Structure

Physi-Chem Properties

Molecular Weight:  300.1
Volume:  302.415
LogP:  3.977
LogD:  3.429
LogS:  -4.088
# Rotatable Bonds:  2
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.755
Synthetic Accessibility Score:  2.902
Fsp3:  0.176
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.964
MDCK Permeability:  1.7447053323849104e-05
Pgp-inhibitor:  0.061
Pgp-substrate:  0.016
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.024
Plasma Protein Binding (PPB):  99.23851776123047%
Volume Distribution (VD):  0.476
Pgp-substrate:  3.2107348442077637%

ADMET: Metabolism

CYP1A2-inhibitor:  0.918
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.409
CYP2C19-substrate:  0.817
CYP2C9-inhibitor:  0.303
CYP2C9-substrate:  0.846
CYP2D6-inhibitor:  0.228
CYP2D6-substrate:  0.924
CYP3A4-inhibitor:  0.303
CYP3A4-substrate:  0.624

ADMET: Excretion

Clearance (CL):  9.581
Half-life (T1/2):  0.569

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.134
Drug-inuced Liver Injury (DILI):  0.549
AMES Toxicity:  0.426
Rat Oral Acute Toxicity:  0.996
Maximum Recommended Daily Dose:  0.826
Skin Sensitization:  0.957
Carcinogencity:  0.634
Eye Corrosion:  0.004
Eye Irritation:  0.921
Respiratory Toxicity:  0.768

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

  Natural Product: NPC37196

Natural Product ID:  NPC37196
Common Name*:   Bauhiniastatin 3
IUPAC Name:   3,7-dimethoxy-2-methylbenzo[b][1]benzoxepine-1,10-diol
Synonyms:   Bauhiniastatin 3
Standard InCHIKey:  ONNAYQNJOKQYOH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H16O5/c1-9-14(21-3)8-10-4-5-11-13(20-2)7-6-12(18)17(11)22-16(10)15(9)19/h4-8,18-19H,1-3H3
SMILES:  Cc1c(cc2C=Cc3c(ccc(c3Oc2c1O)O)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510988
PubChem CID:   11623581
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001910] Benzoxepines
        • [CHEMONTID:0001988] Dibenzoxepines

*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
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. aerial part n.a. PMID[11141127]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[15595606]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562827]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. root n.a. PMID[17480099]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota roots Phitsanulok Province, Thailand 2004-MAY PMID[17480099]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3357 Alnus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2455 Thermopsis mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6828 Purpura aperta Species Muricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9608 Lepraria citrina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8807 Laurentia longiflora n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4382 Elmerrillia papuana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25475 Syphonota geographica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1490 Goldfussia yunnanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9881 Petrosia hebes Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4628 Aloe deltoideodonta Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8977 0tholaena aschenborniana Species Pteridaceae 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
NPT168 Cell Line P388 Mus musculus GI50 = 15.7 ug.mL-1 PMID[550806]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 6.6 ug.mL-1 PMID[550806]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 3.2 ug.mL-1 PMID[550806]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 5.8 ug.mL-1 PMID[550806]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 6.1 ug.mL-1 PMID[550806]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 > 10.0 ug.mL-1 PMID[550806]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 5.8 ug.mL-1 PMID[550806]

☑ 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 NPC37196 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 NPC94236
0.9921 High Similarity NPC161203
0.9762 High Similarity NPC229231
0.969 High Similarity NPC281521
0.969 High Similarity NPC255147
0.969 High Similarity NPC201357
0.9535 High Similarity NPC269528
0.9524 High Similarity NPC216836
0.9453 High Similarity NPC214860
0.938 High Similarity NPC82503
0.9375 High Similarity NPC45824
0.9318 High Similarity NPC476698
0.9297 High Similarity NPC266691
0.9242 High Similarity NPC134968
0.9242 High Similarity NPC472337
0.9237 High Similarity NPC36661
0.9225 High Similarity NPC10225
0.9225 High Similarity NPC58164
0.9219 High Similarity NPC236760
0.9206 High Similarity NPC95168
0.9173 High Similarity NPC472334
0.9173 High Similarity NPC472336
0.9154 High Similarity NPC51840
0.9154 High Similarity NPC234488
0.9154 High Similarity NPC220935
0.9154 High Similarity NPC311680
0.9154 High Similarity NPC299221
0.9147 High Similarity NPC63179
0.9104 High Similarity NPC102904
0.9104 High Similarity NPC326797
0.9104 High Similarity NPC103976
0.9104 High Similarity NPC107551
0.9104 High Similarity NPC474282
0.9104 High Similarity NPC276490
0.9104 High Similarity NPC176051
0.9098 High Similarity NPC261873
0.9098 High Similarity NPC283009
0.9091 High Similarity NPC229442
0.9091 High Similarity NPC168059
0.907 High Similarity NPC210355
0.907 High Similarity NPC50368
0.9062 High Similarity NPC299584
0.9062 High Similarity NPC265483
0.9062 High Similarity NPC82483
0.9051 High Similarity NPC477616
0.9048 High Similarity NPC75713
0.9037 High Similarity NPC25966
0.9037 High Similarity NPC127218
0.9037 High Similarity NPC245207
0.9037 High Similarity NPC319647
0.9023 High Similarity NPC106215
0.9023 High Similarity NPC103967
0.9023 High Similarity NPC310854
0.9015 High Similarity NPC127624
0.9015 High Similarity NPC86655
0.9015 High Similarity NPC6451
0.9015 High Similarity NPC202762
0.9008 High Similarity NPC474481
0.8992 High Similarity NPC476006
0.8992 High Similarity NPC103823
0.8992 High Similarity NPC112596
0.8992 High Similarity NPC44748
0.8992 High Similarity NPC78974
0.8992 High Similarity NPC28730
0.8992 High Similarity NPC223136
0.8992 High Similarity NPC214406
0.8992 High Similarity NPC18924
0.8984 High Similarity NPC183446
0.8971 High Similarity NPC160283
0.8971 High Similarity NPC254759
0.8963 High Similarity NPC73535
0.8963 High Similarity NPC272157
0.8963 High Similarity NPC25111
0.8963 High Similarity NPC90615
0.8963 High Similarity NPC201145
0.8963 High Similarity NPC6262
0.8955 High Similarity NPC474206
0.8955 High Similarity NPC121812
0.8955 High Similarity NPC94750
0.8955 High Similarity NPC112246
0.8955 High Similarity NPC470356
0.8955 High Similarity NPC112939
0.8955 High Similarity NPC195022
0.8947 High Similarity NPC475840
0.8939 High Similarity NPC472597
0.8939 High Similarity NPC45715
0.8939 High Similarity NPC232275
0.8939 High Similarity NPC474356
0.8939 High Similarity NPC12275
0.8923 High Similarity NPC124452
0.8923 High Similarity NPC324112
0.8923 High Similarity NPC159968
0.8923 High Similarity NPC282000
0.8923 High Similarity NPC236791
0.8923 High Similarity NPC74817
0.8923 High Similarity NPC169474
0.8923 High Similarity NPC293054
0.8923 High Similarity NPC82679
0.8923 High Similarity NPC246620
0.8915 High Similarity NPC234400
0.8915 High Similarity NPC60885
0.8906 High Similarity NPC121115
0.8905 High Similarity NPC471389
0.8897 High Similarity NPC292882
0.8897 High Similarity NPC19869
0.8889 High Similarity NPC114155
0.8889 High Similarity NPC306441
0.8889 High Similarity NPC227503
0.8889 High Similarity NPC248727
0.8889 High Similarity NPC270456
0.8889 High Similarity NPC300846
0.8889 High Similarity NPC173660
0.8889 High Similarity NPC16435
0.8889 High Similarity NPC162659
0.8889 High Similarity NPC265433
0.8889 High Similarity NPC476639
0.8889 High Similarity NPC230734
0.8889 High Similarity NPC474639
0.8881 High Similarity NPC317380
0.8872 High Similarity NPC7903
0.8872 High Similarity NPC218884
0.8872 High Similarity NPC35932
0.8872 High Similarity NPC184447
0.8872 High Similarity NPC16208
0.8872 High Similarity NPC160991
0.8864 High Similarity NPC472338
0.8864 High Similarity NPC224157
0.8864 High Similarity NPC91291
0.8864 High Similarity NPC192687
0.8855 High Similarity NPC19694
0.8846 High Similarity NPC245060
0.8841 High Similarity NPC107161
0.8841 High Similarity NPC472335
0.8841 High Similarity NPC472332
0.8837 High Similarity NPC228972
0.8837 High Similarity NPC122792
0.8832 High Similarity NPC73505
0.8832 High Similarity NPC295719
0.8832 High Similarity NPC34431
0.8832 High Similarity NPC165026
0.8832 High Similarity NPC259519
0.8828 High Similarity NPC246967
0.8828 High Similarity NPC135414
0.8828 High Similarity NPC474864
0.8828 High Similarity NPC262253
0.8828 High Similarity NPC473411
0.8828 High Similarity NPC71579
0.8824 High Similarity NPC211549
0.8815 High Similarity NPC260898
0.8815 High Similarity NPC234333
0.8815 High Similarity NPC111655
0.8815 High Similarity NPC61946
0.8815 High Similarity NPC47398
0.8815 High Similarity NPC252095
0.8815 High Similarity NPC151224
0.8806 High Similarity NPC11060
0.8806 High Similarity NPC474810
0.8794 High Similarity NPC178129
0.8788 High Similarity NPC190144
0.8788 High Similarity NPC190629
0.8788 High Similarity NPC210623
0.8788 High Similarity NPC218856
0.8788 High Similarity NPC470258
0.8788 High Similarity NPC273295
0.8788 High Similarity NPC226788
0.8788 High Similarity NPC222004
0.8788 High Similarity NPC202582
0.8788 High Similarity NPC285339
0.8788 High Similarity NPC3439
0.8779 High Similarity NPC470699
0.8769 High Similarity NPC193544
0.8769 High Similarity NPC203133
0.8769 High Similarity NPC17943
0.8769 High Similarity NPC251855
0.8769 High Similarity NPC472093
0.8769 High Similarity NPC298757
0.8769 High Similarity NPC233410
0.8769 High Similarity NPC116907
0.8769 High Similarity NPC117214
0.8769 High Similarity NPC208950
0.8769 High Similarity NPC475169
0.8769 High Similarity NPC221077
0.8769 High Similarity NPC57490
0.8769 High Similarity NPC105925
0.8768 High Similarity NPC247291
0.8768 High Similarity NPC311530
0.8759 High Similarity NPC70682
0.8759 High Similarity NPC212942
0.8759 High Similarity NPC260741
0.8759 High Similarity NPC29868
0.8759 High Similarity NPC471388
0.8759 High Similarity NPC79622
0.875 High Similarity NPC145780
0.875 High Similarity NPC269091
0.875 High Similarity NPC302701
0.8741 High Similarity NPC170694
0.8731 High Similarity NPC470752
0.8723 High Similarity NPC112251
0.8722 High Similarity NPC126836
0.8714 High Similarity NPC45257

  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 NPC37196 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
0.8712 High Similarity NPD1529 Clinical (unspecified phase)
0.8647 High Similarity NPD3027 Phase 3
0.8636 High Similarity NPD1530 Clinical (unspecified phase)
0.8593 High Similarity NPD1612 Clinical (unspecified phase)
0.8593 High Similarity NPD1613 Approved
0.8133 Intermediate Similarity NPD2801 Approved
0.8102 Intermediate Similarity NPD4625 Phase 3
0.8088 Intermediate Similarity NPD3018 Phase 2
0.806 Intermediate Similarity NPD4749 Approved
0.7926 Intermediate Similarity NPD2982 Phase 2
0.7926 Intermediate Similarity NPD2983 Phase 2
0.7919 Intermediate Similarity NPD1653 Approved
0.7899 Intermediate Similarity NPD4908 Phase 1
0.7879 Intermediate Similarity NPD1548 Phase 1
0.7852 Intermediate Similarity NPD2981 Phase 2
0.7829 Intermediate Similarity NPD1934 Approved
0.7786 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD6671 Approved
0.7778 Intermediate Similarity NPD1610 Phase 2
0.7752 Intermediate Similarity NPD228 Approved
0.7698 Intermediate Similarity NPD2861 Phase 2
0.7677 Intermediate Similarity NPD3882 Suspended
0.7664 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD1511 Approved
0.7647 Intermediate Similarity NPD1091 Approved
0.7638 Intermediate Similarity NPD968 Approved
0.7574 Intermediate Similarity NPD3496 Discontinued
0.7552 Intermediate Similarity NPD1558 Phase 1
0.755 Intermediate Similarity NPD1512 Approved
0.75 Intermediate Similarity NPD5283 Phase 1
0.75 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3540 Phase 1
0.7482 Intermediate Similarity NPD6696 Suspended
0.7468 Intermediate Similarity NPD4675 Approved
0.7468 Intermediate Similarity NPD4678 Approved
0.7453 Intermediate Similarity NPD6166 Phase 2
0.7453 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD290 Approved
0.7434 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD5844 Phase 1
0.7415 Intermediate Similarity NPD6100 Approved
0.7415 Intermediate Similarity NPD3539 Phase 1
0.7415 Intermediate Similarity NPD6099 Approved
0.7413 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD422 Phase 1
0.7389 Intermediate Similarity NPD3817 Phase 2
0.7383 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6234 Discontinued
0.7328 Intermediate Similarity NPD4750 Phase 3
0.7317 Intermediate Similarity NPD7054 Approved
0.731 Intermediate Similarity NPD4060 Phase 1
0.7297 Intermediate Similarity NPD1551 Phase 2
0.7273 Intermediate Similarity NPD7472 Approved
0.7273 Intermediate Similarity NPD7074 Phase 3
0.7267 Intermediate Similarity NPD6674 Discontinued
0.7256 Intermediate Similarity NPD3818 Discontinued
0.7246 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1778 Approved
0.7222 Intermediate Similarity NPD6232 Discontinued
0.7219 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3022 Approved
0.7197 Intermediate Similarity NPD3021 Approved
0.719 Intermediate Similarity NPD4357 Discontinued
0.7171 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5402 Approved
0.716 Intermediate Similarity NPD7199 Phase 2
0.7153 Intermediate Similarity NPD5536 Phase 2
0.7152 Intermediate Similarity NPD37 Approved
0.7143 Intermediate Similarity NPD447 Suspended
0.7143 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3705 Approved
0.7143 Intermediate Similarity NPD1611 Approved
0.7143 Intermediate Similarity NPD4123 Phase 3
0.7126 Intermediate Similarity NPD6797 Phase 2
0.7125 Intermediate Similarity NPD4965 Approved
0.7125 Intermediate Similarity NPD4967 Phase 2
0.7125 Intermediate Similarity NPD4966 Approved
0.7121 Intermediate Similarity NPD2684 Approved
0.7113 Intermediate Similarity NPD2922 Phase 1
0.7111 Intermediate Similarity NPD1398 Phase 1
0.7109 Intermediate Similarity NPD1242 Phase 1
0.7107 Intermediate Similarity NPD1465 Phase 2
0.7105 Intermediate Similarity NPD3892 Phase 2
0.7099 Intermediate Similarity NPD5494 Approved
0.7091 Intermediate Similarity NPD7473 Discontinued
0.7083 Intermediate Similarity NPD7251 Discontinued
0.708 Intermediate Similarity NPD7340 Approved
0.7075 Intermediate Similarity NPD3620 Phase 2
0.7075 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2219 Phase 1
0.7059 Intermediate Similarity NPD2677 Approved
0.7054 Intermediate Similarity NPD291 Approved
0.7048 Intermediate Similarity NPD7228 Approved
0.7042 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7549 Discontinued
0.7041 Intermediate Similarity NPD7808 Phase 3
0.7039 Intermediate Similarity NPD1652 Phase 2
0.7039 Intermediate Similarity NPD5177 Phase 3
0.7037 Intermediate Similarity NPD7843 Approved
0.7032 Intermediate Similarity NPD7447 Phase 1
0.7027 Intermediate Similarity NPD230 Phase 1
0.7024 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD5762 Approved
0.702 Intermediate Similarity NPD7266 Discontinued
0.702 Intermediate Similarity NPD5763 Approved
0.7007 Intermediate Similarity NPD6233 Phase 2
0.7007 Intermediate Similarity NPD7157 Approved
0.6993 Remote Similarity NPD8651 Approved
0.6993 Remote Similarity NPD3225 Approved
0.6987 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6984 Remote Similarity NPD9296 Approved
0.698 Remote Similarity NPD1607 Approved
0.6975 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6968 Remote Similarity NPD7212 Phase 2
0.6968 Remote Similarity NPD1774 Approved
0.6968 Remote Similarity NPD7213 Phase 3
0.6968 Remote Similarity NPD6799 Approved
0.6962 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6959 Remote Similarity NPD8053 Approved
0.6959 Remote Similarity NPD8054 Approved
0.6957 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2935 Discontinued
0.6948 Remote Similarity NPD6190 Approved
0.6933 Remote Similarity NPD4536 Approved
0.6933 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4538 Approved
0.6929 Remote Similarity NPD1357 Approved
0.6928 Remote Similarity NPD3060 Approved
0.6923 Remote Similarity NPD940 Approved
0.6923 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6923 Remote Similarity NPD846 Approved
0.6918 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4380 Phase 2
0.6918 Remote Similarity NPD6599 Discontinued
0.6912 Remote Similarity NPD7635 Approved
0.6908 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6908 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6908 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7124 Phase 2
0.6897 Remote Similarity NPD6584 Phase 3
0.6892 Remote Similarity NPD2674 Phase 3
0.6883 Remote Similarity NPD4628 Phase 3
0.6883 Remote Similarity NPD3750 Approved
0.6882 Remote Similarity NPD6559 Discontinued
0.6871 Remote Similarity NPD7095 Approved
0.6871 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6871 Remote Similarity NPD4055 Discovery
0.6871 Remote Similarity NPD7075 Discontinued
0.6863 Remote Similarity NPD1549 Phase 2
0.6859 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6855 Remote Similarity NPD4005 Discontinued
0.6853 Remote Similarity NPD2231 Phase 2
0.6853 Remote Similarity NPD2235 Phase 2
0.6853 Remote Similarity NPD1608 Approved
0.6846 Remote Similarity NPD1240 Approved
0.6842 Remote Similarity NPD6032 Approved
0.6835 Remote Similarity NPD5403 Approved
0.6828 Remote Similarity NPD2797 Approved
0.6824 Remote Similarity NPD3144 Approved
0.6824 Remote Similarity NPD5111 Phase 2
0.6824 Remote Similarity NPD5109 Approved
0.6824 Remote Similarity NPD5110 Phase 2
0.6824 Remote Similarity NPD3145 Approved
0.6824 Remote Similarity NPD6798 Discontinued
0.6818 Remote Similarity NPD4237 Approved
0.6818 Remote Similarity NPD4236 Phase 3
0.6818 Remote Similarity NPD4162 Approved
0.6815 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5585 Approved
0.6807 Remote Similarity NPD3787 Discontinued
0.68 Remote Similarity NPD5124 Phase 1
0.68 Remote Similarity NPD1933 Approved
0.68 Remote Similarity NPD5123 Clinical (unspecified phase)
0.68 Remote Similarity NPD6355 Discontinued
0.6797 Remote Similarity NPD1375 Discontinued
0.6797 Remote Similarity NPD844 Approved
0.679 Remote Similarity NPD5929 Approved
0.679 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5677 Discontinued
0.6786 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6783 Remote Similarity NPD1535 Discovery
0.6776 Remote Similarity NPD7033 Discontinued
0.6776 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5588 Approved
0.6776 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6776 Remote Similarity NPD1510 Phase 2
0.6776 Remote Similarity NPD5960 Phase 3
0.6774 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4110 Phase 3
0.6774 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6090 Discontinued
0.6761 Remote Similarity NPD6516 Phase 2
0.6761 Remote Similarity NPD5846 Approved
0.6761 Remote Similarity NPD4626 Approved
0.6755 Remote Similarity NPD6653 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