Structure

Physi-Chem Properties

Molecular Weight:  258.09
Volume:  231.229
LogP:  -1.364
LogD:  -0.94
LogS:  -0.656
# Rotatable Bonds:  2
TPSA:  124.78
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.463
Synthetic Accessibility Score:  3.448
Fsp3:  0.6
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:  -5.899
MDCK Permeability:  0.00022371664817910641
Pgp-inhibitor:  0.001
Pgp-substrate:  0.024
Human Intestinal Absorption (HIA):  0.764
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.313
Plasma Protein Binding (PPB):  15.974817276000977%
Volume Distribution (VD):  0.35
Pgp-substrate:  75.98640441894531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.121
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.108
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.092
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.072

ADMET: Excretion

Clearance (CL):  8.482
Half-life (T1/2):  0.925

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.717
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.005
Maximum Recommended Daily Dose:  0.004
Skin Sensitization:  0.033
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.027
Respiratory Toxicity:  0.005

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC163352

Natural Product ID:  NPC163352
Common Name*:   Sid112992
IUPAC Name:   1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Synonyms:  
Standard InCHIKey:  DWRXFEITVBNRMK-JAGXHNFQSA-N
Standard InCHI:  InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7+,9-/m1/s1
SMILES:  Cc1cn([C@H]2[C@H]([C@@H]([C@@H](CO)O2)O)O)c(=O)nc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL103283
PubChem CID:   65049
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues
      • [CHEMONTID:0000480] Pyrimidine nucleosides

*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
NPO30675 Vibrio harveyi Species Vibrionaceae Bacteria n.a. n.a. n.a. PMID[23305926]
NPO30675 Vibrio harveyi Species Vibrionaceae Bacteria n.a. n.a. n.a. PMID[25668560]
NPO30675 Vibrio harveyi Species Vibrionaceae Bacteria n.a. n.a. n.a. PMID[311472]

☑ 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
NPT3785 Individual Protein Thymidylate kinase Mycobacterium tuberculosis Ki = 238000.0 nM PMID[508388]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 1000000.0 nM PMID[508391]
NPT1755 Individual Protein Thymidine kinase, cytosolic Homo sapiens Inhibition = 55.1 % PMID[508392]
NPT1755 Individual Protein Thymidine kinase, cytosolic Homo sapiens Inhibition = 22.0 % PMID[508392]
NPT1755 Individual Protein Thymidine kinase, cytosolic Homo sapiens Inhibition = 5.0 % PMID[508392]
NPT1755 Individual Protein Thymidine kinase, cytosolic Homo sapiens IC50 > 1000000.0 nM PMID[508394]
NPT4863 Individual Protein Thymidine kinase, mitochondrial Homo sapiens IC50 = 285000.0 nM PMID[508394]
NPT3787 Individual Protein Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) IC50 = 24000.0 nM PMID[508394]
NPT3800 Individual Protein Deoxynucleoside kinase Drosophila melanogaster IC50 = 65000.0 nM PMID[508394]
NPT6615 Individual Protein Thymidine kinase Varicella-zoster virus (strain Dumas) (HHV-3) (Human herpesvirus 3) IC50 = 17000.0 nM PMID[508394]
NPT1755 Individual Protein Thymidine kinase, cytosolic Homo sapiens IC50 > 1000000.0 nM PMID[508397]
NPT4863 Individual Protein Thymidine kinase, mitochondrial Homo sapiens IC50 = 285000.0 nM PMID[508397]
NPT3788 Individual Protein Thymidine kinase Human herpesvirus 1 IC50 = 24000.0 nM PMID[508397]
NPT3800 Individual Protein Deoxynucleoside kinase Drosophila melanogaster IC50 = 65000.0 nM PMID[508397]
NPT6615 Individual Protein Thymidine kinase Varicella-zoster virus (strain Dumas) (HHV-3) (Human herpesvirus 3) IC50 = 17000.0 nM PMID[508397]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1000000.0 nM PMID[508399]
NPT1864 Cell Line L5178Y Mus musculus ID50 > 100.0 ug ml-1 PMID[508400]
NPT4849 Cell Line P815 Mus musculus ID50 = 13.0 ug ml-1 PMID[508400]
NPT3891 Cell Line S180 Mus musculus Inhibition = 84.0 % PMID[508403]
NPT137 Cell Line L1210 Mus musculus Inhibition = 86.0 % PMID[508403]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 ID50 = 0.64 uM PMID[508389]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 ID50 = 1.65 uM PMID[508389]
NPT27 Others Unspecified Toxicity > 1000.0 uM PMID[508389]
NPT1749 Organism Human herpesvirus 3 Human herpesvirus 3 ID50 = 0.53 uM PMID[508389]
NPT1750 Organism Human herpesvirus 5 Human herpesvirus 5 ID50 > 500.0 uM PMID[508389]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 ID50 > 500.0 uM PMID[508389]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 IC50 > 500.0 ug.mL-1 PMID[508390]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 IC50 = 0.6 ug.mL-1 PMID[508390]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Therapeutic index = 833.0 n.a. PMID[508390]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 ID50 = 10.0 uM PMID[508393]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 ID50 = 19.0 uM PMID[508393]
NPT27 Others Unspecified IC50 = 6.2 nM PMID[508395]
NPT27 Others Unspecified IC50 = 150.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 100.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 55.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 370.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 240.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 120.0 nM PMID[508395]
NPT27 Others Unspecified IC50 = 24400.0 nM PMID[508396]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Inhibition < 90.0 % PMID[508400]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Inhibition > 90.0 % PMID[508400]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Inhibition = 100.0 % PMID[508400]
NPT334 Organism Vaccinia virus Vaccinia virus ID50 = 3.9 10'-6M PMID[508401]
NPT1766 Organism Human herpesvirus 1 strain KOS Human herpesvirus 1 strain KOS ID50 = 3.9 10'-7M PMID[508401]
NPT195 Organism Vesicular stomatitis virus Vesicular stomatitis virus ID50 > 1.0 10'-4M PMID[508401]
NPT195 Organism Vesicular stomatitis virus Vesicular stomatitis virus MIC > 200.0 ug.mL-1 PMID[508402]
NPT334 Organism Vaccinia virus Vaccinia virus MIC = 4.0 ug.mL-1 PMID[508402]
NPT334 Organism Vaccinia virus Vaccinia virus MIC = 2.0 ug.mL-1 PMID[508402]
NPT1766 Organism Human herpesvirus 1 strain KOS Human herpesvirus 1 strain KOS MIC = 0.2 ug.mL-1 PMID[508402]
NPT1766 Organism Human herpesvirus 1 strain KOS Human herpesvirus 1 strain KOS MIC = 0.1 ug.mL-1 PMID[508402]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 MIC = 0.3 ug.mL-1 PMID[508402]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 MIC = 0.4 ug.mL-1 PMID[508402]
NPT27 Others Unspecified MIC = 300.0 ug.mL-1 PMID[508402]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Inhibition = 99.75 % PMID[508403]
NPT2 Others Unspecified Ki = 1000.0 nM PMID[508403]

☑ 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 NPC163352 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 NPC210456
0.9625 High Similarity NPC71339
0.9625 High Similarity NPC112842
0.9059 High Similarity NPC171116
0.8929 High Similarity NPC43246
0.8929 High Similarity NPC89051
0.8851 High Similarity NPC327344
0.8652 High Similarity NPC324516
0.8652 High Similarity NPC318166
0.8571 High Similarity NPC106780
0.8293 Intermediate Similarity NPC329077
0.8242 Intermediate Similarity NPC36985
0.8242 Intermediate Similarity NPC17892
0.8202 Intermediate Similarity NPC315063
0.8152 Intermediate Similarity NPC73765
0.8152 Intermediate Similarity NPC283698
0.8152 Intermediate Similarity NPC317639
0.809 Intermediate Similarity NPC328806
0.7976 Intermediate Similarity NPC325902
0.7912 Intermediate Similarity NPC324390
0.7826 Intermediate Similarity NPC320249
0.7826 Intermediate Similarity NPC322594
0.7363 Intermediate Similarity NPC325723
0.7353 Intermediate Similarity NPC329277
0.7222 Intermediate Similarity NPC319753
0.7212 Intermediate Similarity NPC155087
0.7212 Intermediate Similarity NPC149843
0.7204 Intermediate Similarity NPC190334
0.7204 Intermediate Similarity NPC62927
0.7103 Intermediate Similarity NPC478024
0.6897 Remote Similarity NPC315806
0.6882 Remote Similarity NPC229249
0.67 Remote Similarity NPC226769
0.67 Remote Similarity NPC280946
0.67 Remote Similarity NPC6166
0.6638 Remote Similarity NPC325750
0.6634 Remote Similarity NPC90240
0.6634 Remote Similarity NPC120887
0.6602 Remote Similarity NPC328914
0.6569 Remote Similarity NPC328779
0.6531 Remote Similarity NPC109188
0.6525 Remote Similarity NPC315058
0.6364 Remote Similarity NPC313962
0.6303 Remote Similarity NPC284651
0.6275 Remote Similarity NPC329384
0.6154 Remote Similarity NPC126186
0.6022 Remote Similarity NPC470782
0.6 Remote Similarity NPC316123
0.5904 Remote Similarity NPC293551
0.5876 Remote Similarity NPC470783
0.567 Remote Similarity NPC312315
0.5657 Remote Similarity NPC242077
0.5645 Remote Similarity NPC36254
0.5604 Remote Similarity NPC316445
0.5603 Remote Similarity NPC251122

  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 NPC163352 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
0.9625 High Similarity NPD280 Approved
0.9518 High Similarity NPD755 Phase 3
0.939 High Similarity NPD240 Phase 3
0.9146 High Similarity NPD238 Clinical (unspecified phase)
0.9146 High Similarity NPD239 Phase 2
0.9059 High Similarity NPD841 Approved
0.8929 High Similarity NPD9580 Clinical (unspecified phase)
0.8929 High Similarity NPD9581 Clinical (unspecified phase)
0.8929 High Similarity NPD170 Approved
0.8851 High Similarity NPD251 Approved
0.878 High Similarity NPD9558 Phase 3
0.878 High Similarity NPD9556 Approved
0.8778 High Similarity NPD502 Approved
0.8675 High Similarity NPD9561 Approved
0.8675 High Similarity NPD9560 Approved
0.8571 High Similarity NPD9546 Phase 2
0.8471 Intermediate Similarity NPD9533 Phase 2
0.8444 Intermediate Similarity NPD501 Phase 1
0.8391 Intermediate Similarity NPD241 Discontinued
0.8372 Intermediate Similarity NPD9557 Clinical (unspecified phase)
0.8353 Intermediate Similarity NPD9559 Phase 1
0.8276 Intermediate Similarity NPD9562 Discovery
0.8152 Intermediate Similarity NPD9639 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD9529 Phase 1
0.7935 Intermediate Similarity NPD1686 Approved
0.7912 Intermediate Similarity NPD9565 Discontinued
0.7778 Intermediate Similarity NPD1760 Approved
0.77 Intermediate Similarity NPD1385 Discontinued
0.7576 Intermediate Similarity NPD1061 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD5789 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD762 Discontinued
0.7449 Intermediate Similarity NPD223 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD3129 Phase 3
0.734 Intermediate Similarity NPD500 Discontinued
0.7255 Intermediate Similarity NPD3128 Phase 3
0.7204 Intermediate Similarity NPD9603 Phase 3
0.7204 Intermediate Similarity NPD9602 Phase 3
0.7204 Intermediate Similarity NPD9604 Approved
0.7103 Intermediate Similarity NPD7914 Suspended
0.7083 Intermediate Similarity NPD285 Discontinued
0.7083 Intermediate Similarity NPD6943 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD9573 Phase 2
0.6907 Remote Similarity NPD9585 Discontinued
0.6897 Remote Similarity NPD9653 Clinical (unspecified phase)
0.6882 Remote Similarity NPD205 Approved
0.6882 Remote Similarity NPD9601 Approved
0.6837 Remote Similarity NPD279 Clinical (unspecified phase)
0.6832 Remote Similarity NPD192 Phase 2
0.6829 Remote Similarity NPD9504 Approved
0.6829 Remote Similarity NPD9503 Approved
0.6813 Remote Similarity NPD9429 Discontinued
0.6809 Remote Similarity NPD9555 Phase 2
0.6804 Remote Similarity NPD267 Discontinued
0.68 Remote Similarity NPD514 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7651 Approved
0.6771 Remote Similarity NPD301 Discontinued
0.6757 Remote Similarity NPD3139 Phase 3
0.6742 Remote Similarity NPD9407 Approved
0.6696 Remote Similarity NPD7992 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3138 Phase 3
0.6667 Remote Similarity NPD2691 Clinical (unspecified phase)
0.6602 Remote Similarity NPD1455 Phase 3
0.6602 Remote Similarity NPD1454 Phase 3
0.6602 Remote Similarity NPD765 Discontinued
0.66 Remote Similarity NPD1706 Clinical (unspecified phase)
0.6598 Remote Similarity NPD9554 Approved
0.6598 Remote Similarity NPD9553 Approved
0.6559 Remote Similarity NPD9600 Approved
0.6531 Remote Similarity NPD1331 Approved
0.6436 Remote Similarity NPD215 Discontinued
0.6429 Remote Similarity NPD723 Phase 2
0.6421 Remote Similarity NPD9572 Clinical (unspecified phase)
0.6404 Remote Similarity NPD9405 Approved
0.6355 Remote Similarity NPD2633 Phase 1
0.6348 Remote Similarity NPD7756 Clinical (unspecified phase)
0.6306 Remote Similarity NPD1805 Phase 2
0.6306 Remote Similarity NPD1804 Phase 2
0.6296 Remote Similarity NPD6946 Approved
0.6239 Remote Similarity NPD1428 Phase 2
0.6204 Remote Similarity NPD4743 Phase 2
0.6126 Remote Similarity NPD6693 Phase 3
0.6038 Remote Similarity NPD3121 Phase 2
0.6 Remote Similarity NPD7761 Suspended
0.5983 Remote Similarity NPD6935 Phase 3
0.5983 Remote Similarity NPD6936 Clinical (unspecified phase)
0.5963 Remote Similarity NPD244 Clinical (unspecified phase)
0.596 Remote Similarity NPD9640 Clinical (unspecified phase)
0.5862 Remote Similarity NPD9211 Clinical (unspecified phase)
0.5657 Remote Similarity NPD9644 Approved
0.5657 Remote Similarity NPD9645 Approved
0.5657 Remote Similarity NPD9646 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