Structure

Physi-Chem Properties

Molecular Weight:  293.14
Volume:  313.076
LogP:  4.728
LogD:  3.371
LogS:  -5.75
# Rotatable Bonds:  3
TPSA:  21.7
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.685
Synthetic Accessibility Score:  2.31
Fsp3:  0.263
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.431
MDCK Permeability:  2.6078616429003887e-05
Pgp-inhibitor:  0.676
Pgp-substrate:  0.513
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.986
Plasma Protein Binding (PPB):  93.67986297607422%
Volume Distribution (VD):  3.214
Pgp-substrate:  1.5966488122940063%

ADMET: Metabolism

CYP1A2-inhibitor:  0.985
CYP1A2-substrate:  0.923
CYP2C19-inhibitor:  0.145
CYP2C19-substrate:  0.962
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.849
CYP2D6-inhibitor:  0.988
CYP2D6-substrate:  0.953
CYP3A4-inhibitor:  0.727
CYP3A4-substrate:  0.645

ADMET: Excretion

Clearance (CL):  14.733
Half-life (T1/2):  0.081

ADMET: Toxicity

hERG Blockers:  0.968
Human Hepatotoxicity (H-HT):  0.558
Drug-inuced Liver Injury (DILI):  0.875
AMES Toxicity:  0.873
Rat Oral Acute Toxicity:  0.578
Maximum Recommended Daily Dose:  0.852
Skin Sensitization:  0.92
Carcinogencity:  0.624
Eye Corrosion:  0.01
Eye Irritation:  0.033
Respiratory Toxicity:  0.96

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  Natural Product: NPC145304

Natural Product ID:  NPC145304
Common Name*:   N,N-Dimethyl-2-Naphtho[2,1-G][1,3]Benzodioxol-5-Ylethanamine
IUPAC Name:   N,N-dimethyl-2-naphtho[2,1-g][1,3]benzodioxol-5-ylethanamine
Synonyms:  
Standard InCHIKey:  FXTBDJZGDJJCQU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H19NO2/c1-20(2)10-9-14-11-17-19(22-12-21-17)18-15-6-4-3-5-13(15)7-8-16(14)18/h3-8,11H,9-10,12H2,1-2H3/p+1
SMILES:  C[NH+](C)CCc1cc2c(c3c4ccccc4ccc13)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL492418
PubChem CID:   161379
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0003332] 6,6a-secoaporphines

*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
NPO1179 Anaxagorea luzonensis Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10959592]
NPO755 Phoradendron reichenbachianum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[11488459]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. root n.a. PMID[20030508]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota Aerial parts n.a. n.a. PMID[20426456]
NPO3148 Melianthus major Species Melianthaceae Eukaryota Leaves n.a. n.a. PMID[32663024]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[3728032]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9392886]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12183 Argyreia nervosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11802 Physeter catodon Species Physeteridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12183 Argyreia nervosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11802 Physeter catodon Species Physeteridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12183 Argyreia nervosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11802 Physeter catodon Species Physeteridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12773 Stephania tetrandra Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO755 Phoradendron reichenbachianum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12882 Clitocybe fasciculata Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5783 Acronychia muelleri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11351 Stephania japonica Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1179 Anaxagorea luzonensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21826 Vulpicida juniperinus Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21685 Magnolia coco Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15367 Croton regelianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18003 Leptolyngbya lurida Species Leptolyngbyaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO28111 Lathyrus aphaca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3148 Melianthus major Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2679 Dictyota bartayresiana Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12663 Penicillium implicatum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11802 Physeter catodon Species Physeteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5377 Tapinoma erraticum Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22389 Phelipanche arenaria Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12430 Erythrina chiriquensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12183 Argyreia nervosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12773 Stephania tetrandra Species Menispermaceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[483216]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 12589.3 nM PMID[483216]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[483216]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 7062.7 nM PMID[483216]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 1258.9 nM PMID[483216]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 39810.7 nM PMID[483216]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus Ki = 64.71 nM PMID[483217]
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Ki = 4140.0 nM PMID[483217]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus Ki = 66.0 nM PMID[483217]
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Ki = 6347.0 nM PMID[483217]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 22387.2 nM PMID[483216]
NPT334 Organism Vaccinia virus Vaccinia virus IC50 = 5400.0 nM PMID[483214]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 = 6300.0 nM PMID[483215]
NPT2 Others Unspecified Inhibition = 1.9 % PMID[483215]
NPT2 Others Unspecified Ratio = 0.86 n.a. PMID[483215]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[483216]
NPT2 Others Unspecified Ratio Ki = 96.0 n.a. PMID[483217]
NPT2 Others Unspecified Potency n.a. 17782.8 nM PMID[483216]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[483216]
NPT25760 SINGLE PROTEIN DNA polymerase Vaccinia virus (strain Western Reserve) (VACV) (Vaccinia virus (strainWR)) IC50 = 5400.0 nM PMID[483218]

☑ 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 NPC145304 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
0.9714 High Similarity NPC211296
0.8874 High Similarity NPC266753
0.8874 High Similarity NPC477559
0.8874 High Similarity NPC306902
0.8874 High Similarity NPC160298
0.8874 High Similarity NPC232924
0.8859 High Similarity NPC76079
0.8824 High Similarity NPC100129
0.8776 High Similarity NPC219162
0.8701 High Similarity NPC225774
0.8645 High Similarity NPC24264
0.8645 High Similarity NPC476432
0.8645 High Similarity NPC219341
0.8639 High Similarity NPC90844
0.8639 High Similarity NPC95075
0.8639 High Similarity NPC253883
0.8609 High Similarity NPC244112
0.8601 High Similarity NPC210086
0.859 High Similarity NPC298979
0.859 High Similarity NPC247389
0.8581 High Similarity NPC475959
0.8581 High Similarity NPC167546
0.8581 High Similarity NPC16805
0.8581 High Similarity NPC130941
0.8581 High Similarity NPC302527
0.8535 High Similarity NPC241055
0.8526 High Similarity NPC86144
0.8526 High Similarity NPC304659
0.8523 High Similarity NPC92541
0.8487 Intermediate Similarity NPC41178
0.8487 Intermediate Similarity NPC216459
0.8487 Intermediate Similarity NPC138487
0.8477 Intermediate Similarity NPC114124
0.8471 Intermediate Similarity NPC210918
0.8462 Intermediate Similarity NPC168409
0.8442 Intermediate Similarity NPC477080
0.8431 Intermediate Similarity NPC146288
0.8411 Intermediate Similarity NPC326316
0.8411 Intermediate Similarity NPC81733
0.8406 Intermediate Similarity NPC17348
0.8397 Intermediate Similarity NPC189470
0.8389 Intermediate Similarity NPC144863
0.8366 Intermediate Similarity NPC93593
0.8355 Intermediate Similarity NPC26601
0.8344 Intermediate Similarity NPC179704
0.8333 Intermediate Similarity NPC7018
0.8313 Intermediate Similarity NPC149090
0.8313 Intermediate Similarity NPC19520
0.8312 Intermediate Similarity NPC234392
0.8312 Intermediate Similarity NPC31311
0.8286 Intermediate Similarity NPC177167
0.8272 Intermediate Similarity NPC287588
0.8264 Intermediate Similarity NPC11147
0.825 Intermediate Similarity NPC6152
0.8235 Intermediate Similarity NPC233029
0.8235 Intermediate Similarity NPC210148
0.8221 Intermediate Similarity NPC320223
0.8221 Intermediate Similarity NPC114364
0.8217 Intermediate Similarity NPC60186
0.821 Intermediate Similarity NPC128560
0.821 Intermediate Similarity NPC199465
0.821 Intermediate Similarity NPC229166
0.8194 Intermediate Similarity NPC186063
0.8182 Intermediate Similarity NPC118419
0.8182 Intermediate Similarity NPC249405
0.8171 Intermediate Similarity NPC126284
0.8165 Intermediate Similarity NPC233650
0.8163 Intermediate Similarity NPC314682
0.8158 Intermediate Similarity NPC77359
0.8146 Intermediate Similarity NPC16436
0.8141 Intermediate Similarity NPC476572
0.8137 Intermediate Similarity NPC152212
0.8129 Intermediate Similarity NPC325871
0.8129 Intermediate Similarity NPC99659
0.8117 Intermediate Similarity NPC148898
0.8113 Intermediate Similarity NPC238530
0.8113 Intermediate Similarity NPC232514
0.8113 Intermediate Similarity NPC134858
0.8113 Intermediate Similarity NPC276944
0.8108 Intermediate Similarity NPC188163
0.8108 Intermediate Similarity NPC213206
0.8108 Intermediate Similarity NPC328750
0.8108 Intermediate Similarity NPC474915
0.8095 Intermediate Similarity NPC474904
0.8077 Intermediate Similarity NPC126519
0.8077 Intermediate Similarity NPC203784
0.8077 Intermediate Similarity NPC170503
0.8072 Intermediate Similarity NPC248642
0.8061 Intermediate Similarity NPC267408
0.8049 Intermediate Similarity NPC112575
0.8038 Intermediate Similarity NPC27410
0.8038 Intermediate Similarity NPC166014
0.8028 Intermediate Similarity NPC172403
0.8026 Intermediate Similarity NPC16107
0.8026 Intermediate Similarity NPC210437
0.8026 Intermediate Similarity NPC476151
0.8026 Intermediate Similarity NPC476144
0.8026 Intermediate Similarity NPC51957
0.8026 Intermediate Similarity NPC106295
0.8024 Intermediate Similarity NPC156576
0.8013 Intermediate Similarity NPC78733
0.8012 Intermediate Similarity NPC32413
0.8012 Intermediate Similarity NPC150879
0.8012 Intermediate Similarity NPC474506
0.8012 Intermediate Similarity NPC210140
0.8 Intermediate Similarity NPC294790
0.8 Intermediate Similarity NPC148693
0.8 Intermediate Similarity NPC23219
0.8 Intermediate Similarity NPC227002
0.8 Intermediate Similarity NPC118633
0.7988 Intermediate Similarity NPC477558
0.7988 Intermediate Similarity NPC312531
0.7975 Intermediate Similarity NPC111485
0.7974 Intermediate Similarity NPC7467
0.7974 Intermediate Similarity NPC59907
0.7974 Intermediate Similarity NPC37144
0.7973 Intermediate Similarity NPC196420
0.7971 Intermediate Similarity NPC344161
0.7964 Intermediate Similarity NPC116284
0.7959 Intermediate Similarity NPC231884
0.7959 Intermediate Similarity NPC42793
0.7959 Intermediate Similarity NPC167944
0.7953 Intermediate Similarity NPC302001
0.7952 Intermediate Similarity NPC258695
0.7952 Intermediate Similarity NPC470879
0.7935 Intermediate Similarity NPC52475
0.7931 Intermediate Similarity NPC471983
0.7931 Intermediate Similarity NPC149337
0.7927 Intermediate Similarity NPC474051
0.7922 Intermediate Similarity NPC477565
0.7922 Intermediate Similarity NPC103379
0.7917 Intermediate Similarity NPC135772
0.7917 Intermediate Similarity NPC160193
0.7905 Intermediate Similarity NPC193528
0.7904 Intermediate Similarity NPC155442
0.7904 Intermediate Similarity NPC476574
0.7904 Intermediate Similarity NPC312918
0.7904 Intermediate Similarity NPC477561
0.7895 Intermediate Similarity NPC185838
0.7888 Intermediate Similarity NPC180306
0.7885 Intermediate Similarity NPC18614
0.7883 Intermediate Similarity NPC25648
0.7882 Intermediate Similarity NPC237579
0.7881 Intermediate Similarity NPC476567
0.7881 Intermediate Similarity NPC128019
0.7881 Intermediate Similarity NPC136860
0.7875 Intermediate Similarity NPC24954
0.7871 Intermediate Similarity NPC223125
0.7867 Intermediate Similarity NPC470925
0.7857 Intermediate Similarity NPC80241
0.7857 Intermediate Similarity NPC301641
0.7848 Intermediate Similarity NPC477132
0.7848 Intermediate Similarity NPC477133
0.7848 Intermediate Similarity NPC323443
0.7848 Intermediate Similarity NPC180756
0.7843 Intermediate Similarity NPC473934
0.7826 Intermediate Similarity NPC324144
0.7824 Intermediate Similarity NPC214116
0.7818 Intermediate Similarity NPC285941
0.7818 Intermediate Similarity NPC2314
0.7806 Intermediate Similarity NPC44869
0.7801 Intermediate Similarity NPC298486
0.7792 Intermediate Similarity NPC321505
0.7792 Intermediate Similarity NPC179825
0.7792 Intermediate Similarity NPC191376
0.7791 Intermediate Similarity NPC145832
0.7791 Intermediate Similarity NPC158376
0.7791 Intermediate Similarity NPC306555
0.7791 Intermediate Similarity NPC117188
0.7791 Intermediate Similarity NPC205421
0.7791 Intermediate Similarity NPC474931
0.7791 Intermediate Similarity NPC81218
0.7791 Intermediate Similarity NPC12053
0.7785 Intermediate Similarity NPC123323
0.7785 Intermediate Similarity NPC252107
0.7778 Intermediate Similarity NPC196447
0.7778 Intermediate Similarity NPC96603
0.7778 Intermediate Similarity NPC212794
0.7778 Intermediate Similarity NPC136508
0.7778 Intermediate Similarity NPC130926
0.7778 Intermediate Similarity NPC13504
0.7778 Intermediate Similarity NPC477563
0.7778 Intermediate Similarity NPC78222
0.7778 Intermediate Similarity NPC306843
0.7778 Intermediate Similarity NPC253043
0.7771 Intermediate Similarity NPC223124
0.7771 Intermediate Similarity NPC23080
0.7771 Intermediate Similarity NPC193906
0.7759 Intermediate Similarity NPC162653
0.7758 Intermediate Similarity NPC67978
0.7758 Intermediate Similarity NPC303581
0.7755 Intermediate Similarity NPC228843
0.7751 Intermediate Similarity NPC299990
0.7751 Intermediate Similarity NPC73492
0.7751 Intermediate Similarity NPC476575
0.775 Intermediate Similarity NPC106786
0.7746 Intermediate Similarity NPC249788
0.7742 Intermediate Similarity NPC135538
0.7742 Intermediate Similarity NPC147390
0.7742 Intermediate Similarity NPC476571

  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 NPC145304 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
0.922 High Similarity NPD5084 Clinical (unspecified phase)
0.8503 High Similarity NPD6783 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD5718 Phase 2
0.8108 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD4584 Approved
0.7959 Intermediate Similarity NPD6895 Approved
0.7959 Intermediate Similarity NPD6896 Approved
0.7947 Intermediate Similarity NPD5241 Discontinued
0.777 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD1669 Approved
0.773 Intermediate Similarity NPD3051 Approved
0.7702 Intermediate Similarity NPD7831 Phase 2
0.7702 Intermediate Similarity NPD7833 Phase 2
0.7702 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD4475 Approved
0.7687 Intermediate Similarity NPD4474 Approved
0.7667 Intermediate Similarity NPD4108 Discontinued
0.7654 Intermediate Similarity NPD7400 Phase 3
0.7651 Intermediate Similarity NPD2492 Phase 1
0.7647 Intermediate Similarity NPD5754 Discontinued
0.7647 Intermediate Similarity NPD6331 Phase 2
0.764 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD4481 Phase 3
0.7635 Intermediate Similarity NPD3110 Approved
0.7635 Intermediate Similarity NPD3109 Approved
0.7607 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD4017 Approved
0.7578 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD2970 Approved
0.7576 Intermediate Similarity NPD2969 Approved
0.7548 Intermediate Similarity NPD7124 Phase 2
0.7532 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD2489 Approved
0.753 Intermediate Similarity NPD27 Approved
0.7516 Intermediate Similarity NPD2978 Approved
0.7516 Intermediate Similarity NPD7037 Approved
0.7516 Intermediate Similarity NPD2977 Approved
0.7516 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3705 Approved
0.7469 Intermediate Similarity NPD2563 Approved
0.7469 Intermediate Similarity NPD2560 Approved
0.7468 Intermediate Similarity NPD4727 Phase 1
0.7468 Intermediate Similarity NPD5177 Phase 3
0.7468 Intermediate Similarity NPD6031 Approved
0.7468 Intermediate Similarity NPD6030 Approved
0.7468 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD7905 Discontinued
0.7465 Intermediate Similarity NPD2668 Approved
0.7465 Intermediate Similarity NPD2667 Approved
0.7464 Intermediate Similarity NPD5283 Phase 1
0.7453 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7019 Approved
0.7452 Intermediate Similarity NPD7020 Approved
0.7442 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD2233 Approved
0.7431 Intermediate Similarity NPD2232 Approved
0.7431 Intermediate Similarity NPD2230 Approved
0.7423 Intermediate Similarity NPD6788 Approved
0.7405 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD3443 Approved
0.7394 Intermediate Similarity NPD3444 Approved
0.7394 Intermediate Similarity NPD3445 Approved
0.7391 Intermediate Similarity NPD7110 Phase 1
0.7391 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD2420 Approved
0.7389 Intermediate Similarity NPD2421 Approved
0.7358 Intermediate Similarity NPD3640 Phase 3
0.7358 Intermediate Similarity NPD5976 Discontinued
0.7358 Intermediate Similarity NPD3641 Approved
0.7358 Intermediate Similarity NPD3639 Approved
0.7357 Intermediate Similarity NPD709 Approved
0.7355 Intermediate Similarity NPD3060 Approved
0.7355 Intermediate Similarity NPD4162 Approved
0.7349 Intermediate Similarity NPD7802 Discontinued
0.7346 Intermediate Similarity NPD7298 Approved
0.7338 Intermediate Similarity NPD1375 Discontinued
0.7337 Intermediate Similarity NPD8251 Approved
0.7337 Intermediate Similarity NPD8252 Approved
0.7337 Intermediate Similarity NPD8099 Discontinued
0.7329 Intermediate Similarity NPD6875 Approved
0.7329 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6876 Approved
0.7321 Intermediate Similarity NPD2898 Approved
0.7312 Intermediate Similarity NPD4210 Discontinued
0.7305 Intermediate Similarity NPD6747 Phase 1
0.7305 Intermediate Similarity NPD6071 Discontinued
0.7303 Intermediate Similarity NPD2653 Approved
0.7301 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD8156 Discontinued
0.729 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD2238 Phase 2
0.7284 Intermediate Similarity NPD6873 Phase 2
0.7283 Intermediate Similarity NPD2971 Approved
0.7283 Intermediate Similarity NPD2968 Approved
0.7273 Intermediate Similarity NPD4093 Discontinued
0.7267 Intermediate Similarity NPD7294 Phase 1
0.7261 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD5978 Approved
0.7256 Intermediate Similarity NPD5977 Approved
0.725 Intermediate Similarity NPD1914 Approved
0.7244 Intermediate Similarity NPD6674 Discontinued
0.7244 Intermediate Similarity NPD4237 Approved
0.7244 Intermediate Similarity NPD4236 Phase 3
0.7233 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD6584 Phase 3
0.723 Intermediate Similarity NPD7018 Phase 2
0.7211 Intermediate Similarity NPD2922 Phase 1
0.7203 Intermediate Similarity NPD6581 Approved
0.7203 Intermediate Similarity NPD6580 Approved
0.719 Intermediate Similarity NPD2157 Approved
0.719 Intermediate Similarity NPD4097 Suspended
0.7184 Intermediate Similarity NPD4578 Approved
0.7184 Intermediate Similarity NPD4577 Approved
0.7178 Intermediate Similarity NPD4772 Phase 2
0.7178 Intermediate Similarity NPD4773 Phase 2
0.7169 Intermediate Similarity NPD5604 Discontinued
0.7162 Intermediate Similarity NPD4098 Discontinued
0.7161 Intermediate Similarity NPD4477 Approved
0.7161 Intermediate Similarity NPD2161 Phase 2
0.7161 Intermediate Similarity NPD4476 Approved
0.7153 Intermediate Similarity NPD1651 Approved
0.7153 Intermediate Similarity NPD5691 Approved
0.7153 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5110 Phase 2
0.7152 Intermediate Similarity NPD5111 Phase 2
0.7152 Intermediate Similarity NPD5109 Approved
0.7143 Intermediate Similarity NPD7119 Phase 2
0.7143 Intermediate Similarity NPD6111 Discontinued
0.7143 Intermediate Similarity NPD7427 Discontinued
0.7134 Intermediate Similarity NPD3383 Approved
0.7134 Intermediate Similarity NPD7248 Discontinued
0.7134 Intermediate Similarity NPD3384 Approved
0.7134 Intermediate Similarity NPD3382 Approved
0.7134 Intermediate Similarity NPD5720 Discontinued
0.7126 Intermediate Similarity NPD5709 Phase 3
0.7124 Intermediate Similarity NPD3657 Discovery
0.7119 Intermediate Similarity NPD7906 Approved
0.7115 Intermediate Similarity NPD5865 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6667 Approved
0.7107 Intermediate Similarity NPD6666 Approved
0.7105 Intermediate Similarity NPD2674 Phase 3
0.7103 Intermediate Similarity NPD4626 Approved
0.7089 Intermediate Similarity NPD7466 Approved
0.7088 Intermediate Similarity NPD4420 Approved
0.7086 Intermediate Similarity NPD7313 Approved
0.7086 Intermediate Similarity NPD7281 Phase 3
0.7086 Intermediate Similarity NPD7310 Approved
0.7086 Intermediate Similarity NPD7312 Approved
0.7086 Intermediate Similarity NPD7280 Phase 3
0.7086 Intermediate Similarity NPD7311 Approved
0.7083 Intermediate Similarity NPD4666 Phase 3
0.7083 Intermediate Similarity NPD2486 Discontinued
0.7083 Intermediate Similarity NPD3365 Discontinued
0.7081 Intermediate Similarity NPD6090 Discontinued
0.7066 Intermediate Similarity NPD4055 Discovery
0.7063 Intermediate Similarity NPD7598 Phase 2
0.7062 Intermediate Similarity NPD4663 Approved
0.7059 Intermediate Similarity NPD6225 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3620 Phase 2
0.7055 Intermediate Similarity NPD4005 Discontinued
0.7048 Intermediate Similarity NPD2358 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD8054 Approved
0.7045 Intermediate Similarity NPD7309 Approved
0.7045 Intermediate Similarity NPD8053 Approved
0.7039 Intermediate Similarity NPD1039 Discontinued
0.7039 Intermediate Similarity NPD2488 Approved
0.7039 Intermediate Similarity NPD2490 Approved
0.7034 Intermediate Similarity NPD1357 Approved
0.703 Intermediate Similarity NPD37 Approved
0.7027 Intermediate Similarity NPD6582 Phase 2
0.7027 Intermediate Similarity NPD6583 Phase 3
0.7022 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD3349 Phase 2
0.7021 Intermediate Similarity NPD4859 Phase 1
0.7019 Intermediate Similarity NPD1424 Approved
0.7007 Intermediate Similarity NPD1281 Approved
0.7006 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4166 Phase 2
0.7 Intermediate Similarity NPD4010 Discontinued
0.7 Intermediate Similarity NPD3845 Phase 1
0.6994 Remote Similarity NPD4873 Discontinued
0.6993 Remote Similarity NPD7265 Discontinued
0.6993 Remote Similarity NPD2557 Approved
0.6993 Remote Similarity NPD3532 Approved
0.6993 Remote Similarity NPD3531 Approved
0.6993 Remote Similarity NPD3530 Approved
0.6989 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2154 Approved
0.6987 Remote Similarity NPD2155 Approved
0.6987 Remote Similarity NPD2156 Approved
0.6983 Remote Similarity NPD3408 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