Structure

Physi-Chem Properties

Molecular Weight:  859.48
Volume:  858.685
LogP:  0.481
LogD:  0.374
LogS:  -2.06
# Rotatable Bonds:  16
TPSA:  294.91
# H-Bond Aceptor:  20
# H-Bond Donor:  10
# Rings:  3
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.045
Synthetic Accessibility Score:  6.753
Fsp3:  0.659
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.697
MDCK Permeability:  6.483329343609512e-05
Pgp-inhibitor:  0.772
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.923
20% Bioavailability (F20%):  0.993
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  67.65140533447266%
Volume Distribution (VD):  0.379
Pgp-substrate:  34.19474411010742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.009
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.097
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.062
CYP3A4-inhibitor:  0.045
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  3.141
Half-life (T1/2):  0.585

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.758
Drug-inuced Liver Injury (DILI):  0.929
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.422
Maximum Recommended Daily Dose:  0.882
Skin Sensitization:  0.19
Carcinogencity:  0.029
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.059

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Similar NPs/Drugs  

  Natural Product: NPC138993

Natural Product ID:  NPC138993
Common Name*:   Verproside
IUPAC Name:   [(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 3,4-dihydroxybenzoate
Synonyms:   Verproside
Standard InCHIKey:  DBUOUVZMYWYRRI-YWEKDMGLSA-N
Standard InCHI:  InChI=1S/C22H26O13/c23-6-12-14(27)15(28)16(29)21(32-12)34-20-13-9(3-4-31-20)17(18-22(13,7-24)35-18)33-19(30)8-1-2-10(25)11(26)5-8/h1-5,9,12-18,20-21,23-29H,6-7H2/t9-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1
SMILES:  c1cc(c(cc1C(=O)O[C@H]1[C@@H]2C=CO[C@H]([C@@H]2[C@]2(CO)[C@H]1O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1082144
PubChem CID:   12000799
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:0002207] O-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
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(79)80020-5]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. Brazilian n.a. PMID[10328294]
NPO12175 Iostephane heterophylla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11473422]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[15568764]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota pericarp n.a. n.a. PMID[16038565]
NPO12653 Diacarnus levii Species Podospongiidae Eukaryota n.a. at a depth of -10 M off the coast of Papua New Guinea 1998-JUN PMID[17253866]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[17944538]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18166016]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20232858]
NPO30110 Veronica lavaudiana Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[21568305]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[22823026]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota leaves and stems Ha Long, Quang Ninh province, Vietnam 2014-Jul PMID[25769817]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[29792702]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. PMID[30892891]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. xylem n.a. Database[Article]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4129 Veronica persica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4129 Veronica persica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12047 Solanum unguiculatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9561 Preussia australis Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3432 Tovomita brasiliensis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4923 Ononis hircina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11397 Cladophora rupestris Species Cladophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11255 Veronica thomsonii Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12526 Veronica turrilliana Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13096 Lecidea kochiana Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7323 Lindera pipericarpa Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11491 Vellozia declinans Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12762 Elattostachys apetala Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4129 Veronica persica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10102 Pithecellobium albicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10553 Heterophyllaea pustulata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11674 Viburnum lantanoides Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9908 Adenium somalense Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2576 Eusideroxylon zwageri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1314 Goodenia strophiolata Species Goodeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9254 Scutellaria racemosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14776 Petrosia weinbergi Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5173 Antidesma pentandrum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO396 Ventilago goughii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14462 Jasonia tuberosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12175 Iostephane heterophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7648 Geigeria plumosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1790 Plectranthus comosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12653 Diacarnus levii Species Podospongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1455 Aspergillus caelatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9550 Eritrichium incanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13466 Atroxima afzeliana Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5908 Dianella tasmanica Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5311 Isertia haenkeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26737 Solanum mauritianum Species Solanaceae 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
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Activity = 107.1 % PMID[558513]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Activity = 88.3 % PMID[558513]

☑ 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 NPC138993 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
0.9679 High Similarity NPC130730
0.9679 High Similarity NPC301910
0.9536 High Similarity NPC194705
0.9487 High Similarity NPC206815
0.9487 High Similarity NPC476011
0.9338 High Similarity NPC478236
0.9236 High Similarity NPC474936
0.9226 High Similarity NPC475484
0.9221 High Similarity NPC229354
0.9211 High Similarity NPC478234
0.9205 High Similarity NPC18789
0.9182 High Similarity NPC109990
0.9161 High Similarity NPC478232
0.9119 High Similarity NPC145847
0.9108 High Similarity NPC187205
0.9091 High Similarity NPC158546
0.9091 High Similarity NPC289021
0.9013 High Similarity NPC473867
0.8974 High Similarity NPC229548
0.8974 High Similarity NPC89693
0.8974 High Similarity NPC478241
0.8957 High Similarity NPC21956
0.8951 High Similarity NPC282551
0.8931 High Similarity NPC179914
0.8924 High Similarity NPC475378
0.891 High Similarity NPC478235
0.8903 High Similarity NPC240592
0.8903 High Similarity NPC117346
0.8882 High Similarity NPC77922
0.8882 High Similarity NPC473281
0.8839 High Similarity NPC96599
0.8808 High Similarity NPC46644
0.875 High Similarity NPC49173
0.8735 High Similarity NPC470685
0.8726 High Similarity NPC478249
0.8726 High Similarity NPC269914
0.8688 High Similarity NPC478248
0.8671 High Similarity NPC203664
0.8662 High Similarity NPC147224
0.8659 High Similarity NPC180586
0.8642 High Similarity NPC478265
0.8634 High Similarity NPC104275
0.8634 High Similarity NPC226759
0.8634 High Similarity NPC4747
0.8625 High Similarity NPC156624
0.8625 High Similarity NPC172920
0.8608 High Similarity NPC475379
0.8608 High Similarity NPC140151
0.8599 High Similarity NPC92117
0.859 High Similarity NPC473149
0.8581 High Similarity NPC108455
0.8562 High Similarity NPC472127
0.8562 High Similarity NPC191046
0.8562 High Similarity NPC472128
0.8562 High Similarity NPC194095
0.8562 High Similarity NPC327032
0.8553 High Similarity NPC49597
0.8544 High Similarity NPC69367
0.8535 High Similarity NPC308178
0.8535 High Similarity NPC248257
0.8535 High Similarity NPC120621
0.8526 High Similarity NPC474234
0.8519 High Similarity NPC286919
0.8519 High Similarity NPC475663
0.8516 High Similarity NPC184464
0.8516 High Similarity NPC229036
0.8516 High Similarity NPC478240
0.8516 High Similarity NPC251062
0.8516 High Similarity NPC296659
0.8516 High Similarity NPC202391
0.8481 Intermediate Similarity NPC75945
0.8466 Intermediate Similarity NPC469384
0.8457 Intermediate Similarity NPC471405
0.8452 Intermediate Similarity NPC186296
0.8442 Intermediate Similarity NPC137501
0.8442 Intermediate Similarity NPC7518
0.8442 Intermediate Similarity NPC154262
0.8442 Intermediate Similarity NPC159387
0.8438 Intermediate Similarity NPC134905
0.8438 Intermediate Similarity NPC289438
0.8438 Intermediate Similarity NPC36130
0.8431 Intermediate Similarity NPC220936
0.8431 Intermediate Similarity NPC31745
0.8424 Intermediate Similarity NPC41009
0.8405 Intermediate Similarity NPC472860
0.8405 Intermediate Similarity NPC133984
0.8395 Intermediate Similarity NPC10205
0.8387 Intermediate Similarity NPC296643
0.8385 Intermediate Similarity NPC157898
0.8385 Intermediate Similarity NPC61152
0.8385 Intermediate Similarity NPC3746
0.8385 Intermediate Similarity NPC16024
0.8385 Intermediate Similarity NPC205037
0.8385 Intermediate Similarity NPC44260
0.8375 Intermediate Similarity NPC474620
0.8365 Intermediate Similarity NPC161955
0.8354 Intermediate Similarity NPC74319
0.8354 Intermediate Similarity NPC287872
0.8354 Intermediate Similarity NPC289811
0.8354 Intermediate Similarity NPC160780
0.8344 Intermediate Similarity NPC478266
0.8344 Intermediate Similarity NPC475528
0.8333 Intermediate Similarity NPC237872
0.8333 Intermediate Similarity NPC116104
0.8333 Intermediate Similarity NPC302286
0.8333 Intermediate Similarity NPC88754
0.8333 Intermediate Similarity NPC263397
0.8333 Intermediate Similarity NPC478250
0.8313 Intermediate Similarity NPC205054
0.8304 Intermediate Similarity NPC171706
0.8303 Intermediate Similarity NPC289346
0.8303 Intermediate Similarity NPC239966
0.8303 Intermediate Similarity NPC203020
0.8293 Intermediate Similarity NPC1913
0.8291 Intermediate Similarity NPC475539
0.8291 Intermediate Similarity NPC119773
0.8291 Intermediate Similarity NPC474268
0.8291 Intermediate Similarity NPC143246
0.8282 Intermediate Similarity NPC203757
0.828 Intermediate Similarity NPC226738
0.828 Intermediate Similarity NPC121573
0.828 Intermediate Similarity NPC22176
0.828 Intermediate Similarity NPC190587
0.8272 Intermediate Similarity NPC310661
0.8272 Intermediate Similarity NPC137813
0.8272 Intermediate Similarity NPC105827
0.8258 Intermediate Similarity NPC475299
0.8258 Intermediate Similarity NPC225036
0.8258 Intermediate Similarity NPC105525
0.8258 Intermediate Similarity NPC12218
0.8258 Intermediate Similarity NPC75763
0.8253 Intermediate Similarity NPC311803
0.8253 Intermediate Similarity NPC472859
0.8253 Intermediate Similarity NPC25389
0.825 Intermediate Similarity NPC478242
0.825 Intermediate Similarity NPC111785
0.8247 Intermediate Similarity NPC100558
0.8247 Intermediate Similarity NPC84789
0.8247 Intermediate Similarity NPC310252
0.8247 Intermediate Similarity NPC302583
0.8242 Intermediate Similarity NPC76211
0.8224 Intermediate Similarity NPC114116
0.8217 Intermediate Similarity NPC152796
0.8217 Intermediate Similarity NPC475213
0.8212 Intermediate Similarity NPC475824
0.8204 Intermediate Similarity NPC33298
0.8204 Intermediate Similarity NPC285108
0.8204 Intermediate Similarity NPC90905
0.8204 Intermediate Similarity NPC4013
0.8199 Intermediate Similarity NPC227980
0.8198 Intermediate Similarity NPC469438
0.8194 Intermediate Similarity NPC220942
0.8193 Intermediate Similarity NPC166277
0.8193 Intermediate Similarity NPC208676
0.8193 Intermediate Similarity NPC130489
0.8193 Intermediate Similarity NPC119125
0.8187 Intermediate Similarity NPC189631
0.8182 Intermediate Similarity NPC329997
0.8182 Intermediate Similarity NPC96194
0.8182 Intermediate Similarity NPC471345
0.8182 Intermediate Similarity NPC238419
0.8182 Intermediate Similarity NPC299855
0.8182 Intermediate Similarity NPC172419
0.8182 Intermediate Similarity NPC470572
0.8176 Intermediate Similarity NPC37838
0.8165 Intermediate Similarity NPC194938
0.8165 Intermediate Similarity NPC63304
0.816 Intermediate Similarity NPC44730
0.8158 Intermediate Similarity NPC473924
0.8155 Intermediate Similarity NPC100420
0.8144 Intermediate Similarity NPC477627
0.814 Intermediate Similarity NPC316539
0.8137 Intermediate Similarity NPC42464
0.8137 Intermediate Similarity NPC98809
0.8137 Intermediate Similarity NPC476394
0.8136 Intermediate Similarity NPC189704
0.8121 Intermediate Similarity NPC247629
0.8121 Intermediate Similarity NPC239019
0.8117 Intermediate Similarity NPC476870
0.8117 Intermediate Similarity NPC123988
0.8114 Intermediate Similarity NPC102367
0.8107 Intermediate Similarity NPC472130
0.8107 Intermediate Similarity NPC472131
0.8107 Intermediate Similarity NPC475738
0.8105 Intermediate Similarity NPC254398
0.8101 Intermediate Similarity NPC293154
0.8101 Intermediate Similarity NPC242756
0.8098 Intermediate Similarity NPC267091
0.8095 Intermediate Similarity NPC291957
0.8095 Intermediate Similarity NPC22324
0.8095 Intermediate Similarity NPC14030
0.8092 Intermediate Similarity NPC84482
0.8092 Intermediate Similarity NPC219677
0.8092 Intermediate Similarity NPC469354
0.8092 Intermediate Similarity NPC169645
0.8092 Intermediate Similarity NPC254819
0.809 Intermediate Similarity NPC476067
0.809 Intermediate Similarity NPC475121
0.8089 Intermediate Similarity NPC80098
0.8086 Intermediate Similarity NPC12006

  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 NPC138993 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
0.9379 High Similarity NPD7685 Pre-registration
0.7987 Intermediate Similarity NPD6190 Approved
0.7907 Intermediate Similarity NPD3818 Discontinued
0.7848 Intermediate Similarity NPD7266 Discontinued
0.7784 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD230 Phase 1
0.7753 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD7054 Approved
0.7614 Intermediate Similarity NPD7472 Approved
0.759 Intermediate Similarity NPD1653 Approved
0.7571 Intermediate Similarity NPD6797 Phase 2
0.7544 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD7251 Discontinued
0.7514 Intermediate Similarity NPD7074 Phase 3
0.7455 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD7199 Phase 2
0.7401 Intermediate Similarity NPD7228 Approved
0.7399 Intermediate Similarity NPD6234 Discontinued
0.7389 Intermediate Similarity NPD7808 Phase 3
0.7321 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD37 Approved
0.7283 Intermediate Similarity NPD4965 Approved
0.7283 Intermediate Similarity NPD4967 Phase 2
0.7283 Intermediate Similarity NPD4966 Approved
0.7278 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4628 Phase 3
0.7232 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD1934 Approved
0.7193 Intermediate Similarity NPD4380 Phase 2
0.7171 Intermediate Similarity NPD9545 Approved
0.7168 Intermediate Similarity NPD2801 Approved
0.7168 Intermediate Similarity NPD1465 Phase 2
0.7168 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD9269 Phase 2
0.7158 Intermediate Similarity NPD8313 Approved
0.7158 Intermediate Similarity NPD8312 Approved
0.7152 Intermediate Similarity NPD9494 Approved
0.7143 Intermediate Similarity NPD6559 Discontinued
0.7126 Intermediate Similarity NPD3817 Phase 2
0.7125 Intermediate Similarity NPD3764 Approved
0.7111 Intermediate Similarity NPD7799 Discontinued
0.7095 Intermediate Similarity NPD6166 Phase 2
0.7095 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3882 Suspended
0.7072 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD5844 Phase 1
0.7059 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6653 Approved
0.7041 Intermediate Similarity NPD1511 Approved
0.7022 Intermediate Similarity NPD8127 Discontinued
0.7017 Intermediate Similarity NPD3751 Discontinued
0.6994 Remote Similarity NPD7028 Phase 2
0.6983 Remote Similarity NPD6232 Discontinued
0.6971 Remote Similarity NPD8455 Phase 2
0.6961 Remote Similarity NPD7473 Discontinued
0.6959 Remote Similarity NPD1512 Approved
0.6959 Remote Similarity NPD6273 Approved
0.6957 Remote Similarity NPD7240 Approved
0.6949 Remote Similarity NPD7075 Discontinued
0.6946 Remote Similarity NPD970 Clinical (unspecified phase)
0.6932 Remote Similarity NPD5402 Approved
0.6932 Remote Similarity NPD5353 Approved
0.6903 Remote Similarity NPD9268 Approved
0.6901 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3787 Discontinued
0.6881 Remote Similarity NPD7930 Approved
0.6872 Remote Similarity NPD5494 Approved
0.6864 Remote Similarity NPD8166 Discontinued
0.6864 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6862 Remote Similarity NPD8150 Discontinued
0.6839 Remote Similarity NPD3455 Phase 2
0.6839 Remote Similarity NPD7458 Discontinued
0.6829 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7999 Approved
0.6818 Remote Similarity NPD6801 Discontinued
0.6802 Remote Similarity NPD7435 Discontinued
0.6788 Remote Similarity NPD447 Suspended
0.6786 Remote Similarity NPD6002 Phase 3
0.6786 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6005 Phase 3
0.6786 Remote Similarity NPD6004 Phase 3
0.6784 Remote Similarity NPD7236 Approved
0.678 Remote Similarity NPD7096 Clinical (unspecified phase)
0.678 Remote Similarity NPD5760 Phase 2
0.678 Remote Similarity NPD7819 Suspended
0.678 Remote Similarity NPD5761 Phase 2
0.6772 Remote Similarity NPD8434 Phase 2
0.677 Remote Similarity NPD5647 Approved
0.6768 Remote Similarity NPD8320 Phase 1
0.6768 Remote Similarity NPD8319 Approved
0.6761 Remote Similarity NPD6386 Approved
0.6761 Remote Similarity NPD6385 Approved
0.6736 Remote Similarity NPD6535 Approved
0.6736 Remote Similarity NPD6534 Approved
0.6735 Remote Similarity NPD6777 Approved
0.6735 Remote Similarity NPD6778 Approved
0.6735 Remote Similarity NPD6779 Approved
0.6735 Remote Similarity NPD6776 Approved
0.6735 Remote Similarity NPD6780 Approved
0.6735 Remote Similarity NPD6782 Approved
0.6735 Remote Similarity NPD6781 Approved
0.6727 Remote Similarity NPD943 Approved
0.6724 Remote Similarity NPD5403 Approved
0.6717 Remote Similarity NPD7497 Discontinued
0.6706 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6705 Remote Similarity NPD2533 Approved
0.6705 Remote Similarity NPD2534 Approved
0.6705 Remote Similarity NPD2532 Approved
0.6687 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6687 Remote Similarity NPD1933 Approved
0.6686 Remote Similarity NPD7239 Suspended
0.6684 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1091 Approved
0.6667 Remote Similarity NPD6663 Approved
0.6667 Remote Similarity NPD651 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3750 Approved
0.6667 Remote Similarity NPD7033 Discontinued
0.6667 Remote Similarity NPD4110 Phase 3
0.6667 Remote Similarity NPD1510 Phase 2
0.6647 Remote Similarity NPD6799 Approved
0.6647 Remote Similarity NPD1549 Phase 2
0.6646 Remote Similarity NPD3027 Phase 3
0.6634 Remote Similarity NPD8151 Discontinued
0.6633 Remote Similarity NPD7680 Approved
0.6633 Remote Similarity NPD7700 Phase 2
0.6633 Remote Similarity NPD7699 Phase 2
0.6627 Remote Similarity NPD2935 Discontinued
0.6627 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6627 Remote Similarity NPD1613 Approved
0.6627 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6627 Remote Similarity NPD3620 Phase 2
0.6626 Remote Similarity NPD5736 Approved
0.6609 Remote Similarity NPD5401 Approved
0.6605 Remote Similarity NPD3094 Phase 2
0.6601 Remote Similarity NPD7874 Approved
0.6601 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6765 Approved
0.6596 Remote Similarity NPD6764 Approved
0.6588 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5762 Approved
0.6588 Remote Similarity NPD5763 Approved
0.6588 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6587 Remote Similarity NPD6355 Discontinued
0.6579 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6576 Remote Similarity NPD5242 Approved
0.6575 Remote Similarity NPD3749 Approved
0.6573 Remote Similarity NPD7411 Suspended
0.657 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6569 Remote Similarity NPD7783 Phase 2
0.6569 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6562 Remote Similarity NPD3705 Approved
0.6556 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6556 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6554 Remote Similarity NPD5808 Clinical (unspecified phase)
0.655 Remote Similarity NPD7696 Phase 3
0.655 Remote Similarity NPD7698 Approved
0.655 Remote Similarity NPD7697 Approved
0.654 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6524 Remote Similarity NPD2861 Phase 2
0.6524 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6522 Remote Similarity NPD1608 Approved
0.6517 Remote Similarity NPD7871 Phase 2
0.6517 Remote Similarity NPD7870 Phase 2
0.6517 Remote Similarity NPD6599 Discontinued
0.6514 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6514 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6514 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6513 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6513 Remote Similarity NPD6213 Phase 3
0.6513 Remote Similarity NPD6212 Phase 3
0.6512 Remote Similarity NPD6674 Discontinued
0.6509 Remote Similarity NPD7097 Phase 1
0.6509 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6508 Remote Similarity NPD7038 Approved
0.6508 Remote Similarity NPD7039 Approved
0.6503 Remote Similarity NPD6362 Approved
0.6502 Remote Similarity NPD7701 Phase 2
0.6502 Remote Similarity NPD7585 Approved
0.65 Remote Similarity NPD6823 Phase 2
0.6488 Remote Similarity NPD7801 Approved
0.6478 Remote Similarity NPD1357 Approved
0.6467 Remote Similarity NPD6233 Phase 2
0.6464 Remote Similarity NPD5977 Approved
0.6464 Remote Similarity NPD5978 Approved
0.6461 Remote Similarity NPD3226 Approved
0.6458 Remote Similarity NPD6785 Approved
0.6458 Remote Similarity NPD6784 Approved
0.6453 Remote Similarity NPD7583 Approved
0.6452 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6448 Remote Similarity NPD919 Approved
0.6446 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6433 Remote Similarity NPD1551 Phase 2
0.6433 Remote Similarity NPD2796 Approved
0.6429 Remote Similarity NPD7057 Phase 3

  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