NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	133.06
Volume:	134.96
LogP:	0.526
LogD:	0.542
LogS:	-1.904
# Rotatable Bonds:	0
TPSA:	55.43
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	2.638
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	3.460302104940638e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.098
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.168
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.672
Plasma Protein Binding (PPB):	52.569740295410156%
Volume Distribution (VD):	0.947
Pgp-substrate:	53.65534591674805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	6.579
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.57
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.365
Carcinogencity:	0.962
Eye Corrosion:	0.007
Eye Irritation:	0.956
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC317642

Natural Product ID:	NPC317642
*Common Name:**	1H-Benzimidazol-2-Amine
IUPAC Name:	1H-benzimidazol-2-amine
Synonyms:
Standard InCHIKey:	JWYUFVNJZUSCSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H7N3/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H,(H3,8,9,10)
SMILES:	C1=CC=C2C(=C1)NC(=N2)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL305513
PubChem CID:	13624
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000294] Benzimidazoles

*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
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Kd	1
Ki	2
Others	9
Potency	21

Activity Type	# Activity
Cell Line	2
Individual Protein	16
Organism	4
Others	13
Protein Complex	1
Protein-Protein Interaction	1
SINGLE PROTEIN	3
Uncleic Acid	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1654	Individual Protein	Urokinase-type plasminogen activator	Homo sapiens	IC50	=	200000.0	nM	PMID[573906]
NPT6015	Individual Protein	Pteridine reductase, putative	Trypanosoma brucei brucei (strain 927/4 GUTat10.1)	Ki	=	288000.0	nM	PMID[573909]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	31622.8	nM	PMID[573910]
NPT1098	Individual Protein	Eyes absent homolog 2	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[573911]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[573910]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[573910]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[573910]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[573911]
NPT4106	Individual Protein	Amine oxidase, copper containing	Homo sapiens	IC50	=	4100.0	nM	PMID[573912]
NPT6017	Individual Protein	Amine oxidase, copper containing	Rattus norvegicus	IC50	=	1000.0	nM	PMID[573912]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	177.8	nM	PMID[573911]
NPT1444	Individual Protein	PI3-kinase p110-alpha subunit	Homo sapiens	Inhibition	<	25.0	%	PMID[573917]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	1.1	%	PMID[573919]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	24598.3	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	68346.6	nM	PubChem BioAssay data set
NPT35	Others	n.a.		pKa	=	7.5	n.a.	PMID[573906]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	1902.0	nM	PMID[573907]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	114.0	nM	PMID[573907]
NPT6014	Organism	Trichinella spiralis	Trichinella spiralis	Viability	=	9.0	%	PMID[573907]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	114.82	nM	PMID[573908]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PMID[573910]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	19952.6	nM	PMID[573911]
NPT2	Others	Unspecified		Ki	=	228000.0	nM	PMID[573913]
NPT27	Others	Unspecified		CL	<	3.0	mL.min-1.g-1	PMID[573914]
NPT35	Others	n.a.		pKa_B1	n.a.	7.2	n.a.	PMID[573914]
NPT317	Uncleic Acid	Nucleic Acid		IC50	>	11000000.0	nM	PMID[573915]
NPT35	Others	n.a.		pKa	=	7.5	n.a.	PMID[573916]
NPT6559	Protein Complex	PI3-kinase p110-alpha/p85-alpha	Homo sapiens	Inhibition	<	25.0	%	PMID[573917]
NPT21990	SINGLE PROTEIN	7,8-dihydro-8-oxoguanine triphosphatase	Homo sapiens	IC50	=	44000.0	nM	PMID[573918]
NPT21990	SINGLE PROTEIN	7,8-dihydro-8-oxoguanine triphosphatase	Homo sapiens	Ka	=	5.58	10'4/M	PMID[573918]
NPT21990	SINGLE PROTEIN	7,8-dihydro-8-oxoguanine triphosphatase	Homo sapiens	Kd	=	18000.0	nM	PMID[573918]
NPT2	Others	Unspecified		Potency	n.a.	12328.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30700.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38100.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	77115.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	545.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30264.4	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	43123.8	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	49080.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24250.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24598.3	nM	PubChem BioAssay data set

☑ 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 NPC317642 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	6244
0.1-0.2	21285
0.2-0.3	9113
0.3-0.4	2669
0.4-0.5	2067
0.5-0.6	1086
0.6-0.7	203
0.7-0.8	24
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC134825
0.7347	Intermediate Similarity	NPC229477
0.7222	Intermediate Similarity	NPC474430
0.7193	Intermediate Similarity	NPC314141
0.7155	Intermediate Similarity	NPC125416
0.7143	Intermediate Similarity	NPC271732
0.7109	Intermediate Similarity	NPC216159
0.7091	Intermediate Similarity	NPC313362
0.7021	Intermediate Similarity	NPC301874
0.6791	Remote Similarity	NPC42483
0.6737	Remote Similarity	NPC66775
0.6731	Remote Similarity	NPC173991
0.6594	Remote Similarity	NPC114209
0.6435	Remote Similarity	NPC24060
0.6325	Remote Similarity	NPC302790
0.6325	Remote Similarity	NPC164802
0.6279	Remote Similarity	NPC145754
0.6275	Remote Similarity	NPC307456
0.6261	Remote Similarity	NPC328877
0.6226	Remote Similarity	NPC262295
0.6204	Remote Similarity	NPC92689
0.619	Remote Similarity	NPC475915
0.6179	Remote Similarity	NPC313673
0.6154	Remote Similarity	NPC75999
0.6154	Remote Similarity	NPC15839
0.614	Remote Similarity	NPC326792
0.6122	Remote Similarity	NPC300238
0.6111	Remote Similarity	NPC315403
0.6102	Remote Similarity	NPC434
0.6102	Remote Similarity	NPC20322
0.6102	Remote Similarity	NPC79618
0.6099	Remote Similarity	NPC204141
0.6098	Remote Similarity	NPC143156
0.6098	Remote Similarity	NPC288232
0.6075	Remote Similarity	NPC43655
0.6055	Remote Similarity	NPC191444
0.6053	Remote Similarity	NPC75496
0.6031	Remote Similarity	NPC469949
0.6019	Remote Similarity	NPC111233
0.6019	Remote Similarity	NPC30445
0.5963	Remote Similarity	NPC240134
0.5963	Remote Similarity	NPC176858
0.5963	Remote Similarity	NPC107135
0.5954	Remote Similarity	NPC252794
0.5948	Remote Similarity	NPC291610
0.5942	Remote Similarity	NPC125746
0.5935	Remote Similarity	NPC296163
0.5893	Remote Similarity	NPC322040
0.5893	Remote Similarity	NPC469330
0.5872	Remote Similarity	NPC297532
0.5871	Remote Similarity	NPC314557
0.5846	Remote Similarity	NPC41174
0.5811	Remote Similarity	NPC120070
0.5804	Remote Similarity	NPC108800
0.5796	Remote Similarity	NPC315715
0.5794	Remote Similarity	NPC84268
0.5776	Remote Similarity	NPC213774
0.5766	Remote Similarity	NPC78154
0.5762	Remote Similarity	NPC470204
0.5752	Remote Similarity	NPC476483
0.5748	Remote Similarity	NPC192209
0.5735	Remote Similarity	NPC476687
0.5735	Remote Similarity	NPC476689
0.5735	Remote Similarity	NPC476685
0.5725	Remote Similarity	NPC254698
0.5724	Remote Similarity	NPC253687
0.5724	Remote Similarity	NPC470203
0.5705	Remote Similarity	NPC476297
0.5705	Remote Similarity	NPC476219
0.5683	Remote Similarity	NPC198988
0.568	Remote Similarity	NPC187036
0.5672	Remote Similarity	NPC250361
0.5652	Remote Similarity	NPC316104
0.5652	Remote Similarity	NPC162417
0.5643	Remote Similarity	NPC325252
0.5643	Remote Similarity	NPC218268
0.563	Remote Similarity	NPC209389
0.5625	Remote Similarity	NPC313449
0.5625	Remote Similarity	NPC31651
0.562	Remote Similarity	NPC22079
0.5616	Remote Similarity	NPC143872
0.5614	Remote Similarity	NPC7067
0.5606	Remote Similarity	NPC283130
0.5606	Remote Similarity	NPC328683

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 NPC317642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	710
0.1-0.2	1131
0.2-0.3	1812
0.3-0.4	2183
0.4-0.5	2027
0.5-0.6	971
0.6-0.7	263
0.7-0.8	48
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.802	Intermediate Similarity	NPD9270	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD526	Approved
0.7411	Intermediate Similarity	NPD560	Approved
0.7411	Intermediate Similarity	NPD561	Approved
0.7377	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD462	Approved
0.7282	Intermediate Similarity	NPD463	Approved
0.7282	Intermediate Similarity	NPD464	Approved
0.7273	Intermediate Similarity	NPD1949	Approved
0.7273	Intermediate Similarity	NPD1950	Approved
0.7265	Intermediate Similarity	NPD764	Phase 3
0.7179	Intermediate Similarity	NPD9700	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1515	Discontinued
0.7155	Intermediate Similarity	NPD9719	Approved
0.7155	Intermediate Similarity	NPD5243	Approved
0.7155	Intermediate Similarity	NPD5244	Approved
0.7155	Intermediate Similarity	NPD5245	Approved
0.7155	Intermediate Similarity	NPD9720	Approved
0.7049	Intermediate Similarity	NPD3080	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD541	Approved
0.7034	Intermediate Similarity	NPD726	Discontinued
0.7	Intermediate Similarity	NPD1728	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9527	Approved
0.6942	Remote Similarity	NPD9528	Approved
0.6864	Remote Similarity	NPD2464	Approved
0.6864	Remote Similarity	NPD2463	Approved
0.6864	Remote Similarity	NPD2467	Approved
0.6791	Remote Similarity	NPD9724	Phase 1
0.6696	Remote Similarity	NPD1539	Approved
0.6639	Remote Similarity	NPD202	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD233	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD153	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD909	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1171	Approved
0.6435	Remote Similarity	NPD990	Approved
0.6435	Remote Similarity	NPD993	Approved
0.6422	Remote Similarity	NPD9188	Approved
0.6418	Remote Similarity	NPD2528	Approved
0.6393	Remote Similarity	NPD299	Phase 3
0.6378	Remote Similarity	NPD2143	Discontinued
0.6349	Remote Similarity	NPD2964	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD2033	Phase 2
0.6325	Remote Similarity	NPD477	Phase 1
0.6324	Remote Similarity	NPD7044	Discontinued
0.6288	Remote Similarity	NPD809	Discontinued
0.6281	Remote Similarity	NPD1813	Discontinued
0.6269	Remote Similarity	NPD2867	Approved
0.6269	Remote Similarity	NPD2399	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD9709	Approved
0.6268	Remote Similarity	NPD9708	Approved
0.6262	Remote Similarity	NPD297	Approved
0.6262	Remote Similarity	NPD9350	Approved
0.6262	Remote Similarity	NPD9348	Approved
0.6262	Remote Similarity	NPD9349	Approved
0.6262	Remote Similarity	NPD9351	Phase 3
0.6262	Remote Similarity	NPD9	Approved
0.626	Remote Similarity	NPD4866	Approved
0.626	Remote Similarity	NPD4867	Approved
0.626	Remote Similarity	NPD3841	Phase 3
0.625	Remote Similarity	NPD9304	Approved
0.6207	Remote Similarity	NPD2927	Phase 3
0.617	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD1316	Discontinued
0.6148	Remote Similarity	NPD2032	Discontinued
0.614	Remote Similarity	NPD479	Approved
0.6132	Remote Similarity	NPD305	Approved
0.6132	Remote Similarity	NPD304	Approved
0.6115	Remote Similarity	NPD2129	Approved
0.6111	Remote Similarity	NPD9108	Approved
0.6102	Remote Similarity	NPD1054	Approved
0.6102	Remote Similarity	NPD458	Approved
0.6068	Remote Similarity	NPD156	Phase 3
0.6033	Remote Similarity	NPD3001	Approved
0.6033	Remote Similarity	NPD2999	Approved
0.6031	Remote Similarity	NPD6713	Approved
0.6031	Remote Similarity	NPD6712	Approved
0.6029	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD9598	Discontinued
0.6	Remote Similarity	NPD8128	Discontinued
0.5987	Remote Similarity	NPD773	Approved
0.5986	Remote Similarity	NPD2529	Approved
0.5984	Remote Similarity	NPD1299	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD3625	Discontinued
0.597	Remote Similarity	NPD988	Discontinued
0.5969	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD1720	Phase 2
0.5968	Remote Similarity	NPD1723	Phase 2
0.5966	Remote Similarity	NPD445	Discontinued
0.5966	Remote Similarity	NPD1112	Phase 3
0.5966	Remote Similarity	NPD1111	Phase 3
0.596	Remote Similarity	NPD509	Phase 3
0.5957	Remote Similarity	NPD9254	Phase 3
0.5954	Remote Similarity	NPD1836	Discontinued
0.5954	Remote Similarity	NPD6900	Discontinued
0.5952	Remote Similarity	NPD1216	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD707	Approved
0.5942	Remote Similarity	NPD544	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4811	Discontinued
0.5935	Remote Similarity	NPD1311	Approved
0.5932	Remote Similarity	NPD414	Discontinued
0.5926	Remote Similarity	NPD3652	Approved
0.5921	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6070	Approved
0.592	Remote Similarity	NPD6069	Approved
0.5902	Remote Similarity	NPD3865	Approved
0.5896	Remote Similarity	NPD1619	Phase 3
0.5893	Remote Similarity	NPD243	Approved
0.5893	Remote Similarity	NPD8	Approved
0.589	Remote Similarity	NPD2660	Approved
0.589	Remote Similarity	NPD2128	Phase 1
0.589	Remote Similarity	NPD2662	Approved
0.5882	Remote Similarity	NPD261	Approved
0.5878	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD9352	Approved
0.5873	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD2036	Approved
0.5862	Remote Similarity	NPD499	Phase 3
0.5859	Remote Similarity	NPD6892	Discontinued
0.5857	Remote Similarity	NPD9245	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD174	Discontinued
0.5855	Remote Similarity	NPD1313	Approved
0.5846	Remote Similarity	NPD5787	Discontinued
0.5845	Remote Similarity	NPD2866	Approved
0.5841	Remote Similarity	NPD665	Phase 2
0.5839	Remote Similarity	NPD212	Discontinued
0.5833	Remote Similarity	NPD278	Approved
0.5833	Remote Similarity	NPD6299	Approved
0.5833	Remote Similarity	NPD3240	Phase 2
0.5833	Remote Similarity	NPD6300	Approved
0.5833	Remote Similarity	NPD1569	Phase 2
0.5833	Remote Similarity	NPD1824	Discontinued
0.5833	Remote Similarity	NPD5253	Approved
0.5833	Remote Similarity	NPD9499	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD1015	Phase 2
0.5828	Remote Similarity	NPD1016	Phase 2
0.5821	Remote Similarity	NPD8263	Discontinued
0.5812	Remote Similarity	NPD708	Approved
0.5812	Remote Similarity	NPD4734	Approved
0.5812	Remote Similarity	NPD4735	Approved
0.5809	Remote Similarity	NPD803	Phase 1
0.5806	Remote Similarity	NPD3387	Approved
0.5806	Remote Similarity	NPD453	Phase 1
0.5806	Remote Similarity	NPD452	Phase 1
0.5794	Remote Similarity	NPD1312	Approved
0.5785	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD1342	Approved
0.5778	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD9353	Approved
0.5772	Remote Similarity	NPD2521	Approved
0.5772	Remote Similarity	NPD2519	Approved
0.5772	Remote Similarity	NPD2518	Approved
0.5772	Remote Similarity	NPD3565	Approved
0.5772	Remote Similarity	NPD3036	Approved
0.5772	Remote Similarity	NPD2150	Discontinued
0.5772	Remote Similarity	NPD3566	Approved
0.5764	Remote Similarity	NPD4351	Clinical (unspecified phase)
0.576	Remote Similarity	NPD5629	Discontinued
0.5752	Remote Similarity	NPD1333	Phase 3
0.5752	Remote Similarity	NPD1702	Phase 3
0.5752	Remote Similarity	NPD1394	Approved
0.575	Remote Similarity	NPD3545	Approved
0.575	Remote Similarity	NPD3546	Approved
0.5745	Remote Similarity	NPD758	Approved
0.5739	Remote Similarity	NPD716	Approved
0.5738	Remote Similarity	NPD1107	Approved
0.5738	Remote Similarity	NPD1108	Approved
0.5732	Remote Similarity	NPD7032	Approved
0.5725	Remote Similarity	NPD3462	Approved
0.5725	Remote Similarity	NPD1561	Phase 2
0.5725	Remote Similarity	NPD3461	Approved
0.5724	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD676	Discontinued
0.5714	Remote Similarity	NPD2925	Approved
0.5714	Remote Similarity	NPD1262	Discovery
0.5714	Remote Similarity	NPD2924	Approved
0.5703	Remote Similarity	NPD922	Approved
0.5702	Remote Similarity	NPD4114	Approved
0.5702	Remote Similarity	NPD4115	Approved
0.5694	Remote Similarity	NPD9469	Approved
0.5692	Remote Similarity	NPD678	Discontinued
0.568	Remote Similarity	NPD2914	Approved
0.568	Remote Similarity	NPD2913	Approved
0.568	Remote Similarity	NPD1175	Approved
0.568	Remote Similarity	NPD2587	Approved
0.5659	Remote Similarity	NPD1479	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD412	Approved
0.5641	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD1324	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD4085	Approved
0.5634	Remote Similarity	NPD1902	Approved
0.5634	Remote Similarity	NPD680	Discontinued
0.5634	Remote Similarity	NPD1904	Approved
0.563	Remote Similarity	NPD1396	Approved
0.5625	Remote Similarity	NPD1057	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