Structure

Physi-Chem Properties

Molecular Weight:  272.1
Volume:  273.045
LogP:  2.605
LogD:  2.326
LogS:  -3.77
# Rotatable Bonds:  0
TPSA:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.501
Synthetic Accessibility Score:  5.159
Fsp3:  0.5
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:  -5.127
MDCK Permeability:  7.480028580175713e-05
Pgp-inhibitor:  0.055
Pgp-substrate:  0.02
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.944
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.912
Plasma Protein Binding (PPB):  68.62824249267578%
Volume Distribution (VD):  0.899
Pgp-substrate:  51.99347686767578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.673
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.44
CYP2C9-inhibitor:  0.033
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.026
CYP3A4-inhibitor:  0.81
CYP3A4-substrate:  0.702

ADMET: Excretion

Clearance (CL):  15.173
Half-life (T1/2):  0.297

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.095
Drug-inuced Liver Injury (DILI):  0.321
AMES Toxicity:  0.124
Rat Oral Acute Toxicity:  0.873
Maximum Recommended Daily Dose:  0.097
Skin Sensitization:  0.937
Carcinogencity:  0.894
Eye Corrosion:  0.997
Eye Irritation:  0.945
Respiratory Toxicity:  0.946

Download Data

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

  Natural Product: NPC469371

Natural Product ID:  NPC469371
Common Name*:   Visartiside C
IUPAC Name:   [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-2-[[(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydrochromen-7-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:   Visartiside C
Standard InCHIKey:  DOVKRLBLJULZLC-DFROKGSNSA-N
Standard InCHI:  InChI=1S/C35H36O16/c36-14-26-29(42)30(43)31(51-34-32(44)35(45,16-47-34)15-46-27(41)9-6-17-4-2-1-3-5-17)33(50-26)48-19-11-22(39)28-23(40)13-24(49-25(28)12-19)18-7-8-20(37)21(38)10-18/h1-12,24,26,29-34,36-39,42-45H,13-16H2/b9-6+/t24-,26+,29+,30-,31+,32-,33+,34-,35+/m0/s1
SMILES:  C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(COC(=O)C=CC5=CC=CC=C5)O)O)C6=CC(=C(C=C6)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077014
PubChem CID:   46184804
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-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
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. PMID[20121165]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16561 Viscum articulatum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16561 Viscum articulatum Species Viscaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 14900.0 nM PMID[534808]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 99.7 % PMID[534808]
NPT1 Others Radical scavenging activity ED50 > 100.0 uM PMID[534808]

☑ 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 NPC469371 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
0.9704 High Similarity NPC35924
0.9704 High Similarity NPC199172
0.9639 High Similarity NPC47140
0.9639 High Similarity NPC67134
0.9474 High Similarity NPC156785
0.9474 High Similarity NPC162394
0.9474 High Similarity NPC241781
0.9474 High Similarity NPC470718
0.9419 High Similarity NPC21359
0.9419 High Similarity NPC275977
0.9419 High Similarity NPC470713
0.9419 High Similarity NPC249560
0.9419 High Similarity NPC460984
0.9419 High Similarity NPC25946
0.9419 High Similarity NPC470720
0.9419 High Similarity NPC470717
0.9419 High Similarity NPC223860
0.9412 High Similarity NPC476620
0.9412 High Similarity NPC476622
0.9412 High Similarity NPC476618
0.9412 High Similarity NPC241196
0.9412 High Similarity NPC476619
0.9412 High Similarity NPC476621
0.9412 High Similarity NPC476623
0.9405 High Similarity NPC261254
0.9401 High Similarity NPC105283
0.9364 High Similarity NPC295625
0.9364 High Similarity NPC470719
0.9364 High Similarity NPC473554
0.9364 High Similarity NPC33083
0.9357 High Similarity NPC471030
0.9349 High Similarity NPC472993
0.9349 High Similarity NPC88560
0.9349 High Similarity NPC175230
0.9349 High Similarity NPC172033
0.9345 High Similarity NPC204937
0.9345 High Similarity NPC149011
0.931 High Similarity NPC97817
0.931 High Similarity NPC65489
0.931 High Similarity NPC72554
0.931 High Similarity NPC30011
0.9306 High Similarity NPC231254
0.9298 High Similarity NPC253521
0.9298 High Similarity NPC472387
0.9298 High Similarity NPC120952
0.9298 High Similarity NPC113836
0.9298 High Similarity NPC37668
0.9294 High Similarity NPC214621
0.9294 High Similarity NPC34267
0.9294 High Similarity NPC223426
0.9294 High Similarity NPC81042
0.929 High Similarity NPC180918
0.929 High Similarity NPC235575
0.9286 High Similarity NPC86008
0.9286 High Similarity NPC43587
0.9281 High Similarity NPC8856
0.9277 High Similarity NPC29830
0.9277 High Similarity NPC121290
0.9261 High Similarity NPC264302
0.9253 High Similarity NPC104910
0.9253 High Similarity NPC474093
0.9249 High Similarity NPC97119
0.9249 High Similarity NPC135831
0.9249 High Similarity NPC297503
0.924 High Similarity NPC472991
0.924 High Similarity NPC471669
0.924 High Similarity NPC61904
0.924 High Similarity NPC296018
0.924 High Similarity NPC473862
0.924 High Similarity NPC472992
0.924 High Similarity NPC89127
0.924 High Similarity NPC144097
0.924 High Similarity NPC154741
0.9235 High Similarity NPC25724
0.9231 High Similarity NPC51326
0.9231 High Similarity NPC44328
0.9231 High Similarity NPC105095
0.9231 High Similarity NPC212748
0.9231 High Similarity NPC218488
0.9231 High Similarity NPC177731
0.9231 High Similarity NPC79056
0.9231 High Similarity NPC231194
0.9226 High Similarity NPC45400
0.9217 High Similarity NPC472876
0.92 High Similarity NPC475179
0.9195 High Similarity NPC318119
0.9186 High Similarity NPC217520
0.9186 High Similarity NPC217387
0.9186 High Similarity NPC35167
0.9186 High Similarity NPC293626
0.9186 High Similarity NPC173837
0.9186 High Similarity NPC258044
0.9186 High Similarity NPC139571
0.9186 High Similarity NPC267680
0.9186 High Similarity NPC476773
0.9186 High Similarity NPC196127
0.9186 High Similarity NPC477895
0.9181 High Similarity NPC253685
0.9181 High Similarity NPC198199
0.9176 High Similarity NPC9002
0.9176 High Similarity NPC288152
0.9176 High Similarity NPC257011
0.9176 High Similarity NPC137871
0.9172 High Similarity NPC229687
0.9172 High Similarity NPC293629
0.9172 High Similarity NPC197708
0.9172 High Similarity NPC209296
0.9172 High Similarity NPC195257
0.9172 High Similarity NPC658
0.9167 High Similarity NPC210073
0.9167 High Similarity NPC5778
0.9167 High Similarity NPC236934
0.9167 High Similarity NPC115674
0.9162 High Similarity NPC168822
0.9138 High Similarity NPC132111
0.9138 High Similarity NPC321916
0.9128 High Similarity NPC292019
0.9128 High Similarity NPC202908
0.9128 High Similarity NPC219043
0.9128 High Similarity NPC257714
0.9128 High Similarity NPC14187
0.9128 High Similarity NPC122467
0.9128 High Similarity NPC255799
0.9123 High Similarity NPC208668
0.9118 High Similarity NPC254855
0.9118 High Similarity NPC156869
0.9118 High Similarity NPC136042
0.9118 High Similarity NPC67105
0.9118 High Similarity NPC199079
0.9118 High Similarity NPC476365
0.9118 High Similarity NPC471416
0.9118 High Similarity NPC67326
0.9118 High Similarity NPC78734
0.9118 High Similarity NPC285197
0.9118 High Similarity NPC164704
0.9118 High Similarity NPC255157
0.9118 High Similarity NPC470712
0.9118 High Similarity NPC29958
0.9118 High Similarity NPC76047
0.9118 High Similarity NPC150767
0.9118 High Similarity NPC259896
0.9118 High Similarity NPC210808
0.9118 High Similarity NPC34287
0.9112 High Similarity NPC92565
0.9112 High Similarity NPC275454
0.9112 High Similarity NPC160156
0.9112 High Similarity NPC229729
0.9112 High Similarity NPC149244
0.9112 High Similarity NPC48640
0.9112 High Similarity NPC116745
0.9107 High Similarity NPC165720
0.9102 High Similarity NPC77660
0.9102 High Similarity NPC300537
0.9102 High Similarity NPC189142
0.9102 High Similarity NPC127782
0.9096 High Similarity NPC472724
0.9096 High Similarity NPC160543
0.9096 High Similarity NPC472721
0.9096 High Similarity NPC472720
0.9096 High Similarity NPC200708
0.9096 High Similarity NPC93065
0.9096 High Similarity NPC31208
0.9096 High Similarity NPC469652
0.9091 High Similarity NPC64755
0.9086 High Similarity NPC470455
0.9086 High Similarity NPC470451
0.9086 High Similarity NPC470416
0.908 High Similarity NPC208797
0.908 High Similarity NPC53680
0.9075 High Similarity NPC251417
0.9075 High Similarity NPC267549
0.9075 High Similarity NPC89052
0.907 High Similarity NPC142996
0.907 High Similarity NPC220173
0.907 High Similarity NPC102028
0.907 High Similarity NPC476472
0.907 High Similarity NPC473327
0.907 High Similarity NPC19108
0.907 High Similarity NPC16194
0.907 High Similarity NPC294815
0.9064 High Similarity NPC33054
0.9064 High Similarity NPC471748
0.9064 High Similarity NPC81332
0.9064 High Similarity NPC262580
0.9064 High Similarity NPC102851
0.9064 High Similarity NPC474522
0.9064 High Similarity NPC259152
0.9064 High Similarity NPC470716
0.9064 High Similarity NPC471725
0.9064 High Similarity NPC289396
0.9064 High Similarity NPC245452
0.9064 High Similarity NPC3583
0.9064 High Similarity NPC271848
0.9064 High Similarity NPC203259
0.9064 High Similarity NPC176740
0.9064 High Similarity NPC155877
0.9064 High Similarity NPC301683
0.9064 High Similarity NPC5786
0.9064 High Similarity NPC472386
0.9064 High Similarity NPC134532

  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 NPC469371 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
0.9231 High Similarity NPD7074 Phase 3
0.9231 High Similarity NPD7472 Approved
0.9172 High Similarity NPD7054 Approved
0.9123 High Similarity NPD7251 Discontinued
0.9112 High Similarity NPD3818 Discontinued
0.907 High Similarity NPD7808 Phase 3
0.9064 High Similarity NPD6797 Phase 2
0.8882 High Similarity NPD6167 Clinical (unspecified phase)
0.8882 High Similarity NPD6166 Phase 2
0.8882 High Similarity NPD6168 Clinical (unspecified phase)
0.8862 High Similarity NPD4381 Clinical (unspecified phase)
0.8851 High Similarity NPD4338 Clinical (unspecified phase)
0.8844 High Similarity NPD7993 Clinical (unspecified phase)
0.8802 High Similarity NPD4868 Clinical (unspecified phase)
0.8728 High Similarity NPD7804 Clinical (unspecified phase)
0.858 High Similarity NPD6559 Discontinued
0.8512 High Similarity NPD1934 Approved
0.8483 Intermediate Similarity NPD8313 Approved
0.8483 Intermediate Similarity NPD8312 Approved
0.8462 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8314 Intermediate Similarity NPD7075 Discontinued
0.8284 Intermediate Similarity NPD4380 Phase 2
0.8261 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD3882 Suspended
0.8249 Intermediate Similarity NPD7228 Approved
0.8214 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD3817 Phase 2
0.8144 Intermediate Similarity NPD1511 Approved
0.814 Intermediate Similarity NPD8455 Phase 2
0.814 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD7819 Suspended
0.814 Intermediate Similarity NPD2801 Approved
0.8129 Intermediate Similarity NPD7411 Suspended
0.8114 Intermediate Similarity NPD5494 Approved
0.8101 Intermediate Similarity NPD5844 Phase 1
0.8093 Intermediate Similarity NPD8151 Discontinued
0.8092 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8087 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD7199 Phase 2
0.8066 Intermediate Similarity NPD7685 Pre-registration
0.8054 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD1512 Approved
0.8035 Intermediate Similarity NPD1465 Phase 2
0.8034 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3749 Approved
0.7989 Intermediate Similarity NPD7473 Discontinued
0.7989 Intermediate Similarity NPD5402 Approved
0.7977 Intermediate Similarity NPD6801 Discontinued
0.7966 Intermediate Similarity NPD6959 Discontinued
0.7953 Intermediate Similarity NPD1653 Approved
0.7952 Intermediate Similarity NPD1549 Phase 2
0.7921 Intermediate Similarity NPD6232 Discontinued
0.7895 Intermediate Similarity NPD5403 Approved
0.7892 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7869 Intermediate Similarity NPD7240 Approved
0.7853 Intermediate Similarity NPD6234 Discontinued
0.7845 Intermediate Similarity NPD3751 Discontinued
0.7841 Intermediate Similarity NPD7768 Phase 2
0.7828 Intermediate Similarity NPD7783 Phase 2
0.7828 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD6799 Approved
0.7824 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7266 Discontinued
0.7778 Intermediate Similarity NPD5401 Approved
0.7771 Intermediate Similarity NPD37 Approved
0.7744 Intermediate Similarity NPD7435 Discontinued
0.774 Intermediate Similarity NPD4967 Phase 2
0.774 Intermediate Similarity NPD4966 Approved
0.774 Intermediate Similarity NPD4965 Approved
0.7722 Intermediate Similarity NPD3787 Discontinued
0.7674 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD1510 Phase 2
0.7657 Intermediate Similarity NPD6599 Discontinued
0.7653 Intermediate Similarity NPD7696 Phase 3
0.7653 Intermediate Similarity NPD7698 Approved
0.7653 Intermediate Similarity NPD7697 Approved
0.7619 Intermediate Similarity NPD2796 Approved
0.7614 Intermediate Similarity NPD7871 Phase 2
0.7614 Intermediate Similarity NPD7870 Phase 2
0.7602 Intermediate Similarity NPD6190 Approved
0.76 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7874 Approved
0.759 Intermediate Similarity NPD6782 Approved
0.759 Intermediate Similarity NPD6779 Approved
0.759 Intermediate Similarity NPD6780 Approved
0.759 Intermediate Similarity NPD6777 Approved
0.759 Intermediate Similarity NPD6781 Approved
0.759 Intermediate Similarity NPD6776 Approved
0.759 Intermediate Similarity NPD6778 Approved
0.7588 Intermediate Similarity NPD7701 Phase 2
0.7566 Intermediate Similarity NPD8434 Phase 2
0.7563 Intermediate Similarity NPD7680 Approved
0.7556 Intermediate Similarity NPD919 Approved
0.7544 Intermediate Similarity NPD3750 Approved
0.7538 Intermediate Similarity NPD7584 Approved
0.753 Intermediate Similarity NPD1613 Approved
0.753 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD8320 Phase 1
0.7525 Intermediate Similarity NPD8319 Approved
0.7487 Intermediate Similarity NPD7699 Phase 2
0.7487 Intermediate Similarity NPD7700 Phase 2
0.7486 Intermediate Similarity NPD3926 Phase 2
0.7485 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD8150 Discontinued
0.7471 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4628 Phase 3
0.7425 Intermediate Similarity NPD1240 Approved
0.7425 Intermediate Similarity NPD943 Approved
0.7424 Intermediate Similarity NPD6823 Phase 2
0.7412 Intermediate Similarity NPD1551 Phase 2
0.7401 Intermediate Similarity NPD7458 Discontinued
0.7389 Intermediate Similarity NPD7801 Approved
0.7381 Intermediate Similarity NPD1933 Approved
0.7381 Intermediate Similarity NPD230 Phase 1
0.7371 Intermediate Similarity NPD2534 Approved
0.7371 Intermediate Similarity NPD2532 Approved
0.7371 Intermediate Similarity NPD2533 Approved
0.7337 Intermediate Similarity NPD1607 Approved
0.7333 Intermediate Similarity NPD6534 Approved
0.7333 Intermediate Similarity NPD6535 Approved
0.7327 Intermediate Similarity NPD7585 Approved
0.7326 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD2935 Discontinued
0.7305 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD920 Approved
0.7283 Intermediate Similarity NPD1247 Approved
0.7277 Intermediate Similarity NPD7583 Approved
0.7273 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD3748 Approved
0.7229 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD3226 Approved
0.7198 Intermediate Similarity NPD7930 Approved
0.7189 Intermediate Similarity NPD8127 Discontinued
0.7184 Intermediate Similarity NPD1243 Approved
0.7176 Intermediate Similarity NPD447 Suspended
0.7158 Intermediate Similarity NPD5953 Discontinued
0.7151 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD7286 Phase 2
0.7143 Intermediate Similarity NPD3027 Phase 3
0.7143 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4287 Approved
0.7089 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD2800 Approved
0.7083 Intermediate Similarity NPD6832 Phase 2
0.7069 Intermediate Similarity NPD2344 Approved
0.7065 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7229 Phase 3
0.7022 Intermediate Similarity NPD7390 Discontinued
0.702 Intermediate Similarity NPD6212 Phase 3
0.702 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6213 Phase 3
0.7011 Intermediate Similarity NPD6099 Approved
0.7011 Intermediate Similarity NPD6100 Approved
0.701 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1203 Approved
0.7 Intermediate Similarity NPD2313 Discontinued
0.7 Intermediate Similarity NPD6798 Discontinued
0.7 Intermediate Similarity NPD3764 Approved
0.6995 Remote Similarity NPD7549 Discontinued
0.6995 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7097 Phase 1
0.6991 Remote Similarity NPD8059 Phase 3
0.6991 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6674 Discontinued
0.6984 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6982 Remote Similarity NPD4908 Phase 1
0.6971 Remote Similarity NPD2346 Discontinued
0.6968 Remote Similarity NPD5711 Approved
0.6968 Remote Similarity NPD5710 Approved
0.6954 Remote Similarity NPD2799 Discontinued
0.6954 Remote Similarity NPD651 Clinical (unspecified phase)
0.6949 Remote Similarity NPD8166 Discontinued
0.6919 Remote Similarity NPD5353 Approved
0.6912 Remote Similarity NPD5006 Approved
0.6912 Remote Similarity NPD5005 Approved
0.6911 Remote Similarity NPD7799 Discontinued
0.691 Remote Similarity NPD2309 Approved
0.6901 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6879 Remote Similarity NPD5124 Phase 1
0.6879 Remote Similarity NPD6355 Discontinued
0.6879 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6867 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6867 Remote Similarity NPD1091 Approved
0.686 Remote Similarity NPD6233 Phase 2
0.6856 Remote Similarity NPD7039 Approved
0.6856 Remote Similarity NPD7038 Approved
0.6851 Remote Similarity NPD6273 Approved
0.6848 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8285 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