Structure

Physi-Chem Properties

Molecular Weight:  325.13
Volume:  324.737
LogP:  2.718
LogD:  2.86
LogS:  -2.67
# Rotatable Bonds:  1
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.874
Synthetic Accessibility Score:  3.247
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.893
MDCK Permeability:  2.5509421902825125e-05
Pgp-inhibitor:  0.058
Pgp-substrate:  0.691
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.973
Plasma Protein Binding (PPB):  84.78688049316406%
Volume Distribution (VD):  2.052
Pgp-substrate:  10.239716529846191%

ADMET: Metabolism

CYP1A2-inhibitor:  0.889
CYP1A2-substrate:  0.924
CYP2C19-inhibitor:  0.241
CYP2C19-substrate:  0.835
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.714
CYP2D6-inhibitor:  0.729
CYP2D6-substrate:  0.929
CYP3A4-inhibitor:  0.502
CYP3A4-substrate:  0.883

ADMET: Excretion

Clearance (CL):  18.143
Half-life (T1/2):  0.337

ADMET: Toxicity

hERG Blockers:  0.366
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.497
AMES Toxicity:  0.654
Rat Oral Acute Toxicity:  0.729
Maximum Recommended Daily Dose:  0.963
Skin Sensitization:  0.547
Carcinogencity:  0.593
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.951

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  Natural Product: NPC229166

Natural Product ID:  NPC229166
Common Name*:   Cassythicine
IUPAC Name:   n.a.
Synonyms:   Cassythicine; N-Methylactinodaphnine
Standard InCHIKey:  MPWZJVCAMFAIGV-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3/t13-/m0/s1
SMILES:  COc1cc2c(cc1O)C[C@H]1c3c2c2OCOc2cc3CCN1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464528
PubChem CID:   442194
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO6257 Ficus septica Species Moraceae Eukaryota Stems Tainan Hsien, Taiwan, Republic of China 2000-JAN PMID[16038551]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[18217715]
NPO6257 Ficus septica Species Moraceae Eukaryota leaves n.a. n.a. PMID[19938815]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO22151 Stephania pierrei Species Menispermaceae Eukaryota tubers n.a. n.a. PMID[8254346]
NPO23076 Illigera luzonensis Species Hernandiaceae Eukaryota n.a. n.a. n.a. PMID[9214740]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO32857 cassytha filiformis ii Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[9677264]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13118 Paeonia officinalis Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13118 Paeonia officinalis Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27426 Cassytha melantha Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24130 Cassytha glabella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12080 Metrodorea flavida Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO474 Beilschmiedia kunstleri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20070.1 Crinum stuhlmannii subsp. delagoense Subspecies Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3079 Cassytha filiformis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10161 Macaranga pleiostemona Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13118 Paeonia officinalis Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7346 Ligularia odontomanes Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11817 Seiridium cardinale Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21569 Helichrysum fulvum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15978 Nalanthamala diospyri Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22727 Avena fatua Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8078 Palaquium leiocarpum Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11706 Gordonia terrae Species Gordoniaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12316 Pterospermum lanceolatum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1187 Baccharis scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12193 Metadina trichotoma Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24130 Cassytha glabella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27426 Cassytha melantha Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1863 Alpinia pricei Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23076 Illigera luzonensis Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22151 Stephania pierrei Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16798 Piper sylvaticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11948 Ferulago sylvatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3390 Radermachia sinica n.a. n.a. n.a. 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 7.6 ug ml-1 PMID[502276]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 8.9 ug ml-1 PMID[502276]
NPT91 Cell Line KB Homo sapiens ED50 = 3.0 ug ml-1 PMID[502276]
NPT168 Cell Line P388 Mus musculus ED50 > 5.0 ug ml-1 PMID[502276]
NPT762 Cell Line A-431 Homo sapiens ED50 = 10.5 ug ml-1 PMID[502276]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 6.1 ug ml-1 PMID[502276]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 9.8 ug ml-1 PMID[502276]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 47000.0 nM PMID[502277]
NPT189 Cell Line Vero Chlorocebus aethiops MTC = 31.0 uM PMID[502277]
NPT20967 CELL-LINE Platelet n.a. Activity = 0.0 % PMID[502274]
NPT20967 CELL-LINE Platelet n.a. Activity = 68.1 % PMID[502274]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 68.1 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 16.2 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 51.4 % PMID[502275]
NPT177 Tissue Aorta Rattus norvegicus Activity = 112.9 % PMID[502275]
NPT177 Tissue Aorta Rattus norvegicus Activity = 225.0 % PMID[502275]
NPT177 Tissue Aorta Rattus norvegicus Activity = 98.9 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 69.1 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 82.5 % PMID[502275]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.8 ug ml-1 PMID[502276]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.6 ug ml-1 PMID[502276]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 7.3 ug ml-1 PMID[502276]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.2 ug ml-1 PMID[502276]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 4.8 ug ml-1 PMID[502276]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 2290.0 ng/ml PMID[502276]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 2260.0 ng/ml PMID[502276]
NPT2 Others Unspecified Ratio ED50 = 2.0 n.a. PMID[502276]
NPT2 Others Unspecified Ratio ED50 = 3.0 n.a. PMID[502276]

☑ 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 NPC229166 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC199465
1.0 High Similarity NPC128560
0.9876 High Similarity NPC114364
0.9876 High Similarity NPC320223
0.9695 High Similarity NPC116284
0.9634 High Similarity NPC477561
0.9634 High Similarity NPC155442
0.9634 High Similarity NPC476574
0.9634 High Similarity NPC312918
0.9563 High Similarity NPC298979
0.956 High Similarity NPC212794
0.956 High Similarity NPC78222
0.956 High Similarity NPC477563
0.956 High Similarity NPC16805
0.956 High Similarity NPC302527
0.956 High Similarity NPC196447
0.956 High Similarity NPC167546
0.956 High Similarity NPC136508
0.956 High Similarity NPC13504
0.956 High Similarity NPC306843
0.956 High Similarity NPC253043
0.956 High Similarity NPC96603
0.9518 High Similarity NPC135772
0.95 High Similarity NPC476432
0.95 High Similarity NPC24264
0.9497 High Similarity NPC324144
0.9441 High Similarity NPC81218
0.9441 High Similarity NPC117188
0.9441 High Similarity NPC306555
0.9441 High Similarity NPC145832
0.9441 High Similarity NPC205421
0.9441 High Similarity NPC12053
0.9441 High Similarity NPC247389
0.9441 High Similarity NPC158376
0.9441 High Similarity NPC474931
0.9441 High Similarity NPC210918
0.9437 High Similarity NPC225774
0.9408 High Similarity NPC82763
0.9379 High Similarity NPC219341
0.9349 High Similarity NPC476576
0.9349 High Similarity NPC186546
0.9341 High Similarity NPC248642
0.9337 High Similarity NPC126284
0.9286 High Similarity NPC156576
0.9273 High Similarity NPC477558
0.9268 High Similarity NPC149090
0.9268 High Similarity NPC19520
0.9268 High Similarity NPC239775
0.9255 High Similarity NPC1229
0.925 High Similarity NPC232924
0.925 High Similarity NPC266753
0.925 High Similarity NPC27410
0.925 High Similarity NPC160298
0.925 High Similarity NPC166014
0.925 High Similarity NPC477559
0.925 High Similarity NPC306902
0.9207 High Similarity NPC26240
0.9207 High Similarity NPC6152
0.9207 High Similarity NPC69712
0.9207 High Similarity NPC477562
0.9176 High Similarity NPC57036
0.9119 High Similarity NPC99659
0.9119 High Similarity NPC325871
0.9096 High Similarity NPC192135
0.9096 High Similarity NPC66341
0.9096 High Similarity NPC477020
0.9091 High Similarity NPC118274
0.9091 High Similarity NPC152212
0.9091 High Similarity NPC168753
0.908 High Similarity NPC232514
0.908 High Similarity NPC238530
0.908 High Similarity NPC276944
0.9068 High Similarity NPC111485
0.9064 High Similarity NPC214116
0.9048 High Similarity NPC294790
0.9048 High Similarity NPC118633
0.9048 High Similarity NPC148693
0.9006 High Similarity NPC476572
0.8957 High Similarity NPC60186
0.8916 High Similarity NPC241055
0.8909 High Similarity NPC86144
0.8909 High Similarity NPC476573
0.8909 High Similarity NPC81247
0.8909 High Similarity NPC304659
0.8909 High Similarity NPC35627
0.8889 High Similarity NPC476575
0.8882 High Similarity NPC470879
0.8882 High Similarity NPC474507
0.8882 High Similarity NPC258695
0.8848 High Similarity NPC168409
0.883 High Similarity NPC32413
0.883 High Similarity NPC474506
0.8827 High Similarity NPC186063
0.8824 High Similarity NPC23219
0.8812 High Similarity NPC326316
0.8812 High Similarity NPC81733
0.8788 High Similarity NPC189470
0.8772 High Similarity NPC267408
0.8765 High Similarity NPC148709
0.8765 High Similarity NPC476577
0.8765 High Similarity NPC112575
0.8765 High Similarity NPC173416
0.8757 High Similarity NPC2314
0.875 High Similarity NPC117717
0.8693 High Similarity NPC475754
0.8686 High Similarity NPC237579
0.8686 High Similarity NPC474904
0.8671 High Similarity NPC275132
0.865 High Similarity NPC127674
0.865 High Similarity NPC110416
0.865 High Similarity NPC5238
0.865 High Similarity NPC184026
0.865 High Similarity NPC54379
0.865 High Similarity NPC189266
0.865 High Similarity NPC295691
0.865 High Similarity NPC207757
0.865 High Similarity NPC244112
0.865 High Similarity NPC216459
0.865 High Similarity NPC138487
0.865 High Similarity NPC276588
0.865 High Similarity NPC204828
0.865 High Similarity NPC469817
0.865 High Similarity NPC41178
0.865 High Similarity NPC278799
0.865 High Similarity NPC172765
0.865 High Similarity NPC39701
0.865 High Similarity NPC2413
0.865 High Similarity NPC249797
0.865 High Similarity NPC193949
0.8634 High Similarity NPC151895
0.8634 High Similarity NPC88249
0.8634 High Similarity NPC192768
0.8634 High Similarity NPC220858
0.8634 High Similarity NPC97221
0.8631 High Similarity NPC190332
0.8631 High Similarity NPC210140
0.8631 High Similarity NPC150879
0.8631 High Similarity NPC181653
0.8625 High Similarity NPC147390
0.8625 High Similarity NPC476571
0.8625 High Similarity NPC246587
0.8625 High Similarity NPC428
0.8625 High Similarity NPC24233
0.8625 High Similarity NPC475959
0.8625 High Similarity NPC135538
0.8623 High Similarity NPC24465
0.8598 High Similarity NPC146288
0.8596 High Similarity NPC187678
0.858 High Similarity NPC312531
0.8571 High Similarity NPC264850
0.8571 High Similarity NPC124657
0.8571 High Similarity NPC103379
0.8571 High Similarity NPC13916
0.8571 High Similarity NPC477565
0.8563 High Similarity NPC233718
0.8562 High Similarity NPC321505
0.8562 High Similarity NPC191376
0.8562 High Similarity NPC179825
0.8555 High Similarity NPC32154
0.8554 High Similarity NPC249274
0.8554 High Similarity NPC205167
0.8539 High Similarity NPC478093
0.8539 High Similarity NPC24260
0.8529 High Similarity NPC311991
0.8528 High Similarity NPC233029
0.8528 High Similarity NPC26601
0.8528 High Similarity NPC210148
0.8523 High Similarity NPC320088
0.8521 High Similarity NPC204947
0.8521 High Similarity NPC100566
0.8512 High Similarity NPC134858
0.8494 Intermediate Similarity NPC477080
0.8492 Intermediate Similarity NPC30182
0.8492 Intermediate Similarity NPC478091
0.8492 Intermediate Similarity NPC478092
0.8492 Intermediate Similarity NPC473589
0.8485 Intermediate Similarity NPC170503
0.8485 Intermediate Similarity NPC31311
0.8485 Intermediate Similarity NPC203784
0.8485 Intermediate Similarity NPC234392
0.8485 Intermediate Similarity NPC126519
0.8457 Intermediate Similarity NPC211296
0.8452 Intermediate Similarity NPC233650
0.8452 Intermediate Similarity NPC320104
0.8447 Intermediate Similarity NPC476151
0.8439 Intermediate Similarity NPC237044
0.8439 Intermediate Similarity NPC241704
0.8438 Intermediate Similarity NPC185838
0.8424 Intermediate Similarity NPC76079
0.84 Intermediate Similarity NPC179704
0.8395 Intermediate Similarity NPC130941
0.8391 Intermediate Similarity NPC474325
0.8382 Intermediate Similarity NPC304675
0.8363 Intermediate Similarity NPC204908
0.8363 Intermediate Similarity NPC83198
0.8344 Intermediate Similarity NPC219162
0.8343 Intermediate Similarity NPC474745
0.8343 Intermediate Similarity NPC220961
0.8333 Intermediate Similarity NPC119649
0.8333 Intermediate Similarity NPC235143

  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 NPC229166 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
0.85 High Similarity NPD2420 Approved
0.85 High Similarity NPD2421 Approved
0.8471 Intermediate Similarity NPD27 Approved
0.8471 Intermediate Similarity NPD2489 Approved
0.8462 Intermediate Similarity NPD3051 Approved
0.8412 Intermediate Similarity NPD2970 Approved
0.8412 Intermediate Similarity NPD2969 Approved
0.8315 Intermediate Similarity NPD7906 Approved
0.8221 Intermediate Similarity NPD4584 Approved
0.8192 Intermediate Similarity NPD7312 Approved
0.8192 Intermediate Similarity NPD4578 Approved
0.8192 Intermediate Similarity NPD7311 Approved
0.8192 Intermediate Similarity NPD7310 Approved
0.8192 Intermediate Similarity NPD7313 Approved
0.8192 Intermediate Similarity NPD4577 Approved
0.8187 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8156 Intermediate Similarity NPD4663 Approved
0.8146 Intermediate Similarity NPD8054 Approved
0.8146 Intermediate Similarity NPD7309 Approved
0.8146 Intermediate Similarity NPD8053 Approved
0.8046 Intermediate Similarity NPD4481 Phase 3
0.8046 Intermediate Similarity NPD2898 Approved
0.7931 Intermediate Similarity NPD4010 Discontinued
0.7927 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD2488 Approved
0.7923 Intermediate Similarity NPD2490 Approved
0.7836 Intermediate Similarity NPD2977 Approved
0.7836 Intermediate Similarity NPD2978 Approved
0.7836 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD5241 Discontinued
0.7816 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD7833 Phase 2
0.7803 Intermediate Similarity NPD7831 Phase 2
0.7803 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3845 Phase 1
0.7753 Intermediate Similarity NPD8099 Discontinued
0.7753 Intermediate Similarity NPD8251 Approved
0.7753 Intermediate Similarity NPD8252 Approved
0.7737 Intermediate Similarity NPD3452 Approved
0.7737 Intermediate Similarity NPD2493 Approved
0.7737 Intermediate Similarity NPD3450 Approved
0.7737 Intermediate Similarity NPD2494 Approved
0.7727 Intermediate Similarity NPD6071 Discontinued
0.7709 Intermediate Similarity NPD8156 Discontinued
0.7692 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2560 Approved
0.7688 Intermediate Similarity NPD2563 Approved
0.7674 Intermediate Similarity NPD7298 Approved
0.7665 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.765 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6788 Approved
0.7617 Intermediate Similarity NPD4582 Approved
0.7617 Intermediate Similarity NPD4583 Approved
0.7616 Intermediate Similarity NPD4772 Phase 2
0.7616 Intermediate Similarity NPD4773 Phase 2
0.7602 Intermediate Similarity NPD4017 Approved
0.7596 Intermediate Similarity NPD2968 Approved
0.7596 Intermediate Similarity NPD2971 Approved
0.7574 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD4002 Approved
0.7565 Intermediate Similarity NPD4004 Approved
0.7541 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD2973 Approved
0.7526 Intermediate Similarity NPD2974 Approved
0.7526 Intermediate Similarity NPD2975 Approved
0.7525 Intermediate Similarity NPD7827 Phase 1
0.75 Intermediate Similarity NPD5604 Discontinued
0.7487 Intermediate Similarity NPD4420 Approved
0.7485 Intermediate Similarity NPD3640 Phase 3
0.7485 Intermediate Similarity NPD3639 Approved
0.7485 Intermediate Similarity NPD3641 Approved
0.7474 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD3110 Approved
0.7423 Intermediate Similarity NPD3109 Approved
0.7413 Intermediate Similarity NPD7047 Phase 3
0.7409 Intermediate Similarity NPD4580 Approved
0.7384 Intermediate Similarity NPD6030 Approved
0.7384 Intermediate Similarity NPD6031 Approved
0.7384 Intermediate Similarity NPD4727 Phase 1
0.7366 Intermediate Similarity NPD6997 Phase 2
0.7349 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD4040 Phase 1
0.7346 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5006 Approved
0.7333 Intermediate Similarity NPD5005 Approved
0.7312 Intermediate Similarity NPD7281 Phase 3
0.7312 Intermediate Similarity NPD7280 Phase 3
0.7305 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD4055 Discovery
0.7268 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD3057 Approved
0.7245 Intermediate Similarity NPD3448 Approved
0.7245 Intermediate Similarity NPD2491 Approved
0.7243 Intermediate Similarity NPD6297 Approved
0.7239 Intermediate Similarity NPD5156 Approved
0.7239 Intermediate Similarity NPD5155 Approved
0.7235 Intermediate Similarity NPD5754 Discontinued
0.7225 Intermediate Similarity NPD6090 Discontinued
0.7213 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5582 Discontinued
0.72 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5718 Phase 2
0.7182 Intermediate Similarity NPD6107 Approved
0.7182 Intermediate Similarity NPD7802 Discontinued
0.7178 Intermediate Similarity NPD2606 Approved
0.7178 Intermediate Similarity NPD3594 Approved
0.7178 Intermediate Similarity NPD2605 Approved
0.7178 Intermediate Similarity NPD3595 Approved
0.7176 Intermediate Similarity NPD3060 Approved
0.7176 Intermediate Similarity NPD4236 Phase 3
0.7176 Intermediate Similarity NPD4237 Approved
0.7176 Intermediate Similarity NPD5177 Phase 3
0.7163 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4721 Approved
0.716 Intermediate Similarity NPD4725 Approved
0.716 Intermediate Similarity NPD4726 Approved
0.7157 Intermediate Similarity NPD2972 Approved
0.7157 Intermediate Similarity NPD3533 Approved
0.7152 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2674 Phase 3
0.7143 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1753 Discontinued
0.7143 Intermediate Similarity NPD4166 Phase 2
0.7136 Intermediate Similarity NPD6723 Discontinued
0.7135 Intermediate Similarity NPD42 Phase 2
0.7135 Intermediate Similarity NPD6042 Phase 2
0.7127 Intermediate Similarity NPD4666 Phase 3
0.7117 Intermediate Similarity NPD3636 Approved
0.7117 Intermediate Similarity NPD3637 Approved
0.7117 Intermediate Similarity NPD3635 Approved
0.7102 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD4005 Discontinued
0.7093 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD6853 Approved
0.709 Intermediate Similarity NPD6851 Approved
0.7086 Intermediate Similarity NPD5976 Discontinued
0.7079 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD6674 Discontinued
0.7072 Intermediate Similarity NPD5709 Phase 3
0.7072 Intermediate Similarity NPD7400 Phase 3
0.7069 Intermediate Similarity NPD1424 Approved
0.7065 Intermediate Similarity NPD4859 Phase 1
0.7059 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD4107 Approved
0.7053 Intermediate Similarity NPD3763 Approved
0.7052 Intermediate Similarity NPD6667 Approved
0.7052 Intermediate Similarity NPD6666 Approved
0.7048 Intermediate Similarity NPD4475 Approved
0.7048 Intermediate Similarity NPD4474 Approved
0.7043 Intermediate Similarity NPD4873 Discontinued
0.7041 Intermediate Similarity NPD4108 Discontinued
0.7039 Intermediate Similarity NPD5772 Approved
0.7039 Intermediate Similarity NPD5773 Approved
0.7037 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7037 Approved
0.7011 Intermediate Similarity NPD3124 Discontinued
0.7005 Intermediate Similarity NPD8095 Phase 1
0.6988 Remote Similarity NPD3145 Approved
0.6988 Remote Similarity NPD3144 Approved
0.6986 Remote Similarity NPD7907 Approved
0.6982 Remote Similarity NPD6896 Approved
0.6982 Remote Similarity NPD6895 Approved
0.6978 Remote Similarity NPD6234 Discontinued
0.6971 Remote Similarity NPD4123 Phase 3
0.6971 Remote Similarity NPD4160 Clinical (unspecified phase)
0.697 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5676 Approved
0.6959 Remote Similarity NPD7296 Approved
0.6957 Remote Similarity NPD6747 Phase 1
0.6954 Remote Similarity NPD7124 Phase 2
0.6952 Remote Similarity NPD5313 Approved
0.6952 Remote Similarity NPD5312 Approved
0.6951 Remote Similarity NPD8153 Approved
0.6951 Remote Similarity NPD8152 Approved
0.6935 Remote Similarity NPD4482 Phase 3
0.6927 Remote Similarity NPD6072 Discontinued
0.6923 Remote Similarity NPD2492 Phase 1
0.6923 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6919 Remote Similarity NPD4257 Approved
0.6919 Remote Similarity NPD6687 Approved
0.6919 Remote Similarity NPD4256 Phase 2
0.6919 Remote Similarity NPD6688 Approved
0.6915 Remote Similarity NPD7479 Phase 2
0.6914 Remote Similarity NPD7598 Phase 2
0.6907 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5977 Approved
0.6906 Remote Similarity NPD5978 Approved
0.6898 Remote Similarity NPD7228 Approved
0.6897 Remote Similarity NPD5160 Discontinued
0.6895 Remote Similarity NPD7549 Discontinued
0.6893 Remote Similarity NPD1914 Approved
0.689 Remote Similarity NPD4111 Phase 1
0.689 Remote Similarity NPD4665 Approved
0.689 Remote Similarity NPD8318 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