NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	292.91
Volume:	188.813
LogP:	2.03
LogD:	1.337
LogS:	-2.33
# Rotatable Bonds:	2
TPSA:	46.25
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.88
Synthetic Accessibility Score:	2.29
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:	-4.836
MDCK Permeability:	3.94340131606441e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	93.28497314453125%
Volume Distribution (VD):	1.884
Pgp-substrate:	16.507429122924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.657
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.484
CYP2D6-inhibitor:	0.897
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	1.871
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.873
Carcinogencity:	0.141
Eye Corrosion:	0.915
Eye Irritation:	0.135
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC115803

Natural Product ID:	NPC115803
*Common Name:**	4-(2-Aminoethyl)-2,6-Dibromophenol
IUPAC Name:	4-(2-aminoethyl)-2,6-dibromophenol
Synonyms:
Standard InCHIKey:	WRFLDHTYCUHHFK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9Br2NO/c9-6-3-5(1-2-11)4-7(10)8(6)12/h3-4,12H,1-2,11H2
SMILES:	C(CN)c1cc(c(c(c1)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL415090
PubChem CID:	11833313
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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	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
MIC	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[557119]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	100.0	ug.mL-1	PMID[557119]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[557119]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	>	100.0	ug.mL-1	PMID[557119]

☑ 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 NPC115803 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	304
0.1-0.2	3926
0.2-0.3	13699
0.3-0.4	8944
0.4-0.5	12203
0.5-0.6	2985
0.6-0.7	547
0.7-0.8	81
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC59387
0.8333	Intermediate Similarity	NPC125732
0.8319	Intermediate Similarity	NPC54543
0.8279	Intermediate Similarity	NPC272463
0.8246	Intermediate Similarity	NPC473358
0.824	Intermediate Similarity	NPC474087
0.8077	Intermediate Similarity	NPC474673
0.807	Intermediate Similarity	NPC471495
0.8031	Intermediate Similarity	NPC475735
0.7812	Intermediate Similarity	NPC474091
0.7788	Intermediate Similarity	NPC68055
0.7768	Intermediate Similarity	NPC29601
0.7752	Intermediate Similarity	NPC473724
0.7731	Intermediate Similarity	NPC471488
0.7692	Intermediate Similarity	NPC290566
0.7692	Intermediate Similarity	NPC145638
0.7652	Intermediate Similarity	NPC470471
0.7647	Intermediate Similarity	NPC78530
0.7638	Intermediate Similarity	NPC110131
0.7611	Intermediate Similarity	NPC155847
0.7611	Intermediate Similarity	NPC289381
0.7583	Intermediate Similarity	NPC33244
0.7581	Intermediate Similarity	NPC180207
0.7538	Intermediate Similarity	NPC99280
0.7537	Intermediate Similarity	NPC197045
0.7537	Intermediate Similarity	NPC470470
0.7521	Intermediate Similarity	NPC94217
0.752	Intermediate Similarity	NPC471486
0.75	Intermediate Similarity	NPC146422
0.75	Intermediate Similarity	NPC243404
0.7481	Intermediate Similarity	NPC128877
0.7478	Intermediate Similarity	NPC178902
0.7477	Intermediate Similarity	NPC252149
0.7394	Intermediate Similarity	NPC469711
0.7385	Intermediate Similarity	NPC202776
0.7376	Intermediate Similarity	NPC76412
0.736	Intermediate Similarity	NPC38483
0.7344	Intermediate Similarity	NPC105999
0.7333	Intermediate Similarity	NPC309667
0.7333	Intermediate Similarity	NPC471487
0.7319	Intermediate Similarity	NPC308571
0.7317	Intermediate Similarity	NPC10286
0.7317	Intermediate Similarity	NPC213
0.7293	Intermediate Similarity	NPC166624
0.7288	Intermediate Similarity	NPC231705
0.7287	Intermediate Similarity	NPC213414
0.7281	Intermediate Similarity	NPC107619
0.7273	Intermediate Similarity	NPC47672
0.7273	Intermediate Similarity	NPC135173
0.7266	Intermediate Similarity	NPC470472
0.7258	Intermediate Similarity	NPC281686
0.7258	Intermediate Similarity	NPC188867
0.7258	Intermediate Similarity	NPC106551
0.725	Intermediate Similarity	NPC473372
0.7246	Intermediate Similarity	NPC474128
0.7227	Intermediate Similarity	NPC142297
0.7222	Intermediate Similarity	NPC175313
0.7222	Intermediate Similarity	NPC100395
0.7203	Intermediate Similarity	NPC42383
0.7185	Intermediate Similarity	NPC71888
0.7185	Intermediate Similarity	NPC120114
0.7168	Intermediate Similarity	NPC20142
0.7168	Intermediate Similarity	NPC215351
0.7167	Intermediate Similarity	NPC96224
0.7167	Intermediate Similarity	NPC153690
0.7167	Intermediate Similarity	NPC24101
0.7164	Intermediate Similarity	NPC474753
0.7156	Intermediate Similarity	NPC197783
0.7153	Intermediate Similarity	NPC213471
0.7143	Intermediate Similarity	NPC317784
0.7143	Intermediate Similarity	NPC85276
0.7143	Intermediate Similarity	NPC142638
0.7143	Intermediate Similarity	NPC135349
0.7132	Intermediate Similarity	NPC116562
0.7132	Intermediate Similarity	NPC296202
0.713	Intermediate Similarity	NPC265146
0.7123	Intermediate Similarity	NPC233926
0.7123	Intermediate Similarity	NPC156311
0.7111	Intermediate Similarity	NPC163810
0.7111	Intermediate Similarity	NPC184465
0.7107	Intermediate Similarity	NPC258056
0.7091	Intermediate Similarity	NPC23167
0.7087	Intermediate Similarity	NPC117759
0.7087	Intermediate Similarity	NPC283760
0.7087	Intermediate Similarity	NPC239697
0.7064	Intermediate Similarity	NPC248817
0.7054	Intermediate Similarity	NPC136543
0.7054	Intermediate Similarity	NPC7830
0.7049	Intermediate Similarity	NPC474149
0.7031	Intermediate Similarity	NPC169207
0.7031	Intermediate Similarity	NPC118522
0.7031	Intermediate Similarity	NPC115627
0.7027	Intermediate Similarity	NPC113460
0.7027	Intermediate Similarity	NPC25493
0.7025	Intermediate Similarity	NPC97811
0.7023	Intermediate Similarity	NPC137117
0.7016	Intermediate Similarity	NPC76400
0.7015	Intermediate Similarity	NPC478071
0.7007	Intermediate Similarity	NPC235633
0.6992	Remote Similarity	NPC13004
0.6984	Remote Similarity	NPC79844
0.6983	Remote Similarity	NPC226096
0.6983	Remote Similarity	NPC164514
0.6983	Remote Similarity	NPC108606
0.6983	Remote Similarity	NPC303611
0.6983	Remote Similarity	NPC290515
0.6977	Remote Similarity	NPC318357
0.6972	Remote Similarity	NPC124436
0.697	Remote Similarity	NPC220311
0.6967	Remote Similarity	NPC172046
0.6964	Remote Similarity	NPC258219
0.6964	Remote Similarity	NPC280347
0.6964	Remote Similarity	NPC242240
0.6964	Remote Similarity	NPC123273
0.6964	Remote Similarity	NPC318325
0.6964	Remote Similarity	NPC177420
0.6963	Remote Similarity	NPC11449
0.6944	Remote Similarity	NPC20755
0.6937	Remote Similarity	NPC184169
0.6934	Remote Similarity	NPC303993
0.6929	Remote Similarity	NPC137096
0.6912	Remote Similarity	NPC259017
0.6903	Remote Similarity	NPC151764
0.6903	Remote Similarity	NPC300017
0.6903	Remote Similarity	NPC55561
0.6899	Remote Similarity	NPC474146
0.6875	Remote Similarity	NPC104216
0.687	Remote Similarity	NPC229213
0.6849	Remote Similarity	NPC258222
0.6847	Remote Similarity	NPC155393
0.6842	Remote Similarity	NPC142776
0.6842	Remote Similarity	NPC155908
0.6842	Remote Similarity	NPC45040
0.6842	Remote Similarity	NPC304541
0.6835	Remote Similarity	NPC474587
0.6835	Remote Similarity	NPC475132
0.6825	Remote Similarity	NPC142599
0.6825	Remote Similarity	NPC118202
0.6818	Remote Similarity	NPC13020
0.6818	Remote Similarity	NPC140359
0.6818	Remote Similarity	NPC318777
0.6818	Remote Similarity	NPC473572
0.6818	Remote Similarity	NPC474169
0.6818	Remote Similarity	NPC319826
0.6815	Remote Similarity	NPC150929
0.6814	Remote Similarity	NPC98772
0.6814	Remote Similarity	NPC70436
0.6812	Remote Similarity	NPC471328
0.6807	Remote Similarity	NPC327226
0.6803	Remote Similarity	NPC186469
0.6803	Remote Similarity	NPC475432
0.6794	Remote Similarity	NPC27581
0.6791	Remote Similarity	NPC43706
0.6786	Remote Similarity	NPC307235
0.6786	Remote Similarity	NPC475293
0.6786	Remote Similarity	NPC407
0.6783	Remote Similarity	NPC138117
0.6783	Remote Similarity	NPC325292
0.6772	Remote Similarity	NPC50782
0.6772	Remote Similarity	NPC317254
0.6765	Remote Similarity	NPC474614
0.6746	Remote Similarity	NPC26524
0.6742	Remote Similarity	NPC47790
0.6741	Remote Similarity	NPC159987
0.6741	Remote Similarity	NPC122359
0.6741	Remote Similarity	NPC474147
0.6741	Remote Similarity	NPC78061
0.6741	Remote Similarity	NPC473708
0.6726	Remote Similarity	NPC27974
0.6724	Remote Similarity	NPC316301
0.6724	Remote Similarity	NPC151715
0.6724	Remote Similarity	NPC128062
0.6724	Remote Similarity	NPC27323
0.6719	Remote Similarity	NPC82963
0.6718	Remote Similarity	NPC326079
0.6716	Remote Similarity	NPC318965
0.6714	Remote Similarity	NPC470248
0.6714	Remote Similarity	NPC470249
0.6696	Remote Similarity	NPC270547
0.6696	Remote Similarity	NPC204210
0.6694	Remote Similarity	NPC147000
0.6694	Remote Similarity	NPC150254
0.6694	Remote Similarity	NPC304761
0.6694	Remote Similarity	NPC226778
0.6692	Remote Similarity	NPC84606
0.6667	Remote Similarity	NPC38458
0.6667	Remote Similarity	NPC8392
0.6667	Remote Similarity	NPC274678
0.6667	Remote Similarity	NPC313650
0.6667	Remote Similarity	NPC144682
0.6667	Remote Similarity	NPC283468
0.6667	Remote Similarity	NPC236347
0.6667	Remote Similarity	NPC323775
0.6667	Remote Similarity	NPC311737
0.6667	Remote Similarity	NPC177967
0.6667	Remote Similarity	NPC471237
0.6667	Remote Similarity	NPC26244
0.6644	Remote Similarity	NPC71629
0.6644	Remote Similarity	NPC296085
0.6642	Remote Similarity	NPC474536

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 NPC115803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1158
0.2-0.3	1421
0.3-0.4	3205
0.4-0.5	2329
0.5-0.6	681
0.6-0.7	136
0.7-0.8	10
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD9718	Approved
0.8036	Intermediate Similarity	NPD9610	Approved
0.8036	Intermediate Similarity	NPD9608	Approved
0.7692	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9377	Approved
0.75	Intermediate Similarity	NPD9379	Approved
0.7414	Intermediate Similarity	NPD9244	Approved
0.7258	Intermediate Similarity	NPD9568	Approved
0.72	Intermediate Similarity	NPD318	Approved
0.72	Intermediate Similarity	NPD16	Approved
0.72	Intermediate Similarity	NPD856	Approved
0.72	Intermediate Similarity	NPD317	Approved
0.7097	Intermediate Similarity	NPD9618	Approved
0.7097	Intermediate Similarity	NPD9614	Approved
0.7031	Intermediate Similarity	NPD9384	Approved
0.7031	Intermediate Similarity	NPD9381	Approved
0.7029	Intermediate Similarity	NPD1169	Approved
0.6983	Remote Similarity	NPD9611	Approved
0.6983	Remote Similarity	NPD9609	Approved
0.6983	Remote Similarity	NPD9612	Approved
0.6977	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD111	Approved
0.6929	Remote Similarity	NPD9613	Approved
0.6929	Remote Similarity	NPD9616	Approved
0.6929	Remote Similarity	NPD9615	Approved
0.6905	Remote Similarity	NPD255	Approved
0.6905	Remote Similarity	NPD256	Approved
0.688	Remote Similarity	NPD2234	Approved
0.688	Remote Similarity	NPD2228	Approved
0.688	Remote Similarity	NPD2229	Approved
0.6875	Remote Similarity	NPD316	Approved
0.687	Remote Similarity	NPD2562	Approved
0.687	Remote Similarity	NPD2561	Approved
0.686	Remote Similarity	NPD1445	Approved
0.686	Remote Similarity	NPD1444	Approved
0.6818	Remote Similarity	NPD9622	Approved
0.6767	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5311	Approved
0.6767	Remote Similarity	NPD5310	Approved
0.6765	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2933	Approved
0.6724	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2934	Approved
0.6716	Remote Similarity	NPD3053	Approved
0.6716	Remote Similarity	NPD1129	Approved
0.6716	Remote Similarity	NPD1135	Approved
0.6716	Remote Similarity	NPD1134	Approved
0.6716	Remote Similarity	NPD3055	Approved
0.6716	Remote Similarity	NPD1131	Approved
0.6716	Remote Similarity	NPD1133	Approved
0.6694	Remote Similarity	NPD309	Approved
0.6694	Remote Similarity	NPD10	Approved
0.6694	Remote Similarity	NPD1792	Phase 2
0.6694	Remote Similarity	NPD310	Approved
0.6694	Remote Similarity	NPD315	Approved
0.6694	Remote Similarity	NPD314	Approved
0.6694	Remote Similarity	NPD311	Approved
0.6667	Remote Similarity	NPD7451	Discontinued
0.6667	Remote Similarity	NPD9621	Approved
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD9620	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD2194	Approved
0.6667	Remote Similarity	NPD2195	Approved
0.6667	Remote Similarity	NPD9619	Approved
0.6667	Remote Similarity	NPD1809	Phase 2
0.6618	Remote Similarity	NPD9569	Approved
0.6565	Remote Similarity	NPD4093	Discontinued
0.6562	Remote Similarity	NPD1791	Approved
0.6562	Remote Similarity	NPD1793	Approved
0.6555	Remote Similarity	NPD9273	Approved
0.6522	Remote Similarity	NPD9536	Phase 1
0.6522	Remote Similarity	NPD3136	Phase 2
0.6522	Remote Similarity	NPD9537	Phase 1
0.6519	Remote Similarity	NPD196	Phase 1
0.65	Remote Similarity	NPD3020	Approved
0.6496	Remote Similarity	NPD845	Approved
0.6489	Remote Similarity	NPD5304	Approved
0.6489	Remote Similarity	NPD5303	Approved
0.6475	Remote Similarity	NPD597	Approved
0.6475	Remote Similarity	NPD601	Approved
0.6475	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD598	Approved
0.6434	Remote Similarity	NPD595	Approved
0.6434	Remote Similarity	NPD593	Approved
0.6429	Remote Similarity	NPD1132	Approved
0.6429	Remote Similarity	NPD1136	Approved
0.6429	Remote Similarity	NPD829	Discontinued
0.6429	Remote Similarity	NPD259	Phase 1
0.6429	Remote Similarity	NPD6405	Approved
0.6429	Remote Similarity	NPD1130	Approved
0.6429	Remote Similarity	NPD6407	Approved
0.6423	Remote Similarity	NPD859	Approved
0.6423	Remote Similarity	NPD599	Approved
0.6423	Remote Similarity	NPD858	Approved
0.6423	Remote Similarity	NPD602	Approved
0.6393	Remote Similarity	NPD940	Approved
0.6393	Remote Similarity	NPD846	Approved
0.6391	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1751	Approved
0.6387	Remote Similarity	NPD844	Approved
0.6383	Remote Similarity	NPD3061	Approved
0.6383	Remote Similarity	NPD3059	Approved
0.6383	Remote Similarity	NPD3062	Approved
0.637	Remote Similarity	NPD2235	Phase 2
0.637	Remote Similarity	NPD2231	Phase 2
0.6364	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD555	Phase 2
0.6333	Remote Similarity	NPD288	Approved
0.6324	Remote Similarity	NPD4659	Approved
0.6311	Remote Similarity	NPD1242	Phase 1
0.6304	Remote Similarity	NPD258	Approved
0.6304	Remote Similarity	NPD257	Approved
0.6294	Remote Similarity	NPD3054	Approved
0.6294	Remote Similarity	NPD817	Approved
0.6294	Remote Similarity	NPD823	Approved
0.6294	Remote Similarity	NPD2568	Approved
0.6294	Remote Similarity	NPD5314	Approved
0.6294	Remote Similarity	NPD3052	Approved
0.6289	Remote Similarity	NPD1161	Approved
0.6269	Remote Similarity	NPD2668	Approved
0.6269	Remote Similarity	NPD2667	Approved
0.626	Remote Similarity	NPD854	Approved
0.626	Remote Similarity	NPD855	Approved
0.625	Remote Similarity	NPD3552	Approved
0.625	Remote Similarity	NPD3554	Approved
0.625	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3555	Approved
0.625	Remote Similarity	NPD3553	Approved
0.6241	Remote Similarity	NPD1759	Phase 1
0.6232	Remote Similarity	NPD4103	Phase 2
0.6232	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD600	Approved
0.6214	Remote Similarity	NPD2614	Approved
0.6214	Remote Similarity	NPD596	Approved
0.6207	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD558	Phase 2
0.6179	Remote Similarity	NPD289	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1068	Approved
0.6165	Remote Similarity	NPD1758	Phase 1
0.6164	Remote Similarity	NPD1538	Phase 1
0.6164	Remote Similarity	NPD1523	Approved
0.6164	Remote Similarity	NPD1522	Approved
0.6164	Remote Similarity	NPD7450	Phase 2
0.6164	Remote Similarity	NPD1519	Approved
0.6164	Remote Similarity	NPD1537	Approved
0.6164	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD9570	Approved
0.6143	Remote Similarity	NPD3636	Approved
0.6143	Remote Similarity	NPD3637	Approved
0.6143	Remote Similarity	NPD3635	Approved
0.6134	Remote Similarity	NPD1812	Approved
0.6134	Remote Similarity	NPD1814	Approved
0.6129	Remote Similarity	NPD4818	Approved
0.6129	Remote Similarity	NPD4817	Approved
0.6127	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7978	Discontinued
0.6118	Remote Similarity	NPD2184	Approved
0.6118	Remote Similarity	NPD2183	Approved
0.6111	Remote Similarity	NPD9087	Approved
0.6103	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD1980	Approved
0.6103	Remote Similarity	NPD3421	Phase 3
0.6103	Remote Similarity	NPD1981	Approved
0.6103	Remote Similarity	NPD1983	Approved
0.6099	Remote Similarity	NPD3595	Approved
0.6099	Remote Similarity	NPD3594	Approved
0.6099	Remote Similarity	NPD2606	Approved
0.6099	Remote Similarity	NPD2605	Approved
0.6087	Remote Similarity	NPD2429	Approved
0.6087	Remote Similarity	NPD2428	Approved
0.6087	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4231	Approved
0.608	Remote Similarity	NPD4229	Approved
0.608	Remote Similarity	NPD3683	Approved
0.608	Remote Similarity	NPD3680	Approved
0.608	Remote Similarity	NPD3682	Approved
0.608	Remote Similarity	NPD4658	Approved
0.608	Remote Similarity	NPD4656	Approved
0.608	Remote Similarity	NPD3681	Approved
0.6058	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD5156	Approved
0.6056	Remote Similarity	NPD5155	Approved
0.6047	Remote Similarity	NPD3022	Approved
0.6047	Remote Similarity	NPD3021	Approved
0.6045	Remote Similarity	NPD828	Approved
0.6042	Remote Similarity	NPD825	Approved
0.6042	Remote Similarity	NPD826	Approved
0.604	Remote Similarity	NPD3060	Approved
0.604	Remote Similarity	NPD2209	Approved
0.604	Remote Similarity	NPD2211	Approved
0.6032	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD2497	Approved
0.6031	Remote Similarity	NPD821	Approved
0.6031	Remote Similarity	NPD2496	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