Structure

Physi-Chem Properties

Molecular Weight:  279.09
Volume:  284.638
LogP:  4.023
LogD:  3.137
LogS:  -6.796
# Rotatable Bonds:  2
TPSA:  47.56
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.729
Synthetic Accessibility Score:  2.41
Fsp3:  0.118
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:  -4.916
MDCK Permeability:  2.437955845380202e-05
Pgp-inhibitor:  0.029
Pgp-substrate:  0.741
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.287
Plasma Protein Binding (PPB):  92.89813995361328%
Volume Distribution (VD):  0.754
Pgp-substrate:  6.53672981262207%

ADMET: Metabolism

CYP1A2-inhibitor:  0.964
CYP1A2-substrate:  0.961
CYP2C19-inhibitor:  0.535
CYP2C19-substrate:  0.731
CYP2C9-inhibitor:  0.653
CYP2C9-substrate:  0.87
CYP2D6-inhibitor:  0.545
CYP2D6-substrate:  0.602
CYP3A4-inhibitor:  0.453
CYP3A4-substrate:  0.162

ADMET: Excretion

Clearance (CL):  2.726
Half-life (T1/2):  0.358

ADMET: Toxicity

hERG Blockers:  0.083
Human Hepatotoxicity (H-HT):  0.492
Drug-inuced Liver Injury (DILI):  0.919
AMES Toxicity:  0.857
Rat Oral Acute Toxicity:  0.076
Maximum Recommended Daily Dose:  0.595
Skin Sensitization:  0.876
Carcinogencity:  0.703
Eye Corrosion:  0.007
Eye Irritation:  0.599
Respiratory Toxicity:  0.857

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  Natural Product: NPC265383

Natural Product ID:  NPC265383
Common Name*:   Cepharanone B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YHQIYHDLBZXUON-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H13NO3/c1-20-13-8-11-14-12(18-17(11)19)7-9-5-3-4-6-10(9)15(14)16(13)21-2/h3-8H,1-2H3,(H,18,19)
SMILES:  COc1c(OC)cc2c3c1c1ccccc1cc3N=C2O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL226772
PubChem CID:   162739
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002663] Aristolactams

*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
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[10924192]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10978218]
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. bark n.a. PMID[11101460]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11754613]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14584959]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14643329]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. root n.a. PMID[14750033]
NPO5928 Streptomyces nashvillensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1490884]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15482936]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota whole plant Yunnan Province, China 2002-FEB PMID[16309318]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota whole plant Yunnan Province, China 2002-FEB PMID[16724842]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota stem n.a. n.a. PMID[17081761]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota roots n.a. n.a. PMID[18841903]
NPO26094 Stolonica socialis Species Styelidae Eukaryota n.a. At a depth between 3 and 15 m in Las Lajas (Cdiz, Spain) (3606'11'' N, 525'47'' W) 2003-SEP PMID[20014800]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Roots n.a. n.a. PMID[24359277]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Aerial Parts n.a. n.a. PMID[24387347]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[31642320]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[9548847]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8287 Piper taiwanense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8287 Piper taiwanense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22405 Litsea monopetala Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11010 Melampyrum elatius Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9030 Couroupita guianensis Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17271 Aegialitis annulata Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28938 Artemisia coerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO868 Cephalaria gigantea Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19590 Daedaleopsis tricolor Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5928 Streptomyces nashvillensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3584 Oyedaea buphthalmoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2646 Moschus moschiferus Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO95 Streptomyces ambofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12667 Goniodoma pseudogoniaulax Species Coleophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2400 Streptomyces mediolani Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11715 Polygonum aubertii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27184 Bonellia macrocarpa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13728 Metanarthecium luteoviride Species Nartheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27135 Tubularia larynx Species Tubulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1366 Piptothrix areolare n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4366 Hura crepitans Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2885 Erechtites quadridentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27362 Hypericum elodes Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8287 Piper taiwanense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28066 Aloe speciosa Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27401 Aniba riparia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27953 Eugenia formosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26094 Stolonica socialis Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28133 Geigeria filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27439 Letharia vulpina Species Parmeliaceae 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
NPT1076 Cell Line B-cells IC50 = 7110.0 nM PMID[482831]
NPT148 Cell Line HCT-15 Homo sapiens GI50 > 30000.0 nM PMID[482832]
NPT27 Others Unspecified CC50 = 11100.0 nM PMID[482831]
NPT2 Others Unspecified IC50 = 6960.0 nM PMID[482831]
NPT2 Others Unspecified Ratio CC50/IC50 = 1.0 n.a. PMID[482831]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 > 30000.0 nM PMID[482832]

☑ 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 NPC265383 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
0.9938 High Similarity NPC260118
0.9877 High Similarity NPC215747
0.9877 High Similarity NPC192939
0.9816 High Similarity NPC119579
0.9756 High Similarity NPC28425
0.9755 High Similarity NPC311936
0.9524 High Similarity NPC296742
0.9521 High Similarity NPC69213
0.9521 High Similarity NPC219170
0.9521 High Similarity NPC180253
0.9518 High Similarity NPC276060
0.9464 High Similarity NPC224293
0.9408 High Similarity NPC112676
0.9349 High Similarity NPC22928
0.9191 High Similarity NPC29472
0.9186 High Similarity NPC294244
0.8785 High Similarity NPC159101
0.8268 Intermediate Similarity NPC320088
0.8258 Intermediate Similarity NPC276674
0.8258 Intermediate Similarity NPC33902
0.8239 Intermediate Similarity NPC190461
0.8171 Intermediate Similarity NPC285941
0.8166 Intermediate Similarity NPC235628
0.8144 Intermediate Similarity NPC18614
0.8087 Intermediate Similarity NPC78284
0.8084 Intermediate Similarity NPC52475
0.8022 Intermediate Similarity NPC474904
0.8022 Intermediate Similarity NPC312531
0.8 Intermediate Similarity NPC249405
0.7989 Intermediate Similarity NPC68328
0.791 Intermediate Similarity NPC168153
0.791 Intermediate Similarity NPC231371
0.7784 Intermediate Similarity NPC85661
0.7751 Intermediate Similarity NPC77359
0.774 Intermediate Similarity NPC12053
0.774 Intermediate Similarity NPC81218
0.774 Intermediate Similarity NPC158376
0.774 Intermediate Similarity NPC145832
0.774 Intermediate Similarity NPC474931
0.774 Intermediate Similarity NPC306555
0.774 Intermediate Similarity NPC117188
0.774 Intermediate Similarity NPC205421
0.7738 Intermediate Similarity NPC16436
0.7732 Intermediate Similarity NPC46679
0.7713 Intermediate Similarity NPC162653
0.7692 Intermediate Similarity NPC171882
0.7692 Intermediate Similarity NPC121510
0.7674 Intermediate Similarity NPC10875
0.7674 Intermediate Similarity NPC10730
0.767 Intermediate Similarity NPC1229
0.765 Intermediate Similarity NPC179704
0.7644 Intermediate Similarity NPC476572
0.7627 Intermediate Similarity NPC78222
0.7627 Intermediate Similarity NPC212794
0.7627 Intermediate Similarity NPC136508
0.7627 Intermediate Similarity NPC13504
0.7627 Intermediate Similarity NPC306843
0.7627 Intermediate Similarity NPC253043
0.7627 Intermediate Similarity NPC96603
0.7627 Intermediate Similarity NPC196447
0.7627 Intermediate Similarity NPC477563
0.7616 Intermediate Similarity NPC275027
0.7582 Intermediate Similarity NPC287588
0.7577 Intermediate Similarity NPC38961
0.7576 Intermediate Similarity NPC91234
0.7571 Intermediate Similarity NPC324144
0.7569 Intermediate Similarity NPC228040
0.7569 Intermediate Similarity NPC477020
0.7569 Intermediate Similarity NPC66341
0.7569 Intermediate Similarity NPC192135
0.7561 Intermediate Similarity NPC200888
0.7557 Intermediate Similarity NPC166014
0.7557 Intermediate Similarity NPC27410
0.7551 Intermediate Similarity NPC100573
0.7551 Intermediate Similarity NPC207873
0.7551 Intermediate Similarity NPC90185
0.7541 Intermediate Similarity NPC114364
0.7541 Intermediate Similarity NPC320223
0.7529 Intermediate Similarity NPC99659
0.7529 Intermediate Similarity NPC325871
0.7514 Intermediate Similarity NPC60186
0.75 Intermediate Similarity NPC290227
0.7486 Intermediate Similarity NPC219341
0.7473 Intermediate Similarity NPC474051
0.7463 Intermediate Similarity NPC240684
0.7461 Intermediate Similarity NPC25897
0.7459 Intermediate Similarity NPC168753
0.7459 Intermediate Similarity NPC26240
0.7459 Intermediate Similarity NPC477562
0.7459 Intermediate Similarity NPC118274
0.7459 Intermediate Similarity NPC69712
0.7457 Intermediate Similarity NPC81733
0.7457 Intermediate Similarity NPC326316
0.7449 Intermediate Similarity NPC261388
0.7448 Intermediate Similarity NPC17677
0.7444 Intermediate Similarity NPC298979
0.7444 Intermediate Similarity NPC247389
0.7443 Intermediate Similarity NPC206736
0.7443 Intermediate Similarity NPC195766
0.7432 Intermediate Similarity NPC229166
0.7432 Intermediate Similarity NPC477558
0.7432 Intermediate Similarity NPC128560
0.7432 Intermediate Similarity NPC199465
0.743 Intermediate Similarity NPC225774
0.7421 Intermediate Similarity NPC302001
0.7419 Intermediate Similarity NPC248642
0.7418 Intermediate Similarity NPC239775
0.7405 Intermediate Similarity NPC126284
0.7401 Intermediate Similarity NPC329837
0.7398 Intermediate Similarity NPC156728
0.7398 Intermediate Similarity NPC244606
0.7389 Intermediate Similarity NPC35627
0.7389 Intermediate Similarity NPC24264
0.7389 Intermediate Similarity NPC81247
0.7389 Intermediate Similarity NPC476573
0.7389 Intermediate Similarity NPC476432
0.7381 Intermediate Similarity NPC470090
0.738 Intermediate Similarity NPC135772
0.738 Intermediate Similarity NPC156576
0.7374 Intermediate Similarity NPC19555
0.7368 Intermediate Similarity NPC79213
0.735 Intermediate Similarity NPC186569
0.735 Intermediate Similarity NPC61731
0.7348 Intermediate Similarity NPC150879
0.7333 Intermediate Similarity NPC16805
0.7333 Intermediate Similarity NPC302527
0.7333 Intermediate Similarity NPC167546
0.733 Intermediate Similarity NPC122463
0.733 Intermediate Similarity NPC244112
0.732 Intermediate Similarity NPC212163
0.7318 Intermediate Similarity NPC24954
0.7314 Intermediate Similarity NPC26601
0.7312 Intermediate Similarity NPC474507
0.7299 Intermediate Similarity NPC219383
0.7297 Intermediate Similarity NPC476577
0.7297 Intermediate Similarity NPC148709
0.7297 Intermediate Similarity NPC173416
0.7288 Intermediate Similarity NPC170503
0.7288 Intermediate Similarity NPC203784
0.7288 Intermediate Similarity NPC126519
0.7288 Intermediate Similarity NPC291359
0.7277 Intermediate Similarity NPC227361
0.7277 Intermediate Similarity NPC124658
0.7273 Intermediate Similarity NPC155442
0.7273 Intermediate Similarity NPC476574
0.7273 Intermediate Similarity NPC477561
0.7273 Intermediate Similarity NPC312918
0.7273 Intermediate Similarity NPC228843
0.7273 Intermediate Similarity NPC304183
0.7268 Intermediate Similarity NPC152212
0.7263 Intermediate Similarity NPC477559
0.7263 Intermediate Similarity NPC232924
0.7263 Intermediate Similarity NPC160298
0.7263 Intermediate Similarity NPC306902
0.7263 Intermediate Similarity NPC266753
0.7262 Intermediate Similarity NPC266006
0.7253 Intermediate Similarity NPC210918
0.7246 Intermediate Similarity NPC118121
0.7245 Intermediate Similarity NPC295676
0.7245 Intermediate Similarity NPC471489
0.7241 Intermediate Similarity NPC211296
0.7241 Intermediate Similarity NPC298449
0.7238 Intermediate Similarity NPC169743
0.7236 Intermediate Similarity NPC193777
0.7234 Intermediate Similarity NPC476575
0.7234 Intermediate Similarity NPC116284
0.722 Intermediate Similarity NPC204446
0.7219 Intermediate Similarity NPC105847
0.7219 Intermediate Similarity NPC243759
0.7219 Intermediate Similarity NPC218131
0.7211 Intermediate Similarity NPC57036
0.7209 Intermediate Similarity NPC5462
0.7202 Intermediate Similarity NPC254610
0.72 Intermediate Similarity NPC265473
0.72 Intermediate Similarity NPC276665
0.7198 Intermediate Similarity NPC257354
0.7188 Intermediate Similarity NPC141915
0.7188 Intermediate Similarity NPC114335
0.7188 Intermediate Similarity NPC280964
0.7182 Intermediate Similarity NPC233650
0.7179 Intermediate Similarity NPC23080
0.7179 Intermediate Similarity NPC193906
0.7176 Intermediate Similarity NPC12668
0.7176 Intermediate Similarity NPC308768
0.7174 Intermediate Similarity NPC6152
0.7174 Intermediate Similarity NPC312872
0.716 Intermediate Similarity NPC230919
0.716 Intermediate Similarity NPC200935
0.716 Intermediate Similarity NPC151656
0.716 Intermediate Similarity NPC266453
0.7158 Intermediate Similarity NPC310894
0.7158 Intermediate Similarity NPC204947
0.7157 Intermediate Similarity NPC235076
0.715 Intermediate Similarity NPC308943
0.715 Intermediate Similarity NPC222561
0.715 Intermediate Similarity NPC174049
0.7143 Intermediate Similarity NPC313886
0.7143 Intermediate Similarity NPC219162
0.7143 Intermediate Similarity NPC134858
0.7143 Intermediate Similarity NPC251160

  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 NPC265383 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
0.7719 Intermediate Similarity NPD5617 Suspended
0.7654 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD2883 Discontinued
0.7472 Intermediate Similarity NPD1850 Phase 3
0.7457 Intermediate Similarity NPD5811 Approved
0.7444 Intermediate Similarity NPD4083 Discontinued
0.7443 Intermediate Similarity NPD2358 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD2845 Phase 2
0.7354 Intermediate Similarity NPD2843 Phase 2
0.7337 Intermediate Similarity NPD3920 Phase 2
0.7297 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3778 Approved
0.7216 Intermediate Similarity NPD3296 Phase 1
0.7213 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD950 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD2789 Approved
0.7173 Intermediate Similarity NPD3408 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD4055 Discovery
0.7167 Intermediate Similarity NPD3453 Discontinued
0.7159 Intermediate Similarity NPD4005 Discontinued
0.7135 Intermediate Similarity NPD3812 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD5641 Discontinued
0.7126 Intermediate Similarity NPD4123 Phase 3
0.7112 Intermediate Similarity NPD6184 Discontinued
0.7104 Intermediate Similarity NPD4606 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD3051 Approved
0.7097 Intermediate Similarity NPD5810 Discontinued
0.7086 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5966 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD3236 Phase 3
0.7079 Intermediate Similarity NPD3237 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD2969 Approved
0.7065 Intermediate Similarity NPD2970 Approved
0.7059 Intermediate Similarity NPD7479 Phase 2
0.7056 Intermediate Similarity NPD5599 Discontinued
0.7049 Intermediate Similarity NPD2821 Approved
0.7027 Intermediate Similarity NPD677 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD3763 Approved
0.7006 Intermediate Similarity NPD4003 Phase 3
0.7006 Intermediate Similarity NPD2674 Phase 3
0.6994 Remote Similarity NPD6331 Phase 2
0.6982 Remote Similarity NPD4097 Suspended
0.6979 Remote Similarity NPD4951 Discontinued
0.6974 Remote Similarity NPD7262 Phase 1
0.6959 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6957 Remote Similarity NPD4986 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7034 Discontinued
0.6954 Remote Similarity NPD3301 Approved
0.6954 Remote Similarity NPD5241 Discontinued
0.6943 Remote Similarity NPD3349 Phase 2
0.6935 Remote Similarity NPD27 Approved
0.6935 Remote Similarity NPD2489 Approved
0.6931 Remote Similarity NPD5530 Phase 1
0.6931 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6927 Remote Similarity NPD4678 Approved
0.6927 Remote Similarity NPD4675 Approved
0.6923 Remote Similarity NPD3924 Approved
0.6923 Remote Similarity NPD3922 Approved
0.6923 Remote Similarity NPD3923 Approved
0.6923 Remote Similarity NPD3963 Phase 1
0.6923 Remote Similarity NPD3921 Approved
0.6897 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6889 Remote Similarity NPD980 Clinical (unspecified phase)
0.6879 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2420 Approved
0.6875 Remote Similarity NPD2421 Approved
0.6866 Remote Similarity NPD5848 Clinical (unspecified phase)
0.6866 Remote Similarity NPD6494 Phase 2
0.6862 Remote Similarity NPD7493 Clinical (unspecified phase)
0.686 Remote Similarity NPD2161 Phase 2
0.6856 Remote Similarity NPD5800 Discontinued
0.6856 Remote Similarity NPD7906 Approved
0.6856 Remote Similarity NPD3398 Discontinued
0.685 Remote Similarity NPD6612 Phase 2
0.6845 Remote Similarity NPD3145 Approved
0.6845 Remote Similarity NPD3144 Approved
0.6836 Remote Similarity NPD4584 Approved
0.6829 Remote Similarity NPD1669 Approved
0.6823 Remote Similarity NPD4578 Approved
0.6823 Remote Similarity NPD4577 Approved
0.6813 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6811 Remote Similarity NPD6037 Discontinued
0.6802 Remote Similarity NPD7125 Discontinued
0.6793 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6793 Remote Similarity NPD7831 Phase 2
0.6793 Remote Similarity NPD7833 Phase 2
0.6784 Remote Similarity NPD6527 Approved
0.6784 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6782 Remote Similarity NPD3516 Approved
0.6782 Remote Similarity NPD3515 Approved
0.678 Remote Similarity NPD2752 Clinical (unspecified phase)
0.678 Remote Similarity NPD4357 Discontinued
0.6776 Remote Similarity NPD2563 Approved
0.6776 Remote Similarity NPD2560 Approved
0.6768 Remote Similarity NPD7686 Clinical (unspecified phase)
0.6763 Remote Similarity NPD6522 Clinical (unspecified phase)
0.674 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6736 Remote Similarity NPD7313 Approved
0.6736 Remote Similarity NPD7310 Approved
0.6736 Remote Similarity NPD7546 Discontinued
0.6736 Remote Similarity NPD7311 Approved
0.6736 Remote Similarity NPD7312 Approved
0.6735 Remote Similarity NPD3342 Phase 2
0.6732 Remote Similarity NPD7263 Phase 2
0.6724 Remote Similarity NPD1375 Discontinued
0.6721 Remote Similarity NPD5929 Approved
0.6718 Remote Similarity NPD4663 Approved
0.6706 Remote Similarity NPD7477 Discontinued
0.6705 Remote Similarity NPD5819 Phase 2
0.6703 Remote Similarity NPD5604 Discontinued
0.6703 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6701 Remote Similarity NPD8054 Approved
0.6701 Remote Similarity NPD8053 Approved
0.6701 Remote Similarity NPD7309 Approved
0.6697 Remote Similarity NPD8067 Phase 3
0.6685 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6683 Remote Similarity NPD6491 Clinical (unspecified phase)
0.6683 Remote Similarity NPD4502 Phase 2
0.6682 Remote Similarity NPD5164 Discontinued
0.6667 Remote Similarity NPD6340 Approved
0.6667 Remote Similarity NPD6339 Approved
0.6667 Remote Similarity NPD6031 Approved
0.6667 Remote Similarity NPD4481 Phase 3
0.6667 Remote Similarity NPD2898 Approved
0.6667 Remote Similarity NPD6030 Approved
0.6651 Remote Similarity NPD3816 Phase 1
0.6651 Remote Similarity NPD3815 Phase 1
0.665 Remote Similarity NPD5582 Discontinued
0.665 Remote Similarity NPD5429 Discontinued
0.6649 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6649 Remote Similarity NPD6071 Discontinued
0.6647 Remote Similarity NPD5111 Phase 2
0.6647 Remote Similarity NPD5110 Phase 2
0.6647 Remote Similarity NPD5109 Approved
0.6635 Remote Similarity NPD8149 Discontinued
0.6634 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6633 Remote Similarity NPD6526 Approved
0.6629 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6618 Remote Similarity NPD5658 Approved
0.6617 Remote Similarity NPD4605 Approved
0.6617 Remote Similarity NPD4604 Approved
0.6614 Remote Similarity NPD2216 Approved
0.6614 Remote Similarity NPD2215 Approved
0.6612 Remote Similarity NPD3796 Clinical (unspecified phase)
0.6611 Remote Similarity NPD4319 Phase 2
0.661 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6599 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6597 Remote Similarity NPD8251 Approved
0.6597 Remote Similarity NPD8252 Approved
0.6597 Remote Similarity NPD8099 Discontinued
0.6595 Remote Similarity NPD3557 Approved
0.6595 Remote Similarity NPD3556 Approved
0.6595 Remote Similarity NPD3558 Approved
0.6595 Remote Similarity NPD6063 Approved
0.6595 Remote Similarity NPD3559 Clinical (unspecified phase)
0.6595 Remote Similarity NPD3560 Approved
0.6591 Remote Similarity NPD7153 Discontinued
0.6589 Remote Similarity NPD5930 Phase 3
0.6573 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6573 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6573 Remote Similarity NPD3692 Discontinued
0.6571 Remote Similarity NPD7225 Discontinued
0.657 Remote Similarity NPD7222 Phase 2
0.657 Remote Similarity NPD7452 Approved
0.657 Remote Similarity NPD7453 Approved
0.657 Remote Similarity NPD1558 Phase 1
0.6567 Remote Similarity NPD8249 Clinical (unspecified phase)
0.6562 Remote Similarity NPD8156 Discontinued
0.6559 Remote Similarity NPD7773 Phase 2
0.6559 Remote Similarity NPD6788 Approved
0.6557 Remote Similarity NPD6502 Phase 2
0.655 Remote Similarity NPD2322 Discovery
0.6546 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5938 Phase 3
0.6543 Remote Similarity NPD6746 Phase 2
0.6541 Remote Similarity NPD5773 Approved
0.6541 Remote Similarity NPD5772 Approved
0.654 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6538 Remote Similarity NPD4859 Phase 1
0.6534 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6533 Remote Similarity NPD2488 Approved
0.6533 Remote Similarity NPD2490 Approved
0.6528 Remote Similarity NPD5557 Phase 1
0.6526 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5939 Approved
0.6524 Remote Similarity NPD5936 Approved
0.6522 Remote Similarity NPD5089 Approved
0.6522 Remote Similarity NPD5090 Approved
0.652 Remote Similarity NPD3289 Phase 3
0.652 Remote Similarity NPD3290 Approved
0.6515 Remote Similarity NPD1898 Discontinued
0.6513 Remote Similarity NPD8453 Clinical (unspecified phase)
0.651 Remote Similarity NPD3909 Discontinued
0.6503 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6503 Remote Similarity NPD4017 Approved
0.65 Remote Similarity NPD3634 Approved
0.65 Remote Similarity NPD3633 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