NPASS Compound

Structure

CID98864 OpenBabel06191715442D 21 23 0 0 0 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 21 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 19 21 2 0 0 0 0 20 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.01
Volume:	265.228
LogP:	-0.175
LogD:	0.006
LogS:	-2.461
# Rotatable Bonds:	1
TPSA:	130.83
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	3.946
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.238
MDCK Permeability:	8.184272701328155e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.09
20% Bioavailability (F20%):	0.297
30% Bioavailability (F30%):	0.488

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	53.860557556152344%
Volume Distribution (VD):	0.329
Pgp-substrate:	62.52711486816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	1.054
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.24
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.832

Download Data

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

Natural Product: NPC98864

Natural Product ID:	NPC98864
*Common Name:**	Acidiathiazone A
IUPAC Name:	1,1,5,10-tetraoxo-3,4-dihydro-2H-pyrido[2,3-g][1,4]benzothiazine-7-carboxylic acid
Synonyms:
Standard InCHIKey:	HNRNJVWZIQOLOL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H8N2O6S/c15-9-5-1-2-6(12(17)18)14-7(5)10(16)8-11(9)21(19,20)4-3-13-8/h1-2,13H,3-4H2,(H,17,18)
SMILES:	O=C1c2nc(ccc2C(=O)C2=C1NCCS2(=O)=O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226553
PubChem CID:	11673949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002552] Quinoline carboxylic acids

*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
NPO31025	Aplidium	Genus	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17497807]
NPO32570	aplidium sp.	Species	Polyclinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[17497807]

☑ 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	5
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	73080.0	nM	PMID[545244]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	73000.0	nM	PMID[545245]
NPT2	Others	Unspecified		IC50	=	1550.0	nM	PMID[545244]
NPT2	Others	Unspecified		IC50	=	55900.0	nM	PMID[545244]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	23.0	%	PMID[545244]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1550.0	nM	PMID[545245]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.55	uM	PMID[545245]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	23.0	%	PMID[545245]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	25.0	%	PMID[545245]

☑ 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 NPC98864 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	309
0.1-0.2	3464
0.2-0.3	13338
0.3-0.4	16728
0.4-0.5	4986
0.5-0.6	3001
0.6-0.7	841
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9503	High Similarity	NPC248782
0.9405	High Similarity	NPC473239
0.7838	Intermediate Similarity	NPC470894
0.7594	Intermediate Similarity	NPC41717
0.7563	Intermediate Similarity	NPC469489
0.7473	Intermediate Similarity	NPC322644
0.7382	Intermediate Similarity	NPC273532
0.731	Intermediate Similarity	NPC207851
0.7282	Intermediate Similarity	NPC471944
0.7268	Intermediate Similarity	NPC103361
0.7263	Intermediate Similarity	NPC85443
0.7202	Intermediate Similarity	NPC478141
0.7171	Intermediate Similarity	NPC141454
0.7169	Intermediate Similarity	NPC229893
0.7164	Intermediate Similarity	NPC221873
0.7157	Intermediate Similarity	NPC135950
0.7095	Intermediate Similarity	NPC469563
0.7073	Intermediate Similarity	NPC202812
0.705	Intermediate Similarity	NPC285923
0.7048	Intermediate Similarity	NPC165599
0.7039	Intermediate Similarity	NPC109922
0.7028	Intermediate Similarity	NPC244741
0.7014	Intermediate Similarity	NPC132539
0.701	Intermediate Similarity	NPC114974
0.7009	Intermediate Similarity	NPC469562
0.7009	Intermediate Similarity	NPC220594
0.7005	Intermediate Similarity	NPC473814
0.7005	Intermediate Similarity	NPC78767
0.7005	Intermediate Similarity	NPC74153
0.7	Intermediate Similarity	NPC213914
0.6946	Remote Similarity	NPC206186
0.6942	Remote Similarity	NPC45850
0.6942	Remote Similarity	NPC473821
0.6935	Remote Similarity	NPC302159
0.6935	Remote Similarity	NPC256268
0.6931	Remote Similarity	NPC251391
0.6919	Remote Similarity	NPC57398
0.6908	Remote Similarity	NPC93390
0.6898	Remote Similarity	NPC82370
0.6895	Remote Similarity	NPC477416
0.6895	Remote Similarity	NPC209362
0.6884	Remote Similarity	NPC219848
0.6881	Remote Similarity	NPC477979
0.6878	Remote Similarity	NPC144381
0.6872	Remote Similarity	NPC477516
0.6863	Remote Similarity	NPC278434
0.6862	Remote Similarity	NPC123906
0.6857	Remote Similarity	NPC123395
0.6852	Remote Similarity	NPC309845
0.6847	Remote Similarity	NPC311282
0.6837	Remote Similarity	NPC469578
0.6835	Remote Similarity	NPC89508
0.6832	Remote Similarity	NPC243058
0.681	Remote Similarity	NPC476143
0.6809	Remote Similarity	NPC105811
0.68	Remote Similarity	NPC183662
0.68	Remote Similarity	NPC15573
0.68	Remote Similarity	NPC217372
0.6798	Remote Similarity	NPC203635
0.6794	Remote Similarity	NPC472293
0.6793	Remote Similarity	NPC43477
0.6791	Remote Similarity	NPC467188
0.6789	Remote Similarity	NPC70406
0.6779	Remote Similarity	NPC230403
0.6773	Remote Similarity	NPC322064
0.6768	Remote Similarity	NPC302647
0.6766	Remote Similarity	NPC67659
0.6766	Remote Similarity	NPC219336
0.6759	Remote Similarity	NPC266249
0.6759	Remote Similarity	NPC143075
0.6754	Remote Similarity	NPC312860
0.6742	Remote Similarity	NPC312645
0.6732	Remote Similarity	NPC90415
0.6729	Remote Similarity	NPC476098
0.6729	Remote Similarity	NPC476252
0.6715	Remote Similarity	NPC83111
0.6713	Remote Similarity	NPC270918
0.6699	Remote Similarity	NPC474259
0.6699	Remote Similarity	NPC23476
0.6699	Remote Similarity	NPC477415
0.6698	Remote Similarity	NPC472296
0.6698	Remote Similarity	NPC472297
0.6698	Remote Similarity	NPC88115
0.6697	Remote Similarity	NPC123839
0.6683	Remote Similarity	NPC241025
0.6682	Remote Similarity	NPC106757
0.6667	Remote Similarity	NPC183805
0.6653	Remote Similarity	NPC316110
0.6653	Remote Similarity	NPC313587
0.6653	Remote Similarity	NPC315893
0.6651	Remote Similarity	NPC474916
0.6651	Remote Similarity	NPC472292
0.665	Remote Similarity	NPC469359
0.6649	Remote Similarity	NPC313889
0.6636	Remote Similarity	NPC118940
0.6636	Remote Similarity	NPC469577
0.6636	Remote Similarity	NPC321428
0.6636	Remote Similarity	NPC110182
0.6636	Remote Similarity	NPC475410
0.6635	Remote Similarity	NPC102592
0.6635	Remote Similarity	NPC79356
0.6632	Remote Similarity	NPC33229
0.662	Remote Similarity	NPC314648
0.6619	Remote Similarity	NPC269886
0.6619	Remote Similarity	NPC81802
0.6619	Remote Similarity	NPC247735
0.6619	Remote Similarity	NPC472295
0.6619	Remote Similarity	NPC472210
0.6615	Remote Similarity	NPC474492
0.6614	Remote Similarity	NPC167400
0.6604	Remote Similarity	NPC90229
0.66	Remote Similarity	NPC314254
0.66	Remote Similarity	NPC313966
0.6595	Remote Similarity	NPC475635
0.6592	Remote Similarity	NPC27041
0.659	Remote Similarity	NPC175602
0.6588	Remote Similarity	NPC276517
0.6587	Remote Similarity	NPC103119
0.6584	Remote Similarity	NPC476419
0.6583	Remote Similarity	NPC70949
0.6575	Remote Similarity	NPC472070
0.6574	Remote Similarity	NPC143325
0.6574	Remote Similarity	NPC138562
0.6574	Remote Similarity	NPC317572
0.6573	Remote Similarity	NPC472284
0.6573	Remote Similarity	NPC306376
0.6567	Remote Similarity	NPC252572
0.6566	Remote Similarity	NPC115232
0.6553	Remote Similarity	NPC46895
0.6546	Remote Similarity	NPC229055
0.6546	Remote Similarity	NPC263455
0.6542	Remote Similarity	NPC284338
0.6537	Remote Similarity	NPC477112
0.6535	Remote Similarity	NPC303225
0.6532	Remote Similarity	NPC471741
0.6532	Remote Similarity	NPC317752
0.6528	Remote Similarity	NPC328318
0.6528	Remote Similarity	NPC328596
0.6524	Remote Similarity	NPC138370
0.6522	Remote Similarity	NPC133003
0.652	Remote Similarity	NPC283219
0.6518	Remote Similarity	NPC472285
0.6517	Remote Similarity	NPC249614
0.6514	Remote Similarity	NPC472065
0.6513	Remote Similarity	NPC74357
0.651	Remote Similarity	NPC13432
0.6507	Remote Similarity	NPC255909
0.65	Remote Similarity	NPC61038
0.65	Remote Similarity	NPC325297
0.6497	Remote Similarity	NPC470680
0.6497	Remote Similarity	NPC27904
0.6497	Remote Similarity	NPC100104
0.6488	Remote Similarity	NPC469896
0.6486	Remote Similarity	NPC318299
0.6485	Remote Similarity	NPC191310
0.6484	Remote Similarity	NPC314297
0.6484	Remote Similarity	NPC315545
0.6479	Remote Similarity	NPC472116
0.6477	Remote Similarity	NPC471655
0.6476	Remote Similarity	NPC268966
0.6476	Remote Similarity	NPC324091
0.6473	Remote Similarity	NPC177996
0.6473	Remote Similarity	NPC36405
0.6473	Remote Similarity	NPC147983
0.6468	Remote Similarity	NPC472259
0.6462	Remote Similarity	NPC225622
0.6462	Remote Similarity	NPC221726
0.6462	Remote Similarity	NPC477414
0.646	Remote Similarity	NPC269270
0.6457	Remote Similarity	NPC250448
0.6454	Remote Similarity	NPC473639
0.6453	Remote Similarity	NPC182222
0.6452	Remote Similarity	NPC472069
0.6452	Remote Similarity	NPC472063
0.6452	Remote Similarity	NPC328029
0.6452	Remote Similarity	NPC472062
0.6449	Remote Similarity	NPC106824
0.6449	Remote Similarity	NPC272483
0.6444	Remote Similarity	NPC469727
0.6441	Remote Similarity	NPC220337
0.6439	Remote Similarity	NPC126709
0.6439	Remote Similarity	NPC248041
0.6439	Remote Similarity	NPC164340
0.6438	Remote Similarity	NPC313345
0.6438	Remote Similarity	NPC472064
0.6438	Remote Similarity	NPC314855
0.6438	Remote Similarity	NPC315638
0.6438	Remote Similarity	NPC313796
0.6438	Remote Similarity	NPC317373
0.6432	Remote Similarity	NPC14686
0.6432	Remote Similarity	NPC276657
0.6429	Remote Similarity	NPC209917
0.6429	Remote Similarity	NPC141353
0.6426	Remote Similarity	NPC57453
0.6423	Remote Similarity	NPC74619
0.6422	Remote Similarity	NPC84347
0.6422	Remote Similarity	NPC151635
0.6415	Remote Similarity	NPC216550
0.6411	Remote Similarity	NPC160381
0.6408	Remote Similarity	NPC61011

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 NPC98864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	581
0.2-0.3	966
0.3-0.4	1648
0.4-0.5	3118
0.5-0.6	2214
0.6-0.7	439
0.7-0.8	11
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
0.7407	Intermediate Similarity	NPD6173	Approved
0.726	Intermediate Similarity	NPD4906	Approved
0.726	Intermediate Similarity	NPD4905	Approved
0.726	Intermediate Similarity	NPD4903	Approved
0.7225	Intermediate Similarity	NPD4904	Approved
0.7208	Intermediate Similarity	NPD3178	Discontinued
0.705	Intermediate Similarity	NPD721	Approved
0.7031	Intermediate Similarity	NPD1631	Approved
0.6974	Remote Similarity	NPD1573	Approved
0.6974	Remote Similarity	NPD1575	Approved
0.6959	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1096	Discontinued
0.6875	Remote Similarity	NPD1630	Approved
0.6872	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5901	Discontinued
0.6835	Remote Similarity	NPD3243	Approved
0.6827	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3315	Phase 3
0.6786	Remote Similarity	NPD6753	Phase 1
0.6786	Remote Similarity	NPD6752	Phase 1
0.6782	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4948	Discontinued
0.6766	Remote Similarity	NPD1587	Approved
0.6763	Remote Similarity	NPD2336	Approved
0.6743	Remote Similarity	NPD5416	Discontinued
0.6733	Remote Similarity	NPD1643	Phase 3
0.6731	Remote Similarity	NPD981	Phase 2
0.6714	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3947	Discontinued
0.6682	Remote Similarity	NPD3795	Approved
0.6682	Remote Similarity	NPD7232	Discontinued
0.6682	Remote Similarity	NPD6487	Approved
0.6682	Remote Similarity	NPD6486	Approved
0.6682	Remote Similarity	NPD3794	Approved
0.6667	Remote Similarity	NPD5043	Discontinued
0.6652	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6665	Discontinued
0.6651	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7727	Phase 2
0.6635	Remote Similarity	NPD2307	Discontinued
0.6634	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3394	Approved
0.6622	Remote Similarity	NPD3393	Approved
0.6622	Remote Similarity	NPD3389	Approved
0.6617	Remote Similarity	NPD1586	Approved
0.6614	Remote Similarity	NPD9075	Approved
0.6614	Remote Similarity	NPD9074	Approved
0.6609	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3775	Approved
0.6605	Remote Similarity	NPD3774	Approved
0.6605	Remote Similarity	NPD3773	Approved
0.6601	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5088	Discontinued
0.6592	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4417	Approved
0.659	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1657	Approved
0.6575	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5046	Discontinued
0.6561	Remote Similarity	NPD8096	Phase 3
0.6561	Remote Similarity	NPD8097	Phase 3
0.6558	Remote Similarity	NPD7817	Phase 1
0.6544	Remote Similarity	NPD8115	Approved
0.6544	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8114	Approved
0.654	Remote Similarity	NPD1173	Approved
0.6533	Remote Similarity	NPD6770	Approved
0.6533	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5475	Discontinued
0.6512	Remote Similarity	NPD2912	Approved
0.6512	Remote Similarity	NPD2911	Approved
0.6512	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3280	Approved
0.6496	Remote Similarity	NPD7853	Phase 2
0.6489	Remote Similarity	NPD4429	Discontinued
0.6488	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3353	Approved
0.6462	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2509	Approved
0.6455	Remote Similarity	NPD2510	Approved
0.6455	Remote Similarity	NPD4960	Approved
0.6455	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6376	Discontinued
0.6455	Remote Similarity	NPD4959	Approved
0.6445	Remote Similarity	NPD5042	Phase 1
0.6441	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7010	Phase 3
0.6435	Remote Similarity	NPD3263	Phase 3
0.6425	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4304	Discovery
0.6419	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4397	Phase 1
0.6419	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2844	Phase 3
0.6416	Remote Similarity	NPD7878	Phase 2
0.6414	Remote Similarity	NPD2893	Phase 3
0.6413	Remote Similarity	NPD5866	Approved
0.6409	Remote Similarity	NPD3411	Phase 2
0.6409	Remote Similarity	NPD7562	Approved
0.6409	Remote Similarity	NPD3410	Approved
0.6407	Remote Similarity	NPD4845	Discontinued
0.6402	Remote Similarity	NPD107	Approved
0.6398	Remote Similarity	NPD946	Discontinued
0.6398	Remote Similarity	NPD4499	Approved
0.6395	Remote Similarity	NPD7552	Discontinued
0.6393	Remote Similarity	NPD3379	Phase 2
0.6393	Remote Similarity	NPD3380	Phase 3
0.6379	Remote Similarity	NPD2761	Approved
0.6377	Remote Similarity	NPD1570	Approved
0.6373	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD482	Approved
0.6373	Remote Similarity	NPD6492	Phase 2
0.6373	Remote Similarity	NPD158	Discontinued
0.6368	Remote Similarity	NPD5076	Approved
0.6368	Remote Similarity	NPD5077	Approved
0.6364	Remote Similarity	NPD3082	Discontinued
0.6364	Remote Similarity	NPD8289	Discontinued
0.6359	Remote Similarity	NPD484	Approved
0.6356	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD5022	Discontinued
0.6351	Remote Similarity	NPD6529	Discontinued
0.6351	Remote Similarity	NPD4506	Discontinued
0.6351	Remote Similarity	NPD3968	Approved
0.6346	Remote Similarity	NPD5213	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2381	Approved
0.6341	Remote Similarity	NPD2382	Approved
0.6341	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2380	Approved
0.6337	Remote Similarity	NPD2037	Approved
0.6336	Remote Similarity	NPD7994	Phase 2
0.6335	Remote Similarity	NPD4415	Approved
0.6329	Remote Similarity	NPD2481	Approved
0.6329	Remote Similarity	NPD6452	Discontinued
0.6329	Remote Similarity	NPD2479	Phase 3
0.6329	Remote Similarity	NPD4368	Phase 2
0.6327	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD750	Phase 2
0.6321	Remote Similarity	NPD3321	Discontinued
0.6318	Remote Similarity	NPD8098	Approved
0.6316	Remote Similarity	NPD7404	Approved
0.6316	Remote Similarity	NPD4484	Phase 1
0.6313	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3425	Discontinued
0.6313	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3792	Approved
0.6304	Remote Similarity	NPD2321	Approved
0.63	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.63	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6260	Discontinued
0.6288	Remote Similarity	NPD1996	Discontinued
0.6287	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5020	Approved
0.6281	Remote Similarity	NPD5255	Approved
0.6281	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2431	Approved
0.6275	Remote Similarity	NPD2432	Approved
0.6272	Remote Similarity	NPD7395	Discontinued
0.627	Remote Similarity	NPD3986	Discontinued
0.6268	Remote Similarity	NPD2092	Phase 2
0.6268	Remote Similarity	NPD2094	Phase 2
0.6268	Remote Similarity	NPD2095	Phase 2
0.6262	Remote Similarity	NPD3288	Approved
0.6255	Remote Similarity	NPD3328	Phase 2
0.625	Remote Similarity	NPD4330	Approved
0.625	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4329	Approved
0.625	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5445	Approved
0.6245	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD944	Approved
0.6244	Remote Similarity	NPD1660	Phase 2
0.6239	Remote Similarity	NPD2405	Phase 3
0.6238	Remote Similarity	NPD2096	Phase 2
0.6238	Remote Similarity	NPD2091	Phase 2
0.6234	Remote Similarity	NPD7677	Discontinued
0.6233	Remote Similarity	NPD3351	Approved
0.6228	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD8073	Approved
0.6222	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6152	Phase 1
0.6221	Remote Similarity	NPD6988	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