Structure

Physi-Chem Properties

Molecular Weight:  156.04
Volume:  142.403
LogP:  -0.742
LogD:  -1.521
LogS:  -0.95
# Rotatable Bonds:  1
TPSA:  66.9
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.489
Synthetic Accessibility Score:  4.371
Fsp3:  0.714
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.72
MDCK Permeability:  0.0001971909950952977
Pgp-inhibitor:  0.023
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.04
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.224
Plasma Protein Binding (PPB):  23.63761329650879%
Volume Distribution (VD):  0.97
Pgp-substrate:  83.57755279541016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.278
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.175
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.115
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.195
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.13

ADMET: Excretion

Clearance (CL):  7.407
Half-life (T1/2):  0.857

ADMET: Toxicity

hERG Blockers:  0.093
Human Hepatotoxicity (H-HT):  0.103
Drug-inuced Liver Injury (DILI):  0.833
AMES Toxicity:  0.075
Rat Oral Acute Toxicity:  0.809
Maximum Recommended Daily Dose:  0.015
Skin Sensitization:  0.39
Carcinogencity:  0.272
Eye Corrosion:  0.96
Eye Irritation:  0.941
Respiratory Toxicity:  0.071

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

  Natural Product: NPC159714

Natural Product ID:  NPC159714
Common Name*:   Epoxydon
IUPAC Name:   (1R,2R,6R)-2-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-5-one
Synonyms:   (+)-Epoxydon; Epoxydon
Standard InCHIKey:  VTLJDPHPVHSVGR-QXRNQMCJSA-N
Standard InCHI:  InChI=1S/C7H8O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,4,6-9H,2H2/t4-,6-,7+/m1/s1
SMILES:  OCC1=C[C@@H](O)[C@@H]2[C@H](C1=O)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL477749
PubChem CID:   72629
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0004325] Cyclohexenones

*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
NPO32983 nigrospora sp. psu-f5 Species Trichosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[18646829]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[21953622]
NPO13741 Sisymbrium officinale Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[23193942]
NPO3802 Pisolithus tinctorius Species Pisolithaceae Eukaryota n.a. n.a. n.a. PMID[24997926]
NPO40268 Penicillium concentricum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[28409637]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota Twigs n.a. n.a. PMID[32520551]
NPO3802 Pisolithus tinctorius Species Pisolithaceae Eukaryota n.a. n.a. n.a. PMID[9951730]
NPO13741 Sisymbrium officinale Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15681 Dalbergia obtusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3802 Pisolithus tinctorius Species Pisolithaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13741 Sisymbrium officinale Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14443 Penstemon teucrioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16457 Melaleuca viminea Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23378 Eriocephalus punctulatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15681 Dalbergia obtusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO655 Maximowiczia sonorae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13094 Lippia integrifolia Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3802 Pisolithus tinctorius Species Pisolithaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15045 Ophiorrhiza kunstleri Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6875 Tabebuia chrysantha Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11381 Munchausia speciosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13741 Sisymbrium officinale Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20501 Ips cembrae Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15885 Stachys chrysantha Species Lamiaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 18407.72 nM PMID[515755]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 90157.11 nM PMID[515755]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 65614.53 nM PMID[515755]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 26001.6 nM PMID[515755]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 75509.22 nM PMID[515755]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 61517.69 nM PMID[515755]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 37931.5 nM PMID[515755]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 33265.96 nM PMID[515755]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 17701.09 nM PMID[515755]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 23067.47 nM PMID[515755]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 98855.31 nM PMID[515755]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 77268.06 nM PMID[515755]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 37411.06 nM PMID[515755]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 31117.16 nM PMID[515755]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 21677.04 nM PMID[515755]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 53088.44 nM PMID[515755]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 25176.77 nM PMID[515755]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 39810.72 nM PMID[515755]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 30690.22 nM PMID[515755]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[515755]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 14100.0 nM PMID[515756]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 5700.0 nM PMID[515756]
NPT4395 Organism Rheum x hybridum Rheum x hybridum Activity = 27.0 mm2 PMID[515753]
NPT4396 Organism Sorghum bicolor Sorghum bicolor Activity = 31.0 mm2 PMID[515753]
NPT2233 Organism Sida spinosa Sida spinosa Activity = 25.0 mm2 PMID[515753]
NPT4397 Organism Ipomoea Ipomoea Activity = 51.0 mm2 PMID[515753]
NPT2235 Organism Datura stramonium Datura stramonium Activity = 31.0 mm2 PMID[515753]
NPT2236 Organism Sorghum halepense Sorghum halepense Activity = 37.0 mm2 PMID[515753]
NPT2232 Organism Senna obtusifolia Senna obtusifolia Activity = 17.0 mm2 PMID[515753]
NPT125 Organism Chenopodium album Chenopodium album Activity = 62.0 mm2 PMID[515753]
NPT19 Organism Escherichia coli Escherichia coli IZ = 18.0 mm PMID[515753]
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens IZ = 10.0 mm PMID[515753]
NPT2240 Organism Curtobacterium flaccumfaciens Curtobacterium flaccumfaciens IZ = 12.0 mm PMID[515753]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum IZ = 9.0 mm PMID[515753]
NPT185 Organism Aspergillus flavus Aspergillus flavus IZ = 0.0 mm PMID[515753]
NPT2242 Organism Penicillium chrysogenum Penicillium chrysogenum IZ = 0.0 mm PMID[515753]
NPT2241 Organism Glomerella acutata Glomerella acutata IZ = 10.0 mm PMID[515753]
NPT19 Organism Escherichia coli Escherichia coli IZ = 25.3 mm PMID[515753]
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens IZ = 12.0 mm PMID[515753]
NPT2240 Organism Curtobacterium flaccumfaciens Curtobacterium flaccumfaciens IZ = 20.0 mm PMID[515753]
NPT1286 Organism Pectobacterium carotovorum Pectobacterium carotovorum IZ = 17.0 mm PMID[515753]
NPT185 Organism Aspergillus flavus Aspergillus flavus IZ = 8.0 mm PMID[515753]
NPT2242 Organism Penicillium chrysogenum Penicillium chrysogenum IZ = 10.0 mm PMID[515753]
NPT2241 Organism Glomerella acutata Glomerella acutata IZ = 12.0 mm PMID[515753]
NPT2238 Organism Nasturtium officinale Nasturtium officinale Activity = 41.0 mm2 PMID[515753]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 128.0 ug.mL-1 PMID[515754]

☑ 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 NPC159714 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
1.0 High Similarity NPC221510
0.9615 High Similarity NPC469809
0.961 High Similarity NPC253364
0.9211 High Similarity NPC272267
0.8642 High Similarity NPC47450
0.7979 Intermediate Similarity NPC39996
0.7895 Intermediate Similarity NPC104161
0.7895 Intermediate Similarity NPC118902
0.7895 Intermediate Similarity NPC472072
0.7895 Intermediate Similarity NPC469980
0.7816 Intermediate Similarity NPC196381
0.7805 Intermediate Similarity NPC141195
0.7805 Intermediate Similarity NPC47844
0.7692 Intermediate Similarity NPC327620
0.7667 Intermediate Similarity NPC477684
0.7653 Intermediate Similarity NPC266514
0.759 Intermediate Similarity NPC473536
0.75 Intermediate Similarity NPC187529
0.75 Intermediate Similarity NPC77971
0.7327 Intermediate Similarity NPC87335
0.732 Intermediate Similarity NPC207885
0.7284 Intermediate Similarity NPC107848
0.7262 Intermediate Similarity NPC474197
0.7245 Intermediate Similarity NPC478176
0.7229 Intermediate Similarity NPC474545
0.7229 Intermediate Similarity NPC24590
0.7228 Intermediate Similarity NPC264819
0.7204 Intermediate Similarity NPC476705
0.7191 Intermediate Similarity NPC316819
0.7188 Intermediate Similarity NPC471916
0.7184 Intermediate Similarity NPC317107
0.7143 Intermediate Similarity NPC472007
0.7143 Intermediate Similarity NPC112613
0.7125 Intermediate Similarity NPC251429
0.7115 Intermediate Similarity NPC317687
0.7093 Intermediate Similarity NPC318481
0.7087 Intermediate Similarity NPC89408
0.7083 Intermediate Similarity NPC279722
0.7079 Intermediate Similarity NPC477786
0.7079 Intermediate Similarity NPC477784
0.7079 Intermediate Similarity NPC477785
0.7033 Intermediate Similarity NPC472009
0.7021 Intermediate Similarity NPC303230
0.7021 Intermediate Similarity NPC327760
0.7021 Intermediate Similarity NPC114345
0.7021 Intermediate Similarity NPC6099
0.7011 Intermediate Similarity NPC291260
0.701 Intermediate Similarity NPC20066
0.7 Intermediate Similarity NPC131366
0.7 Intermediate Similarity NPC474251
0.697 Remote Similarity NPC164598
0.697 Remote Similarity NPC474339
0.6962 Remote Similarity NPC475221
0.6939 Remote Similarity NPC306908
0.6939 Remote Similarity NPC281608
0.6939 Remote Similarity NPC300584
0.6939 Remote Similarity NPC475284
0.6915 Remote Similarity NPC471399
0.6897 Remote Similarity NPC68119
0.6897 Remote Similarity NPC13823
0.6893 Remote Similarity NPC322903
0.6882 Remote Similarity NPC119740
0.6882 Remote Similarity NPC476707
0.6882 Remote Similarity NPC476706
0.6882 Remote Similarity NPC150063
0.6882 Remote Similarity NPC287089
0.6882 Remote Similarity NPC472008
0.6875 Remote Similarity NPC121825
0.6869 Remote Similarity NPC475949
0.6867 Remote Similarity NPC202011
0.6854 Remote Similarity NPC67254
0.6842 Remote Similarity NPC142838
0.6842 Remote Similarity NPC475441
0.6824 Remote Similarity NPC326504
0.6809 Remote Similarity NPC14901
0.6809 Remote Similarity NPC130359
0.6796 Remote Similarity NPC469853
0.6782 Remote Similarity NPC475711
0.6778 Remote Similarity NPC310450
0.6778 Remote Similarity NPC474959
0.6778 Remote Similarity NPC11383
0.6778 Remote Similarity NPC475046
0.6774 Remote Similarity NPC471738
0.6774 Remote Similarity NPC23622
0.6771 Remote Similarity NPC469692
0.6771 Remote Similarity NPC469645
0.6768 Remote Similarity NPC161855
0.6744 Remote Similarity NPC473582
0.6744 Remote Similarity NPC161038
0.6742 Remote Similarity NPC162741
0.6742 Remote Similarity NPC91332
0.6739 Remote Similarity NPC182383
0.6737 Remote Similarity NPC274075
0.6735 Remote Similarity NPC94337
0.6735 Remote Similarity NPC473291
0.6733 Remote Similarity NPC471148
0.6703 Remote Similarity NPC286770
0.6703 Remote Similarity NPC185256
0.6703 Remote Similarity NPC284472
0.6703 Remote Similarity NPC229799
0.67 Remote Similarity NPC324667
0.6667 Remote Similarity NPC473687
0.6667 Remote Similarity NPC473624
0.6667 Remote Similarity NPC308412
0.6667 Remote Similarity NPC77089
0.6667 Remote Similarity NPC80650
0.6667 Remote Similarity NPC134807
0.6667 Remote Similarity NPC219498
0.6667 Remote Similarity NPC297440
0.6667 Remote Similarity NPC134885
0.6667 Remote Similarity NPC146852
0.6667 Remote Similarity NPC204686
0.6667 Remote Similarity NPC210218
0.6667 Remote Similarity NPC205615
0.6667 Remote Similarity NPC47937
0.6667 Remote Similarity NPC16279
0.6667 Remote Similarity NPC236176
0.6667 Remote Similarity NPC472755
0.6667 Remote Similarity NPC256640
0.6635 Remote Similarity NPC477513
0.6634 Remote Similarity NPC133907
0.6634 Remote Similarity NPC201718
0.6634 Remote Similarity NPC46998
0.6634 Remote Similarity NPC476270
0.6634 Remote Similarity NPC185141
0.6634 Remote Similarity NPC128733
0.6634 Remote Similarity NPC110443
0.663 Remote Similarity NPC32676
0.6628 Remote Similarity NPC473489
0.6604 Remote Similarity NPC161816
0.6604 Remote Similarity NPC115257
0.6602 Remote Similarity NPC474741
0.66 Remote Similarity NPC471144
0.66 Remote Similarity NPC35717
0.6598 Remote Similarity NPC273579
0.6598 Remote Similarity NPC61275
0.6598 Remote Similarity NPC295204
0.6598 Remote Similarity NPC288240
0.6598 Remote Similarity NPC162205
0.6596 Remote Similarity NPC178215
0.6591 Remote Similarity NPC471061
0.6591 Remote Similarity NPC97173
0.6591 Remote Similarity NPC275530
0.6591 Remote Similarity NPC82666
0.6571 Remote Similarity NPC474664
0.6571 Remote Similarity NPC233379
0.6571 Remote Similarity NPC14862
0.6566 Remote Similarity NPC477921
0.6562 Remote Similarity NPC474232
0.6562 Remote Similarity NPC469464
0.6559 Remote Similarity NPC110710
0.6559 Remote Similarity NPC132496
0.6559 Remote Similarity NPC68303
0.6559 Remote Similarity NPC307126
0.6559 Remote Similarity NPC66346
0.6559 Remote Similarity NPC473651
0.6559 Remote Similarity NPC82795
0.6559 Remote Similarity NPC103284
0.6559 Remote Similarity NPC1083
0.6559 Remote Similarity NPC286338
0.6559 Remote Similarity NPC473478
0.6559 Remote Similarity NPC473669
0.6559 Remote Similarity NPC223871
0.6559 Remote Similarity NPC231009
0.6559 Remote Similarity NPC283085
0.6559 Remote Similarity NPC107986
0.6556 Remote Similarity NPC470945
0.6556 Remote Similarity NPC470947
0.6556 Remote Similarity NPC470946
0.6548 Remote Similarity NPC94488
0.6548 Remote Similarity NPC475982
0.6548 Remote Similarity NPC130618
0.6545 Remote Similarity NPC27999
0.6545 Remote Similarity NPC477116
0.6542 Remote Similarity NPC476023
0.6538 Remote Similarity NPC314244
0.6538 Remote Similarity NPC469852
0.6535 Remote Similarity NPC288876
0.6531 Remote Similarity NPC217624
0.6531 Remote Similarity NPC181393
0.6526 Remote Similarity NPC87189
0.6526 Remote Similarity NPC40376
0.6526 Remote Similarity NPC48338
0.6526 Remote Similarity NPC280621
0.6526 Remote Similarity NPC228415
0.6526 Remote Similarity NPC21208
0.6526 Remote Similarity NPC233551
0.6526 Remote Similarity NPC20339
0.6522 Remote Similarity NPC116543
0.6522 Remote Similarity NPC225049
0.6517 Remote Similarity NPC478122
0.6517 Remote Similarity NPC248775
0.6517 Remote Similarity NPC231739
0.6509 Remote Similarity NPC15218
0.6509 Remote Similarity NPC471400
0.6509 Remote Similarity NPC475922
0.6505 Remote Similarity NPC475871
0.6505 Remote Similarity NPC475945
0.65 Remote Similarity NPC266842
0.6495 Remote Similarity NPC472010

  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 NPC159714 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
0.6889 Remote Similarity NPD6110 Phase 1
0.6562 Remote Similarity NPD46 Approved
0.6562 Remote Similarity NPD6698 Approved
0.6404 Remote Similarity NPD4756 Discovery
0.6292 Remote Similarity NPD818 Approved
0.6292 Remote Similarity NPD819 Approved
0.6275 Remote Similarity NPD4225 Approved
0.6224 Remote Similarity NPD7838 Discovery
0.619 Remote Similarity NPD3704 Approved
0.6162 Remote Similarity NPD7983 Approved
0.6154 Remote Similarity NPD5344 Discontinued
0.6147 Remote Similarity NPD6371 Approved
0.6106 Remote Similarity NPD7115 Discovery
0.6042 Remote Similarity NPD1696 Phase 3
0.604 Remote Similarity NPD5282 Discontinued
0.6024 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6019 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5976 Remote Similarity NPD9120 Clinical (unspecified phase)
0.5946 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5941 Remote Similarity NPD5778 Approved
0.5941 Remote Similarity NPD5779 Approved
0.5814 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5812 Remote Similarity NPD6319 Approved
0.581 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5755 Remote Similarity NPD6648 Approved
0.5714 Remote Similarity NPD4634 Approved
0.5714 Remote Similarity NPD5363 Approved
0.5684 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5678 Remote Similarity NPD6054 Approved
0.5673 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5667 Remote Similarity NPD8328 Phase 3
0.5658 Remote Similarity NPD9005 Phase 3
0.5658 Remote Similarity NPD9003 Clinical (unspecified phase)
0.5658 Remote Similarity NPD9004 Approved
0.563 Remote Similarity NPD6015 Approved
0.563 Remote Similarity NPD6016 Approved
0.561 Remote Similarity NPD8959 Approved

  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