NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	213.01
Volume:	183.932
LogP:	0.255
LogD:	0.501
LogS:	-1.614
# Rotatable Bonds:	2
TPSA:	79.39
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	2.218
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:	-4.9
MDCK Permeability:	1.2334910024947021e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	97.39986419677734%
Volume Distribution (VD):	0.285
Pgp-substrate:	2.7687857151031494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.326
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	5.937
Half-life (T1/2):	0.468

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.773
Carcinogencity:	0.495
Eye Corrosion:	0.679
Eye Irritation:	0.988
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC42979

Natural Product ID:	NPC42979
*Common Name:**	Indoxyl Sulfate
IUPAC Name:	1H-indol-3-yl hydrogen sulfate
Synonyms:
Standard InCHIKey:	BXFFHSIDQOFMLE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)
SMILES:	OS(=O)(=O)Oc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1233636
PubChem CID:	10258
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

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Kd	1
Ki	6
Others	17

Activity Type	# Activity
Individual Protein	17
ORGANISM	2
Others	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1472	Individual Protein	Solute carrier family 22 member 11	Homo sapiens	Ki	=	181000.0	nM	PMID[568352]
NPT1472	Individual Protein	Solute carrier family 22 member 11	Homo sapiens	Ki	=	181300.0	nM	PMID[568352]
NPT589	Individual Protein	Serum albumin	Bos taurus	K	=	1600.0	/s	PMID[568358]
NPT589	Individual Protein	Serum albumin	Bos taurus	K	=	1700.0	/s	PMID[568358]
NPT589	Individual Protein	Serum albumin	Bos taurus	Kd	=	30000.0	nM	PMID[568358]
NPT589	Individual Protein	Serum albumin	Bos taurus	TIME	=	0.0000001861	hr	PMID[568358]
NPT669	Individual Protein	Solute carrier family 22 member 8	Homo sapiens	Ki	=	169000.0	nM	PMID[568352]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	Ki	=	23000.0	nM	PMID[568352]
NPT877	Individual Protein	Solute carrier family 22 member 8	Mus musculus	Activity	=	21.9	%	PMID[568353]
NPT667	Individual Protein	Solute carrier family 22 member 8	Rattus norvegicus	Km	=	158000.0	nM	PMID[568354]
NPT667	Individual Protein	Solute carrier family 22 member 8	Rattus norvegicus	Km	=	174000.0	nM	PMID[568355]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	Km	=	21000.0	nM	PMID[568355]
NPT669	Individual Protein	Solute carrier family 22 member 8	Homo sapiens	Km	=	263000.0	nM	PMID[568355]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	IC50	=	83000.0	nM	PMID[568357]
NPT669	Individual Protein	Solute carrier family 22 member 8	Homo sapiens	Ki	=	168700.0	nM	PMID[568352]
NPT665	Individual Protein	Solute carrier family 22 member 6	Homo sapiens	Ki	=	22700.0	nM	PMID[568352]
NPT2	Others	Unspecified		Drug metabolism	=	100.0	%	PMID[568359]
NPT2	Others	Unspecified		Km	=	216000.0	nM	PMID[568359]
NPT2	Others	Unspecified		Vmax	=	0.02	microM/s	PMID[568359]
NPT2	Others	Unspecified		Kcat	=	2.28	10'5/s	PMID[568359]
NPT2	Others	Unspecified		Activity	=	1060.0	/s/microM	PMID[568359]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	21.24	%	PMID[568360]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.07	%	PMID[568361]

☑ 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 NPC42979 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	731
0.1-0.2	11583
0.2-0.3	7452
0.3-0.4	15216
0.4-0.5	3710
0.5-0.6	2173
0.6-0.7	1504
0.7-0.8	304
0.8-0.85	21
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	NPC224764
0.8647	High Similarity	NPC96890
0.8538	High Similarity	NPC184964
0.8466	Intermediate Similarity	NPC46580
0.8352	Intermediate Similarity	NPC314002
0.8343	Intermediate Similarity	NPC220765
0.8333	Intermediate Similarity	NPC106937
0.8323	Intermediate Similarity	NPC131718
0.8295	Intermediate Similarity	NPC204717
0.8225	Intermediate Similarity	NPC102423
0.8202	Intermediate Similarity	NPC171171
0.8187	Intermediate Similarity	NPC326634
0.8162	Intermediate Similarity	NPC19872
0.814	Intermediate Similarity	NPC314940
0.814	Intermediate Similarity	NPC473764
0.8077	Intermediate Similarity	NPC99666
0.8054	Intermediate Similarity	NPC192315
0.8043	Intermediate Similarity	NPC242209
0.8033	Intermediate Similarity	NPC307963
0.8011	Intermediate Similarity	NPC476167
0.8011	Intermediate Similarity	NPC296527
0.8	Intermediate Similarity	NPC156704
0.7978	Intermediate Similarity	NPC324149
0.7967	Intermediate Similarity	NPC76748
0.7949	Intermediate Similarity	NPC288349
0.7946	Intermediate Similarity	NPC13880
0.7946	Intermediate Similarity	NPC251090
0.7943	Intermediate Similarity	NPC313791
0.7923	Intermediate Similarity	NPC92111
0.7903	Intermediate Similarity	NPC77555
0.7895	Intermediate Similarity	NPC470500
0.7886	Intermediate Similarity	NPC252590
0.7879	Intermediate Similarity	NPC159856
0.7872	Intermediate Similarity	NPC121772
0.7872	Intermediate Similarity	NPC315491
0.7872	Intermediate Similarity	NPC45459
0.7849	Intermediate Similarity	NPC222018
0.7836	Intermediate Similarity	NPC230869
0.7833	Intermediate Similarity	NPC48938
0.7811	Intermediate Similarity	NPC259644
0.7811	Intermediate Similarity	NPC469760
0.7811	Intermediate Similarity	NPC469763
0.7811	Intermediate Similarity	NPC73952
0.7811	Intermediate Similarity	NPC469765
0.7811	Intermediate Similarity	NPC25008
0.7811	Intermediate Similarity	NPC469786
0.7803	Intermediate Similarity	NPC311276
0.7799	Intermediate Similarity	NPC82295
0.7791	Intermediate Similarity	NPC279918
0.7778	Intermediate Similarity	NPC213308
0.7778	Intermediate Similarity	NPC469762
0.7766	Intermediate Similarity	NPC142901
0.7765	Intermediate Similarity	NPC80597
0.7765	Intermediate Similarity	NPC70922
0.7765	Intermediate Similarity	NPC211572
0.7765	Intermediate Similarity	NPC212376
0.7765	Intermediate Similarity	NPC72980
0.7765	Intermediate Similarity	NPC75540
0.7758	Intermediate Similarity	NPC190296
0.7749	Intermediate Similarity	NPC476138
0.7749	Intermediate Similarity	NPC245816
0.7746	Intermediate Similarity	NPC282231
0.774	Intermediate Similarity	NPC474409
0.7719	Intermediate Similarity	NPC469785
0.7719	Intermediate Similarity	NPC141353
0.7714	Intermediate Similarity	NPC160105
0.7713	Intermediate Similarity	NPC267928
0.7692	Intermediate Similarity	NPC5145
0.7692	Intermediate Similarity	NPC284678
0.7692	Intermediate Similarity	NPC105818
0.7692	Intermediate Similarity	NPC24678
0.7665	Intermediate Similarity	NPC314372
0.7647	Intermediate Similarity	NPC84853
0.7644	Intermediate Similarity	NPC232727
0.7641	Intermediate Similarity	NPC185782
0.764	Intermediate Similarity	NPC314603
0.7629	Intermediate Similarity	NPC183777
0.7629	Intermediate Similarity	NPC88008
0.7624	Intermediate Similarity	NPC16352
0.7622	Intermediate Similarity	NPC32771
0.7614	Intermediate Similarity	NPC49954
0.7614	Intermediate Similarity	NPC54988
0.7614	Intermediate Similarity	NPC474561
0.7607	Intermediate Similarity	NPC261195
0.7607	Intermediate Similarity	NPC96102
0.7607	Intermediate Similarity	NPC29886
0.76	Intermediate Similarity	NPC40779
0.7584	Intermediate Similarity	NPC470498
0.7574	Intermediate Similarity	NPC471957
0.7571	Intermediate Similarity	NPC63751
0.7568	Intermediate Similarity	NPC278434
0.7561	Intermediate Similarity	NPC84911
0.7561	Intermediate Similarity	NPC105127
0.7526	Intermediate Similarity	NPC285558
0.7525	Intermediate Similarity	NPC26679
0.75	Intermediate Similarity	NPC84478
0.75	Intermediate Similarity	NPC176538
0.75	Intermediate Similarity	NPC8022
0.75	Intermediate Similarity	NPC470799
0.75	Intermediate Similarity	NPC171787
0.7487	Intermediate Similarity	NPC476287
0.7473	Intermediate Similarity	NPC283219
0.7472	Intermediate Similarity	NPC78020
0.747	Intermediate Similarity	NPC110126
0.747	Intermediate Similarity	NPC73767
0.7446	Intermediate Similarity	NPC212535
0.7442	Intermediate Similarity	NPC216713
0.7437	Intermediate Similarity	NPC128084
0.7437	Intermediate Similarity	NPC316981
0.7436	Intermediate Similarity	NPC475070
0.7433	Intermediate Similarity	NPC242928
0.7429	Intermediate Similarity	NPC92796
0.7429	Intermediate Similarity	NPC135141
0.7425	Intermediate Similarity	NPC469780
0.7425	Intermediate Similarity	NPC469761
0.7425	Intermediate Similarity	NPC469768
0.7425	Intermediate Similarity	NPC469783
0.7425	Intermediate Similarity	NPC469784
0.7425	Intermediate Similarity	NPC279081
0.7425	Intermediate Similarity	NPC469779
0.7425	Intermediate Similarity	NPC469767
0.7425	Intermediate Similarity	NPC230002
0.7418	Intermediate Similarity	NPC248454
0.7418	Intermediate Similarity	NPC111275
0.7416	Intermediate Similarity	NPC49217
0.7403	Intermediate Similarity	NPC110500
0.7403	Intermediate Similarity	NPC149155
0.7403	Intermediate Similarity	NPC203468
0.7401	Intermediate Similarity	NPC194640
0.74	Intermediate Similarity	NPC266931
0.7398	Intermediate Similarity	NPC477113
0.7394	Intermediate Similarity	NPC83111
0.7387	Intermediate Similarity	NPC246518
0.7385	Intermediate Similarity	NPC475774
0.7381	Intermediate Similarity	NPC469766
0.7377	Intermediate Similarity	NPC88363
0.7377	Intermediate Similarity	NPC126709
0.7377	Intermediate Similarity	NPC248041
0.7374	Intermediate Similarity	NPC201700
0.7371	Intermediate Similarity	NPC212742
0.7366	Intermediate Similarity	NPC188387
0.7366	Intermediate Similarity	NPC94943
0.7366	Intermediate Similarity	NPC163421
0.7363	Intermediate Similarity	NPC267885
0.7358	Intermediate Similarity	NPC187558
0.7354	Intermediate Similarity	NPC138370
0.7351	Intermediate Similarity	NPC176127
0.7351	Intermediate Similarity	NPC469358
0.735	Intermediate Similarity	NPC219087
0.7345	Intermediate Similarity	NPC177404
0.734	Intermediate Similarity	NPC264285
0.7337	Intermediate Similarity	NPC167860
0.7337	Intermediate Similarity	NPC123976
0.733	Intermediate Similarity	NPC276517
0.7327	Intermediate Similarity	NPC170114
0.7323	Intermediate Similarity	NPC477111
0.7323	Intermediate Similarity	NPC476465
0.7323	Intermediate Similarity	NPC287208
0.7322	Intermediate Similarity	NPC145885
0.7322	Intermediate Similarity	NPC84827
0.7322	Intermediate Similarity	NPC59269
0.7322	Intermediate Similarity	NPC14113
0.7322	Intermediate Similarity	NPC151939
0.7312	Intermediate Similarity	NPC190007
0.7306	Intermediate Similarity	NPC306376
0.7299	Intermediate Similarity	NPC200214
0.7297	Intermediate Similarity	NPC474798
0.7297	Intermediate Similarity	NPC233936
0.7297	Intermediate Similarity	NPC71037
0.7286	Intermediate Similarity	NPC80596
0.7283	Intermediate Similarity	NPC55772
0.7282	Intermediate Similarity	NPC470501
0.7278	Intermediate Similarity	NPC60553
0.7277	Intermediate Similarity	NPC470549
0.7273	Intermediate Similarity	NPC15102
0.7273	Intermediate Similarity	NPC314954
0.7268	Intermediate Similarity	NPC128823
0.726	Intermediate Similarity	NPC319232
0.726	Intermediate Similarity	NPC24370
0.7258	Intermediate Similarity	NPC163055
0.725	Intermediate Similarity	NPC11464
0.7241	Intermediate Similarity	NPC477110
0.7236	Intermediate Similarity	NPC18348
0.7234	Intermediate Similarity	NPC235684
0.7234	Intermediate Similarity	NPC315555
0.7233	Intermediate Similarity	NPC470502
0.7233	Intermediate Similarity	NPC473317
0.7231	Intermediate Similarity	NPC470497
0.7231	Intermediate Similarity	NPC315957
0.7228	Intermediate Similarity	NPC477610
0.722	Intermediate Similarity	NPC213530
0.722	Intermediate Similarity	NPC193267
0.722	Intermediate Similarity	NPC74360
0.7216	Intermediate Similarity	NPC470499
0.7209	Intermediate Similarity	NPC143872
0.7209	Intermediate Similarity	NPC288838
0.7209	Intermediate Similarity	NPC220523
0.7209	Intermediate Similarity	NPC316069
0.7208	Intermediate Similarity	NPC476098
0.7207	Intermediate Similarity	NPC476118

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 NPC42979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	937
0.2-0.3	554
0.3-0.4	1813
0.4-0.5	2602
0.5-0.6	2144
0.6-0.7	694
0.7-0.8	74
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
0.8333	Intermediate Similarity	NPD802	Phase 2
0.8323	Intermediate Similarity	NPD9705	Discontinued
0.8323	Intermediate Similarity	NPD112	Approved
0.8098	Intermediate Similarity	NPD7948	Phase 1
0.8033	Intermediate Similarity	NPD1038	Approved
0.7935	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD1392	Approved
0.7898	Intermediate Similarity	NPD9690	Approved
0.7872	Intermediate Similarity	NPD484	Approved
0.7838	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5065	Approved
0.7771	Intermediate Similarity	NPD2781	Approved
0.7657	Intermediate Similarity	NPD2782	Approved
0.7657	Intermediate Similarity	NPD2780	Approved
0.7653	Intermediate Similarity	NPD5067	Phase 2
0.7653	Intermediate Similarity	NPD5066	Phase 2
0.763	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7603	Discontinued
0.7544	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD1768	Approved
0.7539	Intermediate Similarity	NPD3825	Phase 3
0.75	Intermediate Similarity	NPD5612	Discontinued
0.7472	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD786	Approved
0.7463	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9695	Approved
0.7426	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD482	Approved
0.7381	Intermediate Similarity	NPD1722	Approved
0.7363	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3330	Phase 1
0.7323	Intermediate Similarity	NPD2189	Approved
0.7323	Intermediate Similarity	NPD2187	Approved
0.7322	Intermediate Similarity	NPD2144	Approved
0.7316	Intermediate Similarity	NPD9689	Approved
0.731	Intermediate Similarity	NPD3003	Approved
0.7278	Intermediate Similarity	NPD1592	Phase 3
0.7258	Intermediate Similarity	NPD2094	Phase 2
0.7258	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2092	Phase 2
0.7258	Intermediate Similarity	NPD2095	Phase 2
0.7249	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6595	Phase 3
0.7241	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1325	Approved
0.7238	Intermediate Similarity	NPD1326	Approved
0.7234	Intermediate Similarity	NPD706	Phase 1
0.7231	Intermediate Similarity	NPD1740	Approved
0.7231	Intermediate Similarity	NPD1739	Approved
0.7228	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD425	Approved
0.7222	Intermediate Similarity	NPD424	Approved
0.7219	Intermediate Similarity	NPD2096	Phase 2
0.7219	Intermediate Similarity	NPD2091	Phase 2
0.7207	Intermediate Similarity	NPD5140	Approved
0.7207	Intermediate Similarity	NPD5138	Approved
0.7204	Intermediate Similarity	NPD3038	Discontinued
0.7191	Intermediate Similarity	NPD1404	Approved
0.7191	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1403	Approved
0.7189	Intermediate Similarity	NPD4076	Approved
0.7189	Intermediate Similarity	NPD4079	Approved
0.715	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD565	Phase 2
0.7143	Intermediate Similarity	NPD2616	Phase 3
0.7143	Intermediate Similarity	NPD2615	Phase 3
0.7136	Intermediate Similarity	NPD7558	Phase 2
0.7135	Intermediate Similarity	NPD6159	Phase 2
0.7135	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3506	Approved
0.7135	Intermediate Similarity	NPD3505	Approved
0.7126	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3100	Discontinued
0.7121	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5903	Approved
0.7108	Intermediate Similarity	NPD5902	Approved
0.7107	Intermediate Similarity	NPD4511	Phase 1
0.7105	Intermediate Similarity	NPD8431	Approved
0.71	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2175	Phase 3
0.7092	Intermediate Similarity	NPD9687	Approved
0.7092	Intermediate Similarity	NPD9688	Approved
0.7092	Intermediate Similarity	NPD2176	Approved
0.7092	Intermediate Similarity	NPD2177	Approved
0.7092	Intermediate Similarity	NPD4548	Discontinued
0.7086	Intermediate Similarity	NPD4462	Approved
0.7086	Intermediate Similarity	NPD2172	Phase 1
0.7086	Intermediate Similarity	NPD4463	Approved
0.7085	Intermediate Similarity	NPD4795	Phase 2
0.7074	Intermediate Similarity	NPD5596	Phase 2
0.7071	Intermediate Similarity	NPD3928	Approved
0.7071	Intermediate Similarity	NPD3931	Approved
0.7065	Intermediate Similarity	NPD750	Phase 2
0.7053	Intermediate Similarity	NPD3402	Phase 1
0.705	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3404	Approved
0.7039	Intermediate Similarity	NPD5255	Approved
0.7033	Intermediate Similarity	NPD2639	Approved
0.7033	Intermediate Similarity	NPD2642	Approved
0.7031	Intermediate Similarity	NPD1213	Phase 3
0.7026	Intermediate Similarity	NPD3477	Phase 2
0.7026	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3178	Discontinued
0.7019	Intermediate Similarity	NPD6242	Discontinued
0.7017	Intermediate Similarity	NPD862	Approved
0.7017	Intermediate Similarity	NPD863	Approved
0.7017	Intermediate Similarity	NPD861	Approved
0.7016	Intermediate Similarity	NPD1034	Phase 3
0.7016	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3814	Phase 1
0.7	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2640	Approved
0.6995	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2641	Approved
0.6985	Remote Similarity	NPD6975	Discontinued
0.6983	Remote Similarity	NPD9383	Approved
0.6983	Remote Similarity	NPD2581	Approved
0.6983	Remote Similarity	NPD2582	Approved
0.6983	Remote Similarity	NPD9382	Approved
0.6965	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7470	Discontinued
0.6959	Remote Similarity	NPD6569	Phase 2
0.6948	Remote Similarity	NPD5559	Phase 2
0.6946	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6290	Phase 2
0.6927	Remote Similarity	NPD8093	Discontinued
0.6927	Remote Similarity	NPD2383	Phase 1
0.6919	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3397	Phase 2
0.6915	Remote Similarity	NPD5901	Discontinued
0.6912	Remote Similarity	NPD4454	Phase 2
0.691	Remote Similarity	NPD2837	Discontinued
0.69	Remote Similarity	NPD8073	Approved
0.6897	Remote Similarity	NPD5658	Approved
0.6897	Remote Similarity	NPD2509	Approved
0.6897	Remote Similarity	NPD2510	Approved
0.689	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4890	Phase 2
0.6885	Remote Similarity	NPD926	Approved
0.6885	Remote Similarity	NPD925	Approved
0.6875	Remote Similarity	NPD4703	Approved
0.6875	Remote Similarity	NPD4702	Approved
0.6875	Remote Similarity	NPD5256	Discontinued
0.6862	Remote Similarity	NPD4071	Approved
0.6862	Remote Similarity	NPD4072	Approved
0.6847	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6985	Discontinued
0.6842	Remote Similarity	NPD4429	Discontinued
0.6842	Remote Similarity	NPD5632	Approved
0.6834	Remote Similarity	NPD5999	Phase 2
0.6832	Remote Similarity	NPD8272	Phase 2
0.6832	Remote Similarity	NPD31	Approved
0.6832	Remote Similarity	NPD4033	Approved
0.6832	Remote Similarity	NPD32	Approved
0.6832	Remote Similarity	NPD4039	Approved
0.6832	Remote Similarity	NPD4122	Approved
0.6832	Remote Similarity	NPD4036	Approved
0.6832	Remote Similarity	NPD4037	Approved
0.6832	Remote Similarity	NPD4038	Approved
0.6832	Remote Similarity	NPD4034	Approved
0.6832	Remote Similarity	NPD4035	Approved
0.6823	Remote Similarity	NPD4889	Approved
0.6823	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4699	Discontinued
0.6821	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1229	Phase 2
0.6813	Remote Similarity	NPD1418	Phase 2
0.681	Remote Similarity	NPD537	Phase 2
0.681	Remote Similarity	NPD534	Phase 2
0.681	Remote Similarity	NPD7194	Discontinued
0.6809	Remote Similarity	NPD2381	Approved
0.6809	Remote Similarity	NPD2382	Approved
0.6809	Remote Similarity	NPD2380	Approved
0.6808	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3395	Approved
0.6802	Remote Similarity	NPD3396	Approved
0.6798	Remote Similarity	NPD3835	Phase 3
0.6798	Remote Similarity	NPD3833	Phase 3
0.6796	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5936	Approved
0.6796	Remote Similarity	NPD4502	Phase 2
0.6796	Remote Similarity	NPD949	Phase 1
0.6796	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5939	Approved
0.6789	Remote Similarity	NPD6452	Discontinued
0.6786	Remote Similarity	NPD4372	Phase 1
0.6782	Remote Similarity	NPD8072	Approved
0.678	Remote Similarity	NPD1661	Suspended
0.6776	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3354	Phase 2

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