Structure

Physi-Chem Properties

Molecular Weight:  194.08
Volume:  173.813
LogP:  -1.801
LogD:  -1.733
LogS:  0.065
# Rotatable Bonds:  3
TPSA:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.394
Synthetic Accessibility Score:  4.063
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.467
MDCK Permeability:  0.0010510783176869154
Pgp-inhibitor:  0.002
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.802
20% Bioavailability (F20%):  0.083
30% Bioavailability (F30%):  0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.302
Plasma Protein Binding (PPB):  15.230670928955078%
Volume Distribution (VD):  0.456
Pgp-substrate:  81.65988159179688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.491
CYP2C19-inhibitor:  0.008
CYP2C19-substrate:  0.515
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.036
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.134
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.08

ADMET: Excretion

Clearance (CL):  4.116
Half-life (T1/2):  0.834

ADMET: Toxicity

hERG Blockers:  0.142
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.168
Rat Oral Acute Toxicity:  0.005
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.326
Carcinogencity:  0.046
Eye Corrosion:  0.005
Eye Irritation:  0.758
Respiratory Toxicity:  0.015

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC230789

Natural Product ID:  NPC230789
Common Name*:   Methyl Beta-D-Fructofuranoside
IUPAC Name:   (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)-2-methoxyoxolane-3,4-diol
Synonyms:   Methyl Beta-D-Fructofuranoside
Standard InCHIKey:  JPHVNZOOBXUCDJ-MVIOUDGNSA-N
Standard InCHI:  InChI=1S/C7H14O6/c1-12-7(3-9)6(11)5(10)4(2-8)13-7/h4-6,8-11H,2-3H2,1H3/t4-,5-,6+,7-/m1/s1
SMILES:  OC[C@H]1O[C@]([C@H]([C@@H]1O)O)(OC)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500884
PubChem CID:   128889
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[15678383]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[16045947]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17711344]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. PMID[19025748]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[19245240]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[20188156]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[22351977]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. Malaysian n.a. PMID[7506311]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10385 Ptelea trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10385 Ptelea trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10385 Ptelea trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6766 Antiphiona pinnatisecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2495 Agave xylonacantha Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9567 Enicosanthum cupulare Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2012 Turnera diffusa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10385 Ptelea trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10991 Maackia tashiroi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9136 Pseudocyclosorus subochthodes Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19826 Helicoverpa armigera Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26103 Streptomyces bobili 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
NPT1 Others Radical scavenging activity IC50 > 30000.0 nM PMID[489540]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 30000.0 nM PMID[489540]

☑ 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 NPC230789 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 NPC252918
0.9556 High Similarity NPC82512
0.9302 High Similarity NPC29721
0.8936 High Similarity NPC323574
0.8723 High Similarity NPC42503
0.8723 High Similarity NPC299781
0.8723 High Similarity NPC157193
0.8723 High Similarity NPC282143
0.8511 High Similarity NPC14144
0.8444 Intermediate Similarity NPC70756
0.8444 Intermediate Similarity NPC320240
0.84 Intermediate Similarity NPC130683
0.84 Intermediate Similarity NPC323361
0.8367 Intermediate Similarity NPC124963
0.8367 Intermediate Similarity NPC23134
0.8367 Intermediate Similarity NPC233726
0.8298 Intermediate Similarity NPC277475
0.8298 Intermediate Similarity NPC321087
0.8222 Intermediate Similarity NPC320189
0.8113 Intermediate Similarity NPC219040
0.8085 Intermediate Similarity NPC289758
0.8085 Intermediate Similarity NPC73906
0.8085 Intermediate Similarity NPC255377
0.8085 Intermediate Similarity NPC285364
0.8085 Intermediate Similarity NPC199857
0.8085 Intermediate Similarity NPC165846
0.8085 Intermediate Similarity NPC21209
0.8085 Intermediate Similarity NPC92246
0.8085 Intermediate Similarity NPC176017
0.8085 Intermediate Similarity NPC69445
0.8 Intermediate Similarity NPC329095
0.8 Intermediate Similarity NPC326533
0.7885 Intermediate Similarity NPC303727
0.7843 Intermediate Similarity NPC103672
0.7843 Intermediate Similarity NPC320043
0.7778 Intermediate Similarity NPC266553
0.7692 Intermediate Similarity NPC58629
0.7692 Intermediate Similarity NPC246558
0.7692 Intermediate Similarity NPC145112
0.7692 Intermediate Similarity NPC67660
0.7692 Intermediate Similarity NPC165198
0.7692 Intermediate Similarity NPC89145
0.7692 Intermediate Similarity NPC242073
0.7692 Intermediate Similarity NPC157514
0.7692 Intermediate Similarity NPC269166
0.7692 Intermediate Similarity NPC107914
0.7679 Intermediate Similarity NPC472026
0.7674 Intermediate Similarity NPC313405
0.7636 Intermediate Similarity NPC290179
0.7636 Intermediate Similarity NPC34877
0.7593 Intermediate Similarity NPC148424
0.75 Intermediate Similarity NPC107091
0.75 Intermediate Similarity NPC207656
0.7455 Intermediate Similarity NPC472025
0.7447 Intermediate Similarity NPC291502
0.7447 Intermediate Similarity NPC317182
0.7447 Intermediate Similarity NPC134252
0.7447 Intermediate Similarity NPC213159
0.7447 Intermediate Similarity NPC86191
0.7447 Intermediate Similarity NPC298699
0.7442 Intermediate Similarity NPC86412
0.7442 Intermediate Similarity NPC192065
0.7442 Intermediate Similarity NPC325034
0.7442 Intermediate Similarity NPC293908
0.7442 Intermediate Similarity NPC66052
0.74 Intermediate Similarity NPC112363
0.7321 Intermediate Similarity NPC320032
0.7321 Intermediate Similarity NPC322855
0.7209 Intermediate Similarity NPC227267
0.72 Intermediate Similarity NPC88638
0.7193 Intermediate Similarity NPC143326
0.7119 Intermediate Similarity NPC268243
0.7115 Intermediate Similarity NPC329128
0.7115 Intermediate Similarity NPC322158
0.7069 Intermediate Similarity NPC477762
0.7069 Intermediate Similarity NPC477750
0.7069 Intermediate Similarity NPC477755
0.7069 Intermediate Similarity NPC477753
0.7069 Intermediate Similarity NPC155457
0.7069 Intermediate Similarity NPC477757
0.7069 Intermediate Similarity NPC477763
0.7037 Intermediate Similarity NPC317501
0.7037 Intermediate Similarity NPC314821
0.7037 Intermediate Similarity NPC317626
0.7018 Intermediate Similarity NPC317023
0.6833 Remote Similarity NPC325773
0.6833 Remote Similarity NPC277570
0.6786 Remote Similarity NPC326557
0.6744 Remote Similarity NPC149070
0.6744 Remote Similarity NPC127074
0.6744 Remote Similarity NPC187058
0.6744 Remote Similarity NPC182541
0.6744 Remote Similarity NPC197207
0.6721 Remote Similarity NPC294813
0.6721 Remote Similarity NPC31496
0.6721 Remote Similarity NPC13143
0.6667 Remote Similarity NPC227707
0.6667 Remote Similarity NPC111882
0.6667 Remote Similarity NPC88278
0.6667 Remote Similarity NPC102981
0.6667 Remote Similarity NPC99573
0.6613 Remote Similarity NPC76881
0.6613 Remote Similarity NPC190418
0.6613 Remote Similarity NPC471761
0.6613 Remote Similarity NPC471760
0.6613 Remote Similarity NPC147292
0.6613 Remote Similarity NPC12040
0.6552 Remote Similarity NPC293692
0.6515 Remote Similarity NPC185419
0.6515 Remote Similarity NPC184550
0.6508 Remote Similarity NPC477756
0.6508 Remote Similarity NPC477764
0.6508 Remote Similarity NPC477751
0.6508 Remote Similarity NPC477752
0.6452 Remote Similarity NPC6848
0.6418 Remote Similarity NPC291228
0.6418 Remote Similarity NPC308096
0.6406 Remote Similarity NPC477754
0.6406 Remote Similarity NPC477760
0.6406 Remote Similarity NPC477759
0.6406 Remote Similarity NPC477758
0.6406 Remote Similarity NPC206601
0.6406 Remote Similarity NPC477761
0.6324 Remote Similarity NPC138273
0.6308 Remote Similarity NPC250619
0.6308 Remote Similarity NPC97736
0.6308 Remote Similarity NPC67099
0.6308 Remote Similarity NPC50228
0.6296 Remote Similarity NPC46254
0.6271 Remote Similarity NPC322148
0.6212 Remote Similarity NPC241265
0.6212 Remote Similarity NPC211428
0.6212 Remote Similarity NPC285003
0.619 Remote Similarity NPC476702
0.6176 Remote Similarity NPC248427
0.6154 Remote Similarity NPC32148
0.6154 Remote Similarity NPC85078
0.6154 Remote Similarity NPC62014
0.6154 Remote Similarity NPC179823
0.6119 Remote Similarity NPC53760
0.6119 Remote Similarity NPC474078
0.6119 Remote Similarity NPC52268
0.6047 Remote Similarity NPC301586
0.6047 Remote Similarity NPC33415
0.6034 Remote Similarity NPC289979
0.6032 Remote Similarity NPC317651
0.6032 Remote Similarity NPC258690
0.6 Remote Similarity NPC220922
0.5942 Remote Similarity NPC225748
0.5942 Remote Similarity NPC9763
0.5942 Remote Similarity NPC206823
0.5942 Remote Similarity NPC470659
0.5942 Remote Similarity NPC39266
0.5942 Remote Similarity NPC163812
0.5942 Remote Similarity NPC169085
0.5942 Remote Similarity NPC470660
0.5926 Remote Similarity NPC8597
0.5926 Remote Similarity NPC314613
0.5915 Remote Similarity NPC279575
0.5902 Remote Similarity NPC476209
0.5902 Remote Similarity NPC182903
0.5882 Remote Similarity NPC471879
0.5873 Remote Similarity NPC172622
0.5857 Remote Similarity NPC472173
0.5857 Remote Similarity NPC472174
0.5857 Remote Similarity NPC166250
0.5857 Remote Similarity NPC308489
0.5846 Remote Similarity NPC250836
0.5833 Remote Similarity NPC188793
0.5821 Remote Similarity NPC473294
0.5821 Remote Similarity NPC471472
0.5818 Remote Similarity NPC247546
0.5818 Remote Similarity NPC172086
0.5814 Remote Similarity NPC272307
0.5814 Remote Similarity NPC320326
0.5806 Remote Similarity NPC174485
0.5763 Remote Similarity NPC469937
0.5763 Remote Similarity NPC23155
0.5763 Remote Similarity NPC320588
0.5763 Remote Similarity NPC53463
0.5758 Remote Similarity NPC322801
0.5758 Remote Similarity NPC291650
0.5758 Remote Similarity NPC129100
0.5735 Remote Similarity NPC223174
0.5735 Remote Similarity NPC327753
0.5735 Remote Similarity NPC327486
0.5714 Remote Similarity NPC325822
0.5714 Remote Similarity NPC55652
0.5714 Remote Similarity NPC61270
0.5714 Remote Similarity NPC132938
0.5694 Remote Similarity NPC477350
0.5694 Remote Similarity NPC229655
0.5694 Remote Similarity NPC326661
0.569 Remote Similarity NPC277878
0.5686 Remote Similarity NPC152008
0.5676 Remote Similarity NPC83248
0.5676 Remote Similarity NPC100204
0.5676 Remote Similarity NPC170595
0.5616 Remote Similarity NPC476782
0.5616 Remote Similarity NPC476783

  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 NPC230789 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
0.9302 High Similarity NPD9006 Approved
0.84 Intermediate Similarity NPD895 Approved
0.84 Intermediate Similarity NPD887 Approved
0.84 Intermediate Similarity NPD894 Approved
0.84 Intermediate Similarity NPD889 Approved
0.8269 Intermediate Similarity NPD2267 Suspended
0.8222 Intermediate Similarity NPD8957 Approved
0.8085 Intermediate Similarity NPD9000 Phase 3
0.8085 Intermediate Similarity NPD8998 Phase 2
0.8085 Intermediate Similarity NPD8993 Phase 1
0.8085 Intermediate Similarity NPD8999 Phase 3
0.8085 Intermediate Similarity NPD8997 Approved
0.8 Intermediate Similarity NPD905 Approved
0.8 Intermediate Similarity NPD904 Phase 3
0.7843 Intermediate Similarity NPD9050 Approved
0.7843 Intermediate Similarity NPD9049 Discontinued
0.7755 Intermediate Similarity NPD8965 Approved
0.7755 Intermediate Similarity NPD8966 Approved
0.7692 Intermediate Similarity NPD888 Phase 3
0.7692 Intermediate Similarity NPD893 Approved
0.7692 Intermediate Similarity NPD891 Phase 3
0.7692 Intermediate Similarity NPD890 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD892 Phase 3
0.75 Intermediate Similarity NPD9219 Approved
0.75 Intermediate Similarity NPD2269 Approved
0.75 Intermediate Similarity NPD9218 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD8958 Phase 2
0.7447 Intermediate Similarity NPD8788 Approved
0.7442 Intermediate Similarity NPD9053 Approved
0.7442 Intermediate Similarity NPD9051 Approved
0.7442 Intermediate Similarity NPD9052 Approved
0.74 Intermediate Similarity NPD9139 Approved
0.7288 Intermediate Similarity NPD1457 Discontinued
0.7119 Intermediate Similarity NPD847 Phase 1
0.7037 Intermediate Similarity NPD9036 Phase 3
0.7037 Intermediate Similarity NPD9035 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8994 Approved
0.6875 Remote Similarity NPD8967 Approved
0.6786 Remote Similarity NPD885 Approved
0.6786 Remote Similarity NPD884 Clinical (unspecified phase)
0.678 Remote Similarity NPD6123 Approved
0.6744 Remote Similarity NPD8814 Phase 3
0.6667 Remote Similarity NPD8995 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8996 Phase 3
0.6316 Remote Similarity NPD7346 Approved
0.6271 Remote Similarity NPD369 Approved
0.6154 Remote Similarity NPD9110 Approved
0.6154 Remote Similarity NPD896 Approved
0.6154 Remote Similarity NPD898 Approved
0.6154 Remote Similarity NPD897 Approved
0.6119 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6047 Remote Similarity NPD8549 Clinical (unspecified phase)
0.6032 Remote Similarity NPD8961 Approved
0.6 Remote Similarity NPD8959 Approved
0.5918 Remote Similarity NPD8976 Approved
0.5918 Remote Similarity NPD8977 Phase 3
0.5818 Remote Similarity NPD9005 Phase 3
0.5818 Remote Similarity NPD9003 Clinical (unspecified phase)
0.5818 Remote Similarity NPD9004 Approved
0.5789 Remote Similarity NPD1400 Approved
0.5789 Remote Similarity NPD1399 Approved
0.5763 Remote Similarity NPD3728 Approved
0.5763 Remote Similarity NPD3730 Approved
0.5758 Remote Similarity NPD9030 Approved
0.5758 Remote Similarity NPD9031 Approved
0.5758 Remote Similarity NPD9032 Approved
0.5758 Remote Similarity NPD9033 Approved
0.5735 Remote Similarity NPD9445 Approved
0.5714 Remote Similarity NPD9061 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3181 Approved
0.569 Remote Similarity NPD66 Approved
0.569 Remote Similarity NPD9007 Approved
0.569 Remote Similarity NPD9008 Approved
0.569 Remote Similarity NPD9011 Approved
0.569 Remote Similarity NPD65 Approved
0.569 Remote Similarity NPD64 Approved
0.569 Remote Similarity NPD72 Approved
0.569 Remote Similarity NPD9009 Approved
0.569 Remote Similarity NPD9010 Approved
0.569 Remote Similarity NPD8960 Approved
0.5686 Remote Similarity NPD7536 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