Structure

Physi-Chem Properties

Molecular Weight:  385.82
Volume:  223.186
LogP:  4.568
LogD:  2.728
LogS:  -5.186
# Rotatable Bonds:  3
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.672
Synthetic Accessibility Score:  3.476
Fsp3:  0.444
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.51
MDCK Permeability:  1.2659248568525072e-05
Pgp-inhibitor:  0.967
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.067
20% Bioavailability (F20%):  0.862
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.119
Plasma Protein Binding (PPB):  97.96306610107422%
Volume Distribution (VD):  1.629
Pgp-substrate:  5.925703048706055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.988
CYP1A2-substrate:  0.221
CYP2C19-inhibitor:  0.898
CYP2C19-substrate:  0.104
CYP2C9-inhibitor:  0.942
CYP2C9-substrate:  0.245
CYP2D6-inhibitor:  0.83
CYP2D6-substrate:  0.083
CYP3A4-inhibitor:  0.46
CYP3A4-substrate:  0.175

ADMET: Excretion

Clearance (CL):  0.758
Half-life (T1/2):  0.229

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.93
Drug-inuced Liver Injury (DILI):  0.811
AMES Toxicity:  0.84
Rat Oral Acute Toxicity:  0.384
Maximum Recommended Daily Dose:  0.077
Skin Sensitization:  0.963
Carcinogencity:  0.797
Eye Corrosion:  0.964
Eye Irritation:  0.982
Respiratory Toxicity:  0.942

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

  Natural Product: NPC217537

Natural Product ID:  NPC217537
Common Name*:   Sid492821
IUPAC Name:   4-bromo-3-butyl-5-(dibromomethylidene)furan-2-one
Synonyms:  
Standard InCHIKey:  VGADRJOQALVEDC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H9Br3O2/c1-2-3-4-5-6(10)7(8(11)12)14-9(5)13/h2-4H2,1H3
SMILES:  CCCCC1=C(C(=C(Br)Br)OC1=O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL450196
PubChem CID:   362385
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO14524 Delisea pulchra Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. PMID[16933872]
NPO14524 Delisea pulchra Species Bonnemaisoniaceae 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 > 20.0 ug ml-1 PMID[549104]
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 10.3 ug ml-1 PMID[549104]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[549104]
NPT168 Cell Line P388 Mus musculus ED50 > 5.0 ug ml-1 PMID[549104]
NPT762 Cell Line A-431 Homo sapiens ED50 = 10.5 ug ml-1 PMID[549104]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 9.3 ug ml-1 PMID[549104]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 8.6 ug ml-1 PMID[549104]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2747.89 nM PMID[549106]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 4365.16 nM PMID[549106]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 11885.02 nM PMID[549106]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10990.06 nM PMID[549106]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1853.53 nM PMID[549106]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 3258.37 nM PMID[549106]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 3706.81 nM PMID[549106]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2254.24 nM PMID[549106]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 3318.94 nM PMID[549106]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 15170.5 nM PMID[549106]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2546.83 nM PMID[549106]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1832.31 nM PMID[549106]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 7961.59 nM PMID[549106]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 4140.0 nM PMID[549106]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 5470.16 nM PMID[549106]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 3169.57 nM PMID[549106]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 16519.62 nM PMID[549106]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 7888.6 nM PMID[549106]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 2741.57 nM PMID[549106]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 3341.95 nM PMID[549106]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 2741.57 nM PMID[549106]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3288.52 nM PMID[549106]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1862.09 nM PMID[549106]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 7620.79 nM PMID[549106]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 9057.33 nM PMID[549106]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 379.31 nM PMID[549106]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 1794.73 nM PMID[549106]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1866.38 nM PMID[549106]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 504.66 nM PMID[549106]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 2792.54 nM PMID[549106]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 8649.68 nM PMID[549106]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 6309.57 nM PMID[549106]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 17060.82 nM PMID[549106]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5636.38 nM PMID[549106]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 3019.95 nM PMID[549106]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 2202.93 nM PMID[549106]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 2494.59 nM PMID[549106]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2612.16 nM PMID[549106]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 3539.97 nM PMID[549106]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 17579.24 nM PMID[549106]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 2074.91 nM PMID[549106]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 4560.37 nM PMID[549106]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 2415.46 nM PMID[549106]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2147.83 nM PMID[549106]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 442.59 nM PMID[549106]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2254.24 nM PMID[549106]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10592.54 nM PMID[549106]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 2483.13 nM PMID[549106]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 6011.74 nM PMID[549106]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 1896.71 nM PMID[549106]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 2454.71 nM PMID[549106]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 3083.19 nM PMID[549106]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 3999.45 nM PMID[549106]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2779.71 nM PMID[549106]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 2094.11 nM PMID[549106]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 3013.01 nM PMID[549106]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 3944.57 nM PMID[549106]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 1963.36 nM PMID[549106]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.4 ug ml-1 PMID[549104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 4.2 ug ml-1 PMID[549104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 12.4 ug ml-1 PMID[549104]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[549104]
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 11.0 mm PMID[549104]
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 13.0 mm PMID[549104]
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 8.0 mm PMID[549104]
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 1.0 mm PMID[549104]
NPT2 Others Unspecified IC50 = 1800.0 nM PMID[549104]
NPT2 Others Unspecified IC50 = 3000.0 nM PMID[549104]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity > 50.0 % PMID[549104]
NPT2 Others Unspecified IC50 >= 200000.0 nM PMID[549104]
NPT2 Others Unspecified IC50 = 14360.0 nM PMID[549105]
NPT1726 Organism Vibrio harveyi Vibrio harveyi GI50 = 20500.0 nM PMID[549105]

☑ 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 NPC217537 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
0.9661 High Similarity NPC53136
0.9661 High Similarity NPC173409
0.8906 High Similarity NPC494
0.8636 High Similarity NPC112983
0.8636 High Similarity NPC162571
0.8571 High Similarity NPC475110
0.8382 Intermediate Similarity NPC177030
0.8235 Intermediate Similarity NPC146583
0.8143 Intermediate Similarity NPC225022
0.8143 Intermediate Similarity NPC238554
0.7826 Intermediate Similarity NPC269103
0.7826 Intermediate Similarity NPC124072
0.7778 Intermediate Similarity NPC228902
0.7778 Intermediate Similarity NPC24827
0.7681 Intermediate Similarity NPC299932
0.7681 Intermediate Similarity NPC475113
0.7568 Intermediate Similarity NPC286816
0.7568 Intermediate Similarity NPC199134
0.7361 Intermediate Similarity NPC188354
0.7231 Intermediate Similarity NPC133600
0.7164 Intermediate Similarity NPC132243
0.7027 Intermediate Similarity NPC469414
0.7027 Intermediate Similarity NPC329826
0.6974 Remote Similarity NPC85743
0.6974 Remote Similarity NPC102065
0.6957 Remote Similarity NPC131174
0.6957 Remote Similarity NPC133904
0.6901 Remote Similarity NPC287705
0.6901 Remote Similarity NPC218477
0.6875 Remote Similarity NPC478117
0.6857 Remote Similarity NPC248125
0.6842 Remote Similarity NPC68156
0.6769 Remote Similarity NPC86948
0.6765 Remote Similarity NPC151648
0.6714 Remote Similarity NPC182794
0.6714 Remote Similarity NPC220766
0.6667 Remote Similarity NPC474823
0.6622 Remote Similarity NPC186531
0.6622 Remote Similarity NPC84038
0.6622 Remote Similarity NPC133098
0.662 Remote Similarity NPC315115
0.662 Remote Similarity NPC191233
0.6618 Remote Similarity NPC429928
0.6615 Remote Similarity NPC173157
0.6575 Remote Similarity NPC475004
0.6575 Remote Similarity NPC232812
0.6575 Remote Similarity NPC473277
0.6533 Remote Similarity NPC474705
0.6533 Remote Similarity NPC144419
0.6528 Remote Similarity NPC203335
0.6528 Remote Similarity NPC21998
0.6486 Remote Similarity NPC37929
0.6486 Remote Similarity NPC64234
0.6486 Remote Similarity NPC67183
0.6479 Remote Similarity NPC471556
0.6479 Remote Similarity NPC470688
0.6471 Remote Similarity NPC286189
0.6438 Remote Similarity NPC470032
0.6438 Remote Similarity NPC79220
0.6438 Remote Similarity NPC313444
0.6429 Remote Similarity NPC44343
0.6429 Remote Similarity NPC155849
0.6429 Remote Similarity NPC68110
0.6429 Remote Similarity NPC473737
0.6429 Remote Similarity NPC179087
0.6429 Remote Similarity NPC210303
0.641 Remote Similarity NPC316324
0.6406 Remote Similarity NPC191643
0.6364 Remote Similarity NPC478194
0.6364 Remote Similarity NPC478193
0.6364 Remote Similarity NPC478191
0.6364 Remote Similarity NPC478192
0.6364 Remote Similarity NPC478195
0.6364 Remote Similarity NPC49028
0.6364 Remote Similarity NPC478196
0.6351 Remote Similarity NPC470693
0.6351 Remote Similarity NPC265574
0.6329 Remote Similarity NPC315765
0.6324 Remote Similarity NPC189700
0.6316 Remote Similarity NPC287878
0.6308 Remote Similarity NPC473784
0.6301 Remote Similarity NPC132286
0.6296 Remote Similarity NPC42470
0.6286 Remote Similarity NPC15193
0.6282 Remote Similarity NPC123360
0.6267 Remote Similarity NPC315597
0.6267 Remote Similarity NPC315285
0.6267 Remote Similarity NPC316029
0.625 Remote Similarity NPC471566
0.625 Remote Similarity NPC476589
0.625 Remote Similarity NPC471565
0.6234 Remote Similarity NPC259599
0.6234 Remote Similarity NPC474758
0.6234 Remote Similarity NPC294434
0.6234 Remote Similarity NPC476355
0.6234 Remote Similarity NPC117746
0.6234 Remote Similarity NPC15499
0.6216 Remote Similarity NPC470256
0.6216 Remote Similarity NPC238223
0.6216 Remote Similarity NPC276290
0.6216 Remote Similarity NPC280374
0.6212 Remote Similarity NPC478120
0.6212 Remote Similarity NPC218486
0.6203 Remote Similarity NPC180290
0.6203 Remote Similarity NPC10572
0.6203 Remote Similarity NPC57744
0.6203 Remote Similarity NPC54996
0.6203 Remote Similarity NPC473825
0.6197 Remote Similarity NPC474658
0.619 Remote Similarity NPC234084
0.619 Remote Similarity NPC135698
0.6184 Remote Similarity NPC163003
0.6167 Remote Similarity NPC103560
0.6164 Remote Similarity NPC37382
0.6164 Remote Similarity NPC116013
0.6154 Remote Similarity NPC329852
0.6143 Remote Similarity NPC309408
0.6143 Remote Similarity NPC79756
0.6143 Remote Similarity NPC130953
0.6125 Remote Similarity NPC299235
0.6125 Remote Similarity NPC471220
0.6125 Remote Similarity NPC128276
0.6118 Remote Similarity NPC469861
0.6118 Remote Similarity NPC469860
0.6118 Remote Similarity NPC130436
0.6111 Remote Similarity NPC475618
0.6104 Remote Similarity NPC269206
0.6104 Remote Similarity NPC295633
0.6104 Remote Similarity NPC58956
0.6094 Remote Similarity NPC236338
0.6081 Remote Similarity NPC472266
0.6081 Remote Similarity NPC225272
0.6081 Remote Similarity NPC194871
0.6076 Remote Similarity NPC27205
0.6049 Remote Similarity NPC63326
0.6049 Remote Similarity NPC63649
0.6049 Remote Similarity NPC472965
0.6049 Remote Similarity NPC178277
0.6049 Remote Similarity NPC265980
0.6049 Remote Similarity NPC150646
0.6049 Remote Similarity NPC264227
0.6029 Remote Similarity NPC221763
0.6029 Remote Similarity NPC150717
0.6026 Remote Similarity NPC470686
0.6026 Remote Similarity NPC140287
0.6024 Remote Similarity NPC8161
0.6 Remote Similarity NPC53581
0.6 Remote Similarity NPC281172
0.6 Remote Similarity NPC15129
0.6 Remote Similarity NPC41780
0.6 Remote Similarity NPC316500
0.6 Remote Similarity NPC187568
0.6 Remote Similarity NPC103987
0.5977 Remote Similarity NPC472302
0.5977 Remote Similarity NPC475739
0.5976 Remote Similarity NPC474510
0.5976 Remote Similarity NPC47653
0.5974 Remote Similarity NPC129665
0.5974 Remote Similarity NPC257618
0.5972 Remote Similarity NPC217940
0.5972 Remote Similarity NPC2328
0.5972 Remote Similarity NPC474774
0.597 Remote Similarity NPC154626
0.5968 Remote Similarity NPC270706
0.5946 Remote Similarity NPC142423
0.5946 Remote Similarity NPC308294
0.5926 Remote Similarity NPC108816
0.5926 Remote Similarity NPC63445
0.5926 Remote Similarity NPC222210
0.5926 Remote Similarity NPC93763
0.5921 Remote Similarity NPC476591
0.5921 Remote Similarity NPC88877
0.5921 Remote Similarity NPC236208
0.5915 Remote Similarity NPC98519
0.5909 Remote Similarity NPC151919
0.5909 Remote Similarity NPC216407
0.5909 Remote Similarity NPC142159
0.5909 Remote Similarity NPC95364
0.5904 Remote Similarity NPC325031
0.5904 Remote Similarity NPC471325
0.5904 Remote Similarity NPC282293
0.589 Remote Similarity NPC471460
0.5875 Remote Similarity NPC235906
0.5875 Remote Similarity NPC473223
0.5875 Remote Similarity NPC271986
0.5873 Remote Similarity NPC128280
0.5854 Remote Similarity NPC270126
0.5854 Remote Similarity NPC471299
0.5846 Remote Similarity NPC27264
0.5833 Remote Similarity NPC94875
0.5833 Remote Similarity NPC173609
0.5833 Remote Similarity NPC473712
0.5833 Remote Similarity NPC473529
0.5833 Remote Similarity NPC68044
0.5833 Remote Similarity NPC221231
0.5833 Remote Similarity NPC65930
0.5833 Remote Similarity NPC475159
0.5833 Remote Similarity NPC471326
0.5833 Remote Similarity NPC11332
0.5833 Remote Similarity NPC145914

  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 NPC217537 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
0.6 Remote Similarity NPD6927 Phase 3
0.5833 Remote Similarity NPD5209 Approved
0.5811 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5802 Remote Similarity NPD4756 Discovery
0.575 Remote Similarity NPD8039 Approved
0.5714 Remote Similarity NPD3174 Discontinued
0.5647 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5645 Remote Similarity NPD9411 Phase 1

  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