NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.16
Volume:	279.962
LogP:	0.33
LogD:	-0.043
LogS:	-1.45
# Rotatable Bonds:	8
TPSA:	84.58
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	2.436
Fsp3:	0.5
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:	-5.594
MDCK Permeability:	3.30116854456719e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	20.260082244873047%
Volume Distribution (VD):	2.359
Pgp-substrate:	78.46871185302734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.761
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	11.04
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.221
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC247018

Natural Product ID:	NPC247018
*Common Name:**	2-[4-[(2R)-2-Hydroxy-3-(Propan-2-Ylamino)Propoxy]Phenyl]Acetamide
IUPAC Name:	2-[4-[(2R)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
Synonyms:	R(+)-Atenolol
Standard InCHIKey:	METKIMKYRPQLGS-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m1/s1
SMILES:	CC(C)NC[C@H](COc1ccc(cc1)CC(=N)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1230004
PubChem CID:	180559
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002363] Phenylacetamides

*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
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	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
AC50	4
Others	9
Potency	14

Activity Type	# Activity
Individual Protein	4
ORGANISM	4
Others	18
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	112201.8	nM	PMID[456442]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[456442]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[456442]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[456444]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[456442]
NPT2	Others	Unspecified		Potency	n.a.	1636.0	nM	PMID[456442]
NPT2	Others	Unspecified		Potency	n.a.	354.8	nM	PMID[456442]
NPT2	Others	Unspecified		Potency	n.a.	354.8	nM	PMID[456443]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[456442]
NPT2	Others	Unspecified		AC50	n.a.	1130.0	nM	PMID[456445]
NPT2	Others	Unspecified		AC50	n.a.	2818.4	nM	PMID[456445]
NPT2	Others	Unspecified		Ac50	n.a.	1.122	uM	PMID[456445]
NPT2	Others	Unspecified		AC50	n.a.	10000.0	nM	PMID[456445]
NPT2	Others	Unspecified		AC50	n.a.	14125.4	nM	PMID[456445]
NPT2	Others	Unspecified		Ac50	n.a.	2.818	uM	PMID[456445]
NPT2	Others	Unspecified		Ac50	n.a.	14.13	uM	PMID[456445]
NPT2	Others	Unspecified		Ac50	n.a.	10.0	uM	PMID[456445]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition index	=	0.05219	n.a.	PMID[456446]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	25.84	%	PMID[456447]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	27.87	%	PMID[456448]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.16	%	PMID[456449]
NPT2	Others	Unspecified		Potency	n.a.	84.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1059.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	29849.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	239.1	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 NPC247018 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	154
0.1-0.2	1120
0.2-0.3	7885
0.3-0.4	10298
0.4-0.5	7689
0.5-0.6	12126
0.6-0.7	3167
0.7-0.8	246
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307123
1.0	High Similarity	NPC97870
0.9516	High Similarity	NPC320242
0.9206	High Similarity	NPC136112
0.9206	High Similarity	NPC141739
0.8467	Intermediate Similarity	NPC318591
0.8467	Intermediate Similarity	NPC231163
0.8417	Intermediate Similarity	NPC204546
0.8102	Intermediate Similarity	NPC274732
0.8031	Intermediate Similarity	NPC26524
0.7958	Intermediate Similarity	NPC212850
0.7958	Intermediate Similarity	NPC189724
0.7958	Intermediate Similarity	NPC83289
0.791	Intermediate Similarity	NPC328267
0.7867	Intermediate Similarity	NPC233926
0.7785	Intermediate Similarity	NPC47672
0.7755	Intermediate Similarity	NPC245974
0.7742	Intermediate Similarity	NPC108875
0.7742	Intermediate Similarity	NPC38079
0.774	Intermediate Similarity	NPC247298
0.7714	Intermediate Similarity	NPC471953
0.768	Intermediate Similarity	NPC470393
0.7656	Intermediate Similarity	NPC46844
0.7638	Intermediate Similarity	NPC97811
0.7634	Intermediate Similarity	NPC10286
0.7634	Intermediate Similarity	NPC213
0.7612	Intermediate Similarity	NPC263835
0.7597	Intermediate Similarity	NPC166837
0.7591	Intermediate Similarity	NPC95733
0.7591	Intermediate Similarity	NPC62101
0.7589	Intermediate Similarity	NPC470392
0.7574	Intermediate Similarity	NPC298486
0.7559	Intermediate Similarity	NPC194034
0.7537	Intermediate Similarity	NPC256369
0.7536	Intermediate Similarity	NPC29477
0.7532	Intermediate Similarity	NPC37205
0.7532	Intermediate Similarity	NPC160931
0.7518	Intermediate Similarity	NPC326599
0.7518	Intermediate Similarity	NPC329595
0.7516	Intermediate Similarity	NPC156311
0.7466	Intermediate Similarity	NPC168861
0.744	Intermediate Similarity	NPC51633
0.7422	Intermediate Similarity	NPC251306
0.7419	Intermediate Similarity	NPC100870
0.7407	Intermediate Similarity	NPC283760
0.7407	Intermediate Similarity	NPC43275
0.7405	Intermediate Similarity	NPC115379
0.7402	Intermediate Similarity	NPC42383
0.74	Intermediate Similarity	NPC132771
0.7391	Intermediate Similarity	NPC13020
0.7391	Intermediate Similarity	NPC211218
0.7391	Intermediate Similarity	NPC140359
0.7381	Intermediate Similarity	NPC192596
0.7364	Intermediate Similarity	NPC146530
0.7353	Intermediate Similarity	NPC321133
0.7351	Intermediate Similarity	NPC324081
0.7348	Intermediate Similarity	NPC301735
0.7343	Intermediate Similarity	NPC208757
0.7338	Intermediate Similarity	NPC206372
0.7338	Intermediate Similarity	NPC203424
0.7329	Intermediate Similarity	NPC204848
0.7329	Intermediate Similarity	NPC41473
0.7329	Intermediate Similarity	NPC14600
0.7329	Intermediate Similarity	NPC312770
0.7329	Intermediate Similarity	NPC160607
0.7305	Intermediate Similarity	NPC191302
0.7305	Intermediate Similarity	NPC153990
0.7299	Intermediate Similarity	NPC83279
0.7297	Intermediate Similarity	NPC195814
0.729	Intermediate Similarity	NPC56635
0.7278	Intermediate Similarity	NPC158900
0.7273	Intermediate Similarity	NPC114102
0.7266	Intermediate Similarity	NPC255253
0.7266	Intermediate Similarity	NPC8302
0.7259	Intermediate Similarity	NPC137096
0.7259	Intermediate Similarity	NPC120075
0.7252	Intermediate Similarity	NPC137685
0.725	Intermediate Similarity	NPC186617
0.7239	Intermediate Similarity	NPC303370
0.7237	Intermediate Similarity	NPC115144
0.7237	Intermediate Similarity	NPC277857
0.7234	Intermediate Similarity	NPC323775
0.7234	Intermediate Similarity	NPC236347
0.7233	Intermediate Similarity	NPC254700
0.7231	Intermediate Similarity	NPC309982
0.7226	Intermediate Similarity	NPC17388
0.7226	Intermediate Similarity	NPC53596
0.7226	Intermediate Similarity	NPC160120
0.7226	Intermediate Similarity	NPC471308
0.7226	Intermediate Similarity	NPC289330
0.7222	Intermediate Similarity	NPC130595
0.7222	Intermediate Similarity	NPC93882
0.7219	Intermediate Similarity	NPC313414
0.7211	Intermediate Similarity	NPC474673
0.7205	Intermediate Similarity	NPC471568
0.7205	Intermediate Similarity	NPC473693
0.7205	Intermediate Similarity	NPC196091
0.72	Intermediate Similarity	NPC78530
0.72	Intermediate Similarity	NPC63628
0.72	Intermediate Similarity	NPC178466
0.7197	Intermediate Similarity	NPC21890
0.7197	Intermediate Similarity	NPC55300
0.7194	Intermediate Similarity	NPC71090
0.7192	Intermediate Similarity	NPC64205
0.7192	Intermediate Similarity	NPC470471
0.719	Intermediate Similarity	NPC76412
0.7188	Intermediate Similarity	NPC226778
0.7188	Intermediate Similarity	NPC147000
0.7188	Intermediate Similarity	NPC150254
0.7188	Intermediate Similarity	NPC304761
0.7185	Intermediate Similarity	NPC258992
0.7183	Intermediate Similarity	NPC186898
0.7183	Intermediate Similarity	NPC198798
0.7176	Intermediate Similarity	NPC474272
0.7176	Intermediate Similarity	NPC145638
0.7176	Intermediate Similarity	NPC290566
0.7176	Intermediate Similarity	NPC24777
0.7174	Intermediate Similarity	NPC318357
0.7174	Intermediate Similarity	NPC183262
0.7172	Intermediate Similarity	NPC313737
0.7172	Intermediate Similarity	NPC6854
0.7172	Intermediate Similarity	NPC285078
0.7164	Intermediate Similarity	NPC235250
0.7164	Intermediate Similarity	NPC118202
0.7162	Intermediate Similarity	NPC299583
0.7154	Intermediate Similarity	NPC186469
0.7153	Intermediate Similarity	NPC163036
0.7152	Intermediate Similarity	NPC294249
0.7143	Intermediate Similarity	NPC258222
0.7143	Intermediate Similarity	NPC165646
0.7133	Intermediate Similarity	NPC271808
0.7133	Intermediate Similarity	NPC155838
0.7132	Intermediate Similarity	NPC164386
0.7132	Intermediate Similarity	NPC323948
0.7132	Intermediate Similarity	NPC473855
0.7125	Intermediate Similarity	NPC469479
0.7123	Intermediate Similarity	NPC218530
0.7122	Intermediate Similarity	NPC127389
0.7122	Intermediate Similarity	NPC290451
0.7122	Intermediate Similarity	NPC211992
0.7114	Intermediate Similarity	NPC477838
0.7114	Intermediate Similarity	NPC477837
0.7113	Intermediate Similarity	NPC301713
0.7111	Intermediate Similarity	NPC317254
0.7109	Intermediate Similarity	NPC305205
0.7107	Intermediate Similarity	NPC22014
0.7103	Intermediate Similarity	NPC214869
0.7101	Intermediate Similarity	NPC41801
0.7101	Intermediate Similarity	NPC60589
0.7101	Intermediate Similarity	NPC469708
0.7097	Intermediate Similarity	NPC476742
0.7097	Intermediate Similarity	NPC469711
0.7095	Intermediate Similarity	NPC470470
0.7095	Intermediate Similarity	NPC253429
0.7095	Intermediate Similarity	NPC214988
0.7092	Intermediate Similarity	NPC94276
0.7092	Intermediate Similarity	NPC48990
0.7092	Intermediate Similarity	NPC293701
0.7092	Intermediate Similarity	NPC114901
0.7092	Intermediate Similarity	NPC109822
0.7083	Intermediate Similarity	NPC262641
0.7083	Intermediate Similarity	NPC52029
0.7083	Intermediate Similarity	NPC195749
0.7083	Intermediate Similarity	NPC35961
0.708	Intermediate Similarity	NPC101503
0.708	Intermediate Similarity	NPC5932
0.7078	Intermediate Similarity	NPC470935
0.7078	Intermediate Similarity	NPC471032
0.7075	Intermediate Similarity	NPC237227
0.7075	Intermediate Similarity	NPC6570
0.7071	Intermediate Similarity	NPC471314
0.7071	Intermediate Similarity	NPC471315
0.707	Intermediate Similarity	NPC2295
0.707	Intermediate Similarity	NPC477564
0.707	Intermediate Similarity	NPC212699
0.707	Intermediate Similarity	NPC207675
0.7063	Intermediate Similarity	NPC157740
0.7063	Intermediate Similarity	NPC107619
0.7063	Intermediate Similarity	NPC99798
0.7063	Intermediate Similarity	NPC251571
0.7063	Intermediate Similarity	NPC313918
0.7051	Intermediate Similarity	NPC76213
0.7051	Intermediate Similarity	NPC476741
0.7051	Intermediate Similarity	NPC277669
0.705	Intermediate Similarity	NPC269242
0.705	Intermediate Similarity	NPC198734
0.705	Intermediate Similarity	NPC469412
0.7047	Intermediate Similarity	NPC36434
0.7042	Intermediate Similarity	NPC194519
0.7034	Intermediate Similarity	NPC308885
0.7034	Intermediate Similarity	NPC255550
0.7032	Intermediate Similarity	NPC60538
0.7032	Intermediate Similarity	NPC207824
0.7031	Intermediate Similarity	NPC327226
0.7029	Intermediate Similarity	NPC135961
0.7029	Intermediate Similarity	NPC311595
0.7029	Intermediate Similarity	NPC24474
0.7025	Intermediate Similarity	NPC319320
0.7025	Intermediate Similarity	NPC287757
0.7023	Intermediate Similarity	NPC258171

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 NPC247018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	107
0.1-0.2	481
0.2-0.3	1168
0.3-0.4	2132
0.4-0.5	2534
0.5-0.6	1785
0.6-0.7	677
0.7-0.8	226
0.8-0.85	23
0.85-0.9	9
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1423	Approved
0.9516	High Similarity	NPD1819	Approved
0.9516	High Similarity	NPD1818	Approved
0.9516	High Similarity	NPD1820	Approved
0.9516	High Similarity	NPD1817	Approved
0.9219	High Similarity	NPD3167	Approved
0.9219	High Similarity	NPD3165	Approved
0.9219	High Similarity	NPD3166	Approved
0.9219	High Similarity	NPD3164	Approved
0.9206	High Similarity	NPD1794	Approved
0.907	High Similarity	NPD3179	Approved
0.907	High Similarity	NPD3180	Approved
0.8815	High Similarity	NPD3175	Clinical (unspecified phase)
0.8676	High Similarity	NPD2239	Approved
0.8676	High Similarity	NPD2240	Approved
0.8647	High Similarity	NPD3163	Approved
0.8647	High Similarity	NPD3162	Approved
0.8615	High Similarity	NPD1770	Clinical (unspecified phase)
0.8582	High Similarity	NPD3985	Discontinued
0.8582	High Similarity	NPD3597	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2156	Approved
0.8467	Intermediate Similarity	NPD2155	Approved
0.8467	Intermediate Similarity	NPD2154	Approved
0.8456	Intermediate Similarity	NPD3052	Approved
0.8456	Intermediate Similarity	NPD3054	Approved
0.8433	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.8359	Intermediate Similarity	NPD1798	Approved
0.8359	Intermediate Similarity	NPD1797	Approved
0.8357	Intermediate Similarity	NPD2460	Phase 3
0.8357	Intermediate Similarity	NPD2458	Approved
0.8357	Intermediate Similarity	NPD2459	Approved
0.8346	Intermediate Similarity	NPD2250	Discontinued
0.8239	Intermediate Similarity	NPD2677	Approved
0.8227	Intermediate Similarity	NPD4162	Approved
0.8194	Intermediate Similarity	NPD6419	Discontinued
0.8194	Intermediate Similarity	NPD3536	Discontinued
0.8138	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD7526	Approved
0.8138	Intermediate Similarity	NPD52	Approved
0.8125	Intermediate Similarity	NPD1774	Approved
0.8095	Intermediate Similarity	NPD821	Approved
0.8088	Intermediate Similarity	NPD5163	Phase 2
0.8074	Intermediate Similarity	NPD5266	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD2874	Phase 2
0.7986	Intermediate Similarity	NPD5160	Discontinued
0.7972	Intermediate Similarity	NPD5061	Approved
0.7972	Intermediate Similarity	NPD5062	Approved
0.7971	Intermediate Similarity	NPD3532	Approved
0.7971	Intermediate Similarity	NPD3530	Approved
0.7971	Intermediate Similarity	NPD3531	Approved
0.7956	Intermediate Similarity	NPD6179	Discontinued
0.791	Intermediate Similarity	NPD2428	Approved
0.791	Intermediate Similarity	NPD2429	Approved
0.7902	Intermediate Similarity	NPD7153	Discontinued
0.7899	Intermediate Similarity	NPD1336	Approved
0.7879	Intermediate Similarity	NPD2554	Approved
0.7879	Intermediate Similarity	NPD2556	Approved
0.7867	Intermediate Similarity	NPD6677	Suspended
0.7847	Intermediate Similarity	NPD1416	Approved
0.7786	Intermediate Similarity	NPD856	Approved
0.7786	Intermediate Similarity	NPD318	Approved
0.7786	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD16	Approved
0.7786	Intermediate Similarity	NPD317	Approved
0.7778	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2684	Approved
0.7778	Intermediate Similarity	NPD3685	Discontinued
0.777	Intermediate Similarity	NPD2236	Approved
0.777	Intermediate Similarity	NPD2676	Approved
0.777	Intermediate Similarity	NPD2675	Approved
0.7763	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1422	Approved
0.7755	Intermediate Similarity	NPD6087	Phase 1
0.7724	Intermediate Similarity	NPD3060	Approved
0.7724	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5745	Approved
0.771	Intermediate Similarity	NPD3596	Phase 2
0.7707	Intermediate Similarity	NPD2215	Approved
0.7707	Intermediate Similarity	NPD2216	Approved
0.7704	Intermediate Similarity	NPD2231	Phase 2
0.7704	Intermediate Similarity	NPD2561	Approved
0.7704	Intermediate Similarity	NPD2235	Phase 2
0.7704	Intermediate Similarity	NPD2562	Approved
0.7703	Intermediate Similarity	NPD4662	Approved
0.7703	Intermediate Similarity	NPD4661	Approved
0.7697	Intermediate Similarity	NPD5722	Discontinued
0.7697	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD593	Approved
0.7692	Intermediate Similarity	NPD595	Approved
0.7669	Intermediate Similarity	NPD3049	Approved
0.7652	Intermediate Similarity	NPD1103	Approved
0.7652	Intermediate Similarity	NPD1102	Approved
0.7647	Intermediate Similarity	NPD6582	Phase 2
0.7647	Intermediate Similarity	NPD5772	Approved
0.7647	Intermediate Similarity	NPD5773	Approved
0.7647	Intermediate Similarity	NPD6583	Phase 3
0.7632	Intermediate Similarity	NPD6072	Discontinued
0.7632	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2649	Approved
0.7616	Intermediate Similarity	NPD2651	Approved
0.7615	Intermediate Similarity	NPD592	Approved
0.7615	Intermediate Similarity	NPD594	Approved
0.7606	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4237	Approved
0.7603	Intermediate Similarity	NPD4236	Phase 3
0.7584	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5746	Approved
0.7568	Intermediate Similarity	NPD3122	Phase 3
0.7559	Intermediate Similarity	NPD290	Approved
0.7554	Intermediate Similarity	NPD4993	Discontinued
0.755	Intermediate Similarity	NPD3687	Approved
0.755	Intermediate Similarity	NPD3686	Approved
0.7538	Intermediate Similarity	NPD7843	Approved
0.7533	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD597	Approved
0.7518	Intermediate Similarity	NPD598	Approved
0.7518	Intermediate Similarity	NPD601	Approved
0.7517	Intermediate Similarity	NPD1725	Approved
0.7516	Intermediate Similarity	NPD4666	Phase 3
0.75	Intermediate Similarity	NPD8031	Discontinued
0.75	Intermediate Similarity	NPD3552	Approved
0.75	Intermediate Similarity	NPD3555	Approved
0.75	Intermediate Similarity	NPD3553	Approved
0.75	Intermediate Similarity	NPD3554	Approved
0.7482	Intermediate Similarity	NPD3690	Phase 2
0.7482	Intermediate Similarity	NPD558	Phase 2
0.7482	Intermediate Similarity	NPD3691	Phase 2
0.7482	Intermediate Similarity	NPD6584	Phase 3
0.7465	Intermediate Similarity	NPD840	Approved
0.7465	Intermediate Similarity	NPD1136	Approved
0.7465	Intermediate Similarity	NPD1130	Approved
0.7465	Intermediate Similarity	NPD1132	Approved
0.7465	Intermediate Similarity	NPD839	Approved
0.7463	Intermediate Similarity	NPD6580	Approved
0.7463	Intermediate Similarity	NPD6581	Approved
0.7452	Intermediate Similarity	NPD5709	Phase 3
0.745	Intermediate Similarity	NPD5756	Phase 2
0.7431	Intermediate Similarity	NPD2223	Approved
0.7431	Intermediate Similarity	NPD2224	Approved
0.7419	Intermediate Similarity	NPD2977	Approved
0.7419	Intermediate Similarity	NPD2978	Approved
0.741	Intermediate Similarity	NPD1129	Approved
0.741	Intermediate Similarity	NPD1131	Approved
0.741	Intermediate Similarity	NPD1133	Approved
0.741	Intermediate Similarity	NPD1135	Approved
0.741	Intermediate Similarity	NPD1134	Approved
0.7407	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2161	Phase 2
0.7394	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1048	Approved
0.7389	Intermediate Similarity	NPD8070	Approved
0.7383	Intermediate Similarity	NPD3692	Discontinued
0.7376	Intermediate Similarity	NPD600	Approved
0.7376	Intermediate Similarity	NPD596	Approved
0.7368	Intermediate Similarity	NPD7157	Approved
0.7368	Intermediate Similarity	NPD2557	Approved
0.7368	Intermediate Similarity	NPD7131	Phase 3
0.7358	Intermediate Similarity	NPD7485	Phase 3
0.7358	Intermediate Similarity	NPD7484	Phase 3
0.7353	Intermediate Similarity	NPD2667	Approved
0.7353	Intermediate Similarity	NPD2668	Approved
0.7351	Intermediate Similarity	NPD2504	Approved
0.7351	Intermediate Similarity	NPD2505	Approved
0.7343	Intermediate Similarity	NPD7477	Discontinued
0.7343	Intermediate Similarity	NPD2245	Discovery
0.7342	Intermediate Similarity	NPD6315	Phase 2
0.7338	Intermediate Similarity	NPD4179	Approved
0.7338	Intermediate Similarity	NPD4180	Approved
0.7333	Intermediate Similarity	NPD316	Approved
0.7333	Intermediate Similarity	NPD5295	Discontinued
0.7329	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3154	Approved
0.7305	Intermediate Similarity	NPD1712	Approved
0.7305	Intermediate Similarity	NPD455	Discontinued
0.7305	Intermediate Similarity	NPD3153	Approved
0.7297	Intermediate Similarity	NPD1391	Approved
0.7279	Intermediate Similarity	NPD6032	Approved
0.7279	Intermediate Similarity	NPD3156	Discontinued
0.7267	Intermediate Similarity	NPD5241	Discontinued
0.7266	Intermediate Similarity	NPD6542	Approved
0.7266	Intermediate Similarity	NPD6543	Approved
0.7266	Intermediate Similarity	NPD6540	Phase 3
0.7266	Intermediate Similarity	NPD6539	Approved
0.7261	Intermediate Similarity	NPD3556	Approved
0.7261	Intermediate Similarity	NPD3560	Approved
0.7261	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3558	Approved
0.7261	Intermediate Similarity	NPD3557	Approved
0.7259	Intermediate Similarity	NPD9616	Approved
0.7259	Intermediate Similarity	NPD9613	Approved
0.7259	Intermediate Similarity	NPD9615	Approved
0.7254	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD776	Approved
0.7244	Intermediate Similarity	NPD5356	Approved
0.7244	Intermediate Similarity	NPD5355	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