NPASS Compound

Structure

NPC244890 OpenBabel07101719152D 21 22 0 0 0 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 12 2 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	481.8
Volume:	302.275
LogP:	4.256
LogD:	2.319
LogS:	-2.614
# Rotatable Bonds:	2
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	3.124
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.402
MDCK Permeability:	1.4907577678968664e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.519
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.25931549072266%
Volume Distribution (VD):	0.517
Pgp-substrate:	0.8933221101760864%

ADMET: Metabolism

CYP1A2-inhibitor:	0.725
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.421
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	3.975
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.958
Carcinogencity:	0.055
Eye Corrosion:	0.004
Eye Irritation:	0.926
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC244890

Natural Product ID:	NPC244890
*Common Name:**	Vidalol A
IUPAC Name:	2-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]benzene-1,3,5-triol
Synonyms:
Standard InCHIKey:	ILWIINNNOSHNIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H9Br3O5/c14-9-4(2-8(19)13(21)11(9)16)1-5-6(17)3-7(18)10(15)12(5)20/h2-3,17-21H,1H2
SMILES:	Oc1cc(O)c(c(c1Cc1cc(O)c(c(c1Br)Br)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476884
PubChem CID:	132036
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO32463	vidalia obtusaloba	Species	Tephritidae	Eukaryota	n.a.	Caribbean	n.a.	Database[Title]

☑ 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

Activity Type	# Activity
Others	1

Activity Type	# Activity
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	Activity	=	96.0	%	PMID[497259]

☑ 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 NPC244890 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	767
0.1-0.2	3097
0.2-0.3	13710
0.3-0.4	7293
0.4-0.5	5703
0.5-0.6	9439
0.6-0.7	2455
0.7-0.8	201
0.8-0.85	19
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC118794
0.9213	High Similarity	NPC220311
0.8947	High Similarity	NPC163560
0.8837	High Similarity	NPC137117
0.881	High Similarity	NPC38483
0.8779	High Similarity	NPC13004
0.875	High Similarity	NPC224663
0.8712	High Similarity	NPC150929
0.8647	High Similarity	NPC474614
0.8623	High Similarity	NPC160932
0.8603	High Similarity	NPC312155
0.8603	High Similarity	NPC245386
0.8582	High Similarity	NPC109346
0.8538	High Similarity	NPC47790
0.8527	High Similarity	NPC471486
0.85	High Similarity	NPC89341
0.8473	Intermediate Similarity	NPC84606
0.8456	Intermediate Similarity	NPC300678
0.8397	Intermediate Similarity	NPC219444
0.8382	Intermediate Similarity	NPC43613
0.837	Intermediate Similarity	NPC85049
0.8309	Intermediate Similarity	NPC226493
0.8309	Intermediate Similarity	NPC160081
0.8288	Intermediate Similarity	NPC152947
0.8286	Intermediate Similarity	NPC271942
0.8209	Intermediate Similarity	NPC142776
0.8182	Intermediate Similarity	NPC136543
0.8156	Intermediate Similarity	NPC156356
0.8031	Intermediate Similarity	NPC268032
0.803	Intermediate Similarity	NPC474146
0.8	Intermediate Similarity	NPC79844
0.7971	Intermediate Similarity	NPC474536
0.7959	Intermediate Similarity	NPC88896
0.7953	Intermediate Similarity	NPC471487
0.7939	Intermediate Similarity	NPC277588
0.7929	Intermediate Similarity	NPC303011
0.7907	Intermediate Similarity	NPC471488
0.7902	Intermediate Similarity	NPC168680
0.7883	Intermediate Similarity	NPC43706
0.7879	Intermediate Similarity	NPC144343
0.7874	Intermediate Similarity	NPC473372
0.7872	Intermediate Similarity	NPC471328
0.7852	Intermediate Similarity	NPC229213
0.7842	Intermediate Similarity	NPC105702
0.7836	Intermediate Similarity	NPC227976
0.7826	Intermediate Similarity	NPC474147
0.7826	Intermediate Similarity	NPC473708
0.782	Intermediate Similarity	NPC191866
0.7795	Intermediate Similarity	NPC471495
0.7795	Intermediate Similarity	NPC105727
0.7795	Intermediate Similarity	NPC58427
0.7795	Intermediate Similarity	NPC114392
0.7795	Intermediate Similarity	NPC34864
0.7794	Intermediate Similarity	NPC474169
0.7794	Intermediate Similarity	NPC473572
0.7786	Intermediate Similarity	NPC50782
0.7786	Intermediate Similarity	NPC472893
0.7761	Intermediate Similarity	NPC472071
0.7727	Intermediate Similarity	NPC474535
0.7717	Intermediate Similarity	NPC176527
0.7704	Intermediate Similarity	NPC24125
0.7687	Intermediate Similarity	NPC117759
0.7687	Intermediate Similarity	NPC217174
0.7677	Intermediate Similarity	NPC475697
0.7674	Intermediate Similarity	NPC473358
0.7647	Intermediate Similarity	NPC39029
0.7647	Intermediate Similarity	NPC237667
0.7626	Intermediate Similarity	NPC134219
0.76	Intermediate Similarity	NPC113862
0.7597	Intermediate Similarity	NPC54543
0.7576	Intermediate Similarity	NPC94217
0.7566	Intermediate Similarity	NPC7398
0.7559	Intermediate Similarity	NPC292452
0.7536	Intermediate Similarity	NPC53567
0.75	Intermediate Similarity	NPC33244
0.7482	Intermediate Similarity	NPC224342
0.748	Intermediate Similarity	NPC30506
0.748	Intermediate Similarity	NPC471511
0.748	Intermediate Similarity	NPC102216
0.7424	Intermediate Similarity	NPC43525
0.7397	Intermediate Similarity	NPC199089
0.7364	Intermediate Similarity	NPC248904
0.7361	Intermediate Similarity	NPC259017
0.7348	Intermediate Similarity	NPC4493
0.7348	Intermediate Similarity	NPC476632
0.7348	Intermediate Similarity	NPC225679
0.7348	Intermediate Similarity	NPC165770
0.7344	Intermediate Similarity	NPC119860
0.7328	Intermediate Similarity	NPC202647
0.7324	Intermediate Similarity	NPC324112
0.7324	Intermediate Similarity	NPC282000
0.7324	Intermediate Similarity	NPC293054
0.7324	Intermediate Similarity	NPC246620
0.7324	Intermediate Similarity	NPC5447
0.7324	Intermediate Similarity	NPC266555
0.7324	Intermediate Similarity	NPC250432
0.7324	Intermediate Similarity	NPC124452
0.7324	Intermediate Similarity	NPC169474
0.7324	Intermediate Similarity	NPC236791
0.7324	Intermediate Similarity	NPC252131
0.7324	Intermediate Similarity	NPC159968
0.7324	Intermediate Similarity	NPC74817
0.7324	Intermediate Similarity	NPC82679
0.7323	Intermediate Similarity	NPC100340
0.7323	Intermediate Similarity	NPC143659
0.7293	Intermediate Similarity	NPC166995
0.7287	Intermediate Similarity	NPC246056
0.7287	Intermediate Similarity	NPC474839
0.7287	Intermediate Similarity	NPC239291
0.7286	Intermediate Similarity	NPC136319
0.7286	Intermediate Similarity	NPC197757
0.7286	Intermediate Similarity	NPC228922
0.7286	Intermediate Similarity	NPC84086
0.7286	Intermediate Similarity	NPC121115
0.7273	Intermediate Similarity	NPC226331
0.7273	Intermediate Similarity	NPC55113
0.7273	Intermediate Similarity	NPC154866
0.7273	Intermediate Similarity	NPC28765
0.7273	Intermediate Similarity	NPC46274
0.7254	Intermediate Similarity	NPC214406
0.7254	Intermediate Similarity	NPC103823
0.7254	Intermediate Similarity	NPC44748
0.7254	Intermediate Similarity	NPC223136
0.7254	Intermediate Similarity	NPC18924
0.7254	Intermediate Similarity	NPC28730
0.7254	Intermediate Similarity	NPC78974
0.7252	Intermediate Similarity	NPC174981
0.7252	Intermediate Similarity	NPC233835
0.7246	Intermediate Similarity	NPC223451
0.7244	Intermediate Similarity	NPC275053
0.7244	Intermediate Similarity	NPC161571
0.7244	Intermediate Similarity	NPC248573
0.7244	Intermediate Similarity	NPC223393
0.7239	Intermediate Similarity	NPC471485
0.7239	Intermediate Similarity	NPC76400
0.7239	Intermediate Similarity	NPC117846
0.7231	Intermediate Similarity	NPC118286
0.7231	Intermediate Similarity	NPC39097
0.7231	Intermediate Similarity	NPC302681
0.7231	Intermediate Similarity	NPC109691
0.7231	Intermediate Similarity	NPC39664
0.7231	Intermediate Similarity	NPC470700
0.7222	Intermediate Similarity	NPC212015
0.7218	Intermediate Similarity	NPC179002
0.7218	Intermediate Similarity	NPC187583
0.7218	Intermediate Similarity	NPC257430
0.7214	Intermediate Similarity	NPC41562
0.7209	Intermediate Similarity	NPC241891
0.7206	Intermediate Similarity	NPC115808
0.7197	Intermediate Similarity	NPC228343
0.7197	Intermediate Similarity	NPC33728
0.7197	Intermediate Similarity	NPC19808
0.7197	Intermediate Similarity	NPC254833
0.7185	Intermediate Similarity	NPC107240
0.7185	Intermediate Similarity	NPC120280
0.7183	Intermediate Similarity	NPC234400
0.7183	Intermediate Similarity	NPC17943
0.7183	Intermediate Similarity	NPC251855
0.7183	Intermediate Similarity	NPC472093
0.7183	Intermediate Similarity	NPC299584
0.7183	Intermediate Similarity	NPC208950
0.7183	Intermediate Similarity	NPC203133
0.7183	Intermediate Similarity	NPC298757
0.7183	Intermediate Similarity	NPC33654
0.7183	Intermediate Similarity	NPC117214
0.7183	Intermediate Similarity	NPC221077
0.7183	Intermediate Similarity	NPC193544
0.7183	Intermediate Similarity	NPC475169
0.7183	Intermediate Similarity	NPC60885
0.7183	Intermediate Similarity	NPC265483
0.7183	Intermediate Similarity	NPC82483
0.7183	Intermediate Similarity	NPC116907
0.7183	Intermediate Similarity	NPC233410
0.7183	Intermediate Similarity	NPC57490
0.7183	Intermediate Similarity	NPC105925
0.7176	Intermediate Similarity	NPC54844
0.7174	Intermediate Similarity	NPC226629
0.7172	Intermediate Similarity	NPC233056
0.7172	Intermediate Similarity	NPC244441
0.7172	Intermediate Similarity	NPC299221
0.7172	Intermediate Similarity	NPC51840
0.7172	Intermediate Similarity	NPC126836
0.7172	Intermediate Similarity	NPC311680
0.7172	Intermediate Similarity	NPC234488
0.7154	Intermediate Similarity	NPC134829
0.7153	Intermediate Similarity	NPC470760
0.7143	Intermediate Similarity	NPC226401
0.7143	Intermediate Similarity	NPC120982
0.7143	Intermediate Similarity	NPC147634
0.7143	Intermediate Similarity	NPC475018
0.7143	Intermediate Similarity	NPC174096
0.7143	Intermediate Similarity	NPC79793
0.7133	Intermediate Similarity	NPC76451
0.7133	Intermediate Similarity	NPC181361
0.7133	Intermediate Similarity	NPC223953
0.7123	Intermediate Similarity	NPC15543
0.7123	Intermediate Similarity	NPC42760
0.7123	Intermediate Similarity	NPC268342
0.7123	Intermediate Similarity	NPC232275
0.7123	Intermediate Similarity	NPC268266

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 NPC244890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	611
0.1-0.2	1107
0.2-0.3	2919
0.3-0.4	2667
0.4-0.5	1309
0.5-0.6	476
0.6-0.7	58
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7324	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1242	Phase 1
0.7197	Intermediate Similarity	NPD3021	Approved
0.7197	Intermediate Similarity	NPD3022	Approved
0.7075	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD943	Approved
0.7075	Intermediate Similarity	NPD1613	Approved
0.7054	Intermediate Similarity	NPD940	Approved
0.7054	Intermediate Similarity	NPD846	Approved
0.6986	Remote Similarity	NPD3027	Phase 3
0.6947	Remote Similarity	NPD9244	Approved
0.694	Remote Similarity	NPD4750	Phase 3
0.6748	Remote Similarity	NPD4288	Approved
0.6552	Remote Similarity	NPD1610	Phase 2
0.6538	Remote Similarity	NPD2860	Approved
0.6538	Remote Similarity	NPD2859	Approved
0.6522	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3020	Approved
0.6509	Remote Similarity	NPD4010	Discontinued
0.6507	Remote Similarity	NPD9269	Phase 2
0.6503	Remote Similarity	NPD1548	Phase 1
0.6475	Remote Similarity	NPD228	Approved
0.6462	Remote Similarity	NPD2933	Approved
0.6462	Remote Similarity	NPD2934	Approved
0.6452	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1169	Approved
0.6438	Remote Similarity	NPD1511	Approved
0.6429	Remote Similarity	NPD9379	Approved
0.6429	Remote Similarity	NPD9377	Approved
0.6412	Remote Similarity	NPD844	Approved
0.64	Remote Similarity	NPD3018	Phase 2
0.6378	Remote Similarity	NPD9094	Approved
0.6364	Remote Similarity	NPD288	Approved
0.6358	Remote Similarity	NPD1512	Approved
0.6358	Remote Similarity	NPD4908	Phase 1
0.6343	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD9381	Approved
0.6301	Remote Similarity	NPD9384	Approved
0.6275	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD230	Phase 1
0.6242	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4749	Approved
0.6242	Remote Similarity	NPD2982	Phase 2
0.6242	Remote Similarity	NPD2983	Phase 2
0.6237	Remote Similarity	NPD8095	Phase 1
0.6233	Remote Similarity	NPD9268	Approved
0.6228	Remote Similarity	NPD1934	Approved
0.6212	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4625	Phase 3
0.62	Remote Similarity	NPD5310	Approved
0.62	Remote Similarity	NPD5311	Approved
0.6194	Remote Similarity	NPD3061	Approved
0.6194	Remote Similarity	NPD3062	Approved
0.6194	Remote Similarity	NPD3059	Approved
0.619	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD2342	Discontinued
0.6174	Remote Similarity	NPD2981	Phase 2
0.6165	Remote Similarity	NPD1809	Phase 2
0.6164	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3053	Approved
0.6159	Remote Similarity	NPD3055	Approved
0.6154	Remote Similarity	NPD5283	Phase 1
0.6133	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD9622	Approved
0.6118	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD5314	Approved
0.6111	Remote Similarity	NPD302	Approved
0.6107	Remote Similarity	NPD422	Phase 1
0.6104	Remote Similarity	NPD9718	Approved
0.6101	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD2801	Approved
0.609	Remote Similarity	NPD1558	Phase 1
0.6084	Remote Similarity	NPD7635	Approved
0.6067	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4287	Approved
0.6065	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7266	Discontinued
0.6061	Remote Similarity	NPD2183	Approved
0.6061	Remote Similarity	NPD2184	Approved
0.6053	Remote Similarity	NPD3094	Phase 2
0.6038	Remote Similarity	NPD1510	Phase 2
0.6026	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3882	Suspended
0.6016	Remote Similarity	NPD111	Approved
0.6015	Remote Similarity	NPD845	Approved
0.6013	Remote Similarity	NPD9621	Approved
0.6013	Remote Similarity	NPD9620	Approved
0.6013	Remote Similarity	NPD258	Approved
0.6013	Remote Similarity	NPD257	Approved
0.6013	Remote Similarity	NPD9619	Approved
0.6013	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2568	Approved
0.6	Remote Similarity	NPD1465	Phase 2
0.6	Remote Similarity	NPD3092	Approved
0.6	Remote Similarity	NPD1201	Approved
0.6	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1653	Approved
0.5987	Remote Similarity	NPD1555	Discontinued
0.5987	Remote Similarity	NPD1240	Approved
0.5987	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD2861	Phase 2
0.5965	Remote Similarity	NPD2296	Approved
0.5963	Remote Similarity	NPD3540	Phase 1
0.5962	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6234	Discontinued
0.5952	Remote Similarity	NPD9093	Approved
0.5948	Remote Similarity	NPD1470	Approved
0.5948	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7390	Discontinued
0.5924	Remote Similarity	NPD6405	Approved
0.5924	Remote Similarity	NPD6407	Approved
0.5915	Remote Similarity	NPD6190	Approved
0.5912	Remote Similarity	NPD817	Approved
0.5912	Remote Similarity	NPD1607	Approved
0.5912	Remote Similarity	NPD823	Approved
0.5906	Remote Similarity	NPD9089	Approved
0.5904	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD3539	Phase 1
0.5886	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD3620	Phase 2
0.5886	Remote Similarity	NPD4060	Phase 1
0.5876	Remote Similarity	NPD6166	Phase 2
0.5876	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD1792	Phase 2
0.5871	Remote Similarity	NPD9569	Approved
0.587	Remote Similarity	NPD3028	Approved
0.5867	Remote Similarity	NPD2286	Discontinued
0.5864	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.586	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.586	Remote Similarity	NPD601	Approved
0.586	Remote Similarity	NPD598	Approved
0.586	Remote Similarity	NPD597	Approved
0.5854	Remote Similarity	NPD3750	Approved
0.585	Remote Similarity	NPD6671	Approved
0.5848	Remote Similarity	NPD37	Approved
0.5844	Remote Similarity	NPD1164	Approved
0.5839	Remote Similarity	NPD9273	Approved
0.5839	Remote Similarity	NPD3091	Approved
0.5828	Remote Similarity	NPD1549	Phase 2
0.5828	Remote Similarity	NPD970	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD1136	Approved
0.5823	Remote Similarity	NPD1130	Approved
0.5823	Remote Similarity	NPD1132	Approved
0.5822	Remote Similarity	NPD2234	Approved
0.5822	Remote Similarity	NPD2229	Approved
0.5822	Remote Similarity	NPD2228	Approved
0.581	Remote Similarity	NPD3818	Discontinued
0.5808	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD5404	Approved
0.5802	Remote Similarity	NPD5408	Approved
0.5802	Remote Similarity	NPD5406	Approved
0.5802	Remote Similarity	NPD9570	Approved
0.5802	Remote Similarity	NPD6100	Approved
0.5802	Remote Similarity	NPD6099	Approved
0.5802	Remote Similarity	NPD5405	Approved
0.58	Remote Similarity	NPD4093	Discontinued
0.5796	Remote Similarity	NPD9536	Phase 1
0.5796	Remote Similarity	NPD9537	Phase 1
0.5793	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD825	Approved
0.5786	Remote Similarity	NPD826	Approved
0.5782	Remote Similarity	NPD497	Approved
0.5775	Remote Similarity	NPD1444	Approved
0.5775	Remote Similarity	NPD1445	Approved
0.5765	Remote Similarity	NPD4005	Discontinued
0.5764	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6232	Discontinued
0.5762	Remote Similarity	NPD4589	Approved
0.5762	Remote Similarity	NPD2932	Approved
0.5762	Remote Similarity	NPD3019	Approved
0.5762	Remote Similarity	NPD4059	Approved
0.5762	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.575	Remote Similarity	NPD275	Approved
0.575	Remote Similarity	NPD274	Approved
0.5749	Remote Similarity	NPD4357	Discontinued
0.5749	Remote Similarity	NPD2421	Approved
0.5749	Remote Similarity	NPD2420	Approved
0.5747	Remote Similarity	NPD4965	Approved
0.5747	Remote Similarity	NPD4966	Approved
0.5747	Remote Similarity	NPD4967	Phase 2
0.5746	Remote Similarity	NPD7074	Phase 3
0.5733	Remote Similarity	NPD5304	Approved
0.5733	Remote Similarity	NPD5303	Approved
0.5731	Remote Similarity	NPD4380	Phase 2
0.573	Remote Similarity	NPD6688	Approved
0.573	Remote Similarity	NPD6687	Approved
0.5723	Remote Similarity	NPD259	Phase 1
0.5723	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD7228	Approved
0.5714	Remote Similarity	NPD7447	Phase 1
0.5714	Remote Similarity	NPD498	Approved
0.5714	Remote Similarity	NPD496	Approved
0.5714	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD495	Approved
0.5714	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4378	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