Structure

Physi-Chem Properties

Molecular Weight:  346.18
Volume:  365.496
LogP:  1.957
LogD:  2.53
LogS:  -3.002
# Rotatable Bonds:  3
TPSA:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.473
Synthetic Accessibility Score:  4.87
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.711
MDCK Permeability:  3.279928569099866e-05
Pgp-inhibitor:  0.491
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.928
20% Bioavailability (F20%):  0.892
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.332
Plasma Protein Binding (PPB):  85.41950225830078%
Volume Distribution (VD):  0.553
Pgp-substrate:  11.859493255615234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.14
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.668
CYP2C19-substrate:  0.422
CYP2C9-inhibitor:  0.664
CYP2C9-substrate:  0.105
CYP2D6-inhibitor:  0.09
CYP2D6-substrate:  0.115
CYP3A4-inhibitor:  0.707
CYP3A4-substrate:  0.253

ADMET: Excretion

Clearance (CL):  9.801
Half-life (T1/2):  0.864

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.767
Drug-inuced Liver Injury (DILI):  0.4
AMES Toxicity:  0.035
Rat Oral Acute Toxicity:  0.889
Maximum Recommended Daily Dose:  0.968
Skin Sensitization:  0.901
Carcinogencity:  0.093
Eye Corrosion:  0.204
Eye Irritation:  0.072
Respiratory Toxicity:  0.955

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  Natural Product: NPC169575

Natural Product ID:  NPC169575
Common Name*:   Nobilin
IUPAC Name:   [(3aR,4S,6E,9S,10Z,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:  
Standard InCHIKey:  QFINJHBXXJQKPB-YVRWQVCISA-N
Standard InCHI:  InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,15-18,21H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10-/t15-,16-,17+,18+/m0/s1
SMILES:  C/C=C(/C)C(=O)O[C@H]1C/C(=C/C[C@@H](/C(=C[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2380798
PubChem CID:   11953937
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001771] Germacranolides 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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24471493]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28116906]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20683 Citrus nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20683 Citrus nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27623 Citrus japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27623.1 Citrus japonica var. margarita Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20683 Citrus nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27623 Citrus japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27623.1 Citrus japonica var. margarita Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT839 Cell Line L6 Rattus norvegicus IC50 = 6640.0 nM PMID[484568]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 4731.51 nM PMID[484567]
NPT27 Others Unspecified IC50 > 30000.0 nM PMID[484567]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 4730.0 nM PMID[484567]
NPT2 Others Unspecified Ratio IC50 = 2.1 n.a. PMID[484568]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 3190.0 nM PMID[484568]

☑ 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 NPC169575 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 NPC40746
0.9747 High Similarity NPC470755
0.9744 High Similarity NPC131669
0.9744 High Similarity NPC473390
0.974 High Similarity NPC24417
0.9625 High Similarity NPC305475
0.9625 High Similarity NPC475461
0.962 High Similarity NPC476804
0.962 High Similarity NPC158756
0.9615 High Similarity NPC229825
0.95 High Similarity NPC255307
0.9494 High Similarity NPC59097
0.9481 High Similarity NPC98557
0.9481 High Similarity NPC167881
0.939 High Similarity NPC475819
0.939 High Similarity NPC476805
0.9383 High Similarity NPC469910
0.9375 High Similarity NPC96259
0.9375 High Similarity NPC141193
0.9375 High Similarity NPC191476
0.9375 High Similarity NPC114979
0.9351 High Similarity NPC196653
0.9351 High Similarity NPC108816
0.9351 High Similarity NPC93763
0.9351 High Similarity NPC471465
0.925 High Similarity NPC116543
0.9241 High Similarity NPC52861
0.9231 High Similarity NPC270126
0.9221 High Similarity NPC476028
0.9221 High Similarity NPC7563
0.9221 High Similarity NPC141789
0.9221 High Similarity NPC171204
0.9221 High Similarity NPC116177
0.9221 High Similarity NPC320630
0.9167 High Similarity NPC475855
0.9157 High Similarity NPC476803
0.9146 High Similarity NPC150755
0.9114 High Similarity NPC281132
0.9091 High Similarity NPC68819
0.9059 High Similarity NPC473321
0.8953 High Similarity NPC295204
0.8953 High Similarity NPC475838
0.8953 High Similarity NPC288240
0.8953 High Similarity NPC125674
0.8953 High Similarity NPC273579
0.8953 High Similarity NPC228451
0.8953 High Similarity NPC162205
0.8941 High Similarity NPC179394
0.8941 High Similarity NPC474232
0.8941 High Similarity NPC473619
0.8941 High Similarity NPC469368
0.8941 High Similarity NPC144133
0.8929 High Similarity NPC473715
0.8861 High Similarity NPC267231
0.8851 High Similarity NPC474247
0.8831 High Similarity NPC476355
0.8795 High Similarity NPC165162
0.875 High Similarity NPC477922
0.875 High Similarity NPC471142
0.8734 High Similarity NPC97516
0.8701 High Similarity NPC269206
0.8701 High Similarity NPC295633
0.8701 High Similarity NPC58956
0.8652 High Similarity NPC279621
0.8652 High Similarity NPC230800
0.8652 High Similarity NPC477921
0.8608 High Similarity NPC123360
0.8605 High Similarity NPC474032
0.859 High Similarity NPC114727
0.859 High Similarity NPC476590
0.859 High Similarity NPC140287
0.8571 High Similarity NPC163003
0.8571 High Similarity NPC21469
0.8523 High Similarity NPC475302
0.8519 High Similarity NPC89128
0.8506 High Similarity NPC129419
0.8434 Intermediate Similarity NPC89555
0.8427 Intermediate Similarity NPC57405
0.8427 Intermediate Similarity NPC303942
0.8391 Intermediate Similarity NPC206001
0.8391 Intermediate Similarity NPC268298
0.8391 Intermediate Similarity NPC218927
0.8391 Intermediate Similarity NPC295312
0.8375 Intermediate Similarity NPC235906
0.8372 Intermediate Similarity NPC160138
0.837 Intermediate Similarity NPC288876
0.8353 Intermediate Similarity NPC261380
0.8333 Intermediate Similarity NPC250315
0.8333 Intermediate Similarity NPC304886
0.8333 Intermediate Similarity NPC471141
0.8315 Intermediate Similarity NPC475912
0.8315 Intermediate Similarity NPC469692
0.8315 Intermediate Similarity NPC469645
0.8313 Intermediate Similarity NPC281949
0.8313 Intermediate Similarity NPC25684
0.8313 Intermediate Similarity NPC141810
0.8313 Intermediate Similarity NPC301477
0.8313 Intermediate Similarity NPC325031
0.8293 Intermediate Similarity NPC470239
0.8293 Intermediate Similarity NPC178277
0.8293 Intermediate Similarity NPC470244
0.8276 Intermediate Similarity NPC477302
0.8276 Intermediate Similarity NPC136879
0.8272 Intermediate Similarity NPC474760
0.8261 Intermediate Similarity NPC471144
0.8256 Intermediate Similarity NPC469483
0.8256 Intermediate Similarity NPC50637
0.825 Intermediate Similarity NPC155587
0.8242 Intermediate Similarity NPC306041
0.8242 Intermediate Similarity NPC473859
0.8222 Intermediate Similarity NPC121825
0.8222 Intermediate Similarity NPC474338
0.8214 Intermediate Similarity NPC474252
0.8214 Intermediate Similarity NPC85772
0.8205 Intermediate Similarity NPC67183
0.8182 Intermediate Similarity NPC166919
0.8161 Intermediate Similarity NPC266957
0.8132 Intermediate Similarity NPC270013
0.8132 Intermediate Similarity NPC14961
0.8132 Intermediate Similarity NPC475659
0.8132 Intermediate Similarity NPC36954
0.8125 Intermediate Similarity NPC48641
0.8118 Intermediate Similarity NPC474703
0.8101 Intermediate Similarity NPC129665
0.8095 Intermediate Similarity NPC470241
0.8095 Intermediate Similarity NPC471325
0.809 Intermediate Similarity NPC473448
0.8077 Intermediate Similarity NPC88877
0.8077 Intermediate Similarity NPC476591
0.8072 Intermediate Similarity NPC475210
0.8072 Intermediate Similarity NPC617
0.8072 Intermediate Similarity NPC19841
0.8068 Intermediate Similarity NPC202672
0.8068 Intermediate Similarity NPC287089
0.8065 Intermediate Similarity NPC141191
0.8065 Intermediate Similarity NPC187268
0.8065 Intermediate Similarity NPC473326
0.8052 Intermediate Similarity NPC194871
0.8049 Intermediate Similarity NPC57744
0.8049 Intermediate Similarity NPC41780
0.8049 Intermediate Similarity NPC470240
0.8049 Intermediate Similarity NPC476794
0.8049 Intermediate Similarity NPC187568
0.8046 Intermediate Similarity NPC107787
0.8046 Intermediate Similarity NPC261721
0.8043 Intermediate Similarity NPC476315
0.8025 Intermediate Similarity NPC329852
0.8023 Intermediate Similarity NPC115786
0.8023 Intermediate Similarity NPC82297
0.8022 Intermediate Similarity NPC81386
0.8022 Intermediate Similarity NPC474035
0.8022 Intermediate Similarity NPC477131
0.8 Intermediate Similarity NPC30515
0.8 Intermediate Similarity NPC300312
0.8 Intermediate Similarity NPC184463
0.8 Intermediate Similarity NPC475925
0.8 Intermediate Similarity NPC261607
0.8 Intermediate Similarity NPC111114
0.8 Intermediate Similarity NPC173609
0.7979 Intermediate Similarity NPC475949
0.7957 Intermediate Similarity NPC169205
0.7957 Intermediate Similarity NPC471462
0.7955 Intermediate Similarity NPC72513
0.7955 Intermediate Similarity NPC237540
0.7955 Intermediate Similarity NPC178215
0.7952 Intermediate Similarity NPC128276
0.7949 Intermediate Similarity NPC470256
0.7931 Intermediate Similarity NPC110710
0.7931 Intermediate Similarity NPC231009
0.7931 Intermediate Similarity NPC107986
0.7931 Intermediate Similarity NPC223871
0.7931 Intermediate Similarity NPC82795
0.7931 Intermediate Similarity NPC473478
0.7931 Intermediate Similarity NPC473651
0.7931 Intermediate Similarity NPC1083
0.7931 Intermediate Similarity NPC66346
0.7931 Intermediate Similarity NPC473669
0.7931 Intermediate Similarity NPC103284
0.7931 Intermediate Similarity NPC78089
0.7931 Intermediate Similarity NPC283085
0.7931 Intermediate Similarity NPC132496
0.7931 Intermediate Similarity NPC215364
0.7931 Intermediate Similarity NPC286338
0.7912 Intermediate Similarity NPC165383
0.7912 Intermediate Similarity NPC212486
0.7912 Intermediate Similarity NPC476300
0.7912 Intermediate Similarity NPC81419
0.7912 Intermediate Similarity NPC179746
0.7907 Intermediate Similarity NPC475947
0.7895 Intermediate Similarity NPC474339
0.7895 Intermediate Similarity NPC164598
0.7895 Intermediate Similarity NPC150923
0.7895 Intermediate Similarity NPC46998
0.7895 Intermediate Similarity NPC185141
0.7895 Intermediate Similarity NPC133907
0.7895 Intermediate Similarity NPC110443
0.7895 Intermediate Similarity NPC128733
0.7889 Intermediate Similarity NPC106510
0.7889 Intermediate Similarity NPC51004
0.7889 Intermediate Similarity NPC476004

  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 NPC169575 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
0.7742 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD7154 Phase 3
0.7692 Intermediate Similarity NPD6698 Approved
0.7692 Intermediate Similarity NPD46 Approved
0.7692 Intermediate Similarity NPD5785 Approved
0.7558 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD5363 Approved
0.7326 Intermediate Similarity NPD4268 Approved
0.7326 Intermediate Similarity NPD4271 Approved
0.732 Intermediate Similarity NPD4225 Approved
0.7303 Intermediate Similarity NPD5362 Discontinued
0.7253 Intermediate Similarity NPD4249 Approved
0.7191 Intermediate Similarity NPD4269 Approved
0.7191 Intermediate Similarity NPD4270 Approved
0.7174 Intermediate Similarity NPD4251 Approved
0.7174 Intermediate Similarity NPD4250 Approved
0.7159 Intermediate Similarity NPD4821 Approved
0.7159 Intermediate Similarity NPD4820 Approved
0.7159 Intermediate Similarity NPD4822 Approved
0.7159 Intermediate Similarity NPD4819 Approved
0.7159 Intermediate Similarity NPD4252 Approved
0.7157 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7838 Discovery
0.7115 Intermediate Similarity NPD6371 Approved
0.7065 Intermediate Similarity NPD5786 Approved
0.7053 Intermediate Similarity NPD7983 Approved
0.7021 Intermediate Similarity NPD1695 Approved
0.7 Intermediate Similarity NPD6435 Approved
0.7 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.697 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1694 Approved
0.6932 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5369 Approved
0.6848 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4756 Discovery
0.6813 Remote Similarity NPD5209 Approved
0.6804 Remote Similarity NPD5778 Approved
0.6804 Remote Similarity NPD5779 Approved
0.6778 Remote Similarity NPD5368 Approved
0.6762 Remote Similarity NPD6686 Approved
0.6739 Remote Similarity NPD5332 Approved
0.6739 Remote Similarity NPD5331 Approved
0.6729 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4790 Discontinued
0.6667 Remote Similarity NPD5370 Suspended
0.66 Remote Similarity NPD7839 Suspended
0.6577 Remote Similarity NPD7115 Discovery
0.6569 Remote Similarity NPD7639 Approved
0.6569 Remote Similarity NPD7640 Approved
0.6566 Remote Similarity NPD5282 Discontinued
0.6531 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6053 Discontinued
0.6505 Remote Similarity NPD5344 Discontinued
0.6495 Remote Similarity NPD6101 Approved
0.6495 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7638 Approved
0.6465 Remote Similarity NPD6399 Phase 3
0.642 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6404 Remote Similarity NPD8039 Approved
0.6364 Remote Similarity NPD7637 Suspended
0.6364 Remote Similarity NPD6411 Approved
0.6353 Remote Similarity NPD4247 Clinical (unspecified phase)
0.625 Remote Similarity NPD6648 Approved
0.6226 Remote Similarity NPD6647 Phase 2
0.6214 Remote Similarity NPD6083 Phase 2
0.6214 Remote Similarity NPD6084 Phase 2
0.6214 Remote Similarity NPD7902 Approved
0.6211 Remote Similarity NPD6110 Phase 1
0.6207 Remote Similarity NPD8517 Approved
0.6207 Remote Similarity NPD8516 Approved
0.6207 Remote Similarity NPD8515 Approved
0.6207 Remote Similarity NPD8513 Phase 3
0.6204 Remote Similarity NPD5697 Approved
0.619 Remote Similarity NPD3197 Phase 1
0.6186 Remote Similarity NPD6422 Discontinued
0.6176 Remote Similarity NPD5695 Phase 3
0.6154 Remote Similarity NPD5696 Approved
0.6147 Remote Similarity NPD6899 Approved
0.6147 Remote Similarity NPD6881 Approved
0.6126 Remote Similarity NPD6649 Approved
0.6126 Remote Similarity NPD6650 Approved
0.6111 Remote Similarity NPD7128 Approved
0.6111 Remote Similarity NPD6675 Approved
0.6111 Remote Similarity NPD5739 Approved
0.6111 Remote Similarity NPD6402 Approved
0.6091 Remote Similarity NPD6373 Approved
0.6091 Remote Similarity NPD6012 Approved
0.6091 Remote Similarity NPD6372 Approved
0.6091 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6091 Remote Similarity NPD6013 Approved
0.6091 Remote Similarity NPD6014 Approved
0.6078 Remote Similarity NPD7748 Approved
0.6071 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6055 Remote Similarity NPD5701 Approved
0.6047 Remote Similarity NPD3704 Approved
0.6047 Remote Similarity NPD7331 Phase 2
0.604 Remote Similarity NPD7515 Phase 2
0.6036 Remote Similarity NPD7102 Approved
0.6036 Remote Similarity NPD6883 Approved
0.6036 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6036 Remote Similarity NPD7290 Approved
0.602 Remote Similarity NPD7334 Approved
0.602 Remote Similarity NPD5330 Approved
0.602 Remote Similarity NPD6409 Approved
0.602 Remote Similarity NPD3618 Phase 1
0.602 Remote Similarity NPD7521 Approved
0.602 Remote Similarity NPD7146 Approved
0.602 Remote Similarity NPD6684 Approved
0.6 Remote Similarity NPD6011 Approved
0.6 Remote Similarity NPD7320 Approved
0.5982 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5982 Remote Similarity NPD8130 Phase 1
0.5982 Remote Similarity NPD6617 Approved
0.5982 Remote Similarity NPD6869 Approved
0.5982 Remote Similarity NPD6847 Approved
0.5981 Remote Similarity NPD5211 Phase 2
0.5981 Remote Similarity NPD7632 Discontinued
0.5979 Remote Similarity NPD3133 Approved
0.5979 Remote Similarity NPD3666 Approved
0.5979 Remote Similarity NPD3665 Phase 1
0.5962 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5952 Remote Similarity NPD368 Approved
0.595 Remote Similarity NPD8074 Phase 3
0.5949 Remote Similarity NPD3172 Approved
0.5938 Remote Similarity NPD3667 Approved
0.5929 Remote Similarity NPD6882 Approved
0.5929 Remote Similarity NPD8297 Approved
0.5922 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5922 Remote Similarity NPD7900 Approved
0.59 Remote Similarity NPD5737 Approved
0.59 Remote Similarity NPD6672 Approved
0.59 Remote Similarity NPD7513 Clinical (unspecified phase)
0.59 Remote Similarity NPD6903 Approved
0.5897 Remote Similarity NPD6927 Phase 3
0.5895 Remote Similarity NPD4695 Discontinued
0.5893 Remote Similarity NPD2067 Discontinued
0.5893 Remote Similarity NPD6421 Discontinued
0.5882 Remote Similarity NPD5693 Phase 1
0.5882 Remote Similarity NPD5281 Approved
0.5882 Remote Similarity NPD5284 Approved
0.5875 Remote Similarity NPD3194 Approved
0.5875 Remote Similarity NPD3195 Phase 2
0.5875 Remote Similarity NPD4266 Approved
0.5875 Remote Similarity NPD3196 Approved
0.5872 Remote Similarity NPD5141 Approved
0.5865 Remote Similarity NPD5210 Approved
0.5865 Remote Similarity NPD4629 Approved
0.5859 Remote Similarity NPD5279 Phase 3
0.5842 Remote Similarity NPD4753 Phase 2
0.5841 Remote Similarity NPD2204 Approved
0.5841 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5833 Remote Similarity NPD7642 Approved
0.5833 Remote Similarity NPD7829 Approved
0.5833 Remote Similarity NPD7830 Approved
0.5818 Remote Similarity NPD6008 Approved
0.5816 Remote Similarity NPD4786 Approved
0.5816 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5812 Remote Similarity NPD7641 Discontinued
0.581 Remote Similarity NPD4228 Discovery
0.5802 Remote Similarity NPD342 Phase 1
0.5794 Remote Similarity NPD5286 Approved
0.5794 Remote Similarity NPD4696 Approved
0.5794 Remote Similarity NPD5285 Approved
0.578 Remote Similarity NPD5738 Clinical (unspecified phase)
0.5776 Remote Similarity NPD6274 Approved
0.5766 Remote Similarity NPD6412 Phase 2
0.5766 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5758 Remote Similarity NPD1696 Phase 3
0.5755 Remote Similarity NPD4755 Approved
0.5747 Remote Similarity NPD7341 Phase 2
0.5738 Remote Similarity NPD7507 Approved
0.5729 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5728 Remote Similarity NPD6079 Approved
0.5728 Remote Similarity NPD8035 Phase 2
0.5728 Remote Similarity NPD8034 Phase 2
0.5726 Remote Similarity NPD7500 Approved
0.5726 Remote Similarity NPD7505 Discontinued
0.5714 Remote Similarity NPD6695 Phase 3
0.5714 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6401 Clinical (unspecified phase)
0.57 Remote Similarity NPD4519 Discontinued
0.57 Remote Similarity NPD4623 Approved
0.5688 Remote Similarity NPD5226 Approved
0.5688 Remote Similarity NPD4633 Approved
0.5688 Remote Similarity NPD5225 Approved
0.5688 Remote Similarity NPD5224 Approved
0.5686 Remote Similarity NPD5328 Approved
0.5684 Remote Similarity NPD3732 Approved
0.5682 Remote Similarity NPD6108 Clinical (unspecified phase)
0.568 Remote Similarity NPD6007 Clinical (unspecified phase)
0.5673 Remote Similarity NPD4202 Approved
0.5673 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5667 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5664 Remote Similarity NPD2182 Approved
0.566 Remote Similarity NPD5221 Approved
0.566 Remote Similarity NPD4697 Phase 3
0.566 Remote Similarity NPD5222 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