Structure

Physi-Chem Properties

Molecular Weight:  260.03
Volume:  202.715
LogP:  -2.595
LogD:  -1.509
LogS:  -0.094
# Rotatable Bonds:  4
TPSA:  153.75
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.334
Synthetic Accessibility Score:  5.429
Fsp3:  1.0
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:  -6.025
MDCK Permeability:  0.001071086386218667
Pgp-inhibitor:  0.003
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.818
20% Bioavailability (F20%):  0.92
30% Bioavailability (F30%):  0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.382
Plasma Protein Binding (PPB):  11.093499183654785%
Volume Distribution (VD):  0.337
Pgp-substrate:  74.74344635009766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.052
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.071
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.119
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  1.481
Half-life (T1/2):  0.871

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.049
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.066
Skin Sensitization:  0.366
Carcinogencity:  0.043
Eye Corrosion:  0.011
Eye Irritation:  0.652
Respiratory Toxicity:  0.119

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Similar NPs/Drugs  

  Natural Product: NPC329095

Natural Product ID:  NPC329095
Common Name*:   [(2R,3S,4S,5R)-3,4,5-Trihydroxy-5-(Hydroxymethyl)Oxolan-2-Yl]Methyl Dihydrogen Phosphate
IUPAC Name:   [(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl dihydrogen phosphate
Synonyms:  
Standard InCHIKey:  BGWGXPAPYGQALX-ARQDHWQXSA-N
Standard InCHI:  InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1
SMILES:  C(C1C(C(C(O1)(CO)O)O)O)OP(=O)(O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL604196
PubChem CID:   440641
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0001540] Monosaccharides
            • [CHEMONTID:0001497] Pentoses
              • [CHEMONTID:0002259] Pentose phosphates

*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
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1172/JCI16309]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1371/journal.pone.0115359]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[10557354]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11034610]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11419736]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11530998]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12812989]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12840027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12878451]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15084647]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1521032]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15230696]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16770722]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1687010]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17116739]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17190852]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18311922]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18544912]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18799520]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19961175]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20506249]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[20581114]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20601097]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. faeces n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. bile n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. urine n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20876113]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[2268561]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[22711758]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23717534]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23752203]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23810710]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23811455]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23868375]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23919613]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24101735]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24399466]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24494566]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24558969]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25114169]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25181601]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25293588]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. PMID[25515814]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8987136]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9192820]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9800648]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4011 Chlamydomonas reinhardtii Species Chlamydomonadaceae 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
NPT1727 Individual Protein Acrosin Homo sapiens Inhibition = 32.0 % PMID[501360]
NPT1727 Individual Protein Acrosin Homo sapiens Inhibition = 7.0 % PMID[501360]
NPT27 Others Unspecified Binding energy = 5.7 kCal mol-1 PMID[501359]

☑ 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 NPC329095 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
0.9792 High Similarity NPC320043
0.9792 High Similarity NPC103672
0.898 High Similarity NPC322158
0.898 High Similarity NPC329128
0.8824 High Similarity NPC317501
0.8824 High Similarity NPC314821
0.8824 High Similarity NPC317626
0.8511 High Similarity NPC29721
0.8 Intermediate Similarity NPC252918
0.8 Intermediate Similarity NPC230789
0.7755 Intermediate Similarity NPC70756
0.7755 Intermediate Similarity NPC320240
0.7692 Intermediate Similarity NPC82512
0.7551 Intermediate Similarity NPC320189
0.7547 Intermediate Similarity NPC323574
0.7455 Intermediate Similarity NPC323361
0.7455 Intermediate Similarity NPC130683
0.7451 Intermediate Similarity NPC176017
0.7451 Intermediate Similarity NPC199857
0.7451 Intermediate Similarity NPC69445
0.7451 Intermediate Similarity NPC21209
0.7451 Intermediate Similarity NPC289758
0.7451 Intermediate Similarity NPC285364
0.7451 Intermediate Similarity NPC73906
0.7451 Intermediate Similarity NPC165846
0.7451 Intermediate Similarity NPC92246
0.7451 Intermediate Similarity NPC255377
0.7358 Intermediate Similarity NPC61270
0.7358 Intermediate Similarity NPC325822
0.7308 Intermediate Similarity NPC277475
0.7308 Intermediate Similarity NPC321087
0.717 Intermediate Similarity NPC14144
0.7143 Intermediate Similarity NPC266553
0.7091 Intermediate Similarity NPC326533
0.7037 Intermediate Similarity NPC157193
0.7037 Intermediate Similarity NPC299781
0.7037 Intermediate Similarity NPC42503
0.7037 Intermediate Similarity NPC282143
0.7 Intermediate Similarity NPC174485
0.6981 Remote Similarity NPC314613
0.6964 Remote Similarity NPC322803
0.6964 Remote Similarity NPC278465
0.6964 Remote Similarity NPC325153
0.6964 Remote Similarity NPC321102
0.6949 Remote Similarity NPC219040
0.6863 Remote Similarity NPC291502
0.6863 Remote Similarity NPC317182
0.6863 Remote Similarity NPC298699
0.6863 Remote Similarity NPC86191
0.6863 Remote Similarity NPC213159
0.6863 Remote Similarity NPC134252
0.6852 Remote Similarity NPC112363
0.6842 Remote Similarity NPC107914
0.6842 Remote Similarity NPC58629
0.6842 Remote Similarity NPC242073
0.6842 Remote Similarity NPC269166
0.6842 Remote Similarity NPC67660
0.6842 Remote Similarity NPC165198
0.6842 Remote Similarity NPC246558
0.6842 Remote Similarity NPC89145
0.6842 Remote Similarity NPC157514
0.6842 Remote Similarity NPC145112
0.6833 Remote Similarity NPC34877
0.6833 Remote Similarity NPC290179
0.6809 Remote Similarity NPC325034
0.6809 Remote Similarity NPC66052
0.6809 Remote Similarity NPC192065
0.6809 Remote Similarity NPC293908
0.6809 Remote Similarity NPC86412
0.6786 Remote Similarity NPC23134
0.6786 Remote Similarity NPC124963
0.6786 Remote Similarity NPC233726
0.6724 Remote Similarity NPC303727
0.6613 Remote Similarity NPC472026
0.6596 Remote Similarity NPC227267
0.65 Remote Similarity NPC3547
0.6452 Remote Similarity NPC323945
0.6406 Remote Similarity NPC268243
0.6393 Remote Similarity NPC472025
0.6364 Remote Similarity NPC88638
0.6349 Remote Similarity NPC320296
0.6327 Remote Similarity NPC313405
0.6296 Remote Similarity NPC207656
0.6296 Remote Similarity NPC107091
0.629 Remote Similarity NPC317023
0.625 Remote Similarity NPC318700
0.625 Remote Similarity NPC188428
0.6232 Remote Similarity NPC321873
0.623 Remote Similarity NPC148424
0.617 Remote Similarity NPC149070
0.617 Remote Similarity NPC321170
0.617 Remote Similarity NPC197207
0.617 Remote Similarity NPC127074
0.617 Remote Similarity NPC182541
0.617 Remote Similarity NPC266566
0.617 Remote Similarity NPC31433
0.617 Remote Similarity NPC187058
0.6154 Remote Similarity NPC102981
0.6154 Remote Similarity NPC111882
0.6154 Remote Similarity NPC88278
0.6154 Remote Similarity NPC227707
0.6154 Remote Similarity NPC99573
0.6129 Remote Similarity NPC293692
0.6094 Remote Similarity NPC477762
0.6094 Remote Similarity NPC477750
0.6094 Remote Similarity NPC477763
0.6094 Remote Similarity NPC477753
0.6094 Remote Similarity NPC477757
0.6094 Remote Similarity NPC477755
0.6032 Remote Similarity NPC322855
0.6032 Remote Similarity NPC320032
0.6 Remote Similarity NPC85078
0.5938 Remote Similarity NPC143326
0.5862 Remote Similarity NPC328954
0.5862 Remote Similarity NPC46254
0.5846 Remote Similarity NPC155457
0.5821 Remote Similarity NPC6848
0.5806 Remote Similarity NPC326557
0.5735 Remote Similarity NPC190418
0.5735 Remote Similarity NPC471761
0.5735 Remote Similarity NPC76881
0.5735 Remote Similarity NPC471760
0.5735 Remote Similarity NPC147292
0.5735 Remote Similarity NPC12040
0.5694 Remote Similarity NPC185419
0.5694 Remote Similarity NPC184550
0.5692 Remote Similarity NPC474627
0.5692 Remote Similarity NPC201338
0.5692 Remote Similarity NPC328786
0.5672 Remote Similarity NPC277570
0.5672 Remote Similarity NPC325773
0.5672 Remote Similarity NPC258690
0.5672 Remote Similarity NPC317651
0.5658 Remote Similarity NPC317263
0.5652 Remote Similarity NPC477764
0.5652 Remote Similarity NPC477756
0.5652 Remote Similarity NPC477751
0.5652 Remote Similarity NPC477752
0.5625 Remote Similarity NPC220922
0.5616 Remote Similarity NPC308096
0.5616 Remote Similarity NPC291228

  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 NPC329095 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
0.9792 High Similarity NPD9049 Discontinued
0.9792 High Similarity NPD9050 Approved
0.8824 High Similarity NPD9036 Phase 3
0.8824 High Similarity NPD9035 Clinical (unspecified phase)
0.8511 High Similarity NPD9006 Approved
0.7551 Intermediate Similarity NPD8957 Approved
0.7455 Intermediate Similarity NPD895 Approved
0.7455 Intermediate Similarity NPD887 Approved
0.7455 Intermediate Similarity NPD894 Approved
0.7455 Intermediate Similarity NPD889 Approved
0.7451 Intermediate Similarity NPD9000 Phase 3
0.7451 Intermediate Similarity NPD8997 Approved
0.7451 Intermediate Similarity NPD8999 Phase 3
0.7451 Intermediate Similarity NPD8993 Phase 1
0.7451 Intermediate Similarity NPD8998 Phase 2
0.7358 Intermediate Similarity NPD9061 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD8966 Approved
0.717 Intermediate Similarity NPD8965 Approved
0.7091 Intermediate Similarity NPD904 Phase 3
0.7091 Intermediate Similarity NPD905 Approved
0.6863 Remote Similarity NPD8788 Approved
0.6852 Remote Similarity NPD9139 Approved
0.6842 Remote Similarity NPD892 Phase 3
0.6842 Remote Similarity NPD890 Clinical (unspecified phase)
0.6842 Remote Similarity NPD893 Approved
0.6842 Remote Similarity NPD891 Phase 3
0.6842 Remote Similarity NPD888 Phase 3
0.6809 Remote Similarity NPD9052 Approved
0.6809 Remote Similarity NPD9053 Approved
0.6809 Remote Similarity NPD9051 Approved
0.678 Remote Similarity NPD2267 Suspended
0.6667 Remote Similarity NPD2269 Approved
0.6538 Remote Similarity NPD8958 Phase 2
0.6481 Remote Similarity NPD8994 Approved
0.6406 Remote Similarity NPD847 Phase 1
0.6296 Remote Similarity NPD9219 Approved
0.6296 Remote Similarity NPD9218 Clinical (unspecified phase)
0.6286 Remote Similarity NPD389 Phase 3
0.625 Remote Similarity NPD9065 Phase 3
0.617 Remote Similarity NPD8814 Phase 3
0.617 Remote Similarity NPD8237 Approved
0.6154 Remote Similarity NPD8995 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8996 Phase 3
0.6094 Remote Similarity NPD6123 Approved
0.6061 Remote Similarity NPD1457 Discontinued
0.6 Remote Similarity NPD9110 Approved
0.5957 Remote Similarity NPD8234 Approved
0.5957 Remote Similarity NPD8235 Approved
0.5957 Remote Similarity NPD8236 Phase 1
0.5932 Remote Similarity NPD8991 Phase 1
0.5806 Remote Similarity NPD884 Clinical (unspecified phase)
0.5806 Remote Similarity NPD885 Approved
0.5741 Remote Similarity NPD8967 Approved
0.5672 Remote Similarity NPD8961 Approved
0.5625 Remote Similarity NPD369 Approved
0.5625 Remote Similarity NPD8959 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