Structure

Physi-Chem Properties

Molecular Weight:  464.1
Volume:  421.937
LogP:  0.298
LogD:  -0.101
LogS:  -3.92
# Rotatable Bonds:  4
TPSA:  210.51
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.245
Synthetic Accessibility Score:  4.027
Fsp3:  0.286
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.357
MDCK Permeability:  8.19832075649174e-06
Pgp-inhibitor:  0.019
Pgp-substrate:  0.589
Human Intestinal Absorption (HIA):  0.565
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  91.9957275390625%
Volume Distribution (VD):  0.825
Pgp-substrate:  11.09682846069336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.225
CYP1A2-substrate:  0.041
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.046
CYP2C9-inhibitor:  0.053
CYP2C9-substrate:  0.195
CYP2D6-inhibitor:  0.154
CYP2D6-substrate:  0.155
CYP3A4-inhibitor:  0.092
CYP3A4-substrate:  0.009

ADMET: Excretion

Clearance (CL):  3.623
Half-life (T1/2):  0.929

ADMET: Toxicity

hERG Blockers:  0.269
Human Hepatotoxicity (H-HT):  0.133
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.82
Rat Oral Acute Toxicity:  0.021
Maximum Recommended Daily Dose:  0.005
Skin Sensitization:  0.617
Carcinogencity:  0.04
Eye Corrosion:  0.003
Eye Irritation:  0.347
Respiratory Toxicity:  0.023

Download Data

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

  Natural Product: NPC197285

Natural Product ID:  NPC197285
Common Name*:   3,5,7-Trihydroxy-2-[4-Hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyphenyl]Chromen-4-One
IUPAC Name:   3,5,7-trihydroxy-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:  
Standard InCHIKey:  YLWQTYZKYGNKPI-HMGRVEAOSA-N
Standard InCHI:  InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-3-7(1-2-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
SMILES:  c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1222354
PubChem CID:   9934142
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides

*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
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae 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
NPT1605 Organism Enterococcus Enterococcus MIC > 128.0 ug.mL-1 PMID[561849]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 128.0 ug.mL-1 PMID[561849]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128.0 ug.mL-1 PMID[561849]
NPT2 Others Unspecified IC50 = 100.0 nM PMID[561849]
NPT1548 Organism Pseudomonas aeruginosa PAO1 Pseudomonas aeruginosa PAO1 MIC = 64.0 ug.mL-1 PMID[561849]
NPT1466 Organism Escherichia coli K12 Escherichia coli K-12 MIC = 32.0 ug.mL-1 PMID[561849]
NPT2 Others Unspecified Ki = 0.05 nM PMID[561849]

☑ 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 NPC197285 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 NPC21100
0.9936 High Similarity NPC277205
0.9873 High Similarity NPC145038
0.9873 High Similarity NPC88789
0.9873 High Similarity NPC219904
0.9873 High Similarity NPC118284
0.9873 High Similarity NPC120099
0.9873 High Similarity NPC56077
0.9873 High Similarity NPC203050
0.9873 High Similarity NPC223747
0.9873 High Similarity NPC276222
0.9873 High Similarity NPC308404
0.9873 High Similarity NPC274618
0.9873 High Similarity NPC253662
0.9873 High Similarity NPC179950
0.9873 High Similarity NPC281131
0.9873 High Similarity NPC225434
0.9872 High Similarity NPC270335
0.9872 High Similarity NPC191306
0.9811 High Similarity NPC285197
0.9811 High Similarity NPC282987
0.9811 High Similarity NPC245014
0.9811 High Similarity NPC206123
0.9811 High Similarity NPC84265
0.981 High Similarity NPC265530
0.981 High Similarity NPC127546
0.981 High Similarity NPC52550
0.981 High Similarity NPC317489
0.981 High Similarity NPC84362
0.981 High Similarity NPC226304
0.981 High Similarity NPC325555
0.981 High Similarity NPC173637
0.981 High Similarity NPC223424
0.9809 High Similarity NPC240431
0.9809 High Similarity NPC22832
0.9809 High Similarity NPC311830
0.9809 High Similarity NPC55786
0.9809 High Similarity NPC19388
0.9808 High Similarity NPC77660
0.9808 High Similarity NPC189142
0.975 High Similarity NPC117260
0.975 High Similarity NPC153755
0.975 High Similarity NPC476405
0.975 High Similarity NPC26230
0.975 High Similarity NPC60735
0.9747 High Similarity NPC254306
0.9747 High Similarity NPC113968
0.9747 High Similarity NPC135599
0.9747 High Similarity NPC277174
0.9747 High Similarity NPC73855
0.9747 High Similarity NPC328940
0.9745 High Similarity NPC309025
0.9745 High Similarity NPC222936
0.9745 High Similarity NPC19709
0.9745 High Similarity NPC168822
0.9745 High Similarity NPC243930
0.9745 High Similarity NPC88023
0.9745 High Similarity NPC284960
0.9689 High Similarity NPC101026
0.9689 High Similarity NPC24043
0.9689 High Similarity NPC4390
0.9689 High Similarity NPC45522
0.9689 High Similarity NPC42773
0.9689 High Similarity NPC21666
0.9689 High Similarity NPC169977
0.9688 High Similarity NPC244776
0.9688 High Similarity NPC67105
0.9688 High Similarity NPC95866
0.9688 High Similarity NPC259896
0.9688 High Similarity NPC235260
0.9688 High Similarity NPC156869
0.9688 High Similarity NPC155763
0.9688 High Similarity NPC20505
0.9688 High Similarity NPC255157
0.9688 High Similarity NPC116864
0.9688 High Similarity NPC254855
0.9688 High Similarity NPC136042
0.9688 High Similarity NPC29958
0.9688 High Similarity NPC67326
0.9686 High Similarity NPC229729
0.9686 High Similarity NPC45618
0.9686 High Similarity NPC92565
0.9686 High Similarity NPC58716
0.9686 High Similarity NPC146792
0.9686 High Similarity NPC275454
0.9686 High Similarity NPC160156
0.9682 High Similarity NPC473043
0.963 High Similarity NPC294815
0.963 High Similarity NPC237435
0.963 High Similarity NPC473327
0.963 High Similarity NPC477848
0.963 High Similarity NPC115760
0.963 High Similarity NPC220173
0.963 High Similarity NPC43211
0.963 High Similarity NPC19108
0.963 High Similarity NPC101191
0.963 High Similarity NPC476472
0.963 High Similarity NPC135277
0.963 High Similarity NPC16194
0.963 High Similarity NPC210094
0.963 High Similarity NPC49344
0.9627 High Similarity NPC175107
0.9627 High Similarity NPC176740
0.9627 High Similarity NPC471725
0.9627 High Similarity NPC134532
0.9627 High Similarity NPC155877
0.9627 High Similarity NPC190003
0.9627 High Similarity NPC33054
0.9627 High Similarity NPC203259
0.9627 High Similarity NPC471748
0.9627 High Similarity NPC245452
0.9625 High Similarity NPC195257
0.9625 High Similarity NPC186807
0.9625 High Similarity NPC52382
0.9625 High Similarity NPC226294
0.9625 High Similarity NPC86008
0.9625 High Similarity NPC227508
0.9625 High Similarity NPC201292
0.9625 High Similarity NPC58053
0.9625 High Similarity NPC209296
0.9625 High Similarity NPC475942
0.9625 High Similarity NPC270578
0.9625 High Similarity NPC93337
0.9625 High Similarity NPC469931
0.9625 High Similarity NPC138927
0.9625 High Similarity NPC45638
0.9625 High Similarity NPC105025
0.9623 High Similarity NPC210073
0.9623 High Similarity NPC115674
0.9623 High Similarity NPC255615
0.9623 High Similarity NPC8856
0.9623 High Similarity NPC67037
0.9623 High Similarity NPC5778
0.9623 High Similarity NPC236934
0.962 High Similarity NPC29830
0.962 High Similarity NPC88043
0.9618 High Similarity NPC182045
0.9571 High Similarity NPC169733
0.9571 High Similarity NPC198324
0.9571 High Similarity NPC233994
0.9571 High Similarity NPC211532
0.9571 High Similarity NPC8573
0.9571 High Similarity NPC219043
0.9571 High Similarity NPC472385
0.9565 High Similarity NPC231194
0.9565 High Similarity NPC51326
0.9565 High Similarity NPC72249
0.9563 High Similarity NPC149244
0.9563 High Similarity NPC48640
0.9563 High Similarity NPC45400
0.956 High Similarity NPC34531
0.956 High Similarity NPC165720
0.9557 High Similarity NPC300537
0.9557 High Similarity NPC127782
0.9554 High Similarity NPC110349
0.9512 High Similarity NPC217520
0.9512 High Similarity NPC251417
0.9512 High Similarity NPC139571
0.9512 High Similarity NPC89052
0.9512 High Similarity NPC168584
0.9512 High Similarity NPC173837
0.9509 High Similarity NPC34267
0.9509 High Similarity NPC81042
0.9509 High Similarity NPC214621
0.9509 High Similarity NPC264735
0.9509 High Similarity NPC253685
0.9509 High Similarity NPC294629
0.9509 High Similarity NPC223426
0.9506 High Similarity NPC307518
0.9506 High Similarity NPC256760
0.9506 High Similarity NPC259152
0.9506 High Similarity NPC254540
0.9506 High Similarity NPC172807
0.9506 High Similarity NPC235575
0.9506 High Similarity NPC180918
0.9506 High Similarity NPC205076
0.9506 High Similarity NPC211594
0.9506 High Similarity NPC48773
0.9506 High Similarity NPC3583
0.9503 High Similarity NPC170675
0.9503 High Similarity NPC229687
0.9503 High Similarity NPC471457
0.9503 High Similarity NPC112755
0.9487 High Similarity NPC261866
0.9487 High Similarity NPC307938
0.9487 High Similarity NPC323593
0.9487 High Similarity NPC203500
0.9455 High Similarity NPC470443
0.9455 High Similarity NPC470444
0.9455 High Similarity NPC110941
0.9455 High Similarity NPC241423
0.9455 High Similarity NPC473571
0.9455 High Similarity NPC192539
0.9455 High Similarity NPC473682
0.9455 High Similarity NPC126784
0.9451 High Similarity NPC122467
0.9451 High Similarity NPC471669
0.9451 High Similarity NPC292019
0.9451 High Similarity NPC202908
0.9451 High Similarity NPC144097

  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 NPC197285 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
0.963 High Similarity NPD4338 Clinical (unspecified phase)
0.9627 High Similarity NPD6797 Phase 2
0.9625 High Similarity NPD7054 Approved
0.9568 High Similarity NPD7251 Discontinued
0.9565 High Similarity NPD7472 Approved
0.9509 High Similarity NPD7808 Phase 3
0.9444 High Similarity NPD7074 Phase 3
0.9441 High Similarity NPD3818 Discontinued
0.9304 High Similarity NPD4381 Clinical (unspecified phase)
0.9198 High Similarity NPD6168 Clinical (unspecified phase)
0.9198 High Similarity NPD6167 Clinical (unspecified phase)
0.9198 High Similarity NPD6166 Phase 2
0.9051 High Similarity NPD1934 Approved
0.903 High Similarity NPD7804 Clinical (unspecified phase)
0.8938 High Similarity NPD3817 Phase 2
0.891 High Similarity NPD1512 Approved
0.8875 High Similarity NPD2801 Approved
0.8875 High Similarity NPD2393 Clinical (unspecified phase)
0.8782 High Similarity NPD1511 Approved
0.8765 High Similarity NPD3882 Suspended
0.8688 High Similarity NPD4380 Phase 2
0.865 High Similarity NPD4868 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD7075 Discontinued
0.848 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD5402 Approved
0.843 Intermediate Similarity NPD6559 Discontinued
0.8385 Intermediate Similarity NPD5403 Approved
0.8375 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD6801 Discontinued
0.8333 Intermediate Similarity NPD1653 Approved
0.8303 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD5401 Approved
0.8228 Intermediate Similarity NPD1549 Phase 2
0.8199 Intermediate Similarity NPD6799 Approved
0.8166 Intermediate Similarity NPD5494 Approved
0.8092 Intermediate Similarity NPD3751 Discontinued
0.8084 Intermediate Similarity NPD1465 Phase 2
0.807 Intermediate Similarity NPD3787 Discontinued
0.8046 Intermediate Similarity NPD5844 Phase 1
0.8038 Intermediate Similarity NPD1510 Phase 2
0.8036 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD7685 Pre-registration
0.7987 Intermediate Similarity NPD2796 Approved
0.7976 Intermediate Similarity NPD7819 Suspended
0.7965 Intermediate Similarity NPD6232 Discontinued
0.7964 Intermediate Similarity NPD7411 Suspended
0.7939 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD7473 Discontinued
0.7927 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD6959 Discontinued
0.7907 Intermediate Similarity NPD7199 Phase 2
0.7904 Intermediate Similarity NPD6599 Discontinued
0.7898 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD1613 Approved
0.7886 Intermediate Similarity NPD7228 Approved
0.7833 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD8312 Approved
0.7821 Intermediate Similarity NPD8313 Approved
0.7791 Intermediate Similarity NPD6234 Discontinued
0.7791 Intermediate Similarity NPD919 Approved
0.7744 Intermediate Similarity NPD6190 Approved
0.7716 Intermediate Similarity NPD7266 Discontinued
0.7714 Intermediate Similarity NPD3926 Phase 2
0.7713 Intermediate Similarity NPD6779 Approved
0.7713 Intermediate Similarity NPD6780 Approved
0.7713 Intermediate Similarity NPD6781 Approved
0.7713 Intermediate Similarity NPD6777 Approved
0.7713 Intermediate Similarity NPD6782 Approved
0.7713 Intermediate Similarity NPD6776 Approved
0.7713 Intermediate Similarity NPD6778 Approved
0.7706 Intermediate Similarity NPD37 Approved
0.7705 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD1247 Approved
0.7683 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD3750 Approved
0.7674 Intermediate Similarity NPD4967 Phase 2
0.7674 Intermediate Similarity NPD4966 Approved
0.7674 Intermediate Similarity NPD4965 Approved
0.7673 Intermediate Similarity NPD943 Approved
0.7673 Intermediate Similarity NPD1240 Approved
0.767 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD7584 Approved
0.7651 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1933 Approved
0.7595 Intermediate Similarity NPD3027 Phase 3
0.7592 Intermediate Similarity NPD7435 Discontinued
0.758 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1607 Approved
0.7558 Intermediate Similarity NPD8455 Phase 2
0.7546 Intermediate Similarity NPD1551 Phase 2
0.7529 Intermediate Similarity NPD3749 Approved
0.7516 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD7697 Approved
0.75 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD7696 Phase 3
0.7487 Intermediate Similarity NPD8151 Discontinued
0.7485 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7768 Phase 2
0.747 Intermediate Similarity NPD4628 Phase 3
0.7461 Intermediate Similarity NPD7870 Phase 2
0.7461 Intermediate Similarity NPD7871 Phase 2
0.746 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6534 Approved
0.7447 Intermediate Similarity NPD6535 Approved
0.7438 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7701 Phase 2
0.7418 Intermediate Similarity NPD7240 Approved
0.7407 Intermediate Similarity NPD447 Suspended
0.7378 Intermediate Similarity NPD3748 Approved
0.736 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7874 Approved
0.7333 Intermediate Similarity NPD2935 Discontinued
0.733 Intermediate Similarity NPD7699 Phase 2
0.733 Intermediate Similarity NPD7700 Phase 2
0.7323 Intermediate Similarity NPD7783 Phase 2
0.7323 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD7801 Approved
0.7308 Intermediate Similarity NPD1091 Approved
0.7305 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD2533 Approved
0.7294 Intermediate Similarity NPD2534 Approved
0.7294 Intermediate Similarity NPD2532 Approved
0.7294 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6823 Phase 2
0.7259 Intermediate Similarity NPD7585 Approved
0.7254 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD8150 Discontinued
0.7209 Intermediate Similarity NPD920 Approved
0.7208 Intermediate Similarity NPD7583 Approved
0.7202 Intermediate Similarity NPD6674 Discontinued
0.7202 Intermediate Similarity NPD2800 Approved
0.7194 Intermediate Similarity NPD8319 Approved
0.7194 Intermediate Similarity NPD8320 Phase 1
0.7193 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5953 Discontinued
0.7173 Intermediate Similarity NPD4363 Phase 3
0.7173 Intermediate Similarity NPD4360 Phase 2
0.7169 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD9494 Approved
0.7126 Intermediate Similarity NPD6099 Approved
0.7126 Intermediate Similarity NPD3226 Approved
0.7126 Intermediate Similarity NPD7458 Discontinued
0.7126 Intermediate Similarity NPD6100 Approved
0.7125 Intermediate Similarity NPD1203 Approved
0.7117 Intermediate Similarity NPD2313 Discontinued
0.7117 Intermediate Similarity NPD6798 Discontinued
0.7113 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD6844 Discontinued
0.7101 Intermediate Similarity NPD1652 Phase 2
0.7101 Intermediate Similarity NPD1243 Approved
0.7099 Intermediate Similarity NPD4908 Phase 1
0.7099 Intermediate Similarity NPD6832 Phase 2
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2798 Approved
0.7073 Intermediate Similarity NPD6233 Phase 2
0.7065 Intermediate Similarity NPD7286 Phase 2
0.7056 Intermediate Similarity NPD7680 Approved
0.7051 Intermediate Similarity NPD1548 Phase 1
0.7048 Intermediate Similarity NPD6651 Approved
0.7035 Intermediate Similarity NPD7390 Discontinued
0.7031 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6213 Phase 3
0.7031 Intermediate Similarity NPD6212 Phase 3
0.7029 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD5353 Approved
0.7019 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6988 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6355 Discontinued
0.6988 Remote Similarity NPD5124 Phase 1
0.6982 Remote Similarity NPD2346 Discontinued
0.6982 Remote Similarity NPD2344 Approved
0.6981 Remote Similarity NPD1610 Phase 2
0.6964 Remote Similarity NPD2799 Discontinued
0.6959 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3225 Approved
0.694 Remote Similarity NPD5242 Approved
0.6937 Remote Similarity NPD9269 Phase 2
0.6923 Remote Similarity NPD8127 Discontinued
0.6919 Remote Similarity NPD2163 Approved
0.6919 Remote Similarity NPD5006 Approved
0.6919 Remote Similarity NPD5005 Approved
0.6911 Remote Similarity NPD6841 Approved
0.6911 Remote Similarity NPD6842 Approved
0.6911 Remote Similarity NPD6843 Phase 3
0.6909 Remote Similarity NPD3268 Approved
0.69 Remote Similarity NPD7211 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