NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.99
Volume:	169.529
LogP:	1.317
LogD:	1.021
LogS:	-1.194
# Rotatable Bonds:	2
TPSA:	46.25
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	2.043
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:	-4.772
MDCK Permeability:	7.37980444682762e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	58.84077453613281%
Volume Distribution (VD):	2.473
Pgp-substrate:	41.10733413696289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	7.282
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.892
Carcinogencity:	0.107
Eye Corrosion:	0.949
Eye Irritation:	0.309
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC59387

Natural Product ID:	NPC59387
*Common Name:**	4-(2-Aminoethyl)-2-Bromophenol
IUPAC Name:	4-(2-aminoethyl)-2-bromophenol
Synonyms:	3'-bromotyramine
Standard InCHIKey:	KIKCGMHGZPBUNQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10BrNO/c9-7-5-6(3-4-10)1-2-8(7)11/h1-2,5,11H,3-4,10H2
SMILES:	NCCc1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450778
PubChem CID:	5323842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO40819	Cnemidocarpa irene	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[33030894]
NPO8796	Cnemidocarpa bicornuta	Species	Styelidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[9644087]
NPO8796	Cnemidocarpa bicornuta	Species	Styelidae	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	46000.0	nM	PMID[533162]

☑ 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 NPC59387 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	287
0.1-0.2	3776
0.2-0.3	13400
0.3-0.4	7742
0.4-0.5	12344
0.5-0.6	4191
0.6-0.7	820
0.7-0.8	125
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC115803
0.8762	High Similarity	NPC125732
0.8607	High Similarity	NPC474087
0.8304	Intermediate Similarity	NPC471495
0.8182	Intermediate Similarity	NPC68055
0.8165	Intermediate Similarity	NPC29601
0.8158	Intermediate Similarity	NPC473358
0.807	Intermediate Similarity	NPC290566
0.807	Intermediate Similarity	NPC145638
0.8016	Intermediate Similarity	NPC474091
0.8	Intermediate Similarity	NPC289381
0.8	Intermediate Similarity	NPC155847
0.7953	Intermediate Similarity	NPC473724
0.7953	Intermediate Similarity	NPC475735
0.7913	Intermediate Similarity	NPC54543
0.7903	Intermediate Similarity	NPC272463
0.7863	Intermediate Similarity	NPC197045
0.7863	Intermediate Similarity	NPC146422
0.7857	Intermediate Similarity	NPC178902
0.7727	Intermediate Similarity	NPC474673
0.7717	Intermediate Similarity	NPC202776
0.7667	Intermediate Similarity	NPC213
0.7667	Intermediate Similarity	NPC10286
0.7658	Intermediate Similarity	NPC107619
0.7652	Intermediate Similarity	NPC231705
0.7619	Intermediate Similarity	NPC175313
0.7615	Intermediate Similarity	NPC166624
0.7607	Intermediate Similarity	NPC473372
0.7603	Intermediate Similarity	NPC106551
0.7603	Intermediate Similarity	NPC281686
0.7603	Intermediate Similarity	NPC188867
0.7586	Intermediate Similarity	NPC142297
0.7574	Intermediate Similarity	NPC78530
0.7565	Intermediate Similarity	NPC42383
0.7557	Intermediate Similarity	NPC243404
0.7547	Intermediate Similarity	NPC197783
0.7542	Intermediate Similarity	NPC471487
0.7524	Intermediate Similarity	NPC265146
0.7521	Intermediate Similarity	NPC24101
0.7521	Intermediate Similarity	NPC153690
0.7521	Intermediate Similarity	NPC96224
0.7481	Intermediate Similarity	NPC474753
0.748	Intermediate Similarity	NPC85276
0.7477	Intermediate Similarity	NPC23167
0.7462	Intermediate Similarity	NPC99280
0.7458	Intermediate Similarity	NPC258056
0.7453	Intermediate Similarity	NPC248817
0.7444	Intermediate Similarity	NPC470471
0.7438	Intermediate Similarity	NPC94217
0.7426	Intermediate Similarity	NPC474128
0.7424	Intermediate Similarity	NPC163810
0.7424	Intermediate Similarity	NPC184465
0.7419	Intermediate Similarity	NPC117759
0.7419	Intermediate Similarity	NPC283760
0.7419	Intermediate Similarity	NPC239697
0.7419	Intermediate Similarity	NPC38483
0.7407	Intermediate Similarity	NPC25493
0.7407	Intermediate Similarity	NPC113460
0.7395	Intermediate Similarity	NPC474149
0.7387	Intermediate Similarity	NPC20142
0.7387	Intermediate Similarity	NPC215351
0.7381	Intermediate Similarity	NPC7830
0.7373	Intermediate Similarity	NPC97811
0.7368	Intermediate Similarity	NPC71888
0.7368	Intermediate Similarity	NPC120114
0.736	Intermediate Similarity	NPC169207
0.736	Intermediate Similarity	NPC115627
0.736	Intermediate Similarity	NPC118522
0.7358	Intermediate Similarity	NPC124436
0.7355	Intermediate Similarity	NPC471488
0.7339	Intermediate Similarity	NPC242240
0.7339	Intermediate Similarity	NPC123273
0.7339	Intermediate Similarity	NPC258219
0.7339	Intermediate Similarity	NPC177420
0.7339	Intermediate Similarity	NPC280347
0.7339	Intermediate Similarity	NPC318325
0.7333	Intermediate Similarity	NPC470470
0.7323	Intermediate Similarity	NPC296202
0.7315	Intermediate Similarity	NPC184169
0.7311	Intermediate Similarity	NPC172046
0.7302	Intermediate Similarity	NPC318357
0.7287	Intermediate Similarity	NPC110131
0.7273	Intermediate Similarity	NPC300017
0.7273	Intermediate Similarity	NPC55561
0.7273	Intermediate Similarity	NPC151764
0.7259	Intermediate Similarity	NPC309667
0.7258	Intermediate Similarity	NPC137096
0.7248	Intermediate Similarity	NPC104216
0.7244	Intermediate Similarity	NPC136543
0.7239	Intermediate Similarity	NPC303993
0.7234	Intermediate Similarity	NPC20755
0.7222	Intermediate Similarity	NPC252149
0.7222	Intermediate Similarity	NPC155393
0.7222	Intermediate Similarity	NPC180207
0.7213	Intermediate Similarity	NPC33244
0.7213	Intermediate Similarity	NPC76400
0.7209	Intermediate Similarity	NPC213414
0.7207	Intermediate Similarity	NPC155908
0.7207	Intermediate Similarity	NPC45040
0.7207	Intermediate Similarity	NPC304541
0.7203	Intermediate Similarity	NPC47672
0.72	Intermediate Similarity	NPC317784
0.72	Intermediate Similarity	NPC142638
0.7196	Intermediate Similarity	NPC319826
0.7193	Intermediate Similarity	NPC303611
0.7193	Intermediate Similarity	NPC290515
0.7193	Intermediate Similarity	NPC226096
0.7193	Intermediate Similarity	NPC108606
0.7193	Intermediate Similarity	NPC164514
0.7183	Intermediate Similarity	NPC76412
0.7182	Intermediate Similarity	NPC98772
0.7177	Intermediate Similarity	NPC79844
0.7165	Intermediate Similarity	NPC471486
0.7156	Intermediate Similarity	NPC407
0.7156	Intermediate Similarity	NPC307235
0.7154	Intermediate Similarity	NPC142599
0.7154	Intermediate Similarity	NPC118202
0.7153	Intermediate Similarity	NPC128877
0.7143	Intermediate Similarity	NPC138117
0.7143	Intermediate Similarity	NPC186469
0.7143	Intermediate Similarity	NPC325292
0.7132	Intermediate Similarity	NPC13020
0.7132	Intermediate Similarity	NPC140359
0.7109	Intermediate Similarity	NPC27581
0.7097	Intermediate Similarity	NPC317254
0.7091	Intermediate Similarity	NPC27974
0.7083	Intermediate Similarity	NPC469711
0.708	Intermediate Similarity	NPC316301
0.708	Intermediate Similarity	NPC128062
0.708	Intermediate Similarity	NPC27323
0.708	Intermediate Similarity	NPC213471
0.708	Intermediate Similarity	NPC151715
0.7077	Intermediate Similarity	NPC137117
0.7073	Intermediate Similarity	NPC26524
0.7071	Intermediate Similarity	NPC470472
0.7055	Intermediate Similarity	NPC156311
0.7055	Intermediate Similarity	NPC233926
0.7054	Intermediate Similarity	NPC229213
0.7054	Intermediate Similarity	NPC204210
0.7054	Intermediate Similarity	NPC270547
0.7045	Intermediate Similarity	NPC78061
0.7045	Intermediate Similarity	NPC159987
0.7045	Intermediate Similarity	NPC122359
0.704	Intermediate Similarity	NPC82963
0.7031	Intermediate Similarity	NPC326079
0.7023	Intermediate Similarity	NPC220311
0.7023	Intermediate Similarity	NPC318965
0.7023	Intermediate Similarity	NPC142776
0.7018	Intermediate Similarity	NPC274678
0.7018	Intermediate Similarity	NPC8392
0.7018	Intermediate Similarity	NPC26244
0.7018	Intermediate Similarity	NPC313650
0.7009	Intermediate Similarity	NPC327226
0.7007	Intermediate Similarity	NPC475132
0.7007	Intermediate Similarity	NPC474587
0.7	Intermediate Similarity	NPC308571
0.7	Intermediate Similarity	NPC474169
0.7	Intermediate Similarity	NPC105999
0.7	Intermediate Similarity	NPC473572
0.7	Intermediate Similarity	NPC318777
0.6991	Remote Similarity	NPC181709
0.6984	Remote Similarity	NPC283468
0.6984	Remote Similarity	NPC311737
0.6984	Remote Similarity	NPC38458
0.6972	Remote Similarity	NPC286904
0.6972	Remote Similarity	NPC150837
0.697	Remote Similarity	NPC236347
0.697	Remote Similarity	NPC323775
0.6966	Remote Similarity	NPC475432
0.6964	Remote Similarity	NPC300478
0.6964	Remote Similarity	NPC192
0.6957	Remote Similarity	NPC132271
0.6957	Remote Similarity	NPC292730
0.6957	Remote Similarity	NPC82664
0.6957	Remote Similarity	NPC475293
0.6957	Remote Similarity	NPC202986
0.6957	Remote Similarity	NPC473388
0.6957	Remote Similarity	NPC216520
0.695	Remote Similarity	NPC135349
0.694	Remote Similarity	NPC478071
0.694	Remote Similarity	NPC135173
0.693	Remote Similarity	NPC81010
0.693	Remote Similarity	NPC32977
0.6929	Remote Similarity	NPC122009
0.6917	Remote Similarity	NPC16031
0.6917	Remote Similarity	NPC145888
0.6917	Remote Similarity	NPC161593
0.6911	Remote Similarity	NPC21890
0.6903	Remote Similarity	NPC306074
0.6897	Remote Similarity	NPC260000
0.6897	Remote Similarity	NPC109955
0.6897	Remote Similarity	NPC225464
0.6897	Remote Similarity	NPC32674
0.6897	Remote Similarity	NPC77492
0.6897	Remote Similarity	NPC315921
0.6891	Remote Similarity	NPC304761
0.6891	Remote Similarity	NPC147000
0.6891	Remote Similarity	NPC226778
0.6891	Remote Similarity	NPC150254
0.6889	Remote Similarity	NPC11449

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 NPC59387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1135
0.2-0.3	1268
0.3-0.4	3057
0.4-0.5	2378
0.5-0.6	883
0.6-0.7	200
0.7-0.8	25
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD9608	Approved
0.844	Intermediate Similarity	NPD9610	Approved
0.8306	Intermediate Similarity	NPD9718	Approved
0.807	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD9377	Approved
0.7863	Intermediate Similarity	NPD9379	Approved
0.7603	Intermediate Similarity	NPD9568	Approved
0.7541	Intermediate Similarity	NPD318	Approved
0.7541	Intermediate Similarity	NPD317	Approved
0.7541	Intermediate Similarity	NPD16	Approved
0.7541	Intermediate Similarity	NPD856	Approved
0.7438	Intermediate Similarity	NPD9614	Approved
0.7438	Intermediate Similarity	NPD9618	Approved
0.736	Intermediate Similarity	NPD9381	Approved
0.736	Intermediate Similarity	NPD9384	Approved
0.7358	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD9616	Approved
0.7258	Intermediate Similarity	NPD9613	Approved
0.7258	Intermediate Similarity	NPD9615	Approved
0.7236	Intermediate Similarity	NPD255	Approved
0.7236	Intermediate Similarity	NPD256	Approved
0.7213	Intermediate Similarity	NPD2234	Approved
0.7213	Intermediate Similarity	NPD2228	Approved
0.7213	Intermediate Similarity	NPD2229	Approved
0.7203	Intermediate Similarity	NPD1445	Approved
0.7203	Intermediate Similarity	NPD1444	Approved
0.72	Intermediate Similarity	NPD316	Approved
0.7193	Intermediate Similarity	NPD9609	Approved
0.7193	Intermediate Similarity	NPD9611	Approved
0.7193	Intermediate Similarity	NPD9612	Approved
0.7188	Intermediate Similarity	NPD2561	Approved
0.7188	Intermediate Similarity	NPD2562	Approved
0.7132	Intermediate Similarity	NPD9622	Approved
0.708	Intermediate Similarity	NPD2934	Approved
0.708	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2933	Approved
0.7077	Intermediate Similarity	NPD5311	Approved
0.7077	Intermediate Similarity	NPD5310	Approved
0.7077	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9244	Approved
0.7031	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1792	Phase 2
0.7023	Intermediate Similarity	NPD1133	Approved
0.7023	Intermediate Similarity	NPD1131	Approved
0.7023	Intermediate Similarity	NPD1129	Approved
0.7023	Intermediate Similarity	NPD1135	Approved
0.7023	Intermediate Similarity	NPD3055	Approved
0.7023	Intermediate Similarity	NPD3053	Approved
0.7023	Intermediate Similarity	NPD1134	Approved
0.7018	Intermediate Similarity	NPD2859	Approved
0.7018	Intermediate Similarity	NPD2860	Approved
0.697	Remote Similarity	NPD9621	Approved
0.697	Remote Similarity	NPD2195	Approved
0.697	Remote Similarity	NPD9619	Approved
0.697	Remote Similarity	NPD2194	Approved
0.697	Remote Similarity	NPD7451	Discontinued
0.697	Remote Similarity	NPD9620	Approved
0.6917	Remote Similarity	NPD9569	Approved
0.6897	Remote Similarity	NPD9273	Approved
0.6891	Remote Similarity	NPD315	Approved
0.6891	Remote Similarity	NPD10	Approved
0.6891	Remote Similarity	NPD309	Approved
0.6891	Remote Similarity	NPD311	Approved
0.6891	Remote Similarity	NPD310	Approved
0.6891	Remote Similarity	NPD314	Approved
0.688	Remote Similarity	NPD1793	Approved
0.688	Remote Similarity	NPD1791	Approved
0.6875	Remote Similarity	NPD4093	Discontinued
0.6838	Remote Similarity	NPD3020	Approved
0.6835	Remote Similarity	NPD1169	Approved
0.6818	Remote Similarity	NPD196	Phase 1
0.6815	Remote Similarity	NPD3136	Phase 2
0.6797	Remote Similarity	NPD5304	Approved
0.6797	Remote Similarity	NPD5303	Approved
0.6765	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD598	Approved
0.6765	Remote Similarity	NPD597	Approved
0.6765	Remote Similarity	NPD601	Approved
0.6746	Remote Similarity	NPD593	Approved
0.6746	Remote Similarity	NPD595	Approved
0.6724	Remote Similarity	NPD1809	Phase 2
0.6724	Remote Similarity	NPD844	Approved
0.6723	Remote Similarity	NPD846	Approved
0.6723	Remote Similarity	NPD940	Approved
0.6715	Remote Similarity	NPD6407	Approved
0.6715	Remote Similarity	NPD6405	Approved
0.6715	Remote Similarity	NPD1132	Approved
0.6715	Remote Similarity	NPD1130	Approved
0.6715	Remote Similarity	NPD1136	Approved
0.6715	Remote Similarity	NPD259	Phase 1
0.6715	Remote Similarity	NPD829	Discontinued
0.6696	Remote Similarity	NPD845	Approved
0.6692	Remote Similarity	NPD1751	Approved
0.6692	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD9537	Phase 1
0.6691	Remote Similarity	NPD9536	Phase 1
0.6667	Remote Similarity	NPD3062	Approved
0.6667	Remote Similarity	NPD288	Approved
0.6667	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD2231	Phase 2
0.6667	Remote Similarity	NPD3061	Approved
0.6667	Remote Similarity	NPD2235	Phase 2
0.6639	Remote Similarity	NPD1242	Phase 1
0.6619	Remote Similarity	NPD555	Phase 2
0.6617	Remote Similarity	NPD4659	Approved
0.6593	Remote Similarity	NPD602	Approved
0.6593	Remote Similarity	NPD257	Approved
0.6593	Remote Similarity	NPD599	Approved
0.6593	Remote Similarity	NPD258	Approved
0.6593	Remote Similarity	NPD858	Approved
0.6593	Remote Similarity	NPD859	Approved
0.6571	Remote Similarity	NPD3054	Approved
0.6571	Remote Similarity	NPD5314	Approved
0.6571	Remote Similarity	NPD3052	Approved
0.6571	Remote Similarity	NPD823	Approved
0.6571	Remote Similarity	NPD817	Approved
0.6571	Remote Similarity	NPD2568	Approved
0.6565	Remote Similarity	NPD2668	Approved
0.6565	Remote Similarity	NPD2667	Approved
0.6541	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1759	Phase 1
0.6525	Remote Similarity	NPD3555	Approved
0.6525	Remote Similarity	NPD3554	Approved
0.6525	Remote Similarity	NPD3553	Approved
0.6525	Remote Similarity	NPD3552	Approved
0.6519	Remote Similarity	NPD4103	Phase 2
0.6519	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.65	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2614	Approved
0.6496	Remote Similarity	NPD600	Approved
0.6496	Remote Similarity	NPD596	Approved
0.6479	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD9087	Approved
0.6471	Remote Similarity	NPD558	Phase 2
0.6462	Remote Similarity	NPD1758	Phase 1
0.6446	Remote Similarity	NPD855	Approved
0.6446	Remote Similarity	NPD854	Approved
0.6434	Remote Similarity	NPD1519	Approved
0.6434	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1537	Approved
0.6434	Remote Similarity	NPD7450	Phase 2
0.6434	Remote Similarity	NPD9570	Approved
0.6434	Remote Similarity	NPD1538	Phase 1
0.6423	Remote Similarity	NPD3636	Approved
0.6423	Remote Similarity	NPD3635	Approved
0.6423	Remote Similarity	NPD3637	Approved
0.6403	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1980	Approved
0.6391	Remote Similarity	NPD3421	Phase 3
0.6391	Remote Similarity	NPD1983	Approved
0.6391	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1981	Approved
0.6389	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7978	Discontinued
0.6389	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3594	Approved
0.6377	Remote Similarity	NPD2606	Approved
0.6377	Remote Similarity	NPD2605	Approved
0.6377	Remote Similarity	NPD3595	Approved
0.6376	Remote Similarity	NPD2183	Approved
0.6376	Remote Similarity	NPD2184	Approved
0.637	Remote Similarity	NPD2429	Approved
0.637	Remote Similarity	NPD2428	Approved
0.637	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3021	Approved
0.6349	Remote Similarity	NPD3022	Approved
0.6343	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5156	Approved
0.6331	Remote Similarity	NPD5155	Approved
0.6328	Remote Similarity	NPD821	Approved
0.6325	Remote Similarity	NPD1814	Approved
0.6325	Remote Similarity	NPD1812	Approved
0.6319	Remote Similarity	NPD1523	Approved
0.6319	Remote Similarity	NPD1522	Approved
0.6316	Remote Similarity	NPD2556	Approved
0.6316	Remote Similarity	NPD2554	Approved
0.6312	Remote Similarity	NPD826	Approved
0.6312	Remote Similarity	NPD825	Approved
0.6311	Remote Similarity	NPD4818	Approved
0.6311	Remote Similarity	NPD4817	Approved
0.6301	Remote Similarity	NPD3060	Approved
0.6299	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1536	Approved
0.6277	Remote Similarity	NPD1819	Approved
0.6277	Remote Similarity	NPD1817	Approved
0.6277	Remote Similarity	NPD1818	Approved
0.6277	Remote Similarity	NPD1820	Approved
0.6268	Remote Similarity	NPD275	Approved
0.6268	Remote Similarity	NPD274	Approved
0.626	Remote Similarity	NPD3682	Approved
0.626	Remote Similarity	NPD4658	Approved
0.626	Remote Similarity	NPD4656	Approved
0.626	Remote Similarity	NPD4231	Approved
0.626	Remote Similarity	NPD3681	Approved
0.626	Remote Similarity	NPD3683	Approved
0.626	Remote Similarity	NPD4229	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