Structure

Physi-Chem Properties

Molecular Weight:  423.98
Volume:  301.816
LogP:  -1.016
LogD:  -0.483
LogS:  -1.445
# Rotatable Bonds:  4
TPSA:  189.43
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.342
Synthetic Accessibility Score:  4.452
Fsp3:  0.5
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.096
MDCK Permeability:  1.67298912856495e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.783
Human Intestinal Absorption (HIA):  0.03
20% Bioavailability (F20%):  0.065
30% Bioavailability (F30%):  0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.149
Plasma Protein Binding (PPB):  40.18506622314453%
Volume Distribution (VD):  1.899
Pgp-substrate:  60.20158386230469%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.802
CYP2C19-inhibitor:  0.026
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.06
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.051

ADMET: Excretion

Clearance (CL):  5.6
Half-life (T1/2):  0.792

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.988
Drug-inuced Liver Injury (DILI):  0.996
AMES Toxicity:  0.961
Rat Oral Acute Toxicity:  0.086
Maximum Recommended Daily Dose:  0.919
Skin Sensitization:  0.644
Carcinogencity:  0.922
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.971

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  Natural Product: NPC472816

Natural Product ID:  NPC472816
Common Name*:   5'-O-Sulfamoyl-2-Bromoadenosine
IUPAC Name:   [(2R,3S,4R,5R)-5-(6-amino-2-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
Synonyms:  
Standard InCHIKey:  VPWOATHUXGHCPI-UUOKFMHZSA-N
Standard InCHI:  InChI=1S/C10H13BrN6O6S/c11-10-15-7(12)4-8(16-10)17(2-14-4)9-6(19)5(18)3(23-9)1-22-24(13,20)21/h2-3,5-6,9,18-19H,1H2,(H2,12,15,16)(H2,13,20,21)/t3-,5-,6-,9-/m1/s1
SMILES:  O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1nc(Br)nc2N)COS(=O)(=O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3586275
PubChem CID:   189495
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues
      • [CHEMONTID:0000479] Purine 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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO28613 Streptomyces calvus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11450 Pseudoceratina purpurea Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28613 Streptomyces calvus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC = 0.2 ug.mL-1 PMID[463215]

☑ 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 NPC472816 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
0.9496 High Similarity NPC21448
0.9496 High Similarity NPC156461
0.9496 High Similarity NPC107374
0.9429 High Similarity NPC189068
0.9429 High Similarity NPC164665
0.9362 High Similarity NPC309832
0.9362 High Similarity NPC269827
0.9362 High Similarity NPC219313
0.9353 High Similarity NPC229974
0.9209 High Similarity NPC161659
0.9209 High Similarity NPC209525
0.9184 High Similarity NPC316618
0.9103 High Similarity NPC85689
0.9103 High Similarity NPC185991
0.9103 High Similarity NPC211025
0.9078 High Similarity NPC314152
0.9071 High Similarity NPC317821
0.9041 High Similarity NPC321814
0.898 High Similarity NPC212551
0.898 High Similarity NPC302778
0.898 High Similarity NPC164952
0.898 High Similarity NPC130586
0.8919 High Similarity NPC174802
0.8897 High Similarity NPC121222
0.8859 High Similarity NPC224076
0.88 High Similarity NPC239737
0.88 High Similarity NPC226245
0.8784 High Similarity NPC207633
0.8732 High Similarity NPC129756
0.8716 High Similarity NPC161224
0.8707 High Similarity NPC136349
0.8649 High Similarity NPC150853
0.8553 High Similarity NPC311197
0.8553 High Similarity NPC54320
0.8553 High Similarity NPC313754
0.8533 High Similarity NPC328479
0.8516 High Similarity NPC323091
0.8487 Intermediate Similarity NPC52238
0.8403 Intermediate Similarity NPC33996
0.8392 Intermediate Similarity NPC320818
0.8258 Intermediate Similarity NPC195140
0.8176 Intermediate Similarity NPC261595
0.816 Intermediate Similarity NPC189261
0.8125 Intermediate Similarity NPC324033
0.8125 Intermediate Similarity NPC321458
0.8113 Intermediate Similarity NPC324484
0.8098 Intermediate Similarity NPC326529
0.8077 Intermediate Similarity NPC93365
0.8063 Intermediate Similarity NPC325906
0.8049 Intermediate Similarity NPC319100
0.8049 Intermediate Similarity NPC324198
0.7963 Intermediate Similarity NPC326082
0.7963 Intermediate Similarity NPC290959
0.7891 Intermediate Similarity NPC61198
0.7823 Intermediate Similarity NPC262926
0.7707 Intermediate Similarity NPC321052
0.7667 Intermediate Similarity NPC30326
0.7665 Intermediate Similarity NPC313897
0.7635 Intermediate Similarity NPC319221
0.7597 Intermediate Similarity NPC89147
0.7597 Intermediate Similarity NPC274384
0.7568 Intermediate Similarity NPC324009
0.7532 Intermediate Similarity NPC211820
0.7532 Intermediate Similarity NPC251233
0.7516 Intermediate Similarity NPC186619
0.7484 Intermediate Similarity NPC177169
0.7457 Intermediate Similarity NPC24589
0.7436 Intermediate Similarity NPC64705
0.7436 Intermediate Similarity NPC232408
0.7429 Intermediate Similarity NPC78941
0.7429 Intermediate Similarity NPC282458
0.7419 Intermediate Similarity NPC318590
0.7372 Intermediate Similarity NPC317746
0.7358 Intermediate Similarity NPC326694
0.7355 Intermediate Similarity NPC315642
0.7355 Intermediate Similarity NPC74306
0.7232 Intermediate Similarity NPC313514
0.7202 Intermediate Similarity NPC33382
0.716 Intermediate Similarity NPC125659
0.716 Intermediate Similarity NPC168702
0.7076 Intermediate Similarity NPC222174
0.7024 Intermediate Similarity NPC14590
0.6974 Remote Similarity NPC104011
0.6964 Remote Similarity NPC321393
0.6952 Remote Similarity NPC276373
0.6915 Remote Similarity NPC5802
0.6878 Remote Similarity NPC157821
0.6871 Remote Similarity NPC327579
0.6667 Remote Similarity NPC476564
0.6667 Remote Similarity NPC57279
0.6645 Remote Similarity NPC246193
0.6571 Remote Similarity NPC174114
0.6571 Remote Similarity NPC87981
0.6567 Remote Similarity NPC250178
0.6536 Remote Similarity NPC248007
0.6438 Remote Similarity NPC312187
0.6438 Remote Similarity NPC4837
0.6359 Remote Similarity NPC103388
0.6346 Remote Similarity NPC107160
0.634 Remote Similarity NPC139776
0.6329 Remote Similarity NPC287876
0.6266 Remote Similarity NPC14330
0.6256 Remote Similarity NPC160666
0.6256 Remote Similarity NPC21461
0.6207 Remote Similarity NPC18335
0.6185 Remote Similarity NPC472834
0.6168 Remote Similarity NPC158055
0.6051 Remote Similarity NPC109322
0.5974 Remote Similarity NPC68938
0.5914 Remote Similarity NPC164845
0.5886 Remote Similarity NPC5707
0.5882 Remote Similarity NPC313547
0.5882 Remote Similarity NPC217656
0.5871 Remote Similarity NPC189314
0.5864 Remote Similarity NPC265111
0.5848 Remote Similarity NPC89139
0.5833 Remote Similarity NPC296437
0.5813 Remote Similarity NPC180493
0.5799 Remote Similarity NPC470266
0.5747 Remote Similarity NPC244700
0.5743 Remote Similarity NPC476561
0.5731 Remote Similarity NPC476528
0.5731 Remote Similarity NPC476433
0.5698 Remote Similarity NPC472833
0.5698 Remote Similarity NPC476013
0.5698 Remote Similarity NPC474986
0.5698 Remote Similarity NPC476522
0.5698 Remote Similarity NPC476520
0.569 Remote Similarity NPC476408
0.5665 Remote Similarity NPC476521
0.5654 Remote Similarity NPC473585
0.5629 Remote Similarity NPC119133
0.5604 Remote Similarity NPC472832
0.5604 Remote Similarity NPC18308

  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 NPC472816 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
0.9496 High Similarity NPD250 Approved
0.9496 High Similarity NPD249 Approved
0.9362 High Similarity NPD186 Discovery
0.9362 High Similarity NPD195 Approved
0.9103 High Similarity NPD283 Approved
0.9078 High Similarity NPD185 Approved
0.898 High Similarity NPD242 Approved
0.898 High Similarity NPD3107 Discontinued
0.898 High Similarity NPD1369 Phase 2
0.898 High Similarity NPD338 Approved
0.898 High Similarity NPD1750 Clinical (unspecified phase)
0.8951 High Similarity NPD166 Approved
0.8936 High Similarity NPD193 Suspended
0.8919 High Similarity NPD339 Approved
0.8859 High Similarity NPD169 Phase 2
0.88 High Similarity NPD2624 Phase 2
0.88 High Similarity NPD1732 Phase 3
0.88 High Similarity NPD2646 Discontinued
0.8707 High Similarity NPD548 Clinical (unspecified phase)
0.8553 High Similarity NPD217 Approved
0.8553 High Similarity NPD216 Approved
0.8553 High Similarity NPD219 Phase 3
0.8553 High Similarity NPD220 Clinical (unspecified phase)
0.8553 High Similarity NPD218 Approved
0.8355 Intermediate Similarity NPD214 Approved
0.8355 Intermediate Similarity NPD213 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD2647 Phase 3
0.8176 Intermediate Similarity NPD247 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD248 Discontinued
0.811 Intermediate Similarity NPD1412 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD5666 Phase 2
0.8077 Intermediate Similarity NPD546 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD1776 Approved
0.8063 Intermediate Similarity NPD7988 Suspended
0.8063 Intermediate Similarity NPD1777 Approved
0.8049 Intermediate Similarity NPD4171 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD9632 Phase 3
0.7904 Intermediate Similarity NPD4716 Approved
0.7902 Intermediate Similarity NPD870 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD252 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD3083 Approved
0.7857 Intermediate Similarity NPD4744 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6417 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD1692 Approved
0.7702 Intermediate Similarity NPD516 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2632 Approved
0.7688 Intermediate Similarity NPD2630 Approved
0.7688 Intermediate Similarity NPD2631 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD549 Approved
0.7674 Intermediate Similarity NPD5684 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD5682 Phase 3
0.7674 Intermediate Similarity NPD5683 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD194 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD536 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD9633 Phase 3
0.7397 Intermediate Similarity NPD9408 Phase 3
0.7375 Intermediate Similarity NPD231 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD7158 Phase 1
0.7355 Intermediate Similarity NPD582 Approved
0.725 Intermediate Similarity NPD3708 Phase 2
0.7232 Intermediate Similarity NPD7138 Phase 2
0.7152 Intermediate Similarity NPD4074 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3085 Phase 1
0.7099 Intermediate Similarity NPD3086 Phase 3
0.7021 Intermediate Similarity NPD2965 Clinical (unspecified phase)
0.6984 Remote Similarity NPD2876 Phase 3
0.6984 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6961 Remote Similarity NPD4054 Clinical (unspecified phase)
0.6951 Remote Similarity NPD9605 Phase 3
0.6918 Remote Similarity NPD9606 Approved
0.6911 Remote Similarity NPD2824 Phase 2
0.6899 Remote Similarity NPD3695 Approved
0.6899 Remote Similarity NPD3696 Approved
0.6871 Remote Similarity NPD9607 Approved
0.6839 Remote Similarity NPD209 Clinical (unspecified phase)
0.6836 Remote Similarity NPD1046 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2903 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2902 Phase 2
0.6753 Remote Similarity NPD4495 Phase 1
0.6728 Remote Similarity NPD171 Discontinued
0.6667 Remote Similarity NPD545 Clinical (unspecified phase)
0.6612 Remote Similarity NPD1063 Phase 2
0.6599 Remote Similarity NPD9374 Approved
0.659 Remote Similarity NPD527 Clinical (unspecified phase)
0.6587 Remote Similarity NPD353 Discontinued
0.6585 Remote Similarity NPD1730 Discontinued
0.6575 Remote Similarity NPD9373 Approved
0.6564 Remote Similarity NPD4240 Approved
0.6561 Remote Similarity NPD547 Clinical (unspecified phase)
0.6536 Remote Similarity NPD9084 Phase 2
0.6533 Remote Similarity NPD307 Approved
0.6497 Remote Similarity NPD282 Approved
0.6478 Remote Similarity NPD1119 Phase 2
0.6407 Remote Similarity NPD775 Approved
0.6386 Remote Similarity NPD5080 Phase 2
0.6364 Remote Similarity NPD207 Discontinued
0.6364 Remote Similarity NPD2152 Clinical (unspecified phase)
0.6341 Remote Similarity NPD1430 Approved
0.6341 Remote Similarity NPD1431 Approved
0.6341 Remote Similarity NPD2253 Discontinued
0.6337 Remote Similarity NPD5079 Phase 2
0.6329 Remote Similarity NPD8829 Clinical (unspecified phase)
0.6312 Remote Similarity NPD1058 Discontinued
0.6312 Remote Similarity NPD9083 Clinical (unspecified phase)
0.6267 Remote Similarity NPD9584 Phase 2
0.6256 Remote Similarity NPD4459 Clinical (unspecified phase)
0.6256 Remote Similarity NPD4458 Phase 2
0.625 Remote Similarity NPD7531 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8836 Approved
0.6203 Remote Similarity NPD1127 Approved
0.6203 Remote Similarity NPD1128 Approved
0.6178 Remote Similarity NPD281 Approved
0.6169 Remote Similarity NPD9409 Discontinued
0.6168 Remote Similarity NPD6840 Approved
0.6159 Remote Similarity NPD1808 Phase 1
0.6159 Remote Similarity NPD799 Phase 1
0.6134 Remote Similarity NPD691 Discontinued
0.6098 Remote Similarity NPD6112 Approved
0.6084 Remote Similarity NPD1118 Discontinued
0.6081 Remote Similarity NPD9416 Phase 3
0.6081 Remote Similarity NPD9417 Phase 3
0.6074 Remote Similarity NPD9484 Clinical (unspecified phase)
0.6067 Remote Similarity NPD9375 Discontinued
0.6051 Remote Similarity NPD798 Discontinued
0.6037 Remote Similarity NPD1120 Approved
0.6037 Remote Similarity NPD1121 Approved
0.6037 Remote Similarity NPD535 Approved
0.5986 Remote Similarity NPD9626 Clinical (unspecified phase)
0.598 Remote Similarity NPD5486 Discontinued
0.5978 Remote Similarity NPD2593 Clinical (unspecified phase)
0.5945 Remote Similarity NPD7502 Clinical (unspecified phase)
0.5938 Remote Similarity NPD515 Phase 1
0.5917 Remote Similarity NPD1117 Clinical (unspecified phase)
0.5906 Remote Similarity NPD1816 Clinical (unspecified phase)
0.5893 Remote Similarity NPD8250 Phase 2
0.5891 Remote Similarity NPD5458 Discontinued
0.5886 Remote Similarity NPD8830 Phase 3
0.5871 Remote Similarity NPD8833 Approved
0.5871 Remote Similarity NPD8831 Approved
0.5844 Remote Similarity NPD9406 Approved
0.5829 Remote Similarity NPD7842 Phase 2
0.5813 Remote Similarity NPD78 Approved
0.5813 Remote Similarity NPD9544 Approved
0.5784 Remote Similarity NPD796 Phase 2
0.578 Remote Similarity NPD5627 Approved
0.5742 Remote Similarity NPD757 Phase 3
0.5732 Remote Similarity NPD9360 Approved
0.5714 Remote Similarity NPD5768 Phase 2
0.5708 Remote Similarity NPD537 Phase 2
0.5708 Remote Similarity NPD534 Phase 2
0.5698 Remote Similarity NPD9704 Approved
0.5672 Remote Similarity NPD5665 Clinical (unspecified phase)
0.5669 Remote Similarity NPD1368 Approved
0.5654 Remote Similarity NPD6381 Phase 2
0.565 Remote Similarity NPD3849 Clinical (unspecified phase)
0.5644 Remote Similarity NPD1775 Approved
0.5644 Remote Similarity NPD1085 Approved
0.5634 Remote Similarity NPD4555 Clinical (unspecified phase)
0.5633 Remote Similarity NPD237 Clinical (unspecified phase)
0.5629 Remote Similarity NPD9291 Approved
0.5625 Remote Similarity NPD2221 Clinical (unspecified phase)
0.5611 Remote Similarity NPD1017 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