NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	171.04
Volume:	160.249
LogP:	0.881
LogD:	0.799
LogS:	-1.828
# Rotatable Bonds:	1
TPSA:	60.16
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	1.659
Fsp3:	0.143
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:	-4.616
MDCK Permeability:	0.00012180456542409956
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	62.69864273071289%
Volume Distribution (VD):	0.568
Pgp-substrate:	31.550804138183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.499
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	0.977
Half-life (T1/2):	0.567

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.352
Maximum Recommended Daily Dose:	0.584
Skin Sensitization:	0.035
Carcinogencity:	0.67
Eye Corrosion:	0.006
Eye Irritation:	0.981
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC302129

Natural Product ID:	NPC302129
*Common Name:**	2-Methylbenzenesulfonimidic Acid
IUPAC Name:	2-methylbenzenesulfonimidic acid
Synonyms:	Toluene-2-Sulfonamide
Standard InCHIKey:	YCMLQMDWSXFTIF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H9NO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)
SMILES:	Cc1ccccc1S(=O)(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL176892
PubChem CID:	90750087 6924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000031] Benzenesulfonamides

*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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Ki	4
Others	7
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	11
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT22604	PROTEIN FAMILY	Carbonic anhydrase	Bos taurus	Log II50	=	0.16	n.a.	PMID[458553]
NPT2	Others	Unspecified		Ki	=	63095734448019.43	nM	PMID[458554]
NPT27	Others	Unspecified		pC	=	0.301	n.a.	PMID[458554]
NPT35	Others	n.a.		LogP	=	3.53	n.a.	PMID[458554]
NPT27	Others	Unspecified		Log 1/C	=	-0.3	n.a.	PMID[458555]
NPT2	Others	Unspecified		Ki	=	16218.1	nM	PMID[458555]
NPT35	Others	n.a.		LogP	=	0.54	n.a.	PMID[458555]
NPT2	Others	Unspecified		FC	=	1.8	n.a.	PMID[458556]
NPT2	Others	Unspecified		Ki	=	625172692.78	nM	PMID[458556]
NPT2	Others	Unspecified		Ki	=	831763771.1	nM	PMID[458556]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	Inhibition	<=	54.0	%	PMID[458557]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	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 NPC302129 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	1076
0.1-0.2	8363
0.2-0.3	17431
0.3-0.4	13247
0.4-0.5	2053
0.5-0.6	411
0.6-0.7	101
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7973	Intermediate Similarity	NPC181786
0.7722	Intermediate Similarity	NPC35599
0.7473	Intermediate Similarity	NPC317400
0.7429	Intermediate Similarity	NPC277704
0.7397	Intermediate Similarity	NPC45255
0.7342	Intermediate Similarity	NPC212463
0.7324	Intermediate Similarity	NPC269586
0.7222	Intermediate Similarity	NPC300345
0.7222	Intermediate Similarity	NPC65873
0.7222	Intermediate Similarity	NPC212114
0.7222	Intermediate Similarity	NPC120441
0.7183	Intermediate Similarity	NPC149436
0.7123	Intermediate Similarity	NPC8235
0.7083	Intermediate Similarity	NPC198841
0.7027	Intermediate Similarity	NPC169110
0.7027	Intermediate Similarity	NPC147062
0.7013	Intermediate Similarity	NPC36440
0.6986	Remote Similarity	NPC469807
0.6979	Remote Similarity	NPC328793
0.6933	Remote Similarity	NPC150196
0.6933	Remote Similarity	NPC135924
0.6933	Remote Similarity	NPC238023
0.6933	Remote Similarity	NPC310758
0.6933	Remote Similarity	NPC248705
0.6933	Remote Similarity	NPC210849
0.6933	Remote Similarity	NPC54368
0.6923	Remote Similarity	NPC52330
0.6892	Remote Similarity	NPC64270
0.6892	Remote Similarity	NPC114327
0.6892	Remote Similarity	NPC36357
0.6842	Remote Similarity	NPC29680
0.6753	Remote Similarity	NPC88566
0.675	Remote Similarity	NPC5324
0.6711	Remote Similarity	NPC246588
0.6667	Remote Similarity	NPC32312
0.6667	Remote Similarity	NPC155172
0.6667	Remote Similarity	NPC198023
0.6625	Remote Similarity	NPC311343
0.6623	Remote Similarity	NPC66517
0.6623	Remote Similarity	NPC22786
0.6623	Remote Similarity	NPC71009
0.6623	Remote Similarity	NPC200745
0.6582	Remote Similarity	NPC178527
0.6579	Remote Similarity	NPC147578
0.6543	Remote Similarity	NPC98880
0.6538	Remote Similarity	NPC113670
0.6538	Remote Similarity	NPC50266
0.6538	Remote Similarity	NPC45756
0.6538	Remote Similarity	NPC21211
0.6512	Remote Similarity	NPC67863
0.6506	Remote Similarity	NPC244738
0.65	Remote Similarity	NPC267443
0.65	Remote Similarity	NPC6107
0.6494	Remote Similarity	NPC200624
0.6484	Remote Similarity	NPC148231
0.6476	Remote Similarity	NPC181390
0.6463	Remote Similarity	NPC229235
0.6463	Remote Similarity	NPC219246
0.6463	Remote Similarity	NPC95289
0.6456	Remote Similarity	NPC291066
0.6452	Remote Similarity	NPC315403
0.6429	Remote Similarity	NPC112609
0.6429	Remote Similarity	NPC113000
0.6429	Remote Similarity	NPC122327
0.642	Remote Similarity	NPC78954
0.642	Remote Similarity	NPC239931
0.642	Remote Similarity	NPC82770
0.6386	Remote Similarity	NPC326200
0.6386	Remote Similarity	NPC155429
0.6386	Remote Similarity	NPC74458
0.6375	Remote Similarity	NPC113837
0.6375	Remote Similarity	NPC289915
0.6364	Remote Similarity	NPC475573
0.6364	Remote Similarity	NPC475289
0.6353	Remote Similarity	NPC276699
0.6341	Remote Similarity	NPC246822
0.6341	Remote Similarity	NPC16190
0.6341	Remote Similarity	NPC169222
0.6341	Remote Similarity	NPC235059
0.6341	Remote Similarity	NPC213570
0.6341	Remote Similarity	NPC200936
0.6341	Remote Similarity	NPC139416
0.6329	Remote Similarity	NPC22627
0.631	Remote Similarity	NPC285679
0.6279	Remote Similarity	NPC139658
0.6279	Remote Similarity	NPC175393
0.6235	Remote Similarity	NPC299134
0.6207	Remote Similarity	NPC3672
0.6207	Remote Similarity	NPC287790
0.6207	Remote Similarity	NPC98269
0.6207	Remote Similarity	NPC325662
0.6207	Remote Similarity	NPC290638
0.619	Remote Similarity	NPC125144
0.619	Remote Similarity	NPC208302
0.619	Remote Similarity	NPC39799
0.619	Remote Similarity	NPC135433
0.619	Remote Similarity	NPC280135
0.619	Remote Similarity	NPC158028
0.619	Remote Similarity	NPC193578
0.619	Remote Similarity	NPC1008
0.619	Remote Similarity	NPC226999
0.619	Remote Similarity	NPC87099
0.619	Remote Similarity	NPC121708
0.618	Remote Similarity	NPC309279
0.6163	Remote Similarity	NPC98976
0.6163	Remote Similarity	NPC206800
0.6163	Remote Similarity	NPC189371
0.6163	Remote Similarity	NPC32203
0.6154	Remote Similarity	NPC125549
0.6154	Remote Similarity	NPC474088
0.6145	Remote Similarity	NPC473206
0.6143	Remote Similarity	NPC11150
0.6136	Remote Similarity	NPC50192
0.6136	Remote Similarity	NPC12857
0.6126	Remote Similarity	NPC476440
0.6118	Remote Similarity	NPC54269
0.6118	Remote Similarity	NPC271437
0.6092	Remote Similarity	NPC271642
0.6092	Remote Similarity	NPC110264
0.6071	Remote Similarity	NPC72670
0.6071	Remote Similarity	NPC251490
0.6071	Remote Similarity	NPC263385
0.6067	Remote Similarity	NPC469894
0.6067	Remote Similarity	NPC167577
0.6067	Remote Similarity	NPC300205
0.6067	Remote Similarity	NPC78517
0.6067	Remote Similarity	NPC170484
0.6064	Remote Similarity	NPC53492
0.6064	Remote Similarity	NPC43655
0.6049	Remote Similarity	NPC264470
0.6047	Remote Similarity	NPC108218
0.6047	Remote Similarity	NPC208075
0.6024	Remote Similarity	NPC22760
0.6023	Remote Similarity	NPC179726
0.6023	Remote Similarity	NPC329318
0.6023	Remote Similarity	NPC298023
0.6	Remote Similarity	NPC121800
0.6	Remote Similarity	NPC192623
0.6	Remote Similarity	NPC328178
0.6	Remote Similarity	NPC164086
0.5977	Remote Similarity	NPC307195
0.5955	Remote Similarity	NPC103488
0.5955	Remote Similarity	NPC76455
0.5955	Remote Similarity	NPC36342
0.5955	Remote Similarity	NPC285470
0.5955	Remote Similarity	NPC2785
0.5955	Remote Similarity	NPC224544
0.5955	Remote Similarity	NPC176228
0.5955	Remote Similarity	NPC137847
0.5952	Remote Similarity	NPC297358
0.5938	Remote Similarity	NPC107135
0.5934	Remote Similarity	NPC242628
0.5934	Remote Similarity	NPC89950
0.5934	Remote Similarity	NPC303245
0.593	Remote Similarity	NPC1901
0.5889	Remote Similarity	NPC272260
0.5876	Remote Similarity	NPC185501
0.587	Remote Similarity	NPC14326
0.587	Remote Similarity	NPC103387
0.587	Remote Similarity	NPC99240
0.587	Remote Similarity	NPC106313
0.587	Remote Similarity	NPC323103
0.5862	Remote Similarity	NPC258492
0.5862	Remote Similarity	NPC96835
0.5851	Remote Similarity	NPC3210
0.5843	Remote Similarity	NPC66655
0.5843	Remote Similarity	NPC3190
0.5843	Remote Similarity	NPC249018
0.5843	Remote Similarity	NPC9796
0.5843	Remote Similarity	NPC245966
0.5824	Remote Similarity	NPC127343
0.5824	Remote Similarity	NPC190567
0.5824	Remote Similarity	NPC477703
0.5824	Remote Similarity	NPC17408
0.5824	Remote Similarity	NPC285716
0.5824	Remote Similarity	NPC157055
0.5806	Remote Similarity	NPC477770
0.5806	Remote Similarity	NPC270507
0.5806	Remote Similarity	NPC288903
0.5761	Remote Similarity	NPC145053
0.5761	Remote Similarity	NPC71795
0.5761	Remote Similarity	NPC100039
0.5761	Remote Similarity	NPC133050
0.5761	Remote Similarity	NPC231986
0.5758	Remote Similarity	NPC473661
0.5745	Remote Similarity	NPC133162
0.5745	Remote Similarity	NPC267704
0.5745	Remote Similarity	NPC95429
0.573	Remote Similarity	NPC78500
0.5714	Remote Similarity	NPC159661
0.5714	Remote Similarity	NPC151405
0.5714	Remote Similarity	NPC139901
0.57	Remote Similarity	NPC71140
0.5699	Remote Similarity	NPC230068
0.5699	Remote Similarity	NPC99394
0.5699	Remote Similarity	NPC87299
0.5699	Remote Similarity	NPC73637
0.5699	Remote Similarity	NPC103326
0.5699	Remote Similarity	NPC121478
0.5699	Remote Similarity	NPC329319

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 NPC302129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	698
0.1-0.2	1075
0.2-0.3	3207
0.3-0.4	2858
0.4-0.5	1007
0.5-0.6	255
0.6-0.7	43
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7882	Intermediate Similarity	NPD9184	Approved
0.7882	Intermediate Similarity	NPD9186	Approved
0.764	Intermediate Similarity	NPD837	Approved
0.7473	Intermediate Similarity	NPD838	Approved
0.7294	Intermediate Similarity	NPD423	Phase 3
0.7111	Intermediate Similarity	NPD2811	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1697	Approved
0.7033	Intermediate Similarity	NPD1007	Discontinued
0.6979	Remote Similarity	NPD9248	Phase 1
0.6915	Remote Similarity	NPD3093	Approved
0.6869	Remote Similarity	NPD1406	Approved
0.6837	Remote Similarity	NPD557	Discovery
0.6737	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1796	Phase 3
0.6667	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1795	Discontinued
0.663	Remote Similarity	NPD1628	Approved
0.663	Remote Similarity	NPD1629	Approved
0.6604	Remote Similarity	NPD4674	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD292	Approved
0.6585	Remote Similarity	NPD294	Approved
0.6571	Remote Similarity	NPD5661	Approved
0.6571	Remote Similarity	NPD5662	Approved
0.6566	Remote Similarity	NPD4321	Approved
0.6543	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD675	Discontinued
0.6538	Remote Similarity	NPD1747	Approved
0.6538	Remote Similarity	NPD1746	Approved
0.6531	Remote Similarity	NPD4737	Phase 2
0.6506	Remote Similarity	NPD9728	Phase 1
0.65	Remote Similarity	NPD1387	Phase 1
0.6465	Remote Similarity	NPD6354	Discontinued
0.6452	Remote Similarity	NPD9108	Approved
0.6429	Remote Similarity	NPD9589	Approved
0.6429	Remote Similarity	NPD9588	Approved
0.6429	Remote Similarity	NPD9591	Approved
0.6429	Remote Similarity	NPD9594	Approved
0.6429	Remote Similarity	NPD9592	Approved
0.6429	Remote Similarity	NPD80	Approved
0.6429	Remote Similarity	NPD9590	Approved
0.6429	Remote Similarity	NPD9593	Approved
0.64	Remote Similarity	NPD1386	Phase 1
0.6354	Remote Similarity	NPD1409	Phase 3
0.6235	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3456	Approved
0.6224	Remote Similarity	NPD3458	Approved
0.6224	Remote Similarity	NPD3457	Approved
0.6224	Remote Similarity	NPD234	Approved
0.6216	Remote Similarity	NPD3675	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD430	Discontinued
0.6211	Remote Similarity	NPD4728	Approved
0.6182	Remote Similarity	NPD4660	Discontinued
0.6163	Remote Similarity	NPD9716	Approved
0.6162	Remote Similarity	NPD9352	Approved
0.6139	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD296	Approved
0.6136	Remote Similarity	NPD295	Approved
0.6136	Remote Similarity	NPD293	Approved
0.6122	Remote Similarity	NPD9260	Approved
0.6122	Remote Similarity	NPD9188	Approved
0.6105	Remote Similarity	NPD9077	Approved
0.6071	Remote Similarity	NPD5569	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD590	Approved
0.6067	Remote Similarity	NPD589	Approved
0.604	Remote Similarity	NPD4008	Approved
0.604	Remote Similarity	NPD784	Discontinued
0.604	Remote Similarity	NPD9353	Approved
0.604	Remote Similarity	NPD4007	Approved
0.6036	Remote Similarity	NPD1596	Approved
0.6023	Remote Similarity	NPD603	Approved
0.6023	Remote Similarity	NPD4144	Approved
0.6023	Remote Similarity	NPD4147	Approved
0.6	Remote Similarity	NPD260	Discontinued
0.5981	Remote Similarity	NPD2298	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD1727	Approved
0.5962	Remote Similarity	NPD2980	Phase 2
0.5955	Remote Similarity	NPD227	Approved
0.5955	Remote Similarity	NPD9397	Approved
0.5955	Remote Similarity	NPD79	Approved
0.5955	Remote Similarity	NPD9393	Approved
0.5955	Remote Similarity	NPD225	Approved
0.5955	Remote Similarity	NPD9564	Approved
0.5955	Remote Similarity	NPD9563	Approved
0.5952	Remote Similarity	NPD1673	Approved
0.5941	Remote Similarity	NPD9304	Approved
0.5929	Remote Similarity	NPD2756	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD507	Approved
0.5889	Remote Similarity	NPD508	Approved
0.5889	Remote Similarity	NPD1053	Approved
0.5889	Remote Similarity	NPD1051	Approved
0.5889	Remote Similarity	NPD1052	Approved
0.5862	Remote Similarity	NPD804	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD9294	Approved
0.5826	Remote Similarity	NPD2338	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD1104	Approved
0.5824	Remote Similarity	NPD3979	Approved
0.5824	Remote Similarity	NPD1617	Discontinued
0.5824	Remote Similarity	NPD5371	Approved
0.5824	Remote Similarity	NPD3904	Approved
0.5824	Remote Similarity	NPD5372	Approved
0.5824	Remote Similarity	NPD3903	Approved
0.5824	Remote Similarity	NPD3981	Approved
0.5812	Remote Similarity	NPD6041	Phase 1
0.5806	Remote Similarity	NPD3971	Phase 1
0.5806	Remote Similarity	NPD2001	Discontinued
0.5806	Remote Similarity	NPD262	Approved
0.5806	Remote Similarity	NPD830	Approved
0.5806	Remote Similarity	NPD831	Approved
0.5806	Remote Similarity	NPD263	Approved
0.5761	Remote Similarity	NPD3035	Approved
0.5761	Remote Similarity	NPD4027	Approved
0.5761	Remote Similarity	NPD472	Approved
0.5761	Remote Similarity	NPD4026	Approved
0.5761	Remote Similarity	NPD226	Approved
0.5755	Remote Similarity	NPD2834	Approved
0.5755	Remote Similarity	NPD2833	Approved
0.5745	Remote Similarity	NPD9395	Approved
0.5745	Remote Similarity	NPD785	Approved
0.5745	Remote Similarity	NPD3427	Approved
0.5745	Remote Similarity	NPD3429	Approved
0.5743	Remote Similarity	NPD157	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5246	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD9538	Approved
0.5714	Remote Similarity	NPD2635	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD744	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD9490	Approved
0.5699	Remote Similarity	NPD4170	Approved
0.5699	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4169	Approved
0.5686	Remote Similarity	NPD716	Approved
0.5684	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD964	Approved
0.567	Remote Similarity	NPD531	Approved
0.567	Remote Similarity	NPD1101	Approved
0.5657	Remote Similarity	NPD530	Approved
0.5652	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD1824	Discontinued
0.5638	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4635	Approved
0.5638	Remote Similarity	NPD9491	Approved
0.562	Remote Similarity	NPD2788	Approved
0.5603	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.56	Remote Similarity	NPD9072	Clinical (unspecified phase)

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