Structure

Physi-Chem Properties

Molecular Weight:  284.2
Volume:  300.704
LogP:  1.981
LogD:  2.316
LogS:  -2.18
# Rotatable Bonds:  3
TPSA:  69.92
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.687
Synthetic Accessibility Score:  4.556
Fsp3:  0.875
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:  -4.609
MDCK Permeability:  1.227853681484703e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.028
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.326
30% Bioavailability (F30%):  0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.697
Plasma Protein Binding (PPB):  28.998790740966797%
Volume Distribution (VD):  0.851
Pgp-substrate:  63.54246139526367%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.743
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.801
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.035
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.064
CYP3A4-inhibitor:  0.115
CYP3A4-substrate:  0.414

ADMET: Excretion

Clearance (CL):  6.365
Half-life (T1/2):  0.185

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.318
Drug-inuced Liver Injury (DILI):  0.483
AMES Toxicity:  0.389
Rat Oral Acute Toxicity:  0.946
Maximum Recommended Daily Dose:  0.066
Skin Sensitization:  0.49
Carcinogencity:  0.959
Eye Corrosion:  0.044
Eye Irritation:  0.259
Respiratory Toxicity:  0.982

Download Data

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

  Natural Product: NPC83702

Natural Product ID:  NPC83702
Common Name*:   Ustusol C
IUPAC Name:   (1S,4R,4aS,8aS)-1,2-bis(hydroxymethyl)-4-methoxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalen-1-ol
Synonyms:   Ustusol C
Standard InCHIKey:  ZPHNAEGQIWXWGS-BFJAYTPKSA-N
Standard InCHI:  InChI=1S/C16H28O4/c1-14(2)6-5-7-15(3)13(14)12(20-4)8-11(9-17)16(15,19)10-18/h8,12-13,17-19H,5-7,9-10H2,1-4H3/t12-,13+,15+,16-/m1/s1
SMILES:  CC1(C)CCC[C@@]2(C)[C@H]1[C@@H](C=C(CO)[C@@]2(CO)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1080769
PubChem CID:   44557563
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001670] Tertiary alcohols

*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
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. DOI[10.1021/np50063a031]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. DOI[10.1021/np50063a031]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. PMID[11277746]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[15165134]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. PMID[16254827]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. PMID[16254827]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. PMID[18179176]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19769341]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota Suberites domuncula n.a. n.a. PMID[19778087]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[19835393]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[21261297]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21348461]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21539300]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21868221]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[22316191]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25679537]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25706180]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25901993]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[2778454]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29286660]
NPO15599 Daldinia concentrica Species n.a. Eukaryota Fruiting Bodies n.a. n.a. PMID[29715021]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8158166]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[Title]
NPO17844 Agaricus integer Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16329 Potebniamyces gallicola Species Phacidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7905 Lepista irina Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16695 Fumaria kraliki Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2550 Trichoderma citrinum Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO84 Isoberlinia angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18073 Justicia trinervia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17304 Sipunculus nudus Species Sipunculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11408 Podocarpus amarus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16215 Umbilicaria cinereorufescens Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2155 Tephroseris integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10770 Ptilota pectinata Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15919 Streptomyces caelestis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9951 Hyella caespitosa Species Hyellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17921 Allium monspessulanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17071 Coeloseira pacifica Species Champiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15545 Veltheimia viridifolia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17375 Ceramium botryocarpum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13789 Paranephelius uniflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14002 Petalostemon purpureum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16923 Cereus chrysacanthus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17218 Helichrysum nudifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28319 Ulva prolifera Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16052 Chromodoris obsoleta Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17339 Macaranga sinensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4336 Echiochilon pauciflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14813 Agaricus silvaticus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28868 Pardachirus pavoninus Species Soleidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25550 Buchenavia tetraphylla Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17602 Arbutus menziesii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28821 Stichopus horrens Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15748 Hypoxis nyasica Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13013 Saccharothrix mutabilis Species Pseudonocardiaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[493780]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 100000.0 nM PMID[493780]

☑ 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 NPC83702 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
0.881 High Similarity NPC255143
0.8556 High Similarity NPC288970
0.8506 High Similarity NPC115607
0.8427 Intermediate Similarity NPC119379
0.8409 Intermediate Similarity NPC295668
0.8409 Intermediate Similarity NPC470817
0.8352 Intermediate Similarity NPC72204
0.8333 Intermediate Similarity NPC65402
0.8333 Intermediate Similarity NPC471408
0.8333 Intermediate Similarity NPC127718
0.8315 Intermediate Similarity NPC41554
0.8315 Intermediate Similarity NPC97404
0.8315 Intermediate Similarity NPC302584
0.8295 Intermediate Similarity NPC470819
0.8295 Intermediate Similarity NPC246028
0.8295 Intermediate Similarity NPC49783
0.8295 Intermediate Similarity NPC97103
0.8295 Intermediate Similarity NPC470361
0.8276 Intermediate Similarity NPC149224
0.8276 Intermediate Similarity NPC476948
0.8261 Intermediate Similarity NPC473244
0.8256 Intermediate Similarity NPC266511
0.8256 Intermediate Similarity NPC290731
0.8256 Intermediate Similarity NPC119001
0.8242 Intermediate Similarity NPC8774
0.8222 Intermediate Similarity NPC67398
0.8222 Intermediate Similarity NPC474792
0.8222 Intermediate Similarity NPC91654
0.8214 Intermediate Similarity NPC471270
0.8214 Intermediate Similarity NPC476646
0.8202 Intermediate Similarity NPC329596
0.8202 Intermediate Similarity NPC220216
0.8202 Intermediate Similarity NPC291484
0.8202 Intermediate Similarity NPC11216
0.8202 Intermediate Similarity NPC191323
0.8202 Intermediate Similarity NPC80561
0.8202 Intermediate Similarity NPC204188
0.8202 Intermediate Similarity NPC3345
0.8193 Intermediate Similarity NPC233295
0.8182 Intermediate Similarity NPC474668
0.8171 Intermediate Similarity NPC130136
0.8161 Intermediate Similarity NPC476217
0.8161 Intermediate Similarity NPC6391
0.8152 Intermediate Similarity NPC284194
0.8152 Intermediate Similarity NPC221801
0.8152 Intermediate Similarity NPC211810
0.8152 Intermediate Similarity NPC471765
0.8152 Intermediate Similarity NPC227583
0.8152 Intermediate Similarity NPC98457
0.8152 Intermediate Similarity NPC12103
0.8148 Intermediate Similarity NPC32832
0.814 Intermediate Similarity NPC185568
0.8132 Intermediate Similarity NPC472416
0.8132 Intermediate Similarity NPC469491
0.8132 Intermediate Similarity NPC472360
0.8125 Intermediate Similarity NPC265485
0.8125 Intermediate Similarity NPC220939
0.8118 Intermediate Similarity NPC155521
0.8111 Intermediate Similarity NPC124374
0.8101 Intermediate Similarity NPC34834
0.8095 Intermediate Similarity NPC474592
0.8095 Intermediate Similarity NPC236707
0.8095 Intermediate Similarity NPC471266
0.8095 Intermediate Similarity NPC96362
0.8095 Intermediate Similarity NPC95124
0.809 Intermediate Similarity NPC187785
0.809 Intermediate Similarity NPC259875
0.809 Intermediate Similarity NPC261320
0.8085 Intermediate Similarity NPC38855
0.8072 Intermediate Similarity NPC167891
0.8072 Intermediate Similarity NPC83351
0.8068 Intermediate Similarity NPC189777
0.8065 Intermediate Similarity NPC261807
0.8049 Intermediate Similarity NPC265588
0.8046 Intermediate Similarity NPC274448
0.8023 Intermediate Similarity NPC23748
0.8023 Intermediate Similarity NPC474634
0.8023 Intermediate Similarity NPC185605
0.8022 Intermediate Similarity NPC310013
0.8022 Intermediate Similarity NPC99653
0.8 Intermediate Similarity NPC475617
0.8 Intermediate Similarity NPC197107
0.8 Intermediate Similarity NPC23954
0.8 Intermediate Similarity NPC472554
0.8 Intermediate Similarity NPC249423
0.7978 Intermediate Similarity NPC133588
0.7975 Intermediate Similarity NPC473893
0.7957 Intermediate Similarity NPC129569
0.7957 Intermediate Similarity NPC103165
0.7957 Intermediate Similarity NPC210717
0.7957 Intermediate Similarity NPC90583
0.7957 Intermediate Similarity NPC57664
0.7955 Intermediate Similarity NPC281316
0.7955 Intermediate Similarity NPC293287
0.7955 Intermediate Similarity NPC152808
0.7955 Intermediate Similarity NPC261266
0.7955 Intermediate Similarity NPC237344
0.7952 Intermediate Similarity NPC477924
0.7952 Intermediate Similarity NPC91594
0.7938 Intermediate Similarity NPC258532
0.7938 Intermediate Similarity NPC473543
0.7935 Intermediate Similarity NPC144202
0.7931 Intermediate Similarity NPC46320
0.7931 Intermediate Similarity NPC205845
0.7927 Intermediate Similarity NPC133580
0.7917 Intermediate Similarity NPC472552
0.7912 Intermediate Similarity NPC210268
0.7907 Intermediate Similarity NPC259858
0.7907 Intermediate Similarity NPC101462
0.7901 Intermediate Similarity NPC259049
0.7895 Intermediate Similarity NPC64348
0.7889 Intermediate Similarity NPC128066
0.7889 Intermediate Similarity NPC20946
0.7882 Intermediate Similarity NPC287749
0.7875 Intermediate Similarity NPC189745
0.7875 Intermediate Similarity NPC92801
0.7872 Intermediate Similarity NPC91197
0.7872 Intermediate Similarity NPC239547
0.7872 Intermediate Similarity NPC26307
0.7872 Intermediate Similarity NPC476893
0.7872 Intermediate Similarity NPC309503
0.7872 Intermediate Similarity NPC155319
0.7872 Intermediate Similarity NPC125551
0.7872 Intermediate Similarity NPC96597
0.7865 Intermediate Similarity NPC470620
0.7865 Intermediate Similarity NPC233744
0.7865 Intermediate Similarity NPC471779
0.7857 Intermediate Similarity NPC477089
0.7849 Intermediate Similarity NPC477969
0.7849 Intermediate Similarity NPC276110
0.7849 Intermediate Similarity NPC135224
0.7841 Intermediate Similarity NPC157257
0.7841 Intermediate Similarity NPC35933
0.7835 Intermediate Similarity NPC474124
0.7835 Intermediate Similarity NPC473523
0.7831 Intermediate Similarity NPC477925
0.7831 Intermediate Similarity NPC274079
0.7831 Intermediate Similarity NPC253190
0.7826 Intermediate Similarity NPC137461
0.7826 Intermediate Similarity NPC27531
0.7821 Intermediate Similarity NPC202017
0.7816 Intermediate Similarity NPC320548
0.7816 Intermediate Similarity NPC49208
0.7812 Intermediate Similarity NPC280991
0.7812 Intermediate Similarity NPC11974
0.7805 Intermediate Similarity NPC201048
0.7805 Intermediate Similarity NPC476366
0.7805 Intermediate Similarity NPC306727
0.7802 Intermediate Similarity NPC48732
0.7791 Intermediate Similarity NPC474683
0.7791 Intermediate Similarity NPC474752
0.7791 Intermediate Similarity NPC209620
0.7791 Intermediate Similarity NPC82986
0.7791 Intermediate Similarity NPC7505
0.7791 Intermediate Similarity NPC23852
0.7791 Intermediate Similarity NPC474731
0.7791 Intermediate Similarity NPC474759
0.7789 Intermediate Similarity NPC476895
0.7778 Intermediate Similarity NPC164022
0.7778 Intermediate Similarity NPC242992
0.7778 Intermediate Similarity NPC67872
0.7778 Intermediate Similarity NPC33053
0.7778 Intermediate Similarity NPC280556
0.7766 Intermediate Similarity NPC165632
0.7765 Intermediate Similarity NPC242767
0.7765 Intermediate Similarity NPC476701
0.7755 Intermediate Similarity NPC296950
0.7755 Intermediate Similarity NPC93352
0.7755 Intermediate Similarity NPC146731
0.7753 Intermediate Similarity NPC471219
0.7753 Intermediate Similarity NPC299068
0.775 Intermediate Similarity NPC471560
0.775 Intermediate Similarity NPC474248
0.7742 Intermediate Similarity NPC182826
0.7742 Intermediate Similarity NPC105490
0.7742 Intermediate Similarity NPC196227
0.7742 Intermediate Similarity NPC105375
0.7742 Intermediate Similarity NPC189513
0.7738 Intermediate Similarity NPC470711
0.7738 Intermediate Similarity NPC471798
0.7738 Intermediate Similarity NPC470758
0.7732 Intermediate Similarity NPC11956
0.7732 Intermediate Similarity NPC475344
0.7732 Intermediate Similarity NPC476471
0.7727 Intermediate Similarity NPC238992
0.7727 Intermediate Similarity NPC102048
0.7727 Intermediate Similarity NPC470077
0.7723 Intermediate Similarity NPC5103
0.7722 Intermediate Similarity NPC114651
0.7722 Intermediate Similarity NPC82337
0.7717 Intermediate Similarity NPC234335
0.7717 Intermediate Similarity NPC116726
0.7717 Intermediate Similarity NPC114389
0.7717 Intermediate Similarity NPC477574
0.7711 Intermediate Similarity NPC477923
0.7711 Intermediate Similarity NPC66566
0.7708 Intermediate Similarity NPC188968
0.7708 Intermediate Similarity NPC471242
0.7708 Intermediate Similarity NPC469942
0.7708 Intermediate Similarity NPC473510

  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 NPC83702 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
0.7727 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7524 Approved
0.7614 Intermediate Similarity NPD6695 Phase 3
0.7473 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6930 Phase 2
0.7471 Intermediate Similarity NPD6931 Approved
0.7356 Intermediate Similarity NPD7645 Phase 2
0.7356 Intermediate Similarity NPD6929 Approved
0.7308 Intermediate Similarity NPD368 Approved
0.7283 Intermediate Similarity NPD7750 Discontinued
0.7273 Intermediate Similarity NPD7514 Phase 3
0.7273 Intermediate Similarity NPD7525 Registered
0.7273 Intermediate Similarity NPD5344 Discontinued
0.7273 Intermediate Similarity NPD7332 Phase 2
0.7245 Intermediate Similarity NPD4225 Approved
0.7209 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6933 Approved
0.7172 Intermediate Similarity NPD7639 Approved
0.7172 Intermediate Similarity NPD7640 Approved
0.7126 Intermediate Similarity NPD6925 Approved
0.7126 Intermediate Similarity NPD5776 Phase 2
0.7093 Intermediate Similarity NPD8264 Approved
0.7093 Intermediate Similarity NPD6942 Approved
0.7093 Intermediate Similarity NPD7339 Approved
0.7071 Intermediate Similarity NPD7638 Approved
0.7065 Intermediate Similarity NPD6893 Approved
0.7045 Intermediate Similarity NPD7145 Approved
0.7 Intermediate Similarity NPD6902 Approved
0.7 Intermediate Similarity NPD6898 Phase 1
0.6979 Remote Similarity NPD7087 Discontinued
0.6977 Remote Similarity NPD6926 Approved
0.6977 Remote Similarity NPD6924 Approved
0.6952 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6932 Approved
0.6857 Remote Similarity NPD6686 Approved
0.6854 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6648 Approved
0.6778 Remote Similarity NPD6683 Phase 2
0.6765 Remote Similarity NPD4159 Approved
0.6757 Remote Similarity NPD7328 Approved
0.6757 Remote Similarity NPD7327 Approved
0.6739 Remote Similarity NPD3667 Approved
0.6726 Remote Similarity NPD8033 Approved
0.6726 Remote Similarity NPD7503 Approved
0.6703 Remote Similarity NPD7509 Discontinued
0.6701 Remote Similarity NPD6698 Approved
0.6701 Remote Similarity NPD46 Approved
0.6701 Remote Similarity NPD7838 Discovery
0.6696 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD7115 Discovery
0.6667 Remote Similarity NPD4732 Discontinued
0.6667 Remote Similarity NPD6640 Phase 3
0.6637 Remote Similarity NPD8377 Approved
0.6637 Remote Similarity NPD8294 Approved
0.6633 Remote Similarity NPD7637 Suspended
0.6604 Remote Similarity NPD6412 Phase 2
0.6598 Remote Similarity NPD6051 Approved
0.6596 Remote Similarity NPD4786 Approved
0.6596 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6591 Remote Similarity NPD4784 Approved
0.6591 Remote Similarity NPD4785 Approved
0.6579 Remote Similarity NPD8296 Approved
0.6579 Remote Similarity NPD8380 Approved
0.6579 Remote Similarity NPD8379 Approved
0.6579 Remote Similarity NPD8335 Approved
0.6579 Remote Similarity NPD8378 Approved
0.6574 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5779 Approved
0.6566 Remote Similarity NPD5778 Approved
0.6552 Remote Similarity NPD4243 Approved
0.6538 Remote Similarity NPD5211 Phase 2
0.6538 Remote Similarity NPD7632 Discontinued
0.6538 Remote Similarity NPD342 Phase 1
0.6531 Remote Similarity NPD3168 Discontinued
0.6522 Remote Similarity NPD4748 Discontinued
0.6512 Remote Similarity NPD6922 Approved
0.6512 Remote Similarity NPD6923 Approved
0.6471 Remote Similarity NPD4755 Approved
0.6458 Remote Similarity NPD3618 Phase 1
0.6455 Remote Similarity NPD6053 Discontinued
0.6437 Remote Similarity NPD7144 Approved
0.6437 Remote Similarity NPD7143 Approved
0.6429 Remote Similarity NPD4753 Phase 2
0.6422 Remote Similarity NPD6371 Approved
0.6422 Remote Similarity NPD4634 Approved
0.6421 Remote Similarity NPD3666 Approved
0.6421 Remote Similarity NPD3133 Approved
0.6421 Remote Similarity NPD3665 Phase 1
0.6415 Remote Similarity NPD5141 Approved
0.6408 Remote Similarity NPD8029 Clinical (unspecified phase)
0.64 Remote Similarity NPD4202 Approved
0.64 Remote Similarity NPD6399 Phase 3
0.6396 Remote Similarity NPD4632 Approved
0.6389 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7150 Approved
0.6364 Remote Similarity NPD7151 Approved
0.6364 Remote Similarity NPD7136 Phase 2
0.6364 Remote Similarity NPD7152 Approved
0.6356 Remote Similarity NPD7507 Approved
0.6346 Remote Similarity NPD4696 Approved
0.6346 Remote Similarity NPD5286 Approved
0.6346 Remote Similarity NPD5285 Approved
0.6346 Remote Similarity NPD4700 Approved
0.6333 Remote Similarity NPD5275 Approved
0.6333 Remote Similarity NPD4190 Phase 3
0.63 Remote Similarity NPD7515 Phase 2
0.63 Remote Similarity NPD7983 Approved
0.6296 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6289 Remote Similarity NPD4519 Discontinued
0.6289 Remote Similarity NPD4623 Approved
0.6263 Remote Similarity NPD5328 Approved
0.625 Remote Similarity NPD3668 Phase 3
0.6237 Remote Similarity NPD4195 Approved
0.6226 Remote Similarity NPD4633 Approved
0.6226 Remote Similarity NPD5226 Approved
0.6226 Remote Similarity NPD5225 Approved
0.6226 Remote Similarity NPD5224 Approved
0.6216 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6207 Remote Similarity NPD7741 Discontinued
0.6207 Remote Similarity NPD6319 Approved
0.6204 Remote Similarity NPD6675 Approved
0.6204 Remote Similarity NPD7128 Approved
0.6204 Remote Similarity NPD6402 Approved
0.6204 Remote Similarity NPD5739 Approved
0.6198 Remote Similarity NPD7319 Approved
0.6182 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6176 Remote Similarity NPD7748 Approved
0.6176 Remote Similarity NPD5282 Discontinued
0.617 Remote Similarity NPD4695 Discontinued
0.617 Remote Similarity NPD4822 Approved
0.617 Remote Similarity NPD4819 Approved
0.617 Remote Similarity NPD4820 Approved
0.617 Remote Similarity NPD4821 Approved
0.6168 Remote Similarity NPD5175 Approved
0.6168 Remote Similarity NPD5174 Approved
0.6154 Remote Similarity NPD8517 Approved
0.6154 Remote Similarity NPD7902 Approved
0.6154 Remote Similarity NPD8515 Approved
0.6154 Remote Similarity NPD8516 Approved
0.6154 Remote Similarity NPD8513 Phase 3
0.6154 Remote Similarity NPD6083 Phase 2
0.6154 Remote Similarity NPD6084 Phase 2
0.6147 Remote Similarity NPD5701 Approved
0.6147 Remote Similarity NPD5697 Approved
0.6146 Remote Similarity NPD6110 Phase 1
0.6139 Remote Similarity NPD6079 Approved
0.6139 Remote Similarity NPD6411 Approved
0.6136 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5223 Approved
0.6122 Remote Similarity NPD4249 Approved
0.6122 Remote Similarity NPD5279 Phase 3
0.6118 Remote Similarity NPD371 Approved
0.6117 Remote Similarity NPD5210 Approved
0.6117 Remote Similarity NPD5695 Phase 3
0.6117 Remote Similarity NPD4629 Approved
0.6106 Remote Similarity NPD8133 Approved
0.6091 Remote Similarity NPD7320 Approved
0.6091 Remote Similarity NPD6881 Approved
0.6091 Remote Similarity NPD6899 Approved
0.6087 Remote Similarity NPD6009 Approved
0.6068 Remote Similarity NPD6054 Approved
0.6068 Remote Similarity NPD6059 Approved
0.6061 Remote Similarity NPD4251 Approved
0.6061 Remote Similarity NPD4250 Approved
0.6058 Remote Similarity NPD4697 Phase 3
0.6058 Remote Similarity NPD5222 Approved
0.6058 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6058 Remote Similarity NPD5221 Approved
0.6055 Remote Similarity NPD4768 Approved
0.6055 Remote Similarity NPD6008 Approved
0.6055 Remote Similarity NPD4767 Approved
0.6049 Remote Similarity NPD4219 Approved
0.6042 Remote Similarity NPD4221 Approved
0.6042 Remote Similarity NPD4223 Phase 3
0.6036 Remote Similarity NPD6012 Approved
0.6036 Remote Similarity NPD6014 Approved
0.6036 Remote Similarity NPD6372 Approved
0.6036 Remote Similarity NPD6013 Approved
0.6036 Remote Similarity NPD6373 Approved
0.602 Remote Similarity NPD1696 Phase 3
0.602 Remote Similarity NPD1694 Approved
0.6019 Remote Similarity NPD4754 Approved
0.6018 Remote Similarity NPD8297 Approved
0.6017 Remote Similarity NPD6016 Approved
0.6017 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD5173 Approved
0.6 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5982 Remote Similarity NPD7290 Approved
0.5982 Remote Similarity NPD6883 Approved
0.5982 Remote Similarity NPD7102 Approved
0.5966 Remote Similarity NPD5126 Approved
0.5966 Remote Similarity NPD5988 Approved
0.5966 Remote Similarity NPD6370 Approved
0.5966 Remote Similarity NPD5125 Phase 3
0.596 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4271 Approved
0.5957 Remote Similarity NPD4268 Approved
0.5948 Remote Similarity NPD8295 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