Structure

Physi-Chem Properties

Molecular Weight:  236.07
Volume:  229.764
LogP:  0.335
LogD:  0.415
LogS:  -2.64
# Rotatable Bonds:  1
TPSA:  76.74
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.787
Synthetic Accessibility Score:  4.046
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.789
MDCK Permeability:  1.3988926184538286e-05
Pgp-inhibitor:  0.191
Pgp-substrate:  0.084
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.848

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.129
Plasma Protein Binding (PPB):  76.05249786376953%
Volume Distribution (VD):  0.689
Pgp-substrate:  23.046449661254883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.883
CYP1A2-substrate:  0.718
CYP2C19-inhibitor:  0.112
CYP2C19-substrate:  0.59
CYP2C9-inhibitor:  0.054
CYP2C9-substrate:  0.906
CYP2D6-inhibitor:  0.069
CYP2D6-substrate:  0.857
CYP3A4-inhibitor:  0.028
CYP3A4-substrate:  0.196

ADMET: Excretion

Clearance (CL):  1.482
Half-life (T1/2):  0.292

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.846
Drug-inuced Liver Injury (DILI):  0.969
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.108
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.163
Carcinogencity:  0.428
Eye Corrosion:  0.004
Eye Irritation:  0.037
Respiratory Toxicity:  0.413

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

  Natural Product: NPC274075

Natural Product ID:  NPC274075
Common Name*:   (2S,3S)-3-Hydroxy-2-Methyl-7-[(E)-Prop-1-Enyl]-2,3-Dihydropyrano[3,2-C]Pyran-4,5-Dione
IUPAC Name:   (2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
Synonyms:  
Standard InCHIKey:  SDKXGAICTNHFCN-DCJAWTJCSA-N
Standard InCHI:  InChI=1S/C12H12O5/c1-3-4-7-5-8-9(12(15)17-7)11(14)10(13)6(2)16-8/h3-6,10,13H,1-2H3/b4-3+/t6-,10-/m0/s1
SMILES:  C/C=C/c1cc2O[C@@H](C)[C@@H](C(=O)c2c(=O)o1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1994984
PubChem CID:   5381458
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003670] Aryl ketones
              • [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO978 Panzerina lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6604 Melanothamnus afaqhusainii Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5641 Dendroctonus frontalis Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2832 Hazunta membranacea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4728 Streptomyces tsukubensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1899 Aria rostellata Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4706 Streptomyces vinaceusdrappus Species Streptomycetaceae Bacteria 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. 15417.0 nM PMID[534110]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 16982.44 nM PMID[534110]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 19678.86 nM PMID[534110]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 16865.53 nM PMID[534110]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 4315.19 nM PMID[534110]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 18620.87 nM PMID[534110]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 14996.85 nM PMID[534110]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 17338.04 nM PMID[534110]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 11967.41 nM PMID[534110]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 8590.14 nM PMID[534110]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 17660.38 nM PMID[534110]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 9705.1 nM PMID[534110]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 15922.09 nM PMID[534110]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 26485.0 nM PMID[534110]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 17579.24 nM PMID[534110]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 17218.69 nM PMID[534110]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 16710.91 nM PMID[534110]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 15958.79 nM PMID[534110]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 19543.39 nM PMID[534110]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10964.78 nM PMID[534110]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 13365.96 nM PMID[534110]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 7906.79 nM PMID[534110]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 14421.15 nM PMID[534110]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 10.0 nM PMID[534110]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 22029.26 nM PMID[534110]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 4092.61 nM PMID[534110]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 15417.0 nM PMID[534110]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 12618.28 nM PMID[534110]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 2773.32 nM PMID[534110]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 16069.41 nM PMID[534110]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 18793.17 nM PMID[534110]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 10280.16 nM PMID[534110]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 19678.86 nM PMID[534110]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 18663.8 nM PMID[534110]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 11246.05 nM PMID[534110]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 7798.3 nM PMID[534110]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 13031.67 nM PMID[534110]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 17179.08 nM PMID[534110]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 4083.19 nM PMID[534110]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 37583.74 nM PMID[534110]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 6745.28 nM PMID[534110]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 21677.04 nM PMID[534110]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 17538.81 nM PMID[534110]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 17298.16 nM PMID[534110]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 2890.68 nM PMID[534110]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 8317.64 nM PMID[534110]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 21037.78 nM PMID[534110]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 14421.15 nM PMID[534110]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 18793.17 nM PMID[534110]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 6280.58 nM PMID[534110]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 5457.58 nM PMID[534110]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 14387.99 nM PMID[534110]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 16904.41 nM PMID[534110]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 15031.42 nM PMID[534110]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 12302.69 nM PMID[534110]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 11428.78 nM PMID[534110]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 17458.22 nM PMID[534110]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 17060.82 nM PMID[534110]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 14.21 % PMID[534111]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = -6.98 % PMID[534111]
NPT20 Organism Candida albicans Candida albicans Inhibition = 1.1 % PMID[534111]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -12.06 % PMID[534111]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = -9.6 % PMID[534111]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 9.46 % PMID[534111]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = -0.66 % PMID[534111]

☑ 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 NPC274075 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
0.8202 Intermediate Similarity NPC474251
0.7865 Intermediate Similarity NPC297440
0.7647 Intermediate Similarity NPC133098
0.7604 Intermediate Similarity NPC327760
0.7586 Intermediate Similarity NPC473948
0.75 Intermediate Similarity NPC199107
0.75 Intermediate Similarity NPC316228
0.75 Intermediate Similarity NPC232969
0.75 Intermediate Similarity NPC271986
0.7429 Intermediate Similarity NPC327106
0.7429 Intermediate Similarity NPC473807
0.7423 Intermediate Similarity NPC32552
0.7423 Intermediate Similarity NPC6099
0.7423 Intermediate Similarity NPC114345
0.7423 Intermediate Similarity NPC303230
0.7416 Intermediate Similarity NPC475711
0.7404 Intermediate Similarity NPC469852
0.74 Intermediate Similarity NPC20066
0.7374 Intermediate Similarity NPC170204
0.7358 Intermediate Similarity NPC38154
0.7333 Intermediate Similarity NPC264391
0.7327 Intermediate Similarity NPC161855
0.7326 Intermediate Similarity NPC202011
0.7315 Intermediate Similarity NPC66108
0.7303 Intermediate Similarity NPC470705
0.73 Intermediate Similarity NPC473291
0.7255 Intermediate Similarity NPC324667
0.7216 Intermediate Similarity NPC87306
0.7212 Intermediate Similarity NPC475871
0.7212 Intermediate Similarity NPC475945
0.7191 Intermediate Similarity NPC478194
0.7191 Intermediate Similarity NPC478193
0.7191 Intermediate Similarity NPC478195
0.7191 Intermediate Similarity NPC161038
0.7191 Intermediate Similarity NPC478196
0.7191 Intermediate Similarity NPC478192
0.7191 Intermediate Similarity NPC478191
0.7188 Intermediate Similarity NPC473248
0.7172 Intermediate Similarity NPC320552
0.7172 Intermediate Similarity NPC282644
0.7172 Intermediate Similarity NPC29798
0.717 Intermediate Similarity NPC266514
0.7158 Intermediate Similarity NPC470124
0.7157 Intermediate Similarity NPC471144
0.7157 Intermediate Similarity NPC35717
0.7157 Intermediate Similarity NPC300584
0.7143 Intermediate Similarity NPC327253
0.7143 Intermediate Similarity NPC473311
0.7143 Intermediate Similarity NPC473455
0.7128 Intermediate Similarity NPC185256
0.7115 Intermediate Similarity NPC149371
0.7115 Intermediate Similarity NPC474747
0.7113 Intermediate Similarity NPC472008
0.7103 Intermediate Similarity NPC264819
0.7093 Intermediate Similarity NPC477117
0.7091 Intermediate Similarity NPC321496
0.7083 Intermediate Similarity NPC112685
0.7083 Intermediate Similarity NPC47937
0.7053 Intermediate Similarity NPC219966
0.7041 Intermediate Similarity NPC14901
0.7041 Intermediate Similarity NPC130359
0.7041 Intermediate Similarity NPC477011
0.7033 Intermediate Similarity NPC275530
0.703 Intermediate Similarity NPC471698
0.7019 Intermediate Similarity NPC474742
0.7019 Intermediate Similarity NPC472753
0.7019 Intermediate Similarity NPC47880
0.7019 Intermediate Similarity NPC469851
0.7019 Intermediate Similarity NPC224172
0.7011 Intermediate Similarity NPC475982
0.701 Intermediate Similarity NPC472007
0.7009 Intermediate Similarity NPC469853
0.7009 Intermediate Similarity NPC474285
0.7009 Intermediate Similarity NPC254538
0.7 Intermediate Similarity NPC61201
0.699 Remote Similarity NPC281608
0.699 Remote Similarity NPC83895
0.699 Remote Similarity NPC187761
0.699 Remote Similarity NPC475284
0.6981 Remote Similarity NPC474741
0.6979 Remote Similarity NPC182383
0.6979 Remote Similarity NPC281172
0.697 Remote Similarity NPC473619
0.697 Remote Similarity NPC131864
0.697 Remote Similarity NPC303451
0.697 Remote Similarity NPC6414
0.697 Remote Similarity NPC475879
0.697 Remote Similarity NPC265856
0.6964 Remote Similarity NPC478216
0.6961 Remote Similarity NPC477921
0.6957 Remote Similarity NPC182292
0.6952 Remote Similarity NPC195510
0.6952 Remote Similarity NPC13171
0.6952 Remote Similarity NPC472754
0.6947 Remote Similarity NPC16488
0.6944 Remote Similarity NPC193765
0.6939 Remote Similarity NPC153570
0.6939 Remote Similarity NPC150063
0.6939 Remote Similarity NPC119740
0.6923 Remote Similarity NPC190400
0.6923 Remote Similarity NPC475949
0.6923 Remote Similarity NPC49392
0.6907 Remote Similarity NPC472009
0.6907 Remote Similarity NPC478112
0.6907 Remote Similarity NPC473687
0.6907 Remote Similarity NPC219498
0.6907 Remote Similarity NPC232555
0.6907 Remote Similarity NPC240695
0.6907 Remote Similarity NPC186332
0.6907 Remote Similarity NPC475581
0.6907 Remote Similarity NPC69082
0.6907 Remote Similarity NPC210218
0.6907 Remote Similarity NPC204686
0.6907 Remote Similarity NPC142117
0.6907 Remote Similarity NPC279267
0.6907 Remote Similarity NPC309211
0.6907 Remote Similarity NPC308412
0.6907 Remote Similarity NPC231096
0.6907 Remote Similarity NPC134807
0.6907 Remote Similarity NPC62118
0.6907 Remote Similarity NPC47220
0.6907 Remote Similarity NPC477010
0.6907 Remote Similarity NPC107717
0.6907 Remote Similarity NPC171174
0.6907 Remote Similarity NPC134885
0.6907 Remote Similarity NPC114694
0.6903 Remote Similarity NPC471145
0.69 Remote Similarity NPC473321
0.6897 Remote Similarity NPC287705
0.6897 Remote Similarity NPC238223
0.6893 Remote Similarity NPC40812
0.6887 Remote Similarity NPC469980
0.6887 Remote Similarity NPC104161
0.6887 Remote Similarity NPC118902
0.6887 Remote Similarity NPC309398
0.6875 Remote Similarity NPC32676
0.6875 Remote Similarity NPC163615
0.6875 Remote Similarity NPC38569
0.6875 Remote Similarity NPC469809
0.6869 Remote Similarity NPC477017
0.6869 Remote Similarity NPC280612
0.6869 Remote Similarity NPC477016
0.6863 Remote Similarity NPC477922
0.6863 Remote Similarity NPC471142
0.6863 Remote Similarity NPC214694
0.686 Remote Similarity NPC475555
0.686 Remote Similarity NPC475675
0.686 Remote Similarity NPC469446
0.6857 Remote Similarity NPC28304
0.6857 Remote Similarity NPC298255
0.6848 Remote Similarity NPC474026
0.6842 Remote Similarity NPC253364
0.6837 Remote Similarity NPC142583
0.6837 Remote Similarity NPC300779
0.6832 Remote Similarity NPC273579
0.6832 Remote Similarity NPC295204
0.6832 Remote Similarity NPC288240
0.6832 Remote Similarity NPC162205
0.6832 Remote Similarity NPC11456
0.6832 Remote Similarity NPC327620
0.6827 Remote Similarity NPC261377
0.6827 Remote Similarity NPC306908
0.6827 Remote Similarity NPC255592
0.6827 Remote Similarity NPC308567
0.6822 Remote Similarity NPC203659
0.6822 Remote Similarity NPC472756
0.6818 Remote Similarity NPC89408
0.6818 Remote Similarity NPC478211
0.6813 Remote Similarity NPC260396
0.6809 Remote Similarity NPC162741
0.6809 Remote Similarity NPC91332
0.6809 Remote Similarity NPC47653
0.6804 Remote Similarity NPC283085
0.6804 Remote Similarity NPC477018
0.6804 Remote Similarity NPC100921
0.6804 Remote Similarity NPC286338
0.6804 Remote Similarity NPC103284
0.6804 Remote Similarity NPC1083
0.6804 Remote Similarity NPC132496
0.6804 Remote Similarity NPC473669
0.6804 Remote Similarity NPC155873
0.6804 Remote Similarity NPC107986
0.6804 Remote Similarity NPC82795
0.6804 Remote Similarity NPC223871
0.6804 Remote Similarity NPC471223
0.6804 Remote Similarity NPC110710
0.6804 Remote Similarity NPC322529
0.6804 Remote Similarity NPC473651
0.6804 Remote Similarity NPC21469
0.6804 Remote Similarity NPC473478
0.6804 Remote Similarity NPC67081
0.6804 Remote Similarity NPC231009
0.6804 Remote Similarity NPC66346
0.68 Remote Similarity NPC313670
0.6796 Remote Similarity NPC255410
0.6792 Remote Similarity NPC235369
0.6792 Remote Similarity NPC473596
0.6792 Remote Similarity NPC310804
0.6792 Remote Similarity NPC261117
0.6786 Remote Similarity NPC478212

  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 NPC274075 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
0.69 Remote Similarity NPD7983 Approved
0.6771 Remote Similarity NPD6110 Phase 1
0.6634 Remote Similarity NPD46 Approved
0.6634 Remote Similarity NPD6698 Approved
0.6591 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6509 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4756 Discovery
0.6471 Remote Similarity NPD7838 Discovery
0.6346 Remote Similarity NPD5778 Approved
0.6346 Remote Similarity NPD5779 Approved
0.625 Remote Similarity NPD7899 Clinical (unspecified phase)
0.625 Remote Similarity NPD8513 Phase 3
0.6226 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6174 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5282 Discontinued
0.6121 Remote Similarity NPD6053 Discontinued
0.6116 Remote Similarity NPD8517 Approved
0.6116 Remote Similarity NPD8516 Approved
0.6116 Remote Similarity NPD8515 Approved
0.6087 Remote Similarity NPD6371 Approved
0.6019 Remote Similarity NPD7839 Suspended
0.6016 Remote Similarity NPD7829 Approved
0.6016 Remote Similarity NPD7830 Approved
0.5984 Remote Similarity NPD8444 Approved
0.5938 Remote Similarity NPD7260 Phase 2
0.593 Remote Similarity NPD8959 Approved
0.5913 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4225 Approved
0.5905 Remote Similarity NPD6101 Approved
0.5905 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5873 Remote Similarity NPD8074 Phase 3
0.5862 Remote Similarity NPD69 Approved
0.5862 Remote Similarity NPD9119 Approved
0.5849 Remote Similarity NPD5785 Approved
0.5842 Remote Similarity NPD5209 Approved
0.5833 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5825 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6411 Approved
0.5794 Remote Similarity NPD8451 Approved
0.5794 Remote Similarity NPD7637 Suspended
0.5785 Remote Similarity NPD7115 Discovery
0.5776 Remote Similarity NPD6686 Approved
0.5772 Remote Similarity NPD6319 Approved
0.5769 Remote Similarity NPD5786 Approved
0.5769 Remote Similarity NPD4249 Approved
0.5761 Remote Similarity NPD3704 Approved
0.576 Remote Similarity NPD7642 Approved
0.5748 Remote Similarity NPD8448 Approved
0.5747 Remote Similarity NPD9118 Approved
0.5738 Remote Similarity NPD7641 Discontinued
0.573 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4251 Approved
0.5714 Remote Similarity NPD3197 Phase 1
0.5714 Remote Similarity NPD4250 Approved
0.5699 Remote Similarity NPD897 Approved
0.5699 Remote Similarity NPD896 Approved
0.5699 Remote Similarity NPD898 Approved
0.5682 Remote Similarity NPD6109 Phase 1
0.5678 Remote Similarity NPD2067 Discontinued
0.5673 Remote Similarity NPD5363 Approved
0.5667 Remote Similarity NPD4632 Approved
0.5664 Remote Similarity NPD5344 Discontinued
0.5644 Remote Similarity NPD4252 Approved
0.5644 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5635 Remote Similarity NPD8328 Phase 3
0.5631 Remote Similarity NPD7154 Phase 3
0.563 Remote Similarity NPD2204 Approved
0.5615 Remote Similarity NPD8392 Approved
0.5615 Remote Similarity NPD8390 Approved
0.5615 Remote Similarity NPD8391 Approved
0.5604 Remote Similarity NPD8961 Approved
0.5603 Remote Similarity NPD5048 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data