Structure

Physi-Chem Properties

Molecular Weight:  233.07
Volume:  223.414
LogP:  1.367
LogD:  1.748
LogS:  -2.565
# Rotatable Bonds:  1
TPSA:  49.69
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.744
Synthetic Accessibility Score:  2.553
Fsp3:  0.25
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:  -4.624
MDCK Permeability:  3.589675179682672e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.971
Plasma Protein Binding (PPB):  90.38077545166016%
Volume Distribution (VD):  1.062
Pgp-substrate:  6.11936616897583%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.919
CYP2C19-inhibitor:  0.644
CYP2C19-substrate:  0.847
CYP2C9-inhibitor:  0.106
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.636
CYP2D6-substrate:  0.906
CYP3A4-inhibitor:  0.862
CYP3A4-substrate:  0.297

ADMET: Excretion

Clearance (CL):  7.056
Half-life (T1/2):  0.652

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.18
Drug-inuced Liver Injury (DILI):  0.247
AMES Toxicity:  0.917
Rat Oral Acute Toxicity:  0.038
Maximum Recommended Daily Dose:  0.162
Skin Sensitization:  0.152
Carcinogencity:  0.96
Eye Corrosion:  0.009
Eye Irritation:  0.561
Respiratory Toxicity:  0.875

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

  Natural Product: NPC287152

Natural Product ID:  NPC287152
Common Name*:   Casimiroin
IUPAC Name:   6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8-one
Synonyms:   Casimiroin
Standard InCHIKey:  DPXXJCMMMXZVSW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H11NO4/c1-13-10(14)5-9(15-2)7-3-4-8-12(11(7)13)17-6-16-8/h3-5H,6H2,1-2H3
SMILES:  Cn1c(=O)cc(c2ccc3c(c12)OCO3)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL492762
PubChem CID:   124075
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000056] Quinolones and derivatives
          • [CHEMONTID:0001716] Hydroquinolones

*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
NPO24038 Casimiroa edulis Species Rutaceae Eukaryota n.a. seed n.a. PMID[10075120]
NPO7344 Spiraea prunifolia Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11473429]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[16499335]
NPO24038 Casimiroa edulis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17228877]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[18484537]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. root n.a. PMID[18484537]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19615910]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[29323912]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[731398]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. root n.a. PMID[731398]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. rhizome n.a. PMID[7714541]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[7760071]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. rhizome n.a. PMID[7798964]
NPO19895 Plectranthus hereroensis Species Lamiaceae Eukaryota Roots n.a. n.a. PMID[7931371]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. PMID[7964801]
NPO23356 Ascodesmis sphaerospora Species Ascodesmidaceae Eukaryota n.a. n.a. n.a. PMID[9868168]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24038 Casimiroa edulis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23588 Ursinia anthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24038 Casimiroa edulis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23628 Imperata cylindrica Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9814 Lactarius fuliginosus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23490 Dalbergia monetaria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23588 Ursinia anthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7344 Spiraea prunifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17492 Amomum reticulatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23356 Ascodesmis sphaerospora Species Ascodesmidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19895 Plectranthus hereroensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24396 Grosvenoria rimbachii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15572 Espeletiopsis purpurascens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23398 Caralluma russeliana Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23911 Alpinia officinarum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24280 Helianthus californicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24038 Casimiroa edulis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23822 Polypodium aureum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23628 Imperata cylindrica Species Poaceae 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 = 3920.0 nM PMID[538948]
NPT366 Individual Protein Quinone reductase 2 Homo sapiens IC50 = 54100.0 nM PMID[538948]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 85810.0 nM PMID[538948]
NPT858 Cell Line LNCaP Homo sapiens IC50 > 85810.0 nM PMID[538948]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 85810.0 nM PMID[538948]

☑ 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 NPC287152 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
0.7941 Intermediate Similarity NPC301163
0.7657 Intermediate Similarity NPC24954
0.7624 Intermediate Similarity NPC5167
0.7619 Intermediate Similarity NPC161804
0.76 Intermediate Similarity NPC87560
0.76 Intermediate Similarity NPC195120
0.7553 Intermediate Similarity NPC254957
0.7537 Intermediate Similarity NPC148124
0.7527 Intermediate Similarity NPC85613
0.7525 Intermediate Similarity NPC157983
0.7525 Intermediate Similarity NPC118154
0.7514 Intermediate Similarity NPC262725
0.7488 Intermediate Similarity NPC99724
0.7396 Intermediate Similarity NPC244338
0.7396 Intermediate Similarity NPC71124
0.7391 Intermediate Similarity NPC248903
0.7391 Intermediate Similarity NPC116096
0.7389 Intermediate Similarity NPC471604
0.7374 Intermediate Similarity NPC231198
0.735 Intermediate Similarity NPC470481
0.735 Intermediate Similarity NPC470482
0.7347 Intermediate Similarity NPC268077
0.7343 Intermediate Similarity NPC26928
0.7337 Intermediate Similarity NPC287588
0.7312 Intermediate Similarity NPC179704
0.7296 Intermediate Similarity NPC207971
0.7289 Intermediate Similarity NPC469808
0.7273 Intermediate Similarity NPC167096
0.7273 Intermediate Similarity NPC169742
0.7268 Intermediate Similarity NPC5374
0.7246 Intermediate Similarity NPC252107
0.7246 Intermediate Similarity NPC470707
0.7231 Intermediate Similarity NPC127178
0.7229 Intermediate Similarity NPC136330
0.7229 Intermediate Similarity NPC255817
0.7229 Intermediate Similarity NPC73883
0.7229 Intermediate Similarity NPC230698
0.7229 Intermediate Similarity NPC277042
0.7229 Intermediate Similarity NPC251454
0.7229 Intermediate Similarity NPC196609
0.7229 Intermediate Similarity NPC205178
0.7211 Intermediate Similarity NPC237579
0.7211 Intermediate Similarity NPC312531
0.7192 Intermediate Similarity NPC148391
0.7186 Intermediate Similarity NPC99078
0.7175 Intermediate Similarity NPC93593
0.7159 Intermediate Similarity NPC471073
0.7159 Intermediate Similarity NPC270811
0.7158 Intermediate Similarity NPC73280
0.7152 Intermediate Similarity NPC217574
0.7151 Intermediate Similarity NPC98416
0.7151 Intermediate Similarity NPC283810
0.7143 Intermediate Similarity NPC220923
0.7143 Intermediate Similarity NPC114468
0.7143 Intermediate Similarity NPC116007
0.7143 Intermediate Similarity NPC268223
0.7129 Intermediate Similarity NPC82541
0.7108 Intermediate Similarity NPC2905
0.7099 Intermediate Similarity NPC250476
0.7098 Intermediate Similarity NPC302001
0.7095 Intermediate Similarity NPC320064
0.709 Intermediate Similarity NPC249405
0.7088 Intermediate Similarity NPC247972
0.7088 Intermediate Similarity NPC306669
0.7087 Intermediate Similarity NPC134702
0.7085 Intermediate Similarity NPC475147
0.7083 Intermediate Similarity NPC7018
0.7083 Intermediate Similarity NPC145446
0.7083 Intermediate Similarity NPC137172
0.7077 Intermediate Similarity NPC472191
0.7067 Intermediate Similarity NPC46259
0.7066 Intermediate Similarity NPC94280
0.7066 Intermediate Similarity NPC159150
0.7066 Intermediate Similarity NPC328419
0.7066 Intermediate Similarity NPC45783
0.7066 Intermediate Similarity NPC193673
0.7066 Intermediate Similarity NPC103947
0.7056 Intermediate Similarity NPC106786
0.7053 Intermediate Similarity NPC83511
0.7045 Intermediate Similarity NPC223125
0.7041 Intermediate Similarity NPC23080
0.7041 Intermediate Similarity NPC193906
0.7041 Intermediate Similarity NPC248505
0.7041 Intermediate Similarity NPC95366
0.7039 Intermediate Similarity NPC126556
0.7029 Intermediate Similarity NPC59907
0.7029 Intermediate Similarity NPC37144
0.7029 Intermediate Similarity NPC475959
0.7026 Intermediate Similarity NPC162653
0.7024 Intermediate Similarity NPC96406
0.7022 Intermediate Similarity NPC470708
0.7011 Intermediate Similarity NPC474324
0.7011 Intermediate Similarity NPC57812
0.701 Intermediate Similarity NPC78284
0.7 Intermediate Similarity NPC163829
0.699 Remote Similarity NPC272706
0.6989 Remote Similarity NPC470739
0.6989 Remote Similarity NPC477640
0.6989 Remote Similarity NPC225597
0.6986 Remote Similarity NPC76478
0.6985 Remote Similarity NPC66815
0.6982 Remote Similarity NPC416184
0.6978 Remote Similarity NPC299582
0.6973 Remote Similarity NPC82533
0.6973 Remote Similarity NPC475845
0.6973 Remote Similarity NPC241055
0.6973 Remote Similarity NPC290759
0.6973 Remote Similarity NPC266176
0.6973 Remote Similarity NPC158148
0.6968 Remote Similarity NPC474470
0.6966 Remote Similarity NPC223124
0.6957 Remote Similarity NPC476002
0.6957 Remote Similarity NPC195636
0.6955 Remote Similarity NPC208364
0.6952 Remote Similarity NPC2314
0.6946 Remote Similarity NPC475133
0.6943 Remote Similarity NPC474904
0.6942 Remote Similarity NPC55470
0.6941 Remote Similarity NPC113236
0.6941 Remote Similarity NPC214036
0.694 Remote Similarity NPC59567
0.694 Remote Similarity NPC218614
0.6935 Remote Similarity NPC474708
0.6935 Remote Similarity NPC474475
0.6923 Remote Similarity NPC477393
0.6923 Remote Similarity NPC180647
0.6923 Remote Similarity NPC182853
0.6919 Remote Similarity NPC247389
0.6912 Remote Similarity NPC219664
0.6905 Remote Similarity NPC7560
0.6905 Remote Similarity NPC118189
0.6901 Remote Similarity NPC13249
0.6895 Remote Similarity NPC220961
0.6891 Remote Similarity NPC477186
0.6889 Remote Similarity NPC216459
0.6889 Remote Similarity NPC41178
0.6889 Remote Similarity NPC138487
0.6885 Remote Similarity NPC70172
0.6882 Remote Similarity NPC58766
0.6882 Remote Similarity NPC475686
0.6881 Remote Similarity NPC158551
0.6875 Remote Similarity NPC156576
0.6872 Remote Similarity NPC148898
0.6865 Remote Similarity NPC219341
0.6865 Remote Similarity NPC24264
0.6865 Remote Similarity NPC476432
0.6862 Remote Similarity NPC4669
0.6861 Remote Similarity NPC477396
0.6857 Remote Similarity NPC476069
0.6851 Remote Similarity NPC146288
0.6845 Remote Similarity NPC318862
0.6845 Remote Similarity NPC119722
0.6845 Remote Similarity NPC203168
0.6842 Remote Similarity NPC472163
0.6842 Remote Similarity NPC190461
0.6842 Remote Similarity NPC197335
0.6842 Remote Similarity NPC225745
0.6832 Remote Similarity NPC473422
0.683 Remote Similarity NPC173250
0.6828 Remote Similarity NPC252960
0.6826 Remote Similarity NPC231382
0.6825 Remote Similarity NPC304675
0.6824 Remote Similarity NPC11147
0.6823 Remote Similarity NPC248642
0.6811 Remote Similarity NPC225774
0.6811 Remote Similarity NPC16805
0.6811 Remote Similarity NPC302527
0.6811 Remote Similarity NPC167546
0.6811 Remote Similarity NPC168409
0.6809 Remote Similarity NPC65403
0.6806 Remote Similarity NPC314659
0.6804 Remote Similarity NPC477259
0.6804 Remote Similarity NPC169387
0.6796 Remote Similarity NPC78733
0.6792 Remote Similarity NPC71539
0.6792 Remote Similarity NPC250960
0.6789 Remote Similarity NPC237044
0.6789 Remote Similarity NPC34770
0.6786 Remote Similarity NPC475597
0.6786 Remote Similarity NPC473716
0.6784 Remote Similarity NPC112937
0.6778 Remote Similarity NPC476580
0.6778 Remote Similarity NPC210148
0.6778 Remote Similarity NPC233029
0.6776 Remote Similarity NPC92191
0.6776 Remote Similarity NPC257763
0.6776 Remote Similarity NPC266994
0.6776 Remote Similarity NPC285254
0.6776 Remote Similarity NPC59028
0.6769 Remote Similarity NPC473569
0.6765 Remote Similarity NPC212123
0.6758 Remote Similarity NPC291173
0.6758 Remote Similarity NPC234392
0.6758 Remote Similarity NPC31311
0.6757 Remote Similarity NPC320104
0.6755 Remote Similarity NPC75958
0.6755 Remote Similarity NPC311991
0.6754 Remote Similarity NPC118633
0.6754 Remote Similarity NPC294790
0.6754 Remote Similarity NPC474325

  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 NPC287152 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
0.7474 Intermediate Similarity NPD5582 Discontinued
0.7423 Intermediate Similarity NPD956 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7263 Phase 2
0.7254 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD2492 Phase 1
0.7053 Intermediate Similarity NPD2899 Discontinued
0.7049 Intermediate Similarity NPD5847 Phase 1
0.7044 Intermediate Similarity NPD683 Approved
0.7043 Intermediate Similarity NPD3793 Phase 3
0.7043 Intermediate Similarity NPD5521 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD5900 Clinical (unspecified phase)
0.6983 Remote Similarity NPD1769 Discontinued
0.698 Remote Similarity NPD4859 Phase 1
0.697 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6961 Remote Similarity NPD4206 Approved
0.6949 Remote Similarity NPD4210 Discontinued
0.69 Remote Similarity NPD3106 Clinical (unspecified phase)
0.6898 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6898 Remote Similarity NPD6625 Approved
0.6891 Remote Similarity NPD3349 Phase 2
0.6881 Remote Similarity NPD4846 Phase 2
0.6863 Remote Similarity NPD3592 Approved
0.6863 Remote Similarity NPD3591 Approved
0.6845 Remote Similarity NPD554 Clinical (unspecified phase)
0.6845 Remote Similarity NPD5966 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3631 Phase 3
0.6802 Remote Similarity NPD6493 Phase 3
0.68 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4237 Approved
0.6782 Remote Similarity NPD4236 Phase 3
0.6771 Remote Similarity NPD7280 Phase 3
0.6771 Remote Similarity NPD7281 Phase 3
0.6769 Remote Similarity NPD7235 Clinical (unspecified phase)
0.676 Remote Similarity NPD814 Clinical (unspecified phase)
0.6758 Remote Similarity NPD2977 Approved
0.6758 Remote Similarity NPD2978 Approved
0.6751 Remote Similarity NPD7125 Discontinued
0.6749 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6737 Remote Similarity NPD3885 Approved
0.6723 Remote Similarity NPD5297 Approved
0.6722 Remote Similarity NPD789 Phase 2
0.6718 Remote Similarity NPD4157 Discontinued
0.67 Remote Similarity NPD4420 Approved
0.67 Remote Similarity NPD5071 Phase 2
0.6698 Remote Similarity NPD7224 Discontinued
0.6698 Remote Similarity NPD7223 Discontinued
0.6684 Remote Similarity NPD2845 Phase 2
0.6684 Remote Similarity NPD2843 Phase 2
0.6667 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6783 Clinical (unspecified phase)
0.665 Remote Similarity NPD5006 Approved
0.665 Remote Similarity NPD5005 Approved
0.6649 Remote Similarity NPD4083 Discontinued
0.6647 Remote Similarity NPD849 Approved
0.6647 Remote Similarity NPD850 Approved
0.6647 Remote Similarity NPD848 Approved
0.6633 Remote Similarity NPD5188 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6629 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6617 Remote Similarity NPD6877 Discontinued
0.6616 Remote Similarity NPD3633 Approved
0.6616 Remote Similarity NPD3634 Approved
0.6598 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5561 Approved
0.6588 Remote Similarity NPD5562 Approved
0.6587 Remote Similarity NPD5645 Phase 3
0.6582 Remote Similarity NPD4084 Clinical (unspecified phase)
0.6578 Remote Similarity NPD5677 Discontinued
0.6576 Remote Similarity NPD5294 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7753 Approved
0.6571 Remote Similarity NPD7752 Approved
0.6561 Remote Similarity NPD5242 Approved
0.6559 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5457 Discontinued
0.6542 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6538 Remote Similarity NPD824 Approved
0.6526 Remote Similarity NPD5858 Discontinued
0.6508 Remote Similarity NPD5186 Approved
0.6508 Remote Similarity NPD5183 Approved
0.6508 Remote Similarity NPD1293 Approved
0.6507 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6505 Remote Similarity NPD19 Approved
0.6505 Remote Similarity NPD1742 Approved
0.6505 Remote Similarity NPD6644 Discontinued
0.6505 Remote Similarity NPD1743 Approved
0.6503 Remote Similarity NPD1337 Clinical (unspecified phase)
0.65 Remote Similarity NPD3442 Approved
0.65 Remote Similarity NPD4123 Phase 3
0.65 Remote Similarity NPD1424 Approved
0.65 Remote Similarity NPD3441 Approved
0.65 Remote Similarity NPD4584 Approved
0.6497 Remote Similarity NPD4515 Suspended
0.6495 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6477 Remote Similarity NPD1375 Discontinued
0.6477 Remote Similarity NPD7479 Phase 2
0.6474 Remote Similarity NPD2216 Approved
0.6474 Remote Similarity NPD2215 Approved
0.6471 Remote Similarity NPD5604 Discontinued
0.6462 Remote Similarity NPD7559 Phase 2
0.6455 Remote Similarity NPD2680 Approved
0.6455 Remote Similarity NPD6457 Approved
0.6455 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6455 Remote Similarity NPD2681 Approved
0.6455 Remote Similarity NPD2821 Approved
0.6455 Remote Similarity NPD3983 Phase 3
0.6452 Remote Similarity NPD1012 Discontinued
0.6445 Remote Similarity NPD7225 Discontinued
0.6443 Remote Similarity NPD6297 Approved
0.6443 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6439 Remote Similarity NPD6238 Discontinued
0.6436 Remote Similarity NPD4796 Discontinued
0.6433 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6432 Remote Similarity NPD8149 Discontinued
0.6432 Remote Similarity NPD7629 Clinical (unspecified phase)
0.6432 Remote Similarity NPD7630 Phase 3
0.6432 Remote Similarity NPD7628 Phase 3
0.6429 Remote Similarity NPD8330 Clinical (unspecified phase)
0.6425 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6425 Remote Similarity NPD5600 Discontinued
0.6422 Remote Similarity NPD1880 Phase 3
0.6422 Remote Similarity NPD3297 Approved
0.6421 Remote Similarity NPD4166 Phase 2
0.6421 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6411 Remote Similarity NPD5950 Discontinued
0.6409 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6409 Remote Similarity NPD3146 Approved
0.6408 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5938 Phase 3
0.6404 Remote Similarity NPD4605 Approved
0.6404 Remote Similarity NPD4604 Approved
0.64 Remote Similarity NPD743 Approved
0.6398 Remote Similarity NPD5773 Approved
0.6398 Remote Similarity NPD5772 Approved
0.6396 Remote Similarity NPD6851 Approved
0.6396 Remote Similarity NPD6853 Approved
0.6389 Remote Similarity NPD3437 Discontinued
0.6378 Remote Similarity NPD6385 Approved
0.6378 Remote Similarity NPD4205 Phase 3
0.6378 Remote Similarity NPD1440 Discontinued
0.6378 Remote Similarity NPD6386 Approved
0.6376 Remote Similarity NPD5566 Clinical (unspecified phase)
0.6374 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6372 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6368 Remote Similarity NPD2247 Approved
0.6368 Remote Similarity NPD3816 Phase 1
0.6368 Remote Similarity NPD2249 Approved
0.6368 Remote Similarity NPD3815 Phase 1
0.6368 Remote Similarity NPD6107 Approved
0.6364 Remote Similarity NPD6339 Approved
0.6364 Remote Similarity NPD6340 Approved
0.6364 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6359 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7805 Phase 3
0.6343 Remote Similarity NPD3763 Approved
0.6341 Remote Similarity NPD5547 Clinical (unspecified phase)
0.634 Remote Similarity NPD5313 Approved
0.634 Remote Similarity NPD5312 Approved
0.6339 Remote Similarity NPD3641 Approved
0.6339 Remote Similarity NPD1670 Discontinued
0.6339 Remote Similarity NPD3640 Phase 3
0.6339 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6339 Remote Similarity NPD6031 Approved
0.6339 Remote Similarity NPD3639 Approved
0.6339 Remote Similarity NPD5976 Discontinued
0.6339 Remote Similarity NPD6030 Approved
0.6333 Remote Similarity NPD5658 Approved
0.6324 Remote Similarity NPD4675 Approved
0.6324 Remote Similarity NPD4678 Approved
0.6323 Remote Similarity NPD4885 Approved
0.6321 Remote Similarity NPD4493 Discontinued
0.6319 Remote Similarity NPD2335 Discontinued
0.6318 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6313 Remote Similarity NPD4586 Phase 3
0.6313 Remote Similarity NPD3060 Approved
0.631 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6304 Remote Similarity NPD1678 Clinical (unspecified phase)
0.6304 Remote Similarity NPD3686 Approved
0.6304 Remote Similarity NPD3687 Approved
0.6302 Remote Similarity NPD2388 Discontinued
0.6301 Remote Similarity NPD3912 Discontinued
0.6301 Remote Similarity NPD5718 Phase 2
0.63 Remote Similarity NPD5620 Clinical (unspecified phase)
0.63 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6298 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6298 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6298 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6294 Remote Similarity NPD1909 Discontinued
0.6294 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6291 Remote Similarity NPD7178 Clinical (unspecified phase)
0.6283 Remote Similarity NPD7126 Discontinued
0.628 Remote Similarity NPD6321 Discontinued
0.6279 Remote Similarity NPD5025 Approved
0.6277 Remote Similarity NPD6063 Approved
0.6277 Remote Similarity NPD2563 Approved
0.6277 Remote Similarity NPD2560 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