Structure

Physi-Chem Properties

Molecular Weight:  372.08
Volume:  358.104
LogP:  4.749
LogD:  2.521
LogS:  -4.144
# Rotatable Bonds:  3
TPSA:  119.36
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.469
Synthetic Accessibility Score:  3.147
Fsp3:  0.211
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.987
MDCK Permeability:  2.012764525716193e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.458
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  98.3616714477539%
Volume Distribution (VD):  0.559
Pgp-substrate:  2.079615831375122%

ADMET: Metabolism

CYP1A2-inhibitor:  0.706
CYP1A2-substrate:  0.716
CYP2C19-inhibitor:  0.405
CYP2C19-substrate:  0.127
CYP2C9-inhibitor:  0.754
CYP2C9-substrate:  0.664
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.183
CYP3A4-inhibitor:  0.311
CYP3A4-substrate:  0.146

ADMET: Excretion

Clearance (CL):  3.022
Half-life (T1/2):  0.406

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.009
Drug-inuced Liver Injury (DILI):  0.384
AMES Toxicity:  0.092
Rat Oral Acute Toxicity:  0.98
Maximum Recommended Daily Dose:  0.933
Skin Sensitization:  0.725
Carcinogencity:  0.029
Eye Corrosion:  0.012
Eye Irritation:  0.949
Respiratory Toxicity:  0.422

Download Data

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

  Natural Product: NPC246716

Natural Product ID:  NPC246716
Common Name*:   Methyl 10-Formyl-3,9-Dihydroxy-1,4,7-Trimethyl-6-Oxobenzo[B][1,4]Benzodioxepine-2-Carboxylate
IUPAC Name:   methyl 10-formyl-3,9-dihydroxy-1,4,7-trimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylate
Synonyms:   NSC-657327
Standard InCHIKey:  HTAATVDZOHXHBE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H16O8/c1-7-5-11(21)10(6-20)17-12(7)19(24)27-16-9(3)14(22)13(18(23)25-4)8(2)15(16)26-17/h5-6,21-22H,1-4H3
SMILES:  Cc1cc(c(C=O)c2c1C(=O)Oc1c(C)c(c(c(C)c1O2)C(=O)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL177021
PubChem CID:   5379546
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001645] Depsides and depsidones

*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
NPO12665 Eunicella verrucosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[1687472]
NPO17287 Lagopsis supina Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24707938]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29192771]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[6114991]
NPO12665 Eunicella verrucosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[7853007]
NPO12930 Apium leptophyllum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8013 Corydalis vaginans Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12930 Apium leptophyllum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12930 Apium leptophyllum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9664 Cortinarius cotoneus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4999 Pentzia grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12066 Mallotus paniculatus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19648 Dalbergia nigrescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10721 Bombax anceps Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11732 Lecanora melanocheila Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12533 Liatris cylindracea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23675 Fumaria microcarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15716 Trichilia hispida Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12665 Eunicella verrucosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9674 Trifolium trichocephalum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17287 Lagopsis supina Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14771 Piper schmidtii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6624 Glycine wightii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12305 Prostanthera sieberi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15799 Phlomis capitata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25377 Ocimum gratissimum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17592 Persea borbonia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12930 Apium leptophyllum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8013 Corydalis vaginans Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26635 Senecio venosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10897 Baccharis ulicina Species Asteraceae 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
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 Inhibition = 96.0 % PMID[470261]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 Inhibition = 97.5 % PMID[470261]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 5400.0 nM PMID[470261]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 4400.0 nM PMID[470261]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 26000.0 nM PMID[470261]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 19998.62 nM PMID[470262]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 45289.76 nM PMID[470262]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 69662.65 nM PMID[470262]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 12531.41 nM PMID[470262]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[470262]

☑ 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 NPC246716 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
0.9937 High Similarity NPC26568
0.9876 High Similarity NPC181523
0.9875 High Similarity NPC20543
0.9875 High Similarity NPC239440
0.9875 High Similarity NPC10576
0.9875 High Similarity NPC1827
0.9874 High Similarity NPC272485
0.9874 High Similarity NPC292788
0.9815 High Similarity NPC139350
0.9693 High Similarity NPC289147
0.9688 High Similarity NPC20216
0.9686 High Similarity NPC156082
0.9636 High Similarity NPC113446
0.963 High Similarity NPC17219
0.9625 High Similarity NPC112981
0.9518 High Similarity NPC470091
0.9518 High Similarity NPC240887
0.9518 High Similarity NPC329161
0.9497 High Similarity NPC143050
0.939 High Similarity NPC109827
0.939 High Similarity NPC124470
0.9383 High Similarity NPC267153
0.9379 High Similarity NPC93739
0.9329 High Similarity NPC49487
0.9329 High Similarity NPC99613
0.9321 High Similarity NPC300984
0.9321 High Similarity NPC284007
0.9321 High Similarity NPC474350
0.9264 High Similarity NPC8070
0.9245 High Similarity NPC149618
0.9245 High Similarity NPC89625
0.9245 High Similarity NPC471800
0.9217 High Similarity NPC158226
0.9207 High Similarity NPC29160
0.9198 High Similarity NPC303565
0.9193 High Similarity NPC83763
0.9193 High Similarity NPC168616
0.9193 High Similarity NPC238381
0.9152 High Similarity NPC234331
0.9096 High Similarity NPC163130
0.9096 High Similarity NPC165979
0.9085 High Similarity NPC197168
0.908 High Similarity NPC66288
0.9068 High Similarity NPC54928
0.9057 High Similarity NPC133856
0.903 High Similarity NPC25361
0.9024 High Similarity NPC108767
0.9018 High Similarity NPC200594
0.9018 High Similarity NPC474287
0.9018 High Similarity NPC475886
0.9018 High Similarity NPC47623
0.9012 High Similarity NPC165977
0.9012 High Similarity NPC217677
0.9 High Similarity NPC273483
0.897 High Similarity NPC270837
0.897 High Similarity NPC234004
0.897 High Similarity NPC236132
0.8963 High Similarity NPC474351
0.8963 High Similarity NPC475883
0.8963 High Similarity NPC474187
0.8963 High Similarity NPC474186
0.8957 High Similarity NPC45846
0.8951 High Similarity NPC146211
0.8951 High Similarity NPC472456
0.8931 High Similarity NPC233267
0.8931 High Similarity NPC291049
0.8909 High Similarity NPC144843
0.8909 High Similarity NPC8300
0.8909 High Similarity NPC294965
0.8902 High Similarity NPC228785
0.8902 High Similarity NPC56085
0.8902 High Similarity NPC14353
0.8882 High Similarity NPC289968
0.8875 High Similarity NPC164527
0.8875 High Similarity NPC213382
0.887 High Similarity NPC214901
0.8868 High Similarity NPC105415
0.8862 High Similarity NPC472452
0.8855 High Similarity NPC7483
0.8848 High Similarity NPC278052
0.8848 High Similarity NPC61010
0.8848 High Similarity NPC40491
0.8841 High Similarity NPC100123
0.8827 High Similarity NPC475895
0.8814 High Similarity NPC220369
0.8812 High Similarity NPC285527
0.8812 High Similarity NPC106334
0.8802 High Similarity NPC85057
0.8802 High Similarity NPC130920
0.8802 High Similarity NPC326520
0.8795 High Similarity NPC229632
0.8788 High Similarity NPC119224
0.8788 High Similarity NPC320359
0.878 High Similarity NPC300727
0.878 High Similarity NPC241904
0.8779 High Similarity NPC207467
0.8765 High Similarity NPC199773
0.8765 High Similarity NPC175978
0.875 High Similarity NPC30027
0.875 High Similarity NPC37870
0.875 High Similarity NPC170245
0.8743 High Similarity NPC477689
0.8743 High Similarity NPC248638
0.8743 High Similarity NPC152659
0.8743 High Similarity NPC236521
0.8743 High Similarity NPC41301
0.8743 High Similarity NPC220313
0.8735 High Similarity NPC266314
0.8728 High Similarity NPC473785
0.8727 High Similarity NPC476242
0.8727 High Similarity NPC85121
0.872 High Similarity NPC274730
0.872 High Similarity NPC142339
0.8712 High Similarity NPC280937
0.8704 High Similarity NPC204350
0.8698 High Similarity NPC6588
0.8698 High Similarity NPC117854
0.8698 High Similarity NPC474024
0.8698 High Similarity NPC477154
0.869 High Similarity NPC275780
0.869 High Similarity NPC472450
0.869 High Similarity NPC239752
0.8683 High Similarity NPC52204
0.8683 High Similarity NPC470694
0.8683 High Similarity NPC25152
0.8679 High Similarity NPC134621
0.8675 High Similarity NPC292415
0.8675 High Similarity NPC299436
0.8675 High Similarity NPC84571
0.8675 High Similarity NPC36217
0.8674 High Similarity NPC154720
0.8667 High Similarity NPC78225
0.8667 High Similarity NPC36852
0.8667 High Similarity NPC44199
0.8667 High Similarity NPC181960
0.8667 High Similarity NPC469584
0.8667 High Similarity NPC262286
0.8667 High Similarity NPC108456
0.8667 High Similarity NPC198163
0.8667 High Similarity NPC476981
0.8667 High Similarity NPC223787
0.8667 High Similarity NPC236796
0.8667 High Similarity NPC263483
0.8663 High Similarity NPC470454
0.8663 High Similarity NPC245975
0.8663 High Similarity NPC199533
0.8659 High Similarity NPC20541
0.8659 High Similarity NPC472909
0.8659 High Similarity NPC82592
0.8659 High Similarity NPC16082
0.8659 High Similarity NPC37392
0.8655 High Similarity NPC475669
0.865 High Similarity NPC217447
0.865 High Similarity NPC475116
0.8642 High Similarity NPC60413
0.8642 High Similarity NPC225129
0.8642 High Similarity NPC119929
0.8639 High Similarity NPC39091
0.8639 High Similarity NPC43319
0.8639 High Similarity NPC272502
0.8634 High Similarity NPC5537
0.8631 High Similarity NPC23298
0.8631 High Similarity NPC207690
0.8631 High Similarity NPC470459
0.8631 High Similarity NPC101769
0.8631 High Similarity NPC475985
0.8631 High Similarity NPC273959
0.8631 High Similarity NPC189473
0.8625 High Similarity NPC237208
0.8625 High Similarity NPC163846
0.8625 High Similarity NPC225173
0.8623 High Similarity NPC103201
0.8623 High Similarity NPC258331
0.8623 High Similarity NPC473106
0.8623 High Similarity NPC311740
0.8623 High Similarity NPC349525
0.8623 High Similarity NPC32694
0.8616 High Similarity NPC95123
0.8616 High Similarity NPC66404
0.8614 High Similarity NPC315157
0.8614 High Similarity NPC250214
0.8614 High Similarity NPC329091
0.8614 High Similarity NPC95936
0.8606 High Similarity NPC191146
0.8606 High Similarity NPC197751
0.8606 High Similarity NPC150227
0.8606 High Similarity NPC227062
0.8606 High Similarity NPC138243
0.8606 High Similarity NPC68093
0.8605 High Similarity NPC233956
0.8598 High Similarity NPC281477
0.8598 High Similarity NPC135522
0.8598 High Similarity NPC276409
0.8598 High Similarity NPC298802
0.8598 High Similarity NPC89474
0.8598 High Similarity NPC75279
0.8598 High Similarity NPC472915
0.8598 High Similarity NPC250822
0.8598 High Similarity NPC186507
0.8596 High Similarity NPC295436

  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 NPC246716 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
0.8909 High Similarity NPD6232 Discontinued
0.8757 High Similarity NPD5844 Phase 1
0.875 High Similarity NPD7473 Discontinued
0.8485 Intermediate Similarity NPD2801 Approved
0.8447 Intermediate Similarity NPD2532 Approved
0.8447 Intermediate Similarity NPD2533 Approved
0.8447 Intermediate Similarity NPD2534 Approved
0.8373 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD7819 Suspended
0.8323 Intermediate Similarity NPD3817 Phase 2
0.8313 Intermediate Similarity NPD1934 Approved
0.8274 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD1465 Phase 2
0.8235 Intermediate Similarity NPD5494 Approved
0.8187 Intermediate Similarity NPD6959 Discontinued
0.8166 Intermediate Similarity NPD3882 Suspended
0.8136 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD3226 Approved
0.8118 Intermediate Similarity NPD7075 Discontinued
0.8081 Intermediate Similarity NPD1247 Approved
0.8075 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD919 Approved
0.8066 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8057 Intermediate Similarity NPD3818 Discontinued
0.8046 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD6166 Phase 2
0.8036 Intermediate Similarity NPD7411 Suspended
0.8 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD6559 Discontinued
0.7976 Intermediate Similarity NPD6599 Discontinued
0.7966 Intermediate Similarity NPD7074 Phase 3
0.795 Intermediate Similarity NPD2935 Discontinued
0.795 Intermediate Similarity NPD1551 Phase 2
0.7941 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1511 Approved
0.791 Intermediate Similarity NPD7054 Approved
0.7895 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6801 Discontinued
0.7882 Intermediate Similarity NPD37 Approved
0.787 Intermediate Similarity NPD4380 Phase 2
0.7865 Intermediate Similarity NPD7472 Approved
0.7861 Intermediate Similarity NPD6234 Discontinued
0.7849 Intermediate Similarity NPD4966 Approved
0.7849 Intermediate Similarity NPD4965 Approved
0.7849 Intermediate Similarity NPD4967 Phase 2
0.7844 Intermediate Similarity NPD1512 Approved
0.7841 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD6799 Approved
0.7829 Intermediate Similarity NPD5711 Approved
0.7829 Intermediate Similarity NPD5710 Approved
0.7821 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD920 Approved
0.7791 Intermediate Similarity NPD5402 Approved
0.7784 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7768 Phase 2
0.7735 Intermediate Similarity NPD7808 Phase 3
0.7722 Intermediate Similarity NPD6797 Phase 2
0.7702 Intermediate Similarity NPD447 Suspended
0.7701 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD3749 Approved
0.7683 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD2346 Discontinued
0.768 Intermediate Similarity NPD7251 Discontinued
0.7679 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD7199 Phase 2
0.7669 Intermediate Similarity NPD2799 Discontinued
0.7654 Intermediate Similarity NPD1607 Approved
0.7651 Intermediate Similarity NPD3750 Approved
0.7651 Intermediate Similarity NPD4628 Phase 3
0.7636 Intermediate Similarity NPD1549 Phase 2
0.7611 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD230 Phase 1
0.7592 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD2800 Approved
0.759 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD3926 Phase 2
0.7584 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD8434 Phase 2
0.7561 Intermediate Similarity NPD1510 Phase 2
0.7561 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD7228 Approved
0.7531 Intermediate Similarity NPD1240 Approved
0.7527 Intermediate Similarity NPD5953 Discontinued
0.7516 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7390 Discontinued
0.7515 Intermediate Similarity NPD2796 Approved
0.7514 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8312 Approved
0.75 Intermediate Similarity NPD8313 Approved
0.7485 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7783 Phase 2
0.744 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD7286 Phase 2
0.7407 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7435 Discontinued
0.7384 Intermediate Similarity NPD5403 Approved
0.738 Intermediate Similarity NPD8150 Discontinued
0.7374 Intermediate Similarity NPD8151 Discontinued
0.7349 Intermediate Similarity NPD3748 Approved
0.7341 Intermediate Similarity NPD1653 Approved
0.7337 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7229 Phase 3
0.732 Intermediate Similarity NPD6776 Approved
0.732 Intermediate Similarity NPD6779 Approved
0.732 Intermediate Similarity NPD6780 Approved
0.732 Intermediate Similarity NPD6781 Approved
0.732 Intermediate Similarity NPD6777 Approved
0.732 Intermediate Similarity NPD6778 Approved
0.732 Intermediate Similarity NPD6782 Approved
0.7317 Intermediate Similarity NPD943 Approved
0.731 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD6100 Approved
0.7305 Intermediate Similarity NPD6099 Approved
0.7299 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD5242 Approved
0.7284 Intermediate Similarity NPD6832 Phase 2
0.7267 Intermediate Similarity NPD5401 Approved
0.7246 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD6651 Approved
0.7212 Intermediate Similarity NPD4060 Phase 1
0.7208 Intermediate Similarity NPD7697 Approved
0.7208 Intermediate Similarity NPD7698 Approved
0.7208 Intermediate Similarity NPD7696 Phase 3
0.7205 Intermediate Similarity NPD1203 Approved
0.7204 Intermediate Similarity NPD7240 Approved
0.7202 Intermediate Similarity NPD5408 Approved
0.7202 Intermediate Similarity NPD5406 Approved
0.7202 Intermediate Similarity NPD5405 Approved
0.7202 Intermediate Similarity NPD5404 Approved
0.7195 Intermediate Similarity NPD2313 Discontinued
0.7193 Intermediate Similarity NPD6190 Approved
0.7182 Intermediate Similarity NPD8127 Discontinued
0.7174 Intermediate Similarity NPD3751 Discontinued
0.7172 Intermediate Similarity NPD7870 Phase 2
0.7172 Intermediate Similarity NPD7871 Phase 2
0.7169 Intermediate Similarity NPD1933 Approved
0.7169 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7874 Approved
0.7164 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3787 Discontinued
0.7134 Intermediate Similarity NPD3027 Phase 3
0.7134 Intermediate Similarity NPD4625 Phase 3
0.7126 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD9494 Approved
0.7117 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1613 Approved
0.7108 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7458 Discontinued
0.7101 Intermediate Similarity NPD4477 Approved
0.7101 Intermediate Similarity NPD4476 Approved
0.7101 Intermediate Similarity NPD2438 Suspended
0.7095 Intermediate Similarity NPD5353 Approved
0.7091 Intermediate Similarity NPD3268 Approved
0.7091 Intermediate Similarity NPD411 Approved
0.7081 Intermediate Similarity NPD7177 Discontinued
0.7074 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD6823 Phase 2
0.7065 Intermediate Similarity NPD7701 Phase 2
0.7062 Intermediate Similarity NPD6535 Approved
0.7062 Intermediate Similarity NPD6534 Approved
0.7059 Intermediate Similarity NPD2344 Approved
0.7059 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4308 Phase 3
0.7037 Intermediate Similarity NPD1283 Approved
0.7035 Intermediate Similarity NPD7003 Approved
0.7029 Intermediate Similarity NPD6273 Approved
0.7022 Intermediate Similarity NPD6386 Approved
0.7022 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD6385 Approved
0.7021 Intermediate Similarity NPD7685 Pre-registration
0.7019 Intermediate Similarity NPD1608 Approved
0.7019 Intermediate Similarity NPD9717 Approved
0.7006 Intermediate Similarity NPD2979 Phase 3
0.7005 Intermediate Similarity NPD8285 Discontinued
0.7 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2797 Approved
0.699 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6984 Remote Similarity NPD7549 Discontinued
0.6978 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7801 Approved
0.6957 Remote Similarity NPD1611 Approved
0.6957 Remote Similarity NPD422 Phase 1
0.6954 Remote Similarity NPD7699 Phase 2
0.6954 Remote Similarity NPD7700 Phase 2
0.6941 Remote Similarity NPD7033 Discontinued
0.6937 Remote Similarity NPD4626 Approved
0.6936 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6936 Remote Similarity NPD4110 Phase 3
0.6931 Remote Similarity NPD7038 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