Structure

Physi-Chem Properties

Molecular Weight:  355.14
Volume:  350.823
LogP:  2.02
LogD:  2.601
LogS:  -2.214
# Rotatable Bonds:  2
TPSA:  60.39
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.894
Synthetic Accessibility Score:  3.428
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.159
MDCK Permeability:  2.8820122679462656e-05
Pgp-inhibitor:  0.149
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  91.62378692626953%
Volume Distribution (VD):  1.719
Pgp-substrate:  5.244521141052246%

ADMET: Metabolism

CYP1A2-inhibitor:  0.656
CYP1A2-substrate:  0.936
CYP2C19-inhibitor:  0.768
CYP2C19-substrate:  0.909
CYP2C9-inhibitor:  0.065
CYP2C9-substrate:  0.704
CYP2D6-inhibitor:  0.923
CYP2D6-substrate:  0.857
CYP3A4-inhibitor:  0.919
CYP3A4-substrate:  0.913

ADMET: Excretion

Clearance (CL):  10.685
Half-life (T1/2):  0.444

ADMET: Toxicity

hERG Blockers:  0.235
Human Hepatotoxicity (H-HT):  0.178
Drug-inuced Liver Injury (DILI):  0.258
AMES Toxicity:  0.243
Rat Oral Acute Toxicity:  0.331
Maximum Recommended Daily Dose:  0.924
Skin Sensitization:  0.104
Carcinogencity:  0.812
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.916

Download Data

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC2314

Natural Product ID:  NPC2314
Common Name*:   FLSSXYPKPLFNLK-RTBURBONSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FLSSXYPKPLFNLK-RTBURBONSA-N
Standard InCHI:  InChI=1S/C20H21NO5/c1-23-15-4-3-12-14(20(15)24-2)9-21-6-5-11-7-16-17(26-10-25-16)8-13(11)18(21)19(12)22/h3-4,7-8,18-19,22H,5-6,9-10H2,1-2H3/t18-,19-/m1/s1
SMILES:  COc1c(OC)ccc2c1CN1CCc3c([C@@H]1[C@@H]2O)cc1c(c3)OCO1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1556795
PubChem CID:   12313750
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[11830162]
NPO29080 Ulex airensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11858751]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[12809361]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO25373 Stereocaulon alpinum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. PMID[18288807]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO26428 Ligularia sagitta Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24913558]
NPO26193 Piper methysticum Species Piperaceae Eukaryota root n.a. n.a. PMID[25597012]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO25373 Stereocaulon alpinum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. PMID[29878768]
NPO22441 Senna spectabilis Species Fabaceae Eukaryota flowers n.a. n.a. PMID[30413343]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO25657 Mezzettia leptopoda Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9868159]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23223 Symphytum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15694 Corydalis cheilanthifolia Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1106 Artabotrys maingayi Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26428 Ligularia sagitta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24480 Diospyros ebenum Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1106 Artabotrys maingayi Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23223 Symphytum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25373 Stereocaulon alpinum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13713 Corydalis campulicarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24087 Psacalium peltatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO511 Corydalis govaniana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26230 Lappula echinata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15694 Corydalis cheilanthifolia Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24480 Diospyros ebenum Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25166 Corydalis ophiocarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26428 Ligularia sagitta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24480 Diospyros ebenum Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23223 Symphytum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25166 Corydalis ophiocarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25624 Teclea sudanica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25657 Mezzettia leptopoda Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26230 Lappula echinata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29080 Ulex airensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24480 Diospyros ebenum Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26428 Ligularia sagitta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22441 Senna spectabilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO336 Chaetomorpha moniligera Species Cladophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24087 Psacalium peltatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8144 Labidiaster annulatus Species Labidiasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15694 Corydalis cheilanthifolia Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25166 Corydalis ophiocarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7177 Inocybe rimosa Species Inocybaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24868 Streptomyces aizunensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25484 Bumelia obtusifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25373 Stereocaulon alpinum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23223 Symphytum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13713 Corydalis campulicarpa Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25881 Stachys plumosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26193 Piper methysticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO511 Corydalis govaniana Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1106 Artabotrys maingayi Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29053 Dictyostelium longosporum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25316 Lasius niger Species Formicidae 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 3548.1 nM PMID[512943]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 100000.0 nM PMID[512943]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 19011.5 nM PMID[512943]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16360.1 nM PMID[512943]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[512943]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 39810.7 nM PMID[512943]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 7943.3 nM PMID[512943]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PMID[512943]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[512943]
NPT2 Others Unspecified Potency n.a. 1258.9 nM PMID[512943]

☑ 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 NPC2314 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
0.9281 High Similarity NPC248642
0.9255 High Similarity NPC276944
0.9255 High Similarity NPC232514
0.9255 High Similarity NPC238530
0.9226 High Similarity NPC156576
0.9207 High Similarity NPC477640
0.9207 High Similarity NPC470739
0.9207 High Similarity NPC225597
0.9177 High Similarity NPC138487
0.9177 High Similarity NPC41178
0.9177 High Similarity NPC216459
0.9162 High Similarity NPC126284
0.9146 High Similarity NPC474475
0.9119 High Similarity NPC146288
0.9102 High Similarity NPC294790
0.9102 High Similarity NPC148693
0.9102 High Similarity NPC118633
0.9085 High Similarity NPC290759
0.9085 High Similarity NPC475686
0.9085 High Similarity NPC266176
0.9085 High Similarity NPC158148
0.9085 High Similarity NPC82533
0.9085 High Similarity NPC58766
0.9006 High Similarity NPC111485
0.9 High Similarity NPC234392
0.9 High Similarity NPC31311
0.8935 High Similarity NPC244554
0.8909 High Similarity NPC100566
0.8895 High Similarity NPC214116
0.8889 High Similarity NPC59028
0.8889 High Similarity NPC92191
0.8876 High Similarity NPC320223
0.8876 High Similarity NPC114364
0.8869 High Similarity NPC187678
0.882 High Similarity NPC207757
0.882 High Similarity NPC276588
0.882 High Similarity NPC278799
0.882 High Similarity NPC127674
0.882 High Similarity NPC189266
0.882 High Similarity NPC110416
0.882 High Similarity NPC295691
0.882 High Similarity NPC204828
0.882 High Similarity NPC172765
0.882 High Similarity NPC54379
0.882 High Similarity NPC5238
0.882 High Similarity NPC469817
0.882 High Similarity NPC2413
0.882 High Similarity NPC39701
0.882 High Similarity NPC249797
0.882 High Similarity NPC184026
0.882 High Similarity NPC193949
0.8817 High Similarity NPC474470
0.8812 High Similarity NPC233029
0.8812 High Similarity NPC210148
0.8802 High Similarity NPC311991
0.8797 High Similarity NPC475959
0.8795 High Similarity NPC190332
0.8795 High Similarity NPC150879
0.8795 High Similarity NPC247389
0.8795 High Similarity NPC181653
0.8757 High Similarity NPC199465
0.8757 High Similarity NPC229166
0.8757 High Similarity NPC49353
0.8757 High Similarity NPC128560
0.8735 High Similarity NPC24264
0.8735 High Similarity NPC476432
0.8735 High Similarity NPC264850
0.8735 High Similarity NPC219341
0.8735 High Similarity NPC13916
0.8734 High Similarity NPC106295
0.8734 High Similarity NPC16107
0.8734 High Similarity NPC51957
0.8734 High Similarity NPC210437
0.8734 High Similarity NPC476144
0.8727 High Similarity NPC320104
0.8721 High Similarity NPC275132
0.8721 High Similarity NPC476575
0.872 High Similarity NPC97072
0.872 High Similarity NPC215829
0.8706 High Similarity NPC241704
0.8683 High Similarity NPC252960
0.8683 High Similarity NPC298979
0.8679 High Similarity NPC7467
0.8675 High Similarity NPC167546
0.8675 High Similarity NPC169743
0.8675 High Similarity NPC16805
0.8675 High Similarity NPC302527
0.8675 High Similarity NPC225774
0.8675 High Similarity NPC24465
0.8623 High Similarity NPC476002
0.8621 High Similarity NPC9867
0.8616 High Similarity NPC476151
0.8614 High Similarity NPC233650
0.8614 High Similarity NPC218614
0.8613 High Similarity NPC233718
0.8606 High Similarity NPC4304
0.8605 High Similarity NPC32154
0.8596 High Similarity NPC237044
0.8589 High Similarity NPC93593
0.8588 High Similarity NPC117717
0.8588 High Similarity NPC24260
0.858 High Similarity NPC75958
0.8571 High Similarity NPC97221
0.8571 High Similarity NPC192768
0.8571 High Similarity NPC88249
0.8571 High Similarity NPC220858
0.8571 High Similarity NPC210918
0.8571 High Similarity NPC151895
0.8563 High Similarity NPC135772
0.8563 High Similarity NPC247972
0.8563 High Similarity NPC134858
0.8547 High Similarity NPC15919
0.8547 High Similarity NPC474325
0.8545 High Similarity NPC477080
0.8538 High Similarity NPC304675
0.8509 High Similarity NPC477565
0.8509 High Similarity NPC103379
0.8506 High Similarity NPC116284
0.8506 High Similarity NPC73492
0.8506 High Similarity NPC299990
0.8497 Intermediate Similarity NPC474745
0.8497 Intermediate Similarity NPC267408
0.8494 Intermediate Similarity NPC266753
0.8494 Intermediate Similarity NPC306902
0.8494 Intermediate Similarity NPC160298
0.8494 Intermediate Similarity NPC232924
0.8494 Intermediate Similarity NPC249274
0.8494 Intermediate Similarity NPC205167
0.8494 Intermediate Similarity NPC477559
0.8491 Intermediate Similarity NPC185838
0.8481 Intermediate Similarity NPC128019
0.8481 Intermediate Similarity NPC136860
0.8481 Intermediate Similarity NPC476567
0.8476 Intermediate Similarity NPC78733
0.8466 Intermediate Similarity NPC148898
0.8462 Intermediate Similarity NPC306555
0.8462 Intermediate Similarity NPC158376
0.8462 Intermediate Similarity NPC210140
0.8462 Intermediate Similarity NPC117188
0.8462 Intermediate Similarity NPC81218
0.8462 Intermediate Similarity NPC205421
0.8462 Intermediate Similarity NPC12053
0.8462 Intermediate Similarity NPC145832
0.8462 Intermediate Similarity NPC474931
0.8457 Intermediate Similarity NPC274026
0.8448 Intermediate Similarity NPC312918
0.8448 Intermediate Similarity NPC476574
0.8448 Intermediate Similarity NPC155442
0.8448 Intermediate Similarity NPC477561
0.8447 Intermediate Similarity NPC147390
0.8447 Intermediate Similarity NPC246587
0.8447 Intermediate Similarity NPC135538
0.8447 Intermediate Similarity NPC428
0.8447 Intermediate Similarity NPC476571
0.8447 Intermediate Similarity NPC24233
0.843 Intermediate Similarity NPC477558
0.8427 Intermediate Similarity NPC475754
0.8424 Intermediate Similarity NPC147091
0.8421 Intermediate Similarity NPC149090
0.8421 Intermediate Similarity NPC65403
0.8421 Intermediate Similarity NPC19520
0.8418 Intermediate Similarity NPC237579
0.8393 Intermediate Similarity NPC59567
0.8385 Intermediate Similarity NPC179825
0.8385 Intermediate Similarity NPC321505
0.8385 Intermediate Similarity NPC191376
0.8373 Intermediate Similarity NPC476572
0.8363 Intermediate Similarity NPC6152
0.8362 Intermediate Similarity NPC57036
0.8354 Intermediate Similarity NPC474915
0.8354 Intermediate Similarity NPC213206
0.8354 Intermediate Similarity NPC188163
0.8354 Intermediate Similarity NPC328750
0.8353 Intermediate Similarity NPC57812
0.8353 Intermediate Similarity NPC474324
0.8352 Intermediate Similarity NPC474746
0.8352 Intermediate Similarity NPC475981
0.8343 Intermediate Similarity NPC477563
0.8343 Intermediate Similarity NPC212794
0.8343 Intermediate Similarity NPC136508
0.8343 Intermediate Similarity NPC78222
0.8343 Intermediate Similarity NPC13504
0.8343 Intermediate Similarity NPC306843
0.8343 Intermediate Similarity NPC196447
0.8343 Intermediate Similarity NPC253043
0.8343 Intermediate Similarity NPC96603
0.8333 Intermediate Similarity NPC60186
0.8306 Intermediate Similarity NPC475654
0.8304 Intermediate Similarity NPC204908
0.8304 Intermediate Similarity NPC83198
0.8304 Intermediate Similarity NPC475845
0.8294 Intermediate Similarity NPC124657
0.8291 Intermediate Similarity NPC314682
0.8284 Intermediate Similarity NPC324144
0.8284 Intermediate Similarity NPC1229
0.8268 Intermediate Similarity NPC281581
0.8268 Intermediate Similarity NPC82763
0.8266 Intermediate Similarity NPC152680
0.8266 Intermediate Similarity NPC232386
0.8266 Intermediate Similarity NPC190783

  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 NPC2314 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
0.8734 High Similarity NPD4584 Approved
0.8537 High Similarity NPD6818 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD2977 Approved
0.8313 Intermediate Similarity NPD2978 Approved
0.8303 Intermediate Similarity NPD4772 Phase 2
0.8303 Intermediate Similarity NPD4773 Phase 2
0.8246 Intermediate Similarity NPD2969 Approved
0.8246 Intermediate Similarity NPD2970 Approved
0.8199 Intermediate Similarity NPD5241 Discontinued
0.8192 Intermediate Similarity NPD8053 Approved
0.8192 Intermediate Similarity NPD8054 Approved
0.8187 Intermediate Similarity NPD6071 Discontinued
0.8187 Intermediate Similarity NPD3051 Approved
0.8161 Intermediate Similarity NPD8156 Discontinued
0.8155 Intermediate Similarity NPD2563 Approved
0.8155 Intermediate Similarity NPD2560 Approved
0.8148 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8103 Intermediate Similarity NPD8251 Approved
0.8103 Intermediate Similarity NPD8252 Approved
0.8103 Intermediate Similarity NPD8099 Discontinued
0.8098 Intermediate Similarity NPD4420 Approved
0.8092 Intermediate Similarity NPD27 Approved
0.8092 Intermediate Similarity NPD2489 Approved
0.8056 Intermediate Similarity NPD7906 Approved
0.8021 Intermediate Similarity NPD5006 Approved
0.8021 Intermediate Similarity NPD5005 Approved
0.8 Intermediate Similarity NPD4663 Approved
0.7965 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD4236 Phase 3
0.7963 Intermediate Similarity NPD4237 Approved
0.7933 Intermediate Similarity NPD4578 Approved
0.7933 Intermediate Similarity NPD4577 Approved
0.7929 Intermediate Similarity NPD7298 Approved
0.7892 Intermediate Similarity NPD5582 Discontinued
0.7886 Intermediate Similarity NPD4481 Phase 3
0.7866 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD7312 Approved
0.7833 Intermediate Similarity NPD7311 Approved
0.7833 Intermediate Similarity NPD7313 Approved
0.7833 Intermediate Similarity NPD7310 Approved
0.7831 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6107 Approved
0.7796 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6788 Approved
0.779 Intermediate Similarity NPD7309 Approved
0.7778 Intermediate Similarity NPD5772 Approved
0.7778 Intermediate Similarity NPD5773 Approved
0.7751 Intermediate Similarity NPD4017 Approved
0.7746 Intermediate Similarity NPD5604 Discontinued
0.7744 Intermediate Similarity NPD3060 Approved
0.7744 Intermediate Similarity NPD5177 Phase 3
0.7738 Intermediate Similarity NPD3641 Approved
0.7738 Intermediate Similarity NPD3640 Phase 3
0.7738 Intermediate Similarity NPD3639 Approved
0.7716 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD2898 Approved
0.767 Intermediate Similarity NPD4010 Discontinued
0.7651 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7833 Phase 2
0.7644 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7831 Phase 2
0.7633 Intermediate Similarity NPD6031 Approved
0.7633 Intermediate Similarity NPD6030 Approved
0.7569 Intermediate Similarity NPD6297 Approved
0.7568 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD2973 Approved
0.7566 Intermediate Similarity NPD2975 Approved
0.7566 Intermediate Similarity NPD2974 Approved
0.7543 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD7280 Phase 3
0.7541 Intermediate Similarity NPD7281 Phase 3
0.7515 Intermediate Similarity NPD4123 Phase 3
0.75 Intermediate Similarity NPD6851 Approved
0.75 Intermediate Similarity NPD3450 Approved
0.75 Intermediate Similarity NPD2493 Approved
0.75 Intermediate Similarity NPD1753 Discontinued
0.75 Intermediate Similarity NPD3452 Approved
0.75 Intermediate Similarity NPD2494 Approved
0.75 Intermediate Similarity NPD6853 Approved
0.7469 Intermediate Similarity NPD2238 Phase 2
0.7459 Intermediate Similarity NPD5312 Approved
0.7459 Intermediate Similarity NPD5313 Approved
0.7456 Intermediate Similarity NPD2421 Approved
0.7456 Intermediate Similarity NPD2420 Approved
0.7448 Intermediate Similarity NPD4580 Approved
0.7442 Intermediate Similarity NPD4005 Discontinued
0.744 Intermediate Similarity NPD2677 Approved
0.7425 Intermediate Similarity NPD4162 Approved
0.7414 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2488 Approved
0.7394 Intermediate Similarity NPD2490 Approved
0.7391 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD4582 Approved
0.7385 Intermediate Similarity NPD4583 Approved
0.7384 Intermediate Similarity NPD4210 Discontinued
0.7374 Intermediate Similarity NPD4166 Phase 2
0.7368 Intermediate Similarity NPD6090 Discontinued
0.7353 Intermediate Similarity NPD3124 Discontinued
0.7351 Intermediate Similarity NPD2971 Approved
0.7351 Intermediate Similarity NPD2968 Approved
0.7346 Intermediate Similarity NPD5718 Phase 2
0.7345 Intermediate Similarity NPD4055 Discovery
0.7337 Intermediate Similarity NPD3692 Discontinued
0.7333 Intermediate Similarity NPD4004 Approved
0.7333 Intermediate Similarity NPD4002 Approved
0.7326 Intermediate Similarity NPD2122 Discontinued
0.7326 Intermediate Similarity NPD5976 Discontinued
0.731 Intermediate Similarity NPD1424 Approved
0.7306 Intermediate Similarity NPD8095 Phase 1
0.7305 Intermediate Similarity NPD1375 Discontinued
0.7305 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5709 Phase 3
0.7301 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4678 Approved
0.7299 Intermediate Similarity NPD4675 Approved
0.7283 Intermediate Similarity NPD3687 Approved
0.7283 Intermediate Similarity NPD3686 Approved
0.7268 Intermediate Similarity NPD42 Phase 2
0.7268 Intermediate Similarity NPD6042 Phase 2
0.7263 Intermediate Similarity NPD4666 Phase 3
0.7263 Intermediate Similarity NPD7296 Approved
0.7263 Intermediate Similarity NPD5677 Discontinued
0.7253 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4103 Phase 2
0.7249 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD5160 Discontinued
0.7222 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7802 Discontinued
0.7219 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7549 Discontinued
0.7195 Intermediate Similarity NPD4474 Approved
0.7195 Intermediate Similarity NPD4475 Approved
0.7193 Intermediate Similarity NPD3122 Phase 3
0.7193 Intermediate Similarity NPD6667 Approved
0.7193 Intermediate Similarity NPD6666 Approved
0.7193 Intermediate Similarity NPD3845 Phase 1
0.7192 Intermediate Similarity NPD7047 Phase 3
0.7189 Intermediate Similarity NPD7007 Discovery
0.7169 Intermediate Similarity NPD823 Approved
0.7169 Intermediate Similarity NPD817 Approved
0.7167 Intermediate Similarity NPD2904 Discontinued
0.7151 Intermediate Similarity NPD7213 Phase 3
0.7151 Intermediate Similarity NPD7212 Phase 2
0.7151 Intermediate Similarity NPD1774 Approved
0.715 Intermediate Similarity NPD6997 Phase 2
0.7135 Intermediate Similarity NPD3885 Approved
0.7129 Intermediate Similarity NPD3815 Phase 1
0.7129 Intermediate Similarity NPD3816 Phase 1
0.7129 Intermediate Similarity NPD7827 Phase 1
0.7126 Intermediate Similarity NPD6896 Approved
0.7126 Intermediate Similarity NPD4727 Phase 1
0.7126 Intermediate Similarity NPD6895 Approved
0.7125 Intermediate Similarity NPD4659 Approved
0.712 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD3383 Approved
0.7119 Intermediate Similarity NPD3384 Approved
0.7119 Intermediate Similarity NPD3382 Approved
0.7112 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7400 Phase 3
0.711 Intermediate Similarity NPD7447 Phase 1
0.7107 Intermediate Similarity NPD3705 Approved
0.7093 Intermediate Similarity NPD7124 Phase 2
0.7093 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2156 Approved
0.7083 Intermediate Similarity NPD2154 Approved
0.7083 Intermediate Similarity NPD2155 Approved
0.7079 Intermediate Similarity NPD5676 Approved
0.7076 Intermediate Similarity NPD6748 Discontinued
0.7074 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD2845 Phase 2
0.7068 Intermediate Similarity NPD2843 Phase 2
0.7066 Intermediate Similarity NPD2492 Phase 1
0.7065 Intermediate Similarity NPD5938 Phase 3
0.7063 Intermediate Similarity NPD2232 Approved
0.7063 Intermediate Similarity NPD2230 Approved
0.7063 Intermediate Similarity NPD2233 Approved
0.7062 Intermediate Similarity NPD6072 Discontinued
0.7059 Intermediate Similarity NPD7039 Approved
0.7059 Intermediate Similarity NPD7038 Approved
0.7059 Intermediate Similarity NPD7037 Approved
0.7059 Intermediate Similarity NPD8152 Approved
0.7059 Intermediate Similarity NPD8153 Approved
0.7053 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD7598 Phase 2
0.7049 Intermediate Similarity NPD6688 Approved
0.7049 Intermediate Similarity NPD6687 Approved
0.7048 Intermediate Similarity NPD3061 Approved
0.7048 Intermediate Similarity NPD3062 Approved
0.7048 Intermediate Similarity NPD3059 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