683 Remote Similarity NPC344161
0.5683 Remote Similarity NPC246214
0.5682 Remote Similarity NPC259554
0.5682 Remote Similarity NPC82016
0.5672 Remote Similarity NPC199462
0.5662 Remote Similarity NPC475815
0.5662 Remote Similarity NPC53906
0.5662 Remote Similarity NPC185541
0.5662 Remote Similarity NPC47194
0.5662 Remote Similarity NPC464
0.5662 Remote Similarity NPC473264
0.5662 Remote Similarity NPC167934
0.5662 Remote Similarity NPC808
0.5662 Remote Similarity NPC283169
0.5652 Remote Similarity NPC206007
0.5652 Remote Similarity NPC329980
0.5649 Remote Similarity NPC151530
0.5649 Remote Similarity NPC157473
0.5649 Remote Similarity NPC258171
0.5649 Remote Similarity NPC227894
0.5646 Remote Similarity NPC82111
0.5646 Remote Similarity NPC227160
0.5639 Remote Similarity NPC94045
0.5639 Remote Similarity NPC168657
0.5639 Remote Similarity NPC106141
0.5639 Remote Similarity NPC183648
0.563 Remote Similarity NPC109241
0.563 Remote Similarity NPC26524
0.563 Remote Similarity NPC204120
0.563 Remote Similarity NPC303522
0.562 Remote Similarity NPC9341
0.562 Remote Similarity NPC33900
0.562 Remote Similarity NPC476031
0.562 Remote Similarity NPC54507
0.562 Remote Similarity NPC476014
0.562 Remote Similarity NPC141090
0.562 Remote Similarity NPC150624
0.562 Remote Similarity NPC229147
0.562 Remote Similarity NPC19290
0.562 Remote Similarity NPC81067
0.562 Remote Similarity NPC85292
0.5615 Remote Similarity NPC473393
0.5615 Remote Similarity NPC307875
0.5615 Remote Similarity NPC17537
0.5614 Remote Similarity NPC299367
0.5612 Remote Similarity NPC119949
0.5606 Remote Similarity NPC146530
0.5606 Remote Similarity NPC309982
0.5603 Remote Similarity NPC216929
0.5603 Remote Similarity NPC312713
0.5603 Remote Similarity NPC172676
0.5603 Remote Similarity NPC126935
0.5603 Remote Similarity NPC65933
0.5603 Remote Similarity NPC57268
0.56 Remote Similarity NPC146316

  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 NPC221877 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
0.6871 Remote Similarity NPD6813 Clinical (unspecified phase)
0.6643 Remote Similarity NPD442 Discontinued
0.6622 Remote Similarity NPD2901 Approved
0.6622 Remote Similarity NPD2900 Approved
0.662 Remote Similarity NPD2862 Discontinued
0.6617 Remote Similarity NPD1244 Clinical (unspecified phase)
0.6617 Remote Similarity NPD1877 Discontinued
0.6565 Remote Similarity NPD446 Clinical (unspecified phase)
0.6494 Remote Similarity NPD1295 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6890 Discontinued
0.6268 Remote Similarity NPD4101 Phase 1
0.6211 Remote Similarity NPD1194 Discontinued
0.6188 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6154 Remote Similarity NPD9295 Approved
0.6071 Remote Similarity NPD1469 Clinical (unspecified phase)
0.6065 Remote Similarity NPD1642 Discontinued
0.6061 Remote Similarity NPD6597 Approved
0.6061 Remote Similarity NPD6598 Approved
0.605 Remote Similarity NPD9365 Approved
0.6047 Remote Similarity NPD5451 Approved
0.6031 Remote Similarity NPD1105 Clinical (unspecified phase)
0.5949 Remote Similarity NPD487 Discontinued
0.5949 Remote Similarity NPD1006 Clinical (unspecified phase)
0.5921 Remote Similarity NPD7440 Discontinued
0.5915 Remote Similarity NPD7015 Phase 2
0.5915 Remote Similarity NPD7016 Phase 3
0.5909 Remote Similarity NPD1279 Clinical (unspecified phase)
0.5906 Remote Similarity NPD5085 Clinical (unspecified phase)
0.5906 Remote Similarity NPD6800 Clinical (unspecified phase)
0.5902 Remote Similarity NPD9296 Approved
0.5871 Remote Similarity NPD8012 Clinical (unspecified phase)
0.5862 Remote Similarity NPD3058 Clinical (unspecified phase)
0.5846 Remote Similarity NPD2684 Approved
0.5828 Remote Similarity NPD3599 Approved
0.5828 Remote Similarity NPD4127 Clinical (unspecified phase)
0.5821 Remote Similarity NPD9299 Approved
0.5817 Remote Similarity NPD6066 Clinical (unspecified phase)
0.5814 Remote Similarity NPD968 Approved
0.5797 Remote Similarity NPD2107 Clinical (unspecified phase)
0.5782 Remote Similarity NPD4340 Discontinued
0.5769 Remote Similarity NPD5373 Approved
0.5769 Remote Similarity NPD290 Approved
0.5769 Remote Similarity NPD5374 Approved
0.5753 Remote Similarity NPD4404 Approved
0.5748 Remote Similarity NPD291 Approved
0.5746 Remote Similarity NPD5283 Phase 1
0.5714 Remote Similarity NPD228 Approved
0.5714 Remote Similarity NPD6374 Clinical (unspecified phase)
0.5706 Remote Similarity NPD2745 Approved
0.5706 Remote Similarity NPD2746 Clinical (unspecified phase)
0.5705 Remote Similarity NPD5886 Approved
0.5705 Remote Similarity NPD41 Approved
0.5705 Remote Similarity NPD2236 Approved
0.5696 Remote Similarity NPD6055 Clinical (unspecified phase)
0.5695 Remote Similarity NPD1803 Phase 3
0.5692 Remote Similarity NPD3134 Approved
0.5689 Remote Similarity NPD730 Discontinued
0.5686 Remote Similarity NPD7976 Clinical (unspecified phase)
0.568 Remote Similarity NPD1672 Phase 2
0.5672 Remote Similarity NPD5535 Approved
0.5672 Remote Similarity NPD821 Approved
0.5672 Remote Similarity NPD7843 Approved
0.5667 Remote Similarity NPD3846 Clinical (unspecified phase)
0.5662 Remote Similarity NPD2557 Approved
0.5655 Remote Similarity NPD682 Discontinued
0.5652 Remote Similarity NPD6581 Approved
0.5652 Remote Similarity NPD7330 Discontinued
0.5652 Remote Similarity NPD6580 Approved
0.5649 Remote Similarity NPD1358 Approved
0.563 Remote Similarity NPD1241 Discontinued
0.563 Remote Similarity NPD1280 Clinical (unspecified phase)
0.5621 Remote Similarity NPD5698 Clinical (unspecified phase)
0.562 Remote Similarity NPD3596 Phase 2
0.5612 Remote Similarity NPD6830 Clinical (unspecified phase)
0.5607 Remote Similarity NPD6734 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