Structure

Physi-Chem Properties

Molecular Weight:  215.06
Volume:  211.988
LogP:  2.961
LogD:  2.908
LogS:  -3.23
# Rotatable Bonds:  1
TPSA:  55.49
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.678
Synthetic Accessibility Score:  2.596
Fsp3:  0.083
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.811
MDCK Permeability:  3.1102819775696844e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.12
Plasma Protein Binding (PPB):  96.76541900634766%
Volume Distribution (VD):  0.498
Pgp-substrate:  3.2277770042419434%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.885
CYP2C19-inhibitor:  0.702
CYP2C19-substrate:  0.294
CYP2C9-inhibitor:  0.699
CYP2C9-substrate:  0.797
CYP2D6-inhibitor:  0.786
CYP2D6-substrate:  0.858
CYP3A4-inhibitor:  0.663
CYP3A4-substrate:  0.237

ADMET: Excretion

Clearance (CL):  11.452
Half-life (T1/2):  0.691

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.063
Drug-inuced Liver Injury (DILI):  0.943
AMES Toxicity:  0.32
Rat Oral Acute Toxicity:  0.389
Maximum Recommended Daily Dose:  0.046
Skin Sensitization:  0.484
Carcinogencity:  0.777
Eye Corrosion:  0.004
Eye Irritation:  0.475
Respiratory Toxicity:  0.942

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  Natural Product: NPC205372

Natural Product ID:  NPC205372
Common Name*:   Robustine
IUPAC Name:   4-methoxyfuro[2,3-b]quinolin-8-ol
Synonyms:   Robustine
Standard InCHIKey:  VGVNNMLKTSWBAR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H9NO3/c1-15-11-7-3-2-4-9(14)10(7)13-12-8(11)5-6-16-12/h2-6,14H,1H3
SMILES:  COc1c2cccc(c2nc2c1cco2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL402862
PubChem CID:   164950
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0002374] Furanoquinolines

*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
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(90)85209-X]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Caribbean n.a. PMID[10021943]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Taiwan n.a. PMID[11277748]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[15921424]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota Leaves n.a. n.a. PMID[17637068]
NPO18723 Zanthoxylum avicennae Species Rutaceae Eukaryota stem wood Pakuashan, Changhua County, Taiwan 2006-Jun PMID[18211005]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[18302336]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. Hainan, China n.a. PMID[19091557]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22432912]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[23806071]
NPO7213 Toddalia asiatica Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24597921]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. China n.a. PMID[25115700]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[26666037]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[26724423]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[26724423]
NPO7175 Eucalyptus robusta Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[27142786]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[28006915]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7798955]
NPO9031 Euonymus europaeus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7213 Toddalia asiatica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18723 Zanthoxylum avicennae Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19347 Dictamnus caucasicus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7175 Eucalyptus robusta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18723 Zanthoxylum avicennae Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7175 Eucalyptus robusta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19347 Dictamnus caucasicus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7213 Toddalia asiatica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9031 Euonymus europaeus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19347 Dictamnus caucasicus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18723 Zanthoxylum avicennae Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7213 Toddalia asiatica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7175 Eucalyptus robusta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25802 Agave deserti Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1267 Acronychia laurifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25201 Aglaia pyramidata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO617 Vicia balansae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26849 Parmelia zollingeri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22264 Inula salsoloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9031 Euonymus europaeus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7213 Toddalia asiatica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO103 Stereocaulon salazinum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1040 Ficus conraui Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25833 Asclepias subulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25259 Schrebera swietenoides Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19347 Dictamnus caucasicus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24918 Jacobaea cannabifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3005 Passiflora morifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7175 Eucalyptus robusta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18723 Zanthoxylum avicennae Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24547 Xanthoria parietina Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28636 Vernonia lilacina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25714 Solanum spirale Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22890 Eutrochium purpureum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26690 Lactarius subpiperatus Species Lactariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1109 Corydalis persica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9324 0techis scutatus Species Elapidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25358 Senecio gilliesi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26789 Tephrosia bidwilli Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26160 Thielavia terricola Species Chaetomiaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[490708]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 18190.0 nM PMID[490708]

☑ 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 NPC205372 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
0.9648 High Similarity NPC131885
0.9275 High Similarity NPC140296
0.9113 High Similarity NPC16066
0.9104 High Similarity NPC269367
0.9074 High Similarity NPC160100
0.8995 High Similarity NPC97746
0.8925 High Similarity NPC34770
0.8818 High Similarity NPC58209
0.8756 High Similarity NPC298436
0.8682 High Similarity NPC166712
0.8643 High Similarity NPC208364
0.8489 Intermediate Similarity NPC173250
0.8451 Intermediate Similarity NPC203373
0.844 Intermediate Similarity NPC217176
0.8426 Intermediate Similarity NPC101312
0.8419 Intermediate Similarity NPC314633
0.8311 Intermediate Similarity NPC188400
0.8268 Intermediate Similarity NPC120513
0.8178 Intermediate Similarity NPC168922
0.8045 Intermediate Similarity NPC179287
0.7965 Intermediate Similarity NPC1608
0.7833 Intermediate Similarity NPC42591
0.7824 Intermediate Similarity NPC187501
0.7811 Intermediate Similarity NPC161801
0.7773 Intermediate Similarity NPC184408
0.7762 Intermediate Similarity NPC112937
0.774 Intermediate Similarity NPC230403
0.7738 Intermediate Similarity NPC208084
0.7721 Intermediate Similarity NPC283117
0.7717 Intermediate Similarity NPC118228
0.7661 Intermediate Similarity NPC294375
0.7645 Intermediate Similarity NPC230683
0.7621 Intermediate Similarity NPC194040
0.7613 Intermediate Similarity NPC247803
0.7596 Intermediate Similarity NPC144381
0.7591 Intermediate Similarity NPC39500
0.7585 Intermediate Similarity NPC66083
0.7581 Intermediate Similarity NPC317572
0.7578 Intermediate Similarity NPC288987
0.7545 Intermediate Similarity NPC225279
0.7545 Intermediate Similarity NPC203168
0.7545 Intermediate Similarity NPC150239
0.7543 Intermediate Similarity NPC6786
0.7543 Intermediate Similarity NPC477587
0.7543 Intermediate Similarity NPC477589
0.7534 Intermediate Similarity NPC219664
0.7489 Intermediate Similarity NPC293151
0.7479 Intermediate Similarity NPC477590
0.7479 Intermediate Similarity NPC477588
0.7479 Intermediate Similarity NPC477585
0.7479 Intermediate Similarity NPC477586
0.7478 Intermediate Similarity NPC474701
0.7477 Intermediate Similarity NPC280714
0.7477 Intermediate Similarity NPC321428
0.7455 Intermediate Similarity NPC174576
0.7455 Intermediate Similarity NPC46561
0.7451 Intermediate Similarity NPC283152
0.7445 Intermediate Similarity NPC51388
0.7431 Intermediate Similarity NPC45190
0.7421 Intermediate Similarity NPC146418
0.7418 Intermediate Similarity NPC185197
0.7417 Intermediate Similarity NPC473188
0.7391 Intermediate Similarity NPC274640
0.7389 Intermediate Similarity NPC174760
0.7387 Intermediate Similarity NPC310211
0.7387 Intermediate Similarity NPC308137
0.7373 Intermediate Similarity NPC66815
0.7358 Intermediate Similarity NPC209981
0.7357 Intermediate Similarity NPC198503
0.7346 Intermediate Similarity NPC45389
0.7339 Intermediate Similarity NPC329631
0.7328 Intermediate Similarity NPC474688
0.7325 Intermediate Similarity NPC144452
0.7324 Intermediate Similarity NPC79293
0.7324 Intermediate Similarity NPC279401
0.7318 Intermediate Similarity NPC249583
0.7317 Intermediate Similarity NPC288943
0.7308 Intermediate Similarity NPC39370
0.73 Intermediate Similarity NPC475844
0.7296 Intermediate Similarity NPC473186
0.7293 Intermediate Similarity NPC94842
0.7289 Intermediate Similarity NPC3207
0.7265 Intermediate Similarity NPC87413
0.7244 Intermediate Similarity NPC116238
0.7207 Intermediate Similarity NPC210828
0.7207 Intermediate Similarity NPC86834
0.72 Intermediate Similarity NPC227824
0.7198 Intermediate Similarity NPC314222
0.7198 Intermediate Similarity NPC196449
0.7195 Intermediate Similarity NPC304183
0.7195 Intermediate Similarity NPC300156
0.7193 Intermediate Similarity NPC148409
0.7188 Intermediate Similarity NPC23294
0.7188 Intermediate Similarity NPC220337
0.7184 Intermediate Similarity NPC303225
0.7182 Intermediate Similarity NPC41216
0.7181 Intermediate Similarity NPC169402
0.7178 Intermediate Similarity NPC118511
0.7175 Intermediate Similarity NPC209769
0.7163 Intermediate Similarity NPC475190
0.7162 Intermediate Similarity NPC469439
0.7162 Intermediate Similarity NPC193238
0.716 Intermediate Similarity NPC165964
0.7156 Intermediate Similarity NPC128823
0.7143 Intermediate Similarity NPC303951
0.7137 Intermediate Similarity NPC8022
0.7137 Intermediate Similarity NPC470799
0.7131 Intermediate Similarity NPC67401
0.7131 Intermediate Similarity NPC473187
0.713 Intermediate Similarity NPC39679
0.7129 Intermediate Similarity NPC478032
0.7124 Intermediate Similarity NPC232225
0.7112 Intermediate Similarity NPC473449
0.7109 Intermediate Similarity NPC320394
0.7109 Intermediate Similarity NPC62069
0.7108 Intermediate Similarity NPC282346
0.7095 Intermediate Similarity NPC291609
0.7095 Intermediate Similarity NPC474798
0.7085 Intermediate Similarity NPC4687
0.7085 Intermediate Similarity NPC53344
0.7076 Intermediate Similarity NPC196718
0.7076 Intermediate Similarity NPC102593
0.7054 Intermediate Similarity NPC124300
0.704 Intermediate Similarity NPC472287
0.704 Intermediate Similarity NPC472286
0.7035 Intermediate Similarity NPC9894
0.7025 Intermediate Similarity NPC316224
0.7012 Intermediate Similarity NPC148889
0.7009 Intermediate Similarity NPC470018
0.7009 Intermediate Similarity NPC270918
0.7004 Intermediate Similarity NPC264176
0.7004 Intermediate Similarity NPC472098
0.7004 Intermediate Similarity NPC38237
0.7004 Intermediate Similarity NPC474428
0.6988 Remote Similarity NPC258048
0.6983 Remote Similarity NPC280799
0.6979 Remote Similarity NPC257851
0.6978 Remote Similarity NPC287208
0.6975 Remote Similarity NPC172222
0.6971 Remote Similarity NPC41501
0.6967 Remote Similarity NPC310618
0.6962 Remote Similarity NPC477112
0.6955 Remote Similarity NPC75179
0.6951 Remote Similarity NPC134637
0.6949 Remote Similarity NPC194740
0.6932 Remote Similarity NPC89549
0.6923 Remote Similarity NPC220408
0.692 Remote Similarity NPC470930
0.6916 Remote Similarity NPC470020
0.6912 Remote Similarity NPC469390
0.69 Remote Similarity NPC89508
0.6898 Remote Similarity NPC242928
0.6898 Remote Similarity NPC72715
0.6887 Remote Similarity NPC325705
0.6887 Remote Similarity NPC52831
0.6886 Remote Similarity NPC218303
0.6883 Remote Similarity NPC312645
0.688 Remote Similarity NPC251071
0.688 Remote Similarity NPC472589
0.6878 Remote Similarity NPC246381
0.6878 Remote Similarity NPC472284
0.6872 Remote Similarity NPC185782
0.6867 Remote Similarity NPC128115
0.6867 Remote Similarity NPC472099
0.6867 Remote Similarity NPC472588
0.6863 Remote Similarity NPC470042
0.686 Remote Similarity NPC474183
0.686 Remote Similarity NPC470784
0.6858 Remote Similarity NPC212123
0.6857 Remote Similarity NPC208522
0.6857 Remote Similarity NPC78609
0.6856 Remote Similarity NPC305542
0.6856 Remote Similarity NPC26679
0.6855 Remote Similarity NPC473800
0.6853 Remote Similarity NPC303658
0.6842 Remote Similarity NPC309845
0.684 Remote Similarity NPC472435
0.6838 Remote Similarity NPC60621
0.6837 Remote Similarity NPC241025
0.6835 Remote Similarity NPC157931
0.6835 Remote Similarity NPC74575
0.6833 Remote Similarity NPC90229
0.6832 Remote Similarity NPC26872
0.6828 Remote Similarity NPC82548
0.6827 Remote Similarity NPC189079
0.6826 Remote Similarity NPC74562
0.6826 Remote Similarity NPC316181
0.6826 Remote Similarity NPC30749
0.6826 Remote Similarity NPC476287
0.6826 Remote Similarity NPC151781
0.6825 Remote Similarity NPC129897
0.6825 Remote Similarity NPC84347
0.682 Remote Similarity NPC110741
0.6818 Remote Similarity NPC184680
0.6814 Remote Similarity NPC26850
0.6813 Remote Similarity NPC53534
0.6809 Remote Similarity NPC478141
0.6806 Remote Similarity NPC61350
0.6805 Remote Similarity NPC182222
0.6805 Remote Similarity NPC253675

  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 NPC205372 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
0.8093 Intermediate Similarity NPD2433 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD2779 Approved
0.7725 Intermediate Similarity NPD2778 Approved
0.7709 Intermediate Similarity NPD1505 Phase 2
0.7686 Intermediate Similarity NPD2951 Discontinued
0.7578 Intermediate Similarity NPD6974 Phase 3
0.7566 Intermediate Similarity NPD3925 Approved
0.7555 Intermediate Similarity NPD1467 Approved
0.7555 Intermediate Similarity NPD1466 Phase 3
0.7534 Intermediate Similarity NPD1166 Clinical (unspecified phase)
0.7511 Intermediate Similarity NPD4898 Clinical (unspecified phase)
0.7478 Intermediate Similarity NPD1867 Approved
0.7448 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD3507 Phase 2
0.7415 Intermediate Similarity NPD6716 Phase 1
0.7399 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4667 Clinical (unspecified phase)
0.738 Intermediate Similarity NPD3263 Phase 3
0.7359 Intermediate Similarity NPD5022 Discontinued
0.7356 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD3945 Discontinued
0.7345 Intermediate Similarity NPD3258 Approved
0.7342 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5416 Discontinued
0.7339 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD6247 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD5512 Phase 3
0.7313 Intermediate Similarity NPD7180 Phase 3
0.7293 Intermediate Similarity NPD7547 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7853 Phase 2
0.7249 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD3257 Approved
0.7225 Intermediate Similarity NPD7395 Discontinued
0.7225 Intermediate Similarity NPD4429 Discontinued
0.7222 Intermediate Similarity NPD7031 Phase 1
0.722 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD4328 Approved
0.7174 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5293 Phase 2
0.7168 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD5429 Discontinued
0.7154 Intermediate Similarity NPD1955 Discontinued
0.7124 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7703 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5443 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD2285 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7417 Discontinued
0.7073 Intermediate Similarity NPD8463 Approved
0.7067 Intermediate Similarity NPD3392 Approved
0.7066 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5479 Discontinued
0.7059 Intermediate Similarity NPD3006 Discontinued
0.7049 Intermediate Similarity NPD8102 Discontinued
0.7046 Intermediate Similarity NPD4373 Phase 2
0.7043 Intermediate Similarity NPD3875 Discontinued
0.7037 Intermediate Similarity NPD5488 Discontinued
0.7018 Intermediate Similarity NPD1638 Discovery
0.7014 Intermediate Similarity NPD4204 Approved
0.7014 Intermediate Similarity NPD4203 Approved
0.7009 Intermediate Similarity NPD7222 Phase 2
0.7004 Intermediate Similarity NPD3746 Discontinued
0.7 Intermediate Similarity NPD5632 Approved
0.6992 Remote Similarity NPD4952 Phase 3
0.6992 Remote Similarity NPD5924 Discontinued
0.6971 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6963 Remote Similarity NPD5256 Discontinued
0.6944 Remote Similarity NPD2565 Phase 2
0.6944 Remote Similarity NPD2564 Approved
0.692 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6456 Discontinued
0.6914 Remote Similarity NPD7022 Phase 2
0.6898 Remote Similarity NPD5817 Discontinued
0.6891 Remote Similarity NPD6962 Phase 2
0.6888 Remote Similarity NPD4368 Phase 2
0.6887 Remote Similarity NPD5922 Phase 3
0.6887 Remote Similarity NPD9510 Approved
0.6886 Remote Similarity NPD4502 Phase 2
0.6885 Remote Similarity NPD6495 Clinical (unspecified phase)
0.6883 Remote Similarity NPD3986 Discontinued
0.6883 Remote Similarity NPD5482 Discontinued
0.6872 Remote Similarity NPD6790 Phase 1
0.6864 Remote Similarity NPD5640 Discontinued
0.6864 Remote Similarity NPD7603 Discontinued
0.6858 Remote Similarity NPD7452 Approved
0.6858 Remote Similarity NPD7453 Approved
0.6846 Remote Similarity NPD3250 Phase 1
0.6842 Remote Similarity NPD2081 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5003 Discontinued
0.6828 Remote Similarity NPD7467 Discontinued
0.6827 Remote Similarity NPD5857 Phase 3
0.6818 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6814 Remote Similarity NPD4305 Clinical (unspecified phase)
0.68 Remote Similarity NPD5532 Phase 2
0.6797 Remote Similarity NPD4897 Phase 2
0.6795 Remote Similarity NPD5850 Phase 3
0.6783 Remote Similarity NPD7069 Discontinued
0.6783 Remote Similarity NPD5866 Approved
0.6778 Remote Similarity NPD1659 Phase 1
0.6776 Remote Similarity NPD1483 Discontinued
0.6774 Remote Similarity NPD1936 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4923 Phase 1
0.6765 Remote Similarity NPD3259 Approved
0.6752 Remote Similarity NPD2884 Phase 1
0.675 Remote Similarity NPD7284 Clinical (unspecified phase)
0.6742 Remote Similarity NPD6590 Discontinued
0.6738 Remote Similarity NPD5164 Discontinued
0.6736 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6734 Remote Similarity NPD3328 Phase 2
0.6733 Remote Similarity NPD6252 Clinical (unspecified phase)
0.6723 Remote Similarity NPD7426 Phase 1
0.6722 Remote Similarity NPD7797 Approved
0.6722 Remote Similarity NPD7796 Approved
0.6721 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6714 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6714 Remote Similarity NPD6159 Phase 2
0.6712 Remote Similarity NPD6550 Discontinued
0.6711 Remote Similarity NPD6321 Discontinued
0.6711 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4369 Phase 2
0.6697 Remote Similarity NPD9363 Approved
0.6697 Remote Similarity NPD9364 Phase 2
0.6696 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6694 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6693 Remote Similarity NPD7803 Approved
0.6682 Remote Similarity NPD1229 Phase 2
0.6682 Remote Similarity NPD6988 Phase 1
0.668 Remote Similarity NPD3809 Discontinued
0.668 Remote Similarity NPD6475 Phase 2
0.6667 Remote Similarity NPD4418 Discontinued
0.6667 Remote Similarity NPD7708 Approved
0.6653 Remote Similarity NPD6242 Discontinued
0.6652 Remote Similarity NPD772 Phase 3
0.6652 Remote Similarity NPD5513 Phase 2
0.6627 Remote Similarity NPD7955 Approved
0.6627 Remote Similarity NPD7956 Approved
0.6624 Remote Similarity NPD5507 Approved
0.6624 Remote Similarity NPD5506 Approved
0.6623 Remote Similarity NPD4467 Phase 2
0.6623 Remote Similarity NPD4465 Phase 2
0.6622 Remote Similarity NPD6874 Approved
0.6622 Remote Similarity NPD2175 Phase 3
0.6622 Remote Similarity NPD2177 Approved
0.6622 Remote Similarity NPD2176 Approved
0.6614 Remote Similarity NPD6961 Discontinued
0.6614 Remote Similarity NPD8101 Phase 3
0.6612 Remote Similarity NPD946 Discontinued
0.6609 Remote Similarity NPD2916 Discontinued
0.6609 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6601 Remote Similarity NPD2311 Clinical (unspecified phase)
0.66 Remote Similarity NPD7868 Clinical (unspecified phase)
0.6596 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6594 Remote Similarity NPD3003 Approved
0.6594 Remote Similarity NPD3842 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6591 Remote Similarity NPD9714 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2792 Approved
0.6582 Remote Similarity NPD8479 Phase 2
0.6579 Remote Similarity NPD2920 Discontinued
0.6573 Remote Similarity NPD4322 Discontinued
0.657 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6568 Remote Similarity NPD1926 Approved
0.6566 Remote Similarity NPD7872 Phase 2
0.6564 Remote Similarity NPD5450 Discontinued
0.6552 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6549 Remote Similarity NPD1768 Approved
0.6545 Remote Similarity NPD5805 Approved
0.654 Remote Similarity NPD2899 Discontinued
0.6527 Remote Similarity NPD8356 Approved
0.6525 Remote Similarity NPD4989 Phase 2
0.6523 Remote Similarity NPD8091 Phase 3
0.6522 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7001 Phase 3
0.6518 Remote Similarity NPD6491 Clinical (unspecified phase)
0.6513 Remote Similarity NPD7924 Phase 2
0.6513 Remote Similarity NPD7925 Phase 2
0.6508 Remote Similarity NPD4558 Phase 2
0.6498 Remote Similarity NPD3354 Phase 2
0.6494 Remote Similarity NPD6290 Phase 2
0.6494 Remote Similarity NPD8100 Phase 3
0.6494 Remote Similarity NPD8359 Phase 2
0.649 Remote Similarity NPD4460 Clinical (unspecified phase)
0.6488 Remote Similarity NPD8430 Approved
0.6483 Remote Similarity NPD5612 Discontinued
0.6478 Remote Similarity NPD8157 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6531 Approved
0.6473 Remote Similarity NPD6530 Approved
0.6471 Remote Similarity NPD4353 Phase 2
0.6471 Remote Similarity NPD6393 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7203 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6468 Remote Similarity NPD9362 Approved
0.6468 Remote Similarity NPD3243 Approved
0.6466 Remote Similarity NPD6376 Discontinued
0.6465 Remote Similarity NPD9690 Approved
0.6458 Remote Similarity NPD6209 Approved
0.6453 Remote Similarity NPD5936 Approved
0.6453 Remote Similarity NPD5939 Approved
0.6452 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6452 Remote Similarity NPD3920 Phase 2

  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