Structure

Physi-Chem Properties

Molecular Weight:  376.25
Volume:  381.599
LogP:  2.203
LogD:  2.636
LogS:  -2.397
# Rotatable Bonds:  6
TPSA:  119.61
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.455
Synthetic Accessibility Score:  4.642
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:  -5.223
MDCK Permeability:  9.903137834044173e-05
Pgp-inhibitor:  0.194
Pgp-substrate:  0.991
Human Intestinal Absorption (HIA):  0.325
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.509

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.12
Plasma Protein Binding (PPB):  76.13780975341797%
Volume Distribution (VD):  0.729
Pgp-substrate:  22.79745864868164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.008
CYP2C19-substrate:  0.772
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.099
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.149
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.143

ADMET: Excretion

Clearance (CL):  3.675
Half-life (T1/2):  0.765

ADMET: Toxicity

hERG Blockers:  0.057
Human Hepatotoxicity (H-HT):  0.262
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.127
Rat Oral Acute Toxicity:  0.016
Maximum Recommended Daily Dose:  0.074
Skin Sensitization:  0.605
Carcinogencity:  0.056
Eye Corrosion:  0.007
Eye Irritation:  0.207
Respiratory Toxicity:  0.164

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  Natural Product: NPC308489

Natural Product ID:  NPC308489
Common Name*:   Myrsinionoside D
IUPAC Name:   (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R)-4-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethylcyclohexyl]butan-2-yl]oxyoxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  IOICPLCBYINMDA-XEDNMXAHSA-N
Standard InCHI:  InChI=1S/C19H36O7/c1-10-7-12(21)8-19(3,4)13(10)6-5-11(2)25-18-17(24)16(23)15(22)14(9-20)26-18/h10-18,20-24H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,16+,17-,18-/m1/s1
SMILES:  C[C@@H]1C[C@@H](CC(C)(C)[C@H]1CC[C@@H](C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3608835
PubChem CID:   10384912
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001766] Fatty acyl glycosides
          • [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO19292 Myrsine seguinii Species Primulaceae Eukaryota n.a. twig n.a. PMID[12005065]
NPO19292 Myrsine seguinii Species Primulaceae Eukaryota n.a. leaf n.a. PMID[12005065]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. aerial part n.a. PMID[12943781]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12951446]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota stems Thailand n.a. PMID[14510595]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. PMID[14738381]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. Argentine n.a. PMID[14738381]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. PMID[21905650]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24697288]
NPO28765 Miliusa balansae Species Annonaceae Eukaryota leaves n.a. n.a. PMID[26238320]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota sclerotia n.a. n.a. PMID[9599285]
NPO28765 Miliusa balansae Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19292 Myrsine seguinii Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28765 Miliusa balansae Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16758 Satureja cuneifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15755 Thymbra spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13548 Chrozophora obliqua Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5269 Coleus garckeanus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11194 Bombus hortorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8499 Osmerus mordax Species Osmeridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5552 Solanum sisymbriifolium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14034 Salvia coulteri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11881 Adenopeltis colliguaya Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16175 Trichia floriformis Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9780 Merremia umbellata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13859 Senecio flavus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13230 Pedicularis condensata Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15858 Phoebe formosana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11599 Elaeagnus commutata Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28765 Miliusa balansae Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13710 Lyophyllum shimeji Species Lyophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16678 Flindersia brayleyana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3391 Jungermannia obovata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15272 Mascarenhasia arborescens Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15015 Meconopsis napaulensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12680 Perityle vaseyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5078 Turraeanthus mannii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12555 Aspergillus quadrilineatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19292 Myrsine seguinii Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16428 Millettia conraui Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15393 Eucalyptus flocktoniae Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13375 Palafoxia rosea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26017 Dalbergia stipulacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24732 Cereus weberi Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14218 Spodoptera littoralis Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15138 Rheum webbianum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16516 Centaurea seridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4935 Dinemasporium strigosum Species Chaetosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4267 Ceratocystis clavigera Species Ceratocystidaceae 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
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 82.0 % PMID[513633]

☑ 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 NPC308489 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
0.9444 High Similarity NPC272841
0.9178 High Similarity NPC177343
0.8831 High Similarity NPC241959
0.8732 High Similarity NPC471879
0.8718 High Similarity NPC474156
0.863 High Similarity NPC166250
0.8608 High Similarity NPC290612
0.85 High Similarity NPC471410
0.85 High Similarity NPC471411
0.8395 Intermediate Similarity NPC43912
0.8395 Intermediate Similarity NPC472396
0.8395 Intermediate Similarity NPC140446
0.831 Intermediate Similarity NPC477758
0.831 Intermediate Similarity NPC477761
0.831 Intermediate Similarity NPC477760
0.831 Intermediate Similarity NPC477759
0.831 Intermediate Similarity NPC477754
0.8293 Intermediate Similarity NPC281004
0.8272 Intermediate Similarity NPC268633
0.825 Intermediate Similarity NPC18953
0.8205 Intermediate Similarity NPC186588
0.8193 Intermediate Similarity NPC473472
0.8193 Intermediate Similarity NPC102725
0.8193 Intermediate Similarity NPC131466
0.8193 Intermediate Similarity NPC82955
0.8169 Intermediate Similarity NPC477756
0.8169 Intermediate Similarity NPC477752
0.8169 Intermediate Similarity NPC477751
0.8169 Intermediate Similarity NPC477764
0.8158 Intermediate Similarity NPC107963
0.8101 Intermediate Similarity NPC16090
0.8095 Intermediate Similarity NPC261990
0.8095 Intermediate Similarity NPC474249
0.8095 Intermediate Similarity NPC279329
0.8095 Intermediate Similarity NPC223143
0.8095 Intermediate Similarity NPC65550
0.8095 Intermediate Similarity NPC473542
0.8056 Intermediate Similarity NPC179823
0.8052 Intermediate Similarity NPC188793
0.8049 Intermediate Similarity NPC107603
0.8026 Intermediate Similarity NPC472950
0.8026 Intermediate Similarity NPC472952
0.8025 Intermediate Similarity NPC166279
0.8 Intermediate Similarity NPC476668
0.8 Intermediate Similarity NPC307167
0.8 Intermediate Similarity NPC204881
0.8 Intermediate Similarity NPC473637
0.8 Intermediate Similarity NPC36372
0.8 Intermediate Similarity NPC229801
0.8 Intermediate Similarity NPC5632
0.8 Intermediate Similarity NPC473830
0.8 Intermediate Similarity NPC210759
0.8 Intermediate Similarity NPC149966
0.8 Intermediate Similarity NPC293609
0.7976 Intermediate Similarity NPC20822
0.7952 Intermediate Similarity NPC62202
0.7952 Intermediate Similarity NPC45833
0.7952 Intermediate Similarity NPC110365
0.7952 Intermediate Similarity NPC213658
0.7949 Intermediate Similarity NPC477577
0.7907 Intermediate Similarity NPC473726
0.7907 Intermediate Similarity NPC297348
0.7907 Intermediate Similarity NPC177834
0.7907 Intermediate Similarity NPC325828
0.7907 Intermediate Similarity NPC171741
0.7907 Intermediate Similarity NPC477547
0.7907 Intermediate Similarity NPC172838
0.7907 Intermediate Similarity NPC277774
0.7907 Intermediate Similarity NPC311246
0.7907 Intermediate Similarity NPC470623
0.7907 Intermediate Similarity NPC144790
0.7907 Intermediate Similarity NPC48339
0.7907 Intermediate Similarity NPC167644
0.7907 Intermediate Similarity NPC477451
0.7907 Intermediate Similarity NPC141769
0.7907 Intermediate Similarity NPC323231
0.7907 Intermediate Similarity NPC476669
0.7907 Intermediate Similarity NPC149400
0.7907 Intermediate Similarity NPC234352
0.7907 Intermediate Similarity NPC137004
0.7907 Intermediate Similarity NPC224003
0.7907 Intermediate Similarity NPC249204
0.7907 Intermediate Similarity NPC250393
0.7907 Intermediate Similarity NPC88962
0.7907 Intermediate Similarity NPC18724
0.7901 Intermediate Similarity NPC474346
0.7901 Intermediate Similarity NPC474284
0.7901 Intermediate Similarity NPC474253
0.7901 Intermediate Similarity NPC475820
0.7901 Intermediate Similarity NPC213737
0.7895 Intermediate Similarity NPC31046
0.7895 Intermediate Similarity NPC200167
0.7895 Intermediate Similarity NPC209666
0.7895 Intermediate Similarity NPC53868
0.7857 Intermediate Similarity NPC470872
0.7831 Intermediate Similarity NPC471240
0.7816 Intermediate Similarity NPC312678
0.7816 Intermediate Similarity NPC309866
0.7816 Intermediate Similarity NPC175
0.7816 Intermediate Similarity NPC477927
0.7816 Intermediate Similarity NPC473774
0.7816 Intermediate Similarity NPC113500
0.7816 Intermediate Similarity NPC294686
0.7816 Intermediate Similarity NPC264101
0.7816 Intermediate Similarity NPC24960
0.7816 Intermediate Similarity NPC148593
0.7816 Intermediate Similarity NPC253268
0.7816 Intermediate Similarity NPC471464
0.7816 Intermediate Similarity NPC473851
0.7816 Intermediate Similarity NPC305160
0.7816 Intermediate Similarity NPC291203
0.7816 Intermediate Similarity NPC72817
0.7816 Intermediate Similarity NPC45959
0.7816 Intermediate Similarity NPC291547
0.7816 Intermediate Similarity NPC77717
0.7816 Intermediate Similarity NPC252253
0.7816 Intermediate Similarity NPC473503
0.7816 Intermediate Similarity NPC30687
0.7816 Intermediate Similarity NPC222731
0.7816 Intermediate Similarity NPC475436
0.7816 Intermediate Similarity NPC305418
0.7816 Intermediate Similarity NPC477224
0.7816 Intermediate Similarity NPC151214
0.7816 Intermediate Similarity NPC3538
0.7816 Intermediate Similarity NPC475325
0.7816 Intermediate Similarity NPC131693
0.7816 Intermediate Similarity NPC191915
0.7816 Intermediate Similarity NPC179859
0.7816 Intermediate Similarity NPC174024
0.7816 Intermediate Similarity NPC471373
0.7816 Intermediate Similarity NPC267238
0.7816 Intermediate Similarity NPC253611
0.7816 Intermediate Similarity NPC217205
0.7805 Intermediate Similarity NPC227260
0.7791 Intermediate Similarity NPC48463
0.7791 Intermediate Similarity NPC59006
0.7791 Intermediate Similarity NPC289361
0.7778 Intermediate Similarity NPC2096
0.7778 Intermediate Similarity NPC470611
0.7778 Intermediate Similarity NPC208912
0.775 Intermediate Similarity NPC471217
0.775 Intermediate Similarity NPC472951
0.775 Intermediate Similarity NPC471216
0.775 Intermediate Similarity NPC472943
0.7738 Intermediate Similarity NPC161928
0.7738 Intermediate Similarity NPC210658
0.7727 Intermediate Similarity NPC107962
0.7727 Intermediate Similarity NPC473067
0.7727 Intermediate Similarity NPC477494
0.7727 Intermediate Similarity NPC205129
0.7727 Intermediate Similarity NPC211354
0.7727 Intermediate Similarity NPC57964
0.7727 Intermediate Similarity NPC473610
0.7727 Intermediate Similarity NPC106701
0.7727 Intermediate Similarity NPC19400
0.7727 Intermediate Similarity NPC474399
0.7727 Intermediate Similarity NPC206003
0.7727 Intermediate Similarity NPC6295
0.7727 Intermediate Similarity NPC471429
0.7727 Intermediate Similarity NPC473064
0.7727 Intermediate Similarity NPC475351
0.7727 Intermediate Similarity NPC471424
0.7727 Intermediate Similarity NPC107188
0.7727 Intermediate Similarity NPC473065
0.7727 Intermediate Similarity NPC473727
0.7727 Intermediate Similarity NPC94582
0.7727 Intermediate Similarity NPC92196
0.7727 Intermediate Similarity NPC471425
0.7727 Intermediate Similarity NPC189575
0.7727 Intermediate Similarity NPC469710
0.7711 Intermediate Similarity NPC232044
0.7711 Intermediate Similarity NPC273290
0.7711 Intermediate Similarity NPC235402
0.7701 Intermediate Similarity NPC475307
0.7692 Intermediate Similarity NPC279575
0.7683 Intermediate Similarity NPC470070
0.7662 Intermediate Similarity NPC470151
0.7654 Intermediate Similarity NPC71541
0.7654 Intermediate Similarity NPC216941
0.7647 Intermediate Similarity NPC148424
0.7647 Intermediate Similarity NPC128475
0.764 Intermediate Similarity NPC128572
0.764 Intermediate Similarity NPC472989
0.764 Intermediate Similarity NPC287483
0.764 Intermediate Similarity NPC97700
0.764 Intermediate Similarity NPC195297
0.764 Intermediate Similarity NPC473287
0.764 Intermediate Similarity NPC470864
0.764 Intermediate Similarity NPC160426
0.764 Intermediate Similarity NPC116756
0.764 Intermediate Similarity NPC139271
0.764 Intermediate Similarity NPC30856
0.764 Intermediate Similarity NPC304011
0.764 Intermediate Similarity NPC142264
0.764 Intermediate Similarity NPC203434
0.764 Intermediate Similarity NPC470863
0.764 Intermediate Similarity NPC238796
0.764 Intermediate Similarity NPC84111
0.764 Intermediate Similarity NPC252056
0.764 Intermediate Similarity NPC90583

  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 NPC308489 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
0.7907 Intermediate Similarity NPD8171 Discontinued
0.7895 Intermediate Similarity NPD1810 Approved
0.7895 Intermediate Similarity NPD1811 Approved
0.7733 Intermediate Similarity NPD7532 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6928 Phase 2
0.75 Intermediate Similarity NPD2687 Approved
0.75 Intermediate Similarity NPD2254 Approved
0.75 Intermediate Similarity NPD2686 Approved
0.7397 Intermediate Similarity NPD371 Approved
0.7083 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3669 Approved
0.7059 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6812 Remote Similarity NPD2269 Approved
0.68 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6714 Remote Similarity NPD891 Phase 3
0.6714 Remote Similarity NPD890 Clinical (unspecified phase)
0.6714 Remote Similarity NPD888 Phase 3
0.6714 Remote Similarity NPD892 Phase 3
0.6714 Remote Similarity NPD893 Approved
0.6667 Remote Similarity NPD905 Approved
0.6667 Remote Similarity NPD904 Phase 3
0.6667 Remote Similarity NPD2267 Suspended
0.66 Remote Similarity NPD6412 Phase 2
0.6538 Remote Similarity NPD8133 Approved
0.6535 Remote Similarity NPD6686 Approved
0.6533 Remote Similarity NPD6123 Approved
0.6479 Remote Similarity NPD895 Approved
0.6479 Remote Similarity NPD889 Approved
0.6479 Remote Similarity NPD887 Approved
0.6479 Remote Similarity NPD894 Approved
0.6437 Remote Similarity NPD1779 Approved
0.6437 Remote Similarity NPD1780 Approved
0.6421 Remote Similarity NPD7991 Discontinued
0.6415 Remote Similarity NPD6940 Discontinued
0.6355 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7328 Approved
0.6296 Remote Similarity NPD7327 Approved
0.6279 Remote Similarity NPD6118 Approved
0.6279 Remote Similarity NPD6114 Approved
0.6279 Remote Similarity NPD6697 Approved
0.6279 Remote Similarity NPD6115 Approved
0.6239 Remote Similarity NPD7516 Approved
0.6182 Remote Similarity NPD8377 Approved
0.6182 Remote Similarity NPD8294 Approved
0.6176 Remote Similarity NPD9000 Phase 3
0.6176 Remote Similarity NPD8997 Approved
0.6176 Remote Similarity NPD8998 Phase 2
0.6176 Remote Similarity NPD8993 Phase 1
0.6176 Remote Similarity NPD8999 Phase 3
0.6164 Remote Similarity NPD7346 Approved
0.6163 Remote Similarity NPD6116 Phase 1
0.6126 Remote Similarity NPD8378 Approved
0.6126 Remote Similarity NPD8379 Approved
0.6126 Remote Similarity NPD8296 Approved
0.6126 Remote Similarity NPD8033 Approved
0.6126 Remote Similarity NPD8380 Approved
0.6126 Remote Similarity NPD8335 Approved
0.6058 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6058 Remote Similarity NPD8174 Phase 2
0.6047 Remote Similarity NPD6117 Approved
0.6024 Remote Similarity NPD4787 Phase 1
0.6022 Remote Similarity NPD7524 Approved
0.6018 Remote Similarity NPD8328 Phase 3
0.6 Remote Similarity NPD8966 Approved
0.6 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6 Remote Similarity NPD8965 Approved
0.5982 Remote Similarity NPD7503 Approved
0.5952 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5952 Remote Similarity NPD4808 Clinical (unspecified phase)
0.593 Remote Similarity NPD3703 Phase 2
0.5913 Remote Similarity NPD7507 Approved
0.5904 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5904 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8086 Approved
0.5882 Remote Similarity NPD8139 Approved
0.5882 Remote Similarity NPD8084 Approved
0.5882 Remote Similarity NPD8138 Approved
0.5882 Remote Similarity NPD8082 Approved
0.5882 Remote Similarity NPD8085 Approved
0.5882 Remote Similarity NPD8083 Approved
0.587 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5857 Remote Similarity NPD385 Approved
0.5857 Remote Similarity NPD384 Approved
0.5843 Remote Similarity NPD7645 Phase 2
0.5833 Remote Similarity NPD3168 Discontinued
0.5825 Remote Similarity NPD8276 Approved
0.5825 Remote Similarity NPD8275 Approved
0.5789 Remote Similarity NPD6370 Approved
0.5778 Remote Similarity NPD7525 Registered
0.5769 Remote Similarity NPD8081 Approved
0.5763 Remote Similarity NPD7319 Approved
0.5761 Remote Similarity NPD6695 Phase 3
0.575 Remote Similarity NPD847 Phase 1
0.5735 Remote Similarity NPD8788 Approved
0.5714 Remote Similarity NPD388 Approved
0.5714 Remote Similarity NPD386 Approved
0.5714 Remote Similarity NPD8393 Approved
0.5714 Remote Similarity NPD369 Approved
0.5701 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5698 Remote Similarity NPD3181 Approved
0.566 Remote Similarity NPD8140 Approved
0.566 Remote Similarity NPD8307 Discontinued
0.5647 Remote Similarity NPD4244 Approved
0.5647 Remote Similarity NPD4245 Approved
0.5631 Remote Similarity NPD5344 Discontinued
0.5619 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5619 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5614 Remote Similarity NPD6054 Approved
0.5614 Remote Similarity NPD6059 Approved
0.561 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5603 Remote Similarity NPD6067 Discontinued
0.56 Remote Similarity NPD9036 Phase 3
0.56 Remote Similarity NPD9035 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