Structure

Physi-Chem Properties

Molecular Weight:  476.13
Volume:  447.739
LogP:  1.463
LogD:  1.118
LogS:  -2.655
# Rotatable Bonds:  6
TPSA:  175.37
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.203
Synthetic Accessibility Score:  4.302
Fsp3:  0.348
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.308
MDCK Permeability:  7.1298009061138146e-06
Pgp-inhibitor:  0.005
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.767
20% Bioavailability (F20%):  0.987
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.063
Plasma Protein Binding (PPB):  95.9780044555664%
Volume Distribution (VD):  0.498
Pgp-substrate:  5.484654903411865%

ADMET: Metabolism

CYP1A2-inhibitor:  0.101
CYP1A2-substrate:  0.041
CYP2C19-inhibitor:  0.143
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.541
CYP2C9-substrate:  0.294
CYP2D6-inhibitor:  0.258
CYP2D6-substrate:  0.202
CYP3A4-inhibitor:  0.177
CYP3A4-substrate:  0.129

ADMET: Excretion

Clearance (CL):  12.017
Half-life (T1/2):  0.927

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.073
Drug-inuced Liver Injury (DILI):  0.094
AMES Toxicity:  0.759
Rat Oral Acute Toxicity:  0.629
Maximum Recommended Daily Dose:  0.102
Skin Sensitization:  0.973
Carcinogencity:  0.346
Eye Corrosion:  0.004
Eye Irritation:  0.912
Respiratory Toxicity:  0.039

Download Data

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  Natural Product: NPC78363

Natural Product ID:  NPC78363
Common Name*:   Plantasioside
IUPAC Name:   [(2S,4aR,6R,7S,8S,8aR)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-6-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   Plantasioside
Standard InCHIKey:  PAPHRQZMDUSBBD-CILOSVJESA-N
Standard InCHI:  InChI=1S/C23H24O11/c24-13-4-1-11(7-15(13)26)2-6-19(28)31-10-18-20(29)21(30)22-23(34-18)32-9-17(33-22)12-3-5-14(25)16(27)8-12/h1-8,17-18,20-27,29-30H,9-10H2/b6-2+/t17-,18-,20-,21+,22-,23-/m1/s1
SMILES:  c1cc(c(cc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]2[C@H](OC[C@H](c3ccc(c(c3)O)O)O2)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL228185
PubChem CID:   44423103
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11858748]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1367520]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15974609]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota stem bark n.a. n.a. PMID[17461599]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[19093848]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota n.a. stem n.a. PMID[20961093]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota Stem bark Lu Mountain, Jiangxi Province, China 2004-AUG PMID[20961093]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21381678]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22118684]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[24840014]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26692349]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26697686]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[31180680]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33089690]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8626236]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15718 Lindera sericea Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11243 Exochorda giraldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13460 Asphodeline damascena Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2667 Acacia lasiopetala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29322 Rhodanthe maryonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27134 Euphrasia rubra Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8556 Eucalyptus kitsoniana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21851 Chaetomella raphigera Species Chaetomellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10527 Cyathula tomentosa Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15621 Lethasterias fusca Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26381 Bombus pascuorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15513 Pseudocyphellaria rubella Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13225 Spergula japonica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22101 Himantoglossum hircinum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15806 Rhododendron campylocarpum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO255 Solanum pseudopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26951 Gymnopus androsaceus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1777 Toddalia aculeata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9299.3 Hordeum vulgare var. distichon Varieties Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28240 0tholaena lemmonii Species Pteridaceae 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
NPT180 Cell Line HCT-8 Homo sapiens IC50 = 3400.0 nM PMID[547472]

☑ 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 NPC78363 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
0.9847 High Similarity NPC260425
0.9774 High Similarity NPC476385
0.9774 High Similarity NPC134405
0.9773 High Similarity NPC476383
0.9773 High Similarity NPC89105
0.9773 High Similarity NPC81515
0.9773 High Similarity NPC197316
0.9773 High Similarity NPC68092
0.9773 High Similarity NPC64141
0.9773 High Similarity NPC205195
0.9773 High Similarity NPC472350
0.9769 High Similarity NPC287597
0.9769 High Similarity NPC34293
0.9769 High Similarity NPC886
0.9701 High Similarity NPC265648
0.9701 High Similarity NPC222433
0.9627 High Similarity NPC476377
0.9627 High Similarity NPC47471
0.9552 High Similarity NPC473799
0.9552 High Similarity NPC475530
0.9545 High Similarity NPC476870
0.9489 High Similarity NPC252292
0.9489 High Similarity NPC34927
0.9489 High Similarity NPC34587
0.9489 High Similarity NPC476382
0.9489 High Similarity NPC100998
0.9485 High Similarity NPC247032
0.9485 High Similarity NPC264632
0.9485 High Similarity NPC476380
0.9485 High Similarity NPC76406
0.9485 High Similarity NPC269141
0.9485 High Similarity NPC105005
0.9485 High Similarity NPC476375
0.9485 High Similarity NPC476378
0.9485 High Similarity NPC205864
0.9485 High Similarity NPC112
0.9485 High Similarity NPC96795
0.9485 High Similarity NPC476397
0.9485 High Similarity NPC175214
0.9485 High Similarity NPC298257
0.9485 High Similarity NPC476381
0.9485 High Similarity NPC476384
0.9485 High Similarity NPC119537
0.9478 High Similarity NPC321638
0.9478 High Similarity NPC328273
0.9478 High Similarity NPC321184
0.9478 High Similarity NPC171134
0.9466 High Similarity NPC473285
0.9416 High Similarity NPC141455
0.9416 High Similarity NPC296954
0.9416 High Similarity NPC196063
0.9416 High Similarity NPC300894
0.9416 High Similarity NPC64195
0.9412 High Similarity NPC140502
0.9403 High Similarity NPC476376
0.9385 High Similarity NPC477293
0.9385 High Similarity NPC229784
0.9385 High Similarity NPC477294
0.9353 High Similarity NPC232992
0.9338 High Similarity NPC186406
0.9318 High Similarity NPC254275
0.9308 High Similarity NPC232880
0.9281 High Similarity NPC229505
0.9275 High Similarity NPC476867
0.9242 High Similarity NPC235294
0.9242 High Similarity NPC246869
0.9242 High Similarity NPC225384
0.9242 High Similarity NPC138777
0.9242 High Similarity NPC46137
0.9242 High Similarity NPC219677
0.9231 High Similarity NPC476873
0.9231 High Similarity NPC288416
0.922 High Similarity NPC94871
0.922 High Similarity NPC476398
0.922 High Similarity NPC259347
0.922 High Similarity NPC471062
0.922 High Similarity NPC306890
0.922 High Similarity NPC476386
0.922 High Similarity NPC473427
0.922 High Similarity NPC470933
0.9209 High Similarity NPC476866
0.9209 High Similarity NPC476869
0.9209 High Similarity NPC476868
0.9209 High Similarity NPC476864
0.9203 High Similarity NPC40305
0.9203 High Similarity NPC478239
0.9173 High Similarity NPC473924
0.9155 High Similarity NPC257970
0.9155 High Similarity NPC188393
0.9155 High Similarity NPC470927
0.9155 High Similarity NPC470934
0.9143 High Similarity NPC476865
0.9137 High Similarity NPC292443
0.9137 High Similarity NPC232228
0.913 High Similarity NPC157816
0.9124 High Similarity NPC202700
0.9104 High Similarity NPC254398
0.9091 High Similarity NPC184092
0.9077 High Similarity NPC83218
0.9077 High Similarity NPC126991
0.9044 High Similarity NPC157554
0.9037 High Similarity NPC471883
0.9008 High Similarity NPC471157
0.9007 High Similarity NPC199928
0.9 High Similarity NPC110063
0.8971 High Similarity NPC263829
0.8971 High Similarity NPC123988
0.8955 High Similarity NPC478255
0.8951 High Similarity NPC106138
0.8939 High Similarity NPC79715
0.8939 High Similarity NPC231607
0.8939 High Similarity NPC108659
0.8939 High Similarity NPC264900
0.8936 High Similarity NPC262182
0.8936 High Similarity NPC287615
0.8936 High Similarity NPC216819
0.8936 High Similarity NPC83743
0.8913 High Similarity NPC100389
0.8913 High Similarity NPC226005
0.8905 High Similarity NPC471665
0.8905 High Similarity NPC470572
0.8905 High Similarity NPC186418
0.8905 High Similarity NPC471664
0.8897 High Similarity NPC478268
0.8897 High Similarity NPC135127
0.8897 High Similarity NPC106818
0.8889 High Similarity NPC476871
0.8881 High Similarity NPC3460
0.8881 High Similarity NPC473138
0.8881 High Similarity NPC261122
0.8881 High Similarity NPC199311
0.8881 High Similarity NPC201148
0.8881 High Similarity NPC192763
0.8881 High Similarity NPC215095
0.8881 High Similarity NPC28651
0.8881 High Similarity NPC80732
0.8881 High Similarity NPC28776
0.8881 High Similarity NPC210611
0.8881 High Similarity NPC300262
0.8872 High Similarity NPC148982
0.8872 High Similarity NPC225307
0.8864 High Similarity NPC94179
0.8857 High Similarity NPC296643
0.8849 High Similarity NPC106944
0.8846 High Similarity NPC52097
0.8841 High Similarity NPC302583
0.8841 High Similarity NPC126206
0.8841 High Similarity NPC310252
0.8841 High Similarity NPC100558
0.8841 High Similarity NPC84789
0.8836 High Similarity NPC471874
0.8836 High Similarity NPC87403
0.8828 High Similarity NPC140151
0.8819 High Similarity NPC478242
0.8797 High Similarity NPC106677
0.8777 High Similarity NPC220942
0.8769 High Similarity NPC147654
0.8769 High Similarity NPC266045
0.8769 High Similarity NPC11724
0.8768 High Similarity NPC199459
0.8768 High Similarity NPC52277
0.8768 High Similarity NPC177035
0.8768 High Similarity NPC471345
0.8768 High Similarity NPC37468
0.8767 High Similarity NPC176186
0.8767 High Similarity NPC169404
0.8767 High Similarity NPC53587
0.8759 High Similarity NPC35731
0.875 High Similarity NPC23677
0.875 High Similarity NPC478237
0.8723 High Similarity NPC145319
0.8722 High Similarity NPC252114
0.8707 High Similarity NPC150442
0.8705 High Similarity NPC470413
0.8705 High Similarity NPC138738
0.8699 High Similarity NPC125823
0.8699 High Similarity NPC85192
0.8699 High Similarity NPC143480
0.8699 High Similarity NPC7145
0.8692 High Similarity NPC476872
0.869 High Similarity NPC90896
0.869 High Similarity NPC283839
0.869 High Similarity NPC92117
0.8686 High Similarity NPC28637
0.8676 High Similarity NPC65942
0.8676 High Similarity NPC248307
0.8662 High Similarity NPC113680
0.8662 High Similarity NPC278961
0.8658 High Similarity NPC11411
0.8647 High Similarity NPC90318
0.8639 High Similarity NPC289967
0.8639 High Similarity NPC476352
0.8639 High Similarity NPC472611
0.8639 High Similarity NPC472612
0.8639 High Similarity NPC215060
0.8633 High Similarity NPC154485
0.8633 High Similarity NPC471872
0.8633 High Similarity NPC166180
0.8623 High Similarity NPC106406
0.8621 High Similarity NPC248257

  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 NPC78363 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
0.9773 High Similarity NPD7266 Discontinued
0.8435 Intermediate Similarity NPD1653 Approved
0.8276 Intermediate Similarity NPD6190 Approved
0.7888 Intermediate Similarity NPD7054 Approved
0.7872 Intermediate Similarity NPD3027 Phase 3
0.7853 Intermediate Similarity NPD7685 Pre-registration
0.784 Intermediate Similarity NPD7074 Phase 3
0.784 Intermediate Similarity NPD7472 Approved
0.7832 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7832 Intermediate Similarity NPD1613 Approved
0.7826 Intermediate Similarity NPD7228 Approved
0.7821 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6797 Phase 2
0.7744 Intermediate Similarity NPD7251 Discontinued
0.7716 Intermediate Similarity NPD3818 Discontinued
0.7682 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD6234 Discontinued
0.759 Intermediate Similarity NPD7808 Phase 3
0.758 Intermediate Similarity NPD8455 Phase 2
0.7571 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD1091 Approved
0.7552 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD230 Phase 1
0.7516 Intermediate Similarity NPD37 Approved
0.7484 Intermediate Similarity NPD4965 Approved
0.7484 Intermediate Similarity NPD4966 Approved
0.7484 Intermediate Similarity NPD4967 Phase 2
0.7483 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD6674 Discontinued
0.7378 Intermediate Similarity NPD6166 Phase 2
0.7378 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD8166 Discontinued
0.7337 Intermediate Similarity NPD8312 Approved
0.7337 Intermediate Similarity NPD8313 Approved
0.7321 Intermediate Similarity NPD6559 Discontinued
0.7321 Intermediate Similarity NPD7240 Approved
0.7308 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3705 Approved
0.7296 Intermediate Similarity NPD1934 Approved
0.7285 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD4380 Phase 2
0.7255 Intermediate Similarity NPD4628 Phase 3
0.725 Intermediate Similarity NPD1465 Phase 2
0.725 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD3021 Approved
0.7239 Intermediate Similarity NPD3022 Approved
0.7215 Intermediate Similarity NPD3455 Phase 2
0.7214 Intermediate Similarity NPD1357 Approved
0.7195 Intermediate Similarity NPD7199 Phase 2
0.7181 Intermediate Similarity NPD4340 Discontinued
0.7163 Intermediate Similarity NPD5125 Phase 3
0.7163 Intermediate Similarity NPD5126 Approved
0.7143 Intermediate Similarity NPD5844 Phase 1
0.7132 Intermediate Similarity NPD969 Suspended
0.7132 Intermediate Similarity NPD228 Approved
0.7126 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD2861 Phase 2
0.7114 Intermediate Similarity NPD4060 Phase 1
0.7099 Intermediate Similarity NPD3817 Phase 2
0.7099 Intermediate Similarity NPD5402 Approved
0.7095 Intermediate Similarity NPD3764 Approved
0.7086 Intermediate Similarity NPD7097 Phase 1
0.7078 Intermediate Similarity NPD1652 Phase 2
0.7071 Intermediate Similarity NPD5536 Phase 2
0.7051 Intermediate Similarity NPD5058 Phase 3
0.7047 Intermediate Similarity NPD6233 Phase 2
0.7045 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD2977 Approved
0.7037 Intermediate Similarity NPD2801 Approved
0.7037 Intermediate Similarity NPD2978 Approved
0.7021 Intermediate Similarity NPD9545 Approved
0.7012 Intermediate Similarity NPD7075 Discontinued
0.7006 Intermediate Similarity NPD1511 Approved
0.7006 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.6988 Remote Similarity NPD8127 Discontinued
0.6982 Remote Similarity NPD3751 Discontinued
0.6981 Remote Similarity NPD5403 Approved
0.6963 Remote Similarity NPD1358 Approved
0.6962 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4908 Phase 1
0.6954 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5124 Phase 1
0.6951 Remote Similarity NPD3882 Suspended
0.694 Remote Similarity NPD7680 Approved
0.6918 Remote Similarity NPD1512 Approved
0.6913 Remote Similarity NPD7095 Approved
0.6906 Remote Similarity NPD5283 Phase 1
0.6897 Remote Similarity NPD9269 Phase 2
0.6887 Remote Similarity NPD3620 Phase 2
0.6887 Remote Similarity NPD3062 Approved
0.6887 Remote Similarity NPD3059 Approved
0.6887 Remote Similarity NPD3061 Approved
0.6887 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6883 Remote Similarity NPD2935 Discontinued
0.6875 Remote Similarity NPD3496 Discontinued
0.6867 Remote Similarity NPD6798 Discontinued
0.6867 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6863 Remote Similarity NPD4538 Approved
0.6863 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6863 Remote Similarity NPD4536 Approved
0.6859 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6855 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6855 Remote Similarity NPD5401 Approved
0.6849 Remote Similarity NPD2983 Phase 2
0.6849 Remote Similarity NPD2982 Phase 2
0.6845 Remote Similarity NPD3787 Discontinued
0.6845 Remote Similarity NPD6232 Discontinued
0.6842 Remote Similarity NPD1933 Approved
0.6832 Remote Similarity NPD3687 Approved
0.6832 Remote Similarity NPD3686 Approved
0.6829 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6828 Remote Similarity NPD422 Phase 1
0.6828 Remote Similarity NPD1610 Phase 2
0.6818 Remote Similarity NPD5588 Approved
0.6818 Remote Similarity NPD5960 Phase 3
0.6815 Remote Similarity NPD3750 Approved
0.6806 Remote Similarity NPD9381 Approved
0.6806 Remote Similarity NPD9384 Approved
0.6803 Remote Similarity NPD3225 Approved
0.6797 Remote Similarity NPD5314 Approved
0.6797 Remote Similarity NPD6653 Approved
0.679 Remote Similarity NPD7458 Discontinued
0.6783 Remote Similarity NPD1548 Phase 1
0.6782 Remote Similarity NPD7549 Discontinued
0.6781 Remote Similarity NPD2981 Phase 2
0.6779 Remote Similarity NPD9494 Approved
0.6779 Remote Similarity NPD3018 Phase 2
0.6776 Remote Similarity NPD943 Approved
0.6776 Remote Similarity NPD1558 Phase 1
0.6774 Remote Similarity NPD9570 Approved
0.6768 Remote Similarity NPD6801 Discontinued
0.6768 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3134 Approved
0.6757 Remote Similarity NPD3094 Phase 2
0.6755 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6752 Remote Similarity NPD3060 Approved
0.6752 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6732 Remote Similarity NPD6355 Discontinued
0.6731 Remote Similarity NPD5763 Approved
0.6731 Remote Similarity NPD5762 Approved
0.6727 Remote Similarity NPD7819 Suspended
0.6726 Remote Similarity NPD5494 Approved
0.6725 Remote Similarity NPD7473 Discontinued
0.6724 Remote Similarity NPD7039 Approved
0.6724 Remote Similarity NPD7038 Approved
0.6723 Remote Similarity NPD8150 Discontinued
0.672 Remote Similarity NPD8319 Approved
0.672 Remote Similarity NPD8320 Phase 1
0.6714 Remote Similarity NPD5535 Approved
0.6714 Remote Similarity NPD7843 Approved
0.6711 Remote Similarity NPD4062 Phase 3
0.671 Remote Similarity NPD4108 Discontinued
0.671 Remote Similarity NPD7033 Discontinued
0.6709 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6709 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6709 Remote Similarity NPD4110 Phase 3
0.6708 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6385 Approved
0.6707 Remote Similarity NPD7411 Suspended
0.6707 Remote Similarity NPD6386 Approved
0.6705 Remote Similarity NPD7090 Clinical (unspecified phase)
0.669 Remote Similarity NPD4626 Approved
0.669 Remote Similarity NPD7157 Approved
0.6688 Remote Similarity NPD1549 Phase 2
0.6687 Remote Similarity NPD6799 Approved
0.6687 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6687 Remote Similarity NPD4357 Discontinued
0.6685 Remote Similarity NPD6843 Phase 3
0.6685 Remote Similarity NPD6842 Approved
0.6685 Remote Similarity NPD6535 Approved
0.6685 Remote Similarity NPD6841 Approved
0.6685 Remote Similarity NPD6534 Approved
0.6667 Remote Similarity NPD4140 Approved
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD826 Approved
0.6667 Remote Similarity NPD825 Approved
0.6667 Remote Similarity NPD7699 Phase 2
0.6667 Remote Similarity NPD8151 Discontinued
0.6667 Remote Similarity NPD2684 Approved
0.6667 Remote Similarity NPD7700 Phase 2
0.6646 Remote Similarity NPD4237 Approved
0.6646 Remote Similarity NPD3536 Discontinued
0.6646 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4236 Phase 3
0.6646 Remote Similarity NPD7028 Phase 2
0.6646 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6642 Remote Similarity NPD1242 Phase 1
0.6641 Remote Similarity NPD2934 Approved
0.6641 Remote Similarity NPD2933 Approved
0.6627 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6625 Remote Similarity NPD6783 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