Structure

Physi-Chem Properties

Molecular Weight:  254.02
Volume:  205.948
LogP:  -1.785
LogD:  -1.145
LogS:  -0.114
# Rotatable Bonds:  3
TPSA:  141.36
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.459
Synthetic Accessibility Score:  5.094
Fsp3:  0.571
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:  -6.065
MDCK Permeability:  0.00041643535951152444
Pgp-inhibitor:  0.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.881
20% Bioavailability (F20%):  0.277
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.541
Plasma Protein Binding (PPB):  12.01597785949707%
Volume Distribution (VD):  0.258
Pgp-substrate:  66.59494018554688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.02
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.604
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.102
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.006

ADMET: Excretion

Clearance (CL):  1.551
Half-life (T1/2):  0.881

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.654
Drug-inuced Liver Injury (DILI):  0.053
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.002
Maximum Recommended Daily Dose:  0.817
Skin Sensitization:  0.43
Carcinogencity:  0.122
Eye Corrosion:  0.018
Eye Irritation:  0.798
Respiratory Toxicity:  0.428

Download Data

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

  Natural Product: NPC316819

Natural Product ID:  NPC316819
Common Name*:   (3R,4S,5R)-4,5-Dihydroxy-3-Phosphonooxycyclohexene-1-Carboxylic Acid
IUPAC Name:   (3R,4S,5R)-4,5-dihydroxy-3-phosphonooxycyclohexene-1-carboxylic acid
Synonyms:  
Standard InCHIKey:  QYOJSKGCWNAKGW-PBXRRBTRSA-N
Standard InCHI:  InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m1/s1
SMILES:  O[C@H]1[C@H](O)CC(=C[C@H]1OP(=O)(O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL95193
PubChem CID:   121947
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000402] Organic phosphoric acids and derivatives
        • [CHEMONTID:0000408] Phosphate esters
          • [CHEMONTID:0003457] Alkyl phosphates
            • [CHEMONTID:0003458] Monoalkyl 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
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1016/0006-291X(79)91731-5]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1093/emboj/18.8.2021]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1091286]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[10977898]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1100617]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11745165]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11750815]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12369847]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12467448]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12805358]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. ChEBI[131529]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13610867]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13831814]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[14973046]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15031653]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15292242]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15610037]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1644759]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[16630633]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[170247]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[17765195]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[179975]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19026742]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19514719]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19561621]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21437340]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21988831]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22289691]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22855027]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23537328]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23676670]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[241475]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24206068]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24783849]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24831709]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24939187]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24966042]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24967680]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[2543976]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[25867074]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26195826]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26337258]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26670289]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26826371]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[29897754]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30302998]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[318639]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[3283102]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[398096]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4877125]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4879561]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4908789]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[5332408]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6102982]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6284709]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6338507]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7042909]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7601837]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[8852895]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[9470222]
NPO730 Escherichia coli Species Enterobacteriaceae 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
NPT3015 Individual Protein 5-enolpyruvylshikimate-3-phosphate synthase Escherichia coli K-12 Kd = 7000.0 nM PMID[501765]
NPT3015 Individual Protein 5-enolpyruvylshikimate-3-phosphate synthase Escherichia coli K-12 Kd = 7000.0 nM PMID[501766]
NPT3015 Individual Protein 5-enolpyruvylshikimate-3-phosphate synthase Escherichia coli K-12 Kd = 7000.0 nM PMID[501767]
NPT3015 Individual Protein 5-enolpyruvylshikimate-3-phosphate synthase Escherichia coli K-12 Kd = 8000.0 nM PMID[501768]

☑ 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 NPC316819 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
0.9103 High Similarity NPC47844
0.9103 High Similarity NPC141195
0.907 High Similarity NPC327620
0.7191 Intermediate Similarity NPC221510
0.7191 Intermediate Similarity NPC159714
0.7111 Intermediate Similarity NPC253364
0.7065 Intermediate Similarity NPC77971
0.7021 Intermediate Similarity NPC473715
0.6989 Remote Similarity NPC112685
0.6979 Remote Similarity NPC473321
0.6979 Remote Similarity NPC303230
0.6979 Remote Similarity NPC6099
0.6979 Remote Similarity NPC114345
0.697 Remote Similarity NPC20066
0.6957 Remote Similarity NPC469809
0.6951 Remote Similarity NPC472072
0.6947 Remote Similarity NPC280612
0.6947 Remote Similarity NPC477011
0.6915 Remote Similarity NPC178215
0.6907 Remote Similarity NPC11456
0.6907 Remote Similarity NPC273579
0.6907 Remote Similarity NPC288240
0.6907 Remote Similarity NPC162205
0.6907 Remote Similarity NPC295204
0.69 Remote Similarity NPC300584
0.6889 Remote Similarity NPC470947
0.6889 Remote Similarity NPC470945
0.6889 Remote Similarity NPC470946
0.6882 Remote Similarity NPC21469
0.6882 Remote Similarity NPC182383
0.6875 Remote Similarity NPC471399
0.6875 Remote Similarity NPC473619
0.686 Remote Similarity NPC325627
0.6842 Remote Similarity NPC40376
0.6842 Remote Similarity NPC89001
0.6842 Remote Similarity NPC20339
0.6842 Remote Similarity NPC48338
0.6842 Remote Similarity NPC21208
0.6842 Remote Similarity NPC233551
0.6842 Remote Similarity NPC280621
0.6809 Remote Similarity NPC103523
0.6809 Remote Similarity NPC47937
0.6809 Remote Similarity NPC134865
0.6804 Remote Similarity NPC142838
0.6804 Remote Similarity NPC327760
0.6774 Remote Similarity NPC474251
0.6771 Remote Similarity NPC477016
0.6771 Remote Similarity NPC139418
0.6771 Remote Similarity NPC477017
0.6768 Remote Similarity NPC36954
0.6768 Remote Similarity NPC471142
0.6739 Remote Similarity NPC47450
0.6735 Remote Similarity NPC475912
0.6702 Remote Similarity NPC82795
0.6702 Remote Similarity NPC473669
0.6702 Remote Similarity NPC473478
0.6702 Remote Similarity NPC283085
0.6702 Remote Similarity NPC477014
0.6702 Remote Similarity NPC231009
0.6702 Remote Similarity NPC477013
0.6702 Remote Similarity NPC107986
0.6702 Remote Similarity NPC286338
0.6702 Remote Similarity NPC473651
0.6702 Remote Similarity NPC110710
0.6702 Remote Similarity NPC103284
0.6702 Remote Similarity NPC1083
0.6702 Remote Similarity NPC223871
0.6702 Remote Similarity NPC132496
0.6702 Remote Similarity NPC66346
0.6701 Remote Similarity NPC473904
0.6701 Remote Similarity NPC265856
0.6701 Remote Similarity NPC239517
0.6701 Remote Similarity NPC166554
0.67 Remote Similarity NPC477921
0.6699 Remote Similarity NPC39996
0.6667 Remote Similarity NPC116543
0.6667 Remote Similarity NPC196227
0.6634 Remote Similarity NPC40812
0.6632 Remote Similarity NPC171174
0.6632 Remote Similarity NPC477015
0.6632 Remote Similarity NPC107717
0.6632 Remote Similarity NPC134885
0.6632 Remote Similarity NPC232555
0.6632 Remote Similarity NPC69082
0.6632 Remote Similarity NPC240695
0.6632 Remote Similarity NPC279267
0.6632 Remote Similarity NPC231096
0.6632 Remote Similarity NPC142117
0.6632 Remote Similarity NPC475581
0.6632 Remote Similarity NPC62118
0.6632 Remote Similarity NPC134807
0.6632 Remote Similarity NPC204686
0.6632 Remote Similarity NPC210218
0.6632 Remote Similarity NPC219498
0.6632 Remote Similarity NPC473687
0.6632 Remote Similarity NPC114694
0.6632 Remote Similarity NPC308412
0.663 Remote Similarity NPC297440
0.6628 Remote Similarity NPC202011
0.66 Remote Similarity NPC270013
0.66 Remote Similarity NPC14961
0.66 Remote Similarity NPC477922
0.6598 Remote Similarity NPC473504
0.6598 Remote Similarity NPC14901
0.6598 Remote Similarity NPC42598
0.6598 Remote Similarity NPC40066
0.6598 Remote Similarity NPC93794
0.6598 Remote Similarity NPC91067
0.6598 Remote Similarity NPC130359
0.6598 Remote Similarity NPC318963
0.6598 Remote Similarity NPC81778
0.6598 Remote Similarity NPC20621
0.6596 Remote Similarity NPC163093
0.6596 Remote Similarity NPC219966
0.6596 Remote Similarity NPC472326
0.6569 Remote Similarity NPC471144
0.6566 Remote Similarity NPC476300
0.6559 Remote Similarity NPC313677
0.6556 Remote Similarity NPC272267
0.6556 Remote Similarity NPC471061
0.6556 Remote Similarity NPC475711
0.6535 Remote Similarity NPC476315
0.6531 Remote Similarity NPC474232
0.6526 Remote Similarity NPC137033
0.6526 Remote Similarity NPC187529
0.6526 Remote Similarity NPC329838
0.6526 Remote Similarity NPC471567
0.6526 Remote Similarity NPC477018
0.6526 Remote Similarity NPC329615
0.6526 Remote Similarity NPC100921
0.6526 Remote Similarity NPC120398
0.65 Remote Similarity NPC470957
0.65 Remote Similarity NPC81386
0.65 Remote Similarity NPC57405
0.65 Remote Similarity NPC71589
0.65 Remote Similarity NPC474035
0.65 Remote Similarity NPC470958
0.65 Remote Similarity NPC303942
0.6495 Remote Similarity NPC169511
0.6495 Remote Similarity NPC475819
0.6495 Remote Similarity NPC320458
0.6495 Remote Similarity NPC133730
0.6495 Remote Similarity NPC136879
0.6495 Remote Similarity NPC234077
0.6495 Remote Similarity NPC81045
0.6495 Remote Similarity NPC261952
0.6495 Remote Similarity NPC172821
0.6495 Remote Similarity NPC472008
0.6495 Remote Similarity NPC61257
0.6495 Remote Similarity NPC287164
0.6495 Remote Similarity NPC320569
0.6495 Remote Similarity NPC202672
0.6495 Remote Similarity NPC151403
0.6495 Remote Similarity NPC473905
0.6495 Remote Similarity NPC39754
0.6495 Remote Similarity NPC191929
0.6495 Remote Similarity NPC171135
0.6495 Remote Similarity NPC100454
0.6495 Remote Similarity NPC274446
0.6495 Remote Similarity NPC242364
0.6489 Remote Similarity NPC315559
0.6489 Remote Similarity NPC169575
0.6489 Remote Similarity NPC40746
0.6484 Remote Similarity NPC317263
0.6476 Remote Similarity NPC469980
0.6476 Remote Similarity NPC118902
0.6476 Remote Similarity NPC104161
0.6471 Remote Similarity NPC26500
0.6471 Remote Similarity NPC99619
0.6465 Remote Similarity NPC30515
0.6465 Remote Similarity NPC116726
0.6465 Remote Similarity NPC184463
0.6458 Remote Similarity NPC309211
0.6458 Remote Similarity NPC164393
0.6458 Remote Similarity NPC469910
0.6458 Remote Similarity NPC477010
0.6452 Remote Similarity NPC24417
0.6437 Remote Similarity NPC107848
0.6429 Remote Similarity NPC323477
0.6429 Remote Similarity NPC206001
0.6429 Remote Similarity NPC295312
0.6429 Remote Similarity NPC473100
0.6429 Remote Similarity NPC218927
0.6429 Remote Similarity NPC474032
0.6421 Remote Similarity NPC472957
0.6421 Remote Similarity NPC472958
0.6421 Remote Similarity NPC243618
0.6421 Remote Similarity NPC70424
0.6421 Remote Similarity NPC156804
0.6413 Remote Similarity NPC246458
0.6413 Remote Similarity NPC180725
0.6408 Remote Similarity NPC83895
0.6408 Remote Similarity NPC308567
0.6408 Remote Similarity NPC473326
0.6408 Remote Similarity NPC255592
0.6408 Remote Similarity NPC187761
0.6408 Remote Similarity NPC261377
0.64 Remote Similarity NPC212486
0.64 Remote Similarity NPC179746
0.64 Remote Similarity NPC81419

  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 NPC316819 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
0.6531 Remote Similarity NPD6698 Approved
0.6531 Remote Similarity NPD46 Approved
0.6465 Remote Similarity NPD7983 Approved
0.6279 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5778 Approved
0.6238 Remote Similarity NPD5779 Approved
0.6196 Remote Similarity NPD4756 Discovery
0.5946 Remote Similarity NPD4730 Approved
0.5946 Remote Similarity NPD4729 Approved
0.5909 Remote Similarity NPD4768 Approved
0.5909 Remote Similarity NPD4767 Approved
0.5905 Remote Similarity NPD7839 Suspended
0.5882 Remote Similarity NPD7838 Discovery
0.5859 Remote Similarity NPD5363 Approved
0.5854 Remote Similarity NPD73 Approved
0.5841 Remote Similarity NPD5248 Approved
0.5841 Remote Similarity NPD5249 Phase 3
0.5841 Remote Similarity NPD5251 Approved
0.5841 Remote Similarity NPD5247 Approved
0.5841 Remote Similarity NPD5250 Approved
0.5816 Remote Similarity NPD6110 Phase 1
0.581 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5794 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4225 Approved
0.575 Remote Similarity NPD8515 Approved
0.575 Remote Similarity NPD8517 Approved
0.575 Remote Similarity NPD8513 Phase 3
0.575 Remote Similarity NPD8516 Approved
0.5747 Remote Similarity NPD3197 Phase 1
0.5714 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6371 Approved
0.57 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5688 Remote Similarity NPD5344 Discontinued
0.5664 Remote Similarity NPD6686 Approved
0.5657 Remote Similarity NPD7154 Phase 3
0.5644 Remote Similarity NPD5786 Approved
0.5632 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5631 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5631 Remote Similarity NPD6101 Approved
0.5625 Remote Similarity NPD4268 Approved
0.5625 Remote Similarity NPD4271 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