NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.0
Volume:	182.614
LogP:	0.817
LogD:	-0.264
LogS:	-2.032
# Rotatable Bonds:	2
TPSA:	82.22
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	2.724
Fsp3:	0.0
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:	-4.617
MDCK Permeability:	2.1470041247084737e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	98.23369598388672%
Volume Distribution (VD):	0.325
Pgp-substrate:	1.7074564695358276%

ADMET: Metabolism

CYP1A2-inhibitor:	0.585
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.407
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	2.981
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.844
Carcinogencity:	0.513
Eye Corrosion:	0.382
Eye Irritation:	0.986
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC224764

Natural Product ID:	NPC224764
*Common Name:**	Potassium;1H-Indol-3-Yl Sulfate
IUPAC Name:	potassium;1H-indol-3-yl sulfate
Synonyms:
Standard InCHIKey:	MDAWATNFDJIBBD-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C8H7NO4S.K/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8;/h1-5,9H,(H,10,11,12);/q;+1/p-1
SMILES:	[O-]S(=O)(=O)Oc1c[nH]c2c1cccc2.[K+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1452061
PubChem CID:	5177095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0004258] Arylsulfates

*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
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087.1	Pteridium aquilinum var. latiusculum	Varieties	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087.1	Pteridium aquilinum var. latiusculum	Varieties	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31050	Isatis indigotica	Species	Brassicaceae	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
AC50	2
EC50	1
Potency	12

Activity Type	# Activity
Individual Protein	10
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	19952.6	nM	PMID[487605]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	10000.0	nM	PMID[487605]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PMID[487605]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[487605]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[487605]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[487605]
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	1338.0	nM	PMID[487605]
NPT2867	Individual Protein	Protein RecA	Mycobacterium tuberculosis	EC50	=	155.0	nM	PMID[487605]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	11995.5	nM	PMID[487605]
NPT2866	Individual Protein	Replicative DNA helicase	Mycobacterium tuberculosis	AC50	=	5480.0	nM	PMID[487605]
NPT2	Others	Unspecified		Potency	=	1458.1	nM	PMID[487605]
NPT2	Others	Unspecified		Potency	n.a.	16360.1	nM	PMID[487605]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[487605]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	7375.3	nM	PMID[487605]
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PMID[487605]

☑ 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 NPC224764 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	855
0.1-0.2	12478
0.2-0.3	6886
0.3-0.4	14957
0.4-0.5	3598
0.5-0.6	2102
0.6-0.7	1515
0.7-0.8	285
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9874	High Similarity	NPC42979
0.8639	High Similarity	NPC96890
0.8529	High Similarity	NPC184964
0.8457	Intermediate Similarity	NPC46580
0.8343	Intermediate Similarity	NPC314002
0.8333	Intermediate Similarity	NPC220765
0.8324	Intermediate Similarity	NPC106937
0.8313	Intermediate Similarity	NPC131718
0.8286	Intermediate Similarity	NPC204717
0.8251	Intermediate Similarity	NPC19872
0.8214	Intermediate Similarity	NPC102423
0.8192	Intermediate Similarity	NPC171171
0.8177	Intermediate Similarity	NPC326634
0.8129	Intermediate Similarity	NPC473764
0.8129	Intermediate Similarity	NPC314940
0.8101	Intermediate Similarity	NPC296527
0.8066	Intermediate Similarity	NPC99666
0.8056	Intermediate Similarity	NPC76748
0.8043	Intermediate Similarity	NPC192315
0.8033	Intermediate Similarity	NPC13880
0.8033	Intermediate Similarity	NPC242209
0.8022	Intermediate Similarity	NPC307963
0.8011	Intermediate Similarity	NPC92111
0.8	Intermediate Similarity	NPC476167
0.7989	Intermediate Similarity	NPC156704
0.7967	Intermediate Similarity	NPC324149
0.7957	Intermediate Similarity	NPC121772
0.7938	Intermediate Similarity	NPC288349
0.7935	Intermediate Similarity	NPC251090
0.7931	Intermediate Similarity	NPC313791
0.7898	Intermediate Similarity	NPC82295
0.7892	Intermediate Similarity	NPC77555
0.7884	Intermediate Similarity	NPC470500
0.7874	Intermediate Similarity	NPC252590
0.7866	Intermediate Similarity	NPC159856
0.7861	Intermediate Similarity	NPC45459
0.7861	Intermediate Similarity	NPC315491
0.7838	Intermediate Similarity	NPC222018
0.7831	Intermediate Similarity	NPC476138
0.7831	Intermediate Similarity	NPC245816
0.7824	Intermediate Similarity	NPC230869
0.7821	Intermediate Similarity	NPC48938
0.7798	Intermediate Similarity	NPC469765
0.7798	Intermediate Similarity	NPC469786
0.7798	Intermediate Similarity	NPC25008
0.7798	Intermediate Similarity	NPC469763
0.7798	Intermediate Similarity	NPC73952
0.7798	Intermediate Similarity	NPC469760
0.7798	Intermediate Similarity	NPC259644
0.7796	Intermediate Similarity	NPC267928
0.7791	Intermediate Similarity	NPC311276
0.7778	Intermediate Similarity	NPC279918
0.7778	Intermediate Similarity	NPC284678
0.7766	Intermediate Similarity	NPC213308
0.7765	Intermediate Similarity	NPC469762
0.7755	Intermediate Similarity	NPC142901
0.7753	Intermediate Similarity	NPC72980
0.7751	Intermediate Similarity	NPC80597
0.7751	Intermediate Similarity	NPC211572
0.7751	Intermediate Similarity	NPC70922
0.7751	Intermediate Similarity	NPC212376
0.7751	Intermediate Similarity	NPC75540
0.7744	Intermediate Similarity	NPC190296
0.7733	Intermediate Similarity	NPC282231
0.773	Intermediate Similarity	NPC84853
0.7727	Intermediate Similarity	NPC474409
0.7725	Intermediate Similarity	NPC232727
0.772	Intermediate Similarity	NPC185782
0.7706	Intermediate Similarity	NPC469785
0.7706	Intermediate Similarity	NPC141353
0.7702	Intermediate Similarity	NPC29886
0.7702	Intermediate Similarity	NPC96102
0.7702	Intermediate Similarity	NPC261195
0.7701	Intermediate Similarity	NPC160105
0.768	Intermediate Similarity	NPC5145
0.7679	Intermediate Similarity	NPC24678
0.7679	Intermediate Similarity	NPC105818
0.7654	Intermediate Similarity	NPC105127
0.7654	Intermediate Similarity	NPC84911
0.7651	Intermediate Similarity	NPC314372
0.7627	Intermediate Similarity	NPC314603
0.7617	Intermediate Similarity	NPC183777
0.7617	Intermediate Similarity	NPC88008
0.7609	Intermediate Similarity	NPC32771
0.7604	Intermediate Similarity	NPC285558
0.7602	Intermediate Similarity	NPC26679
0.76	Intermediate Similarity	NPC474561
0.76	Intermediate Similarity	NPC54988
0.76	Intermediate Similarity	NPC49954
0.7586	Intermediate Similarity	NPC40779
0.7582	Intermediate Similarity	NPC84478
0.7579	Intermediate Similarity	NPC176538
0.7571	Intermediate Similarity	NPC470498
0.7563	Intermediate Similarity	NPC476287
0.7561	Intermediate Similarity	NPC110126
0.7561	Intermediate Similarity	NPC73767
0.756	Intermediate Similarity	NPC471957
0.7557	Intermediate Similarity	NPC63751
0.7554	Intermediate Similarity	NPC278434
0.7525	Intermediate Similarity	NPC16352
0.7515	Intermediate Similarity	NPC279081
0.7515	Intermediate Similarity	NPC469780
0.7515	Intermediate Similarity	NPC469767
0.7515	Intermediate Similarity	NPC230002
0.7515	Intermediate Similarity	NPC469761
0.7515	Intermediate Similarity	NPC469783
0.7515	Intermediate Similarity	NPC469784
0.7515	Intermediate Similarity	NPC469768
0.7515	Intermediate Similarity	NPC469779
0.7514	Intermediate Similarity	NPC242928
0.7487	Intermediate Similarity	NPC171787
0.7487	Intermediate Similarity	NPC8022
0.7487	Intermediate Similarity	NPC470799
0.747	Intermediate Similarity	NPC469766
0.7459	Intermediate Similarity	NPC283219
0.7458	Intermediate Similarity	NPC78020
0.7435	Intermediate Similarity	NPC187558
0.7433	Intermediate Similarity	NPC138370
0.7432	Intermediate Similarity	NPC212535
0.7432	Intermediate Similarity	NPC176127
0.7427	Intermediate Similarity	NPC216713
0.7424	Intermediate Similarity	NPC128084
0.7424	Intermediate Similarity	NPC316981
0.7423	Intermediate Similarity	NPC475070
0.7414	Intermediate Similarity	NPC92796
0.7414	Intermediate Similarity	NPC135141
0.7411	Intermediate Similarity	NPC167860
0.7411	Intermediate Similarity	NPC123976
0.7403	Intermediate Similarity	NPC111275
0.7403	Intermediate Similarity	NPC84827
0.7403	Intermediate Similarity	NPC145885
0.7403	Intermediate Similarity	NPC248454
0.7403	Intermediate Similarity	NPC14113
0.7401	Intermediate Similarity	NPC49217
0.74	Intermediate Similarity	NPC170114
0.7398	Intermediate Similarity	NPC287208
0.7398	Intermediate Similarity	NPC476465
0.7389	Intermediate Similarity	NPC149155
0.7389	Intermediate Similarity	NPC203468
0.7389	Intermediate Similarity	NPC110500
0.7387	Intermediate Similarity	NPC266931
0.7386	Intermediate Similarity	NPC194640
0.7385	Intermediate Similarity	NPC477113
0.7384	Intermediate Similarity	NPC200214
0.738	Intermediate Similarity	NPC83111
0.7377	Intermediate Similarity	NPC474798
0.7374	Intermediate Similarity	NPC246518
0.7371	Intermediate Similarity	NPC475774
0.7363	Intermediate Similarity	NPC88363
0.7363	Intermediate Similarity	NPC126709
0.7363	Intermediate Similarity	NPC248041
0.736	Intermediate Similarity	NPC201700
0.7356	Intermediate Similarity	NPC212742
0.7351	Intermediate Similarity	NPC163421
0.7351	Intermediate Similarity	NPC188387
0.7351	Intermediate Similarity	NPC94943
0.735	Intermediate Similarity	NPC470549
0.7348	Intermediate Similarity	NPC267885
0.7343	Intermediate Similarity	NPC314954
0.7337	Intermediate Similarity	NPC469358
0.7337	Intermediate Similarity	NPC219087
0.733	Intermediate Similarity	NPC177404
0.7327	Intermediate Similarity	NPC264285
0.7316	Intermediate Similarity	NPC276517
0.731	Intermediate Similarity	NPC477111
0.7308	Intermediate Similarity	NPC151939
0.7308	Intermediate Similarity	NPC59269
0.7306	Intermediate Similarity	NPC315957
0.7297	Intermediate Similarity	NPC190007
0.7294	Intermediate Similarity	NPC143872
0.7294	Intermediate Similarity	NPC288838
0.7294	Intermediate Similarity	NPC316069
0.7292	Intermediate Similarity	NPC306376
0.7288	Intermediate Similarity	NPC118511
0.7283	Intermediate Similarity	NPC233936
0.7283	Intermediate Similarity	NPC71037
0.7283	Intermediate Similarity	NPC26872
0.7273	Intermediate Similarity	NPC80596
0.7268	Intermediate Similarity	NPC55772
0.7268	Intermediate Similarity	NPC470501
0.7262	Intermediate Similarity	NPC60553
0.7258	Intermediate Similarity	NPC15102
0.7254	Intermediate Similarity	NPC128823
0.7251	Intermediate Similarity	NPC469811
0.7246	Intermediate Similarity	NPC319232
0.7246	Intermediate Similarity	NPC24370
0.7243	Intermediate Similarity	NPC163055
0.7238	Intermediate Similarity	NPC469554
0.7238	Intermediate Similarity	NPC101543
0.7238	Intermediate Similarity	NPC196718
0.7238	Intermediate Similarity	NPC102593
0.7236	Intermediate Similarity	NPC11464
0.7231	Intermediate Similarity	NPC473761
0.7228	Intermediate Similarity	NPC477110
0.7225	Intermediate Similarity	NPC470823
0.7222	Intermediate Similarity	NPC18348
0.722	Intermediate Similarity	NPC470502
0.722	Intermediate Similarity	NPC473317
0.7219	Intermediate Similarity	NPC235684
0.7219	Intermediate Similarity	NPC315555

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 NPC224764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	957
0.2-0.3	514
0.3-0.4	1841
0.4-0.5	2616
0.5-0.6	2117
0.6-0.7	677
0.7-0.8	61
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD9705	Discontinued
0.8424	Intermediate Similarity	NPD112	Approved
0.8324	Intermediate Similarity	NPD802	Phase 2
0.8087	Intermediate Similarity	NPD7948	Phase 1
0.8022	Intermediate Similarity	NPD1038	Approved
0.7923	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1392	Approved
0.7886	Intermediate Similarity	NPD9690	Approved
0.7861	Intermediate Similarity	NPD484	Approved
0.7784	Intermediate Similarity	NPD5065	Approved
0.7746	Intermediate Similarity	NPD2782	Approved
0.7746	Intermediate Similarity	NPD2780	Approved
0.7702	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD2781	Approved
0.7641	Intermediate Similarity	NPD5067	Phase 2
0.7641	Intermediate Similarity	NPD5066	Phase 2
0.7619	Intermediate Similarity	NPD3825	Phase 3
0.7616	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7603	Discontinued
0.7561	Intermediate Similarity	NPD786	Approved
0.7529	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1768	Approved
0.7487	Intermediate Similarity	NPD5612	Discontinued
0.747	Intermediate Similarity	NPD1722	Approved
0.7458	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9695	Approved
0.7413	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD2187	Approved
0.7398	Intermediate Similarity	NPD2189	Approved
0.7389	Intermediate Similarity	NPD482	Approved
0.7348	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3330	Phase 1
0.7308	Intermediate Similarity	NPD2144	Approved
0.7306	Intermediate Similarity	NPD1740	Approved
0.7306	Intermediate Similarity	NPD1739	Approved
0.7302	Intermediate Similarity	NPD9689	Approved
0.7296	Intermediate Similarity	NPD3003	Approved
0.7273	Intermediate Similarity	NPD1404	Approved
0.7273	Intermediate Similarity	NPD1403	Approved
0.7262	Intermediate Similarity	NPD1592	Phase 3
0.7243	Intermediate Similarity	NPD2094	Phase 2
0.7243	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2095	Phase 2
0.7243	Intermediate Similarity	NPD2092	Phase 2
0.7234	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6595	Phase 3
0.7228	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD565	Phase 2
0.7222	Intermediate Similarity	NPD1325	Approved
0.7222	Intermediate Similarity	NPD1326	Approved
0.7219	Intermediate Similarity	NPD706	Phase 1
0.7214	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3100	Discontinued
0.7209	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD424	Approved
0.7207	Intermediate Similarity	NPD425	Approved
0.7204	Intermediate Similarity	NPD2096	Phase 2
0.7204	Intermediate Similarity	NPD2091	Phase 2
0.7194	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5140	Approved
0.7191	Intermediate Similarity	NPD5138	Approved
0.7189	Intermediate Similarity	NPD3038	Discontinued
0.7175	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4076	Approved
0.7174	Intermediate Similarity	NPD4079	Approved
0.7168	Intermediate Similarity	NPD2172	Phase 1
0.7165	Intermediate Similarity	NPD4548	Discontinued
0.7157	Intermediate Similarity	NPD4795	Phase 2
0.7129	Intermediate Similarity	NPD2615	Phase 3
0.7129	Intermediate Similarity	NPD2616	Phase 3
0.7123	Intermediate Similarity	NPD7558	Phase 2
0.7122	Intermediate Similarity	NPD3402	Phase 1
0.712	Intermediate Similarity	NPD3506	Approved
0.712	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3505	Approved
0.712	Intermediate Similarity	NPD6159	Phase 2
0.7111	Intermediate Similarity	NPD2642	Approved
0.7111	Intermediate Similarity	NPD2639	Approved
0.7098	Intermediate Similarity	NPD3477	Phase 2
0.7098	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5903	Approved
0.7094	Intermediate Similarity	NPD5902	Approved
0.7092	Intermediate Similarity	NPD4511	Phase 1
0.709	Intermediate Similarity	NPD1034	Phase 3
0.709	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8431	Approved
0.7087	Intermediate Similarity	NPD6242	Discontinued
0.7085	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2175	Phase 3
0.7077	Intermediate Similarity	NPD2177	Approved
0.7077	Intermediate Similarity	NPD9688	Approved
0.7077	Intermediate Similarity	NPD9687	Approved
0.7077	Intermediate Similarity	NPD2176	Approved
0.7072	Intermediate Similarity	NPD2641	Approved
0.7072	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2640	Approved
0.7069	Intermediate Similarity	NPD4462	Approved
0.7069	Intermediate Similarity	NPD4463	Approved
0.7062	Intermediate Similarity	NPD2581	Approved
0.7062	Intermediate Similarity	NPD2582	Approved
0.7059	Intermediate Similarity	NPD5596	Phase 2
0.7056	Intermediate Similarity	NPD3928	Approved
0.7056	Intermediate Similarity	NPD3931	Approved
0.7049	Intermediate Similarity	NPD750	Phase 2
0.7035	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3404	Approved
0.7022	Intermediate Similarity	NPD5255	Approved
0.7016	Intermediate Similarity	NPD1213	Phase 3
0.7015	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5559	Phase 2
0.7005	Intermediate Similarity	NPD3178	Discontinued
0.7	Intermediate Similarity	NPD863	Approved
0.7	Intermediate Similarity	NPD861	Approved
0.7	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD862	Approved
0.699	Remote Similarity	NPD3814	Phase 1
0.699	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2837	Discontinued
0.6985	Remote Similarity	NPD3397	Phase 2
0.6984	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6975	Discontinued
0.6966	Remote Similarity	NPD9383	Approved
0.6966	Remote Similarity	NPD9382	Approved
0.6965	Remote Similarity	NPD5658	Approved
0.6965	Remote Similarity	NPD2509	Approved
0.6965	Remote Similarity	NPD2510	Approved
0.6957	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5256	Discontinued
0.6946	Remote Similarity	NPD7470	Discontinued
0.6943	Remote Similarity	NPD6569	Phase 2
0.6935	Remote Similarity	NPD4071	Approved
0.6935	Remote Similarity	NPD4072	Approved
0.6915	Remote Similarity	NPD6290	Phase 2
0.6912	Remote Similarity	NPD8093	Discontinued
0.6911	Remote Similarity	NPD2383	Phase 1
0.6908	Remote Similarity	NPD4429	Discontinued
0.6908	Remote Similarity	NPD5632	Approved
0.6904	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5901	Discontinued
0.6898	Remote Similarity	NPD4454	Phase 2
0.6895	Remote Similarity	NPD4889	Approved
0.6895	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1418	Phase 2
0.6884	Remote Similarity	NPD8073	Approved
0.6881	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3835	Phase 3
0.6875	Remote Similarity	NPD3833	Phase 3
0.6872	Remote Similarity	NPD4890	Phase 2
0.6868	Remote Similarity	NPD926	Approved
0.6868	Remote Similarity	NPD925	Approved
0.6857	Remote Similarity	NPD4702	Approved
0.6857	Remote Similarity	NPD4703	Approved
0.6856	Remote Similarity	NPD4372	Phase 1
0.6832	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6985	Discontinued
0.6823	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3006	Discontinued
0.6818	Remote Similarity	NPD5999	Phase 2
0.6816	Remote Similarity	NPD8272	Phase 2
0.6816	Remote Similarity	NPD31	Approved
0.6816	Remote Similarity	NPD4122	Approved
0.6816	Remote Similarity	NPD4033	Approved
0.6816	Remote Similarity	NPD4039	Approved
0.6816	Remote Similarity	NPD4038	Approved
0.6816	Remote Similarity	NPD32	Approved
0.6816	Remote Similarity	NPD4034	Approved
0.6816	Remote Similarity	NPD4036	Approved
0.6816	Remote Similarity	NPD4035	Approved
0.6816	Remote Similarity	NPD4037	Approved
0.6813	Remote Similarity	NPD3323	Discontinued
0.6804	Remote Similarity	NPD4699	Discontinued
0.6804	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5913	Phase 3
0.6804	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1229	Phase 2
0.6802	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7194	Discontinued
0.6794	Remote Similarity	NPD537	Phase 2
0.6794	Remote Similarity	NPD534	Phase 2
0.6792	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2382	Approved
0.6791	Remote Similarity	NPD4075	Phase 2
0.6791	Remote Similarity	NPD2381	Approved
0.6791	Remote Similarity	NPD2380	Approved
0.6789	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD991	Phase 2
0.6786	Remote Similarity	NPD3395	Approved
0.6786	Remote Similarity	NPD4418	Discontinued
0.6786	Remote Similarity	NPD3396	Approved
0.6782	Remote Similarity	NPD8403	Phase 1
0.678	Remote Similarity	NPD5939	Approved
0.678	Remote Similarity	NPD949	Phase 1

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