NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	277.05
Volume:	258.41
LogP:	1.88
LogD:	1.715
LogS:	-3.169
# Rotatable Bonds:	3
TPSA:	100.85
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	2.772
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.924
MDCK Permeability:	1.0642304914654233e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.081
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.72

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	98.42213439941406%
Volume Distribution (VD):	0.617
Pgp-substrate:	2.0552167892456055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.124
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.263
CYP2C9-substrate:	0.796
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.36
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	6.02
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.808
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.649
Skin Sensitization:	0.205
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.08
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC473778

Natural Product ID:	NPC473778
*Common Name:**	BKOGPYGCVVUVLM-MKMNVTDBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BKOGPYGCVVUVLM-MKMNVTDBSA-N
Standard InCHI:	InChI=1S/C12H11N3O3S/c1-6(14-15-12(13)19)10-8(16)4-2-7-3-5-9(17)18-11(7)10/h2-5,16H,1H3,(H3,13,15,19)/b14-6+
SMILES:	SC(=N)N/N=C(/c1c(O)ccc2c1oc(=O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451599
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO33433	adina cordifolia	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18675491]

☑ 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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	4460000.0	nM	PMID[469159]

☑ 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 NPC473778 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	333
0.1-0.2	2401
0.2-0.3	6953
0.3-0.4	11463
0.4-0.5	5690
0.5-0.6	8161
0.6-0.7	5515
0.7-0.8	2151
0.8-0.85	28
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8812	High Similarity	NPC474902
0.8812	High Similarity	NPC474919
0.8282	Intermediate Similarity	NPC474881
0.8252	Intermediate Similarity	NPC93219
0.8252	Intermediate Similarity	NPC244495
0.8138	Intermediate Similarity	NPC243688
0.7972	Intermediate Similarity	NPC52247
0.7867	Intermediate Similarity	NPC194277
0.7852	Intermediate Similarity	NPC32463
0.7847	Intermediate Similarity	NPC187868
0.7838	Intermediate Similarity	NPC185066
0.7832	Intermediate Similarity	NPC247553
0.7829	Intermediate Similarity	NPC475411
0.7815	Intermediate Similarity	NPC163557
0.7793	Intermediate Similarity	NPC96286
0.7793	Intermediate Similarity	NPC248429
0.7778	Intermediate Similarity	NPC302107
0.7755	Intermediate Similarity	NPC168259
0.774	Intermediate Similarity	NPC472518
0.7697	Intermediate Similarity	NPC31849
0.7687	Intermediate Similarity	NPC111347
0.7687	Intermediate Similarity	NPC201667
0.7687	Intermediate Similarity	NPC73413
0.7671	Intermediate Similarity	NPC13007
0.7671	Intermediate Similarity	NPC257188
0.7647	Intermediate Similarity	NPC204353
0.7647	Intermediate Similarity	NPC131950
0.7647	Intermediate Similarity	NPC50896
0.7647	Intermediate Similarity	NPC326600
0.7619	Intermediate Similarity	NPC109675
0.7619	Intermediate Similarity	NPC273772
0.7603	Intermediate Similarity	NPC144418
0.7584	Intermediate Similarity	NPC188327
0.7584	Intermediate Similarity	NPC234109
0.7569	Intermediate Similarity	NPC152306
0.7569	Intermediate Similarity	NPC265547
0.7569	Intermediate Similarity	NPC96705
0.7568	Intermediate Similarity	NPC291899
0.7568	Intermediate Similarity	NPC27671
0.7564	Intermediate Similarity	NPC221046
0.7564	Intermediate Similarity	NPC332594
0.755	Intermediate Similarity	NPC168710
0.755	Intermediate Similarity	NPC474289
0.7548	Intermediate Similarity	NPC38099
0.7548	Intermediate Similarity	NPC26954
0.7533	Intermediate Similarity	NPC258567
0.7533	Intermediate Similarity	NPC224774
0.7533	Intermediate Similarity	NPC121740
0.7532	Intermediate Similarity	NPC62366
0.7532	Intermediate Similarity	NPC253574
0.7532	Intermediate Similarity	NPC98179
0.7517	Intermediate Similarity	NPC471827
0.7517	Intermediate Similarity	NPC471828
0.7517	Intermediate Similarity	NPC281356
0.7517	Intermediate Similarity	NPC298796
0.75	Intermediate Similarity	NPC212124
0.75	Intermediate Similarity	NPC154176
0.75	Intermediate Similarity	NPC173350
0.75	Intermediate Similarity	NPC290605
0.75	Intermediate Similarity	NPC281014
0.75	Intermediate Similarity	NPC225106
0.75	Intermediate Similarity	NPC294456
0.75	Intermediate Similarity	NPC184861
0.7484	Intermediate Similarity	NPC33986
0.7483	Intermediate Similarity	NPC199204
0.7483	Intermediate Similarity	NPC469453
0.7483	Intermediate Similarity	NPC472519
0.7468	Intermediate Similarity	NPC183642
0.7468	Intermediate Similarity	NPC310370
0.7467	Intermediate Similarity	NPC471826
0.7452	Intermediate Similarity	NPC151946
0.7452	Intermediate Similarity	NPC279573
0.7451	Intermediate Similarity	NPC37009
0.7451	Intermediate Similarity	NPC66430
0.7436	Intermediate Similarity	NPC188380
0.7436	Intermediate Similarity	NPC78746
0.7436	Intermediate Similarity	NPC224543
0.7431	Intermediate Similarity	NPC128633
0.7419	Intermediate Similarity	NPC213173
0.7419	Intermediate Similarity	NPC180716
0.7419	Intermediate Similarity	NPC224475
0.7415	Intermediate Similarity	NPC235190
0.7415	Intermediate Similarity	NPC180006
0.7415	Intermediate Similarity	NPC163200
0.7415	Intermediate Similarity	NPC319378
0.74	Intermediate Similarity	NPC202594
0.74	Intermediate Similarity	NPC232692
0.7389	Intermediate Similarity	NPC153818
0.7389	Intermediate Similarity	NPC232246
0.7389	Intermediate Similarity	NPC155963
0.7386	Intermediate Similarity	NPC80170
0.7386	Intermediate Similarity	NPC113098
0.7383	Intermediate Similarity	NPC315807
0.7372	Intermediate Similarity	NPC472525
0.7372	Intermediate Similarity	NPC61499
0.7368	Intermediate Similarity	NPC157212
0.7358	Intermediate Similarity	NPC152771
0.7358	Intermediate Similarity	NPC195357
0.7358	Intermediate Similarity	NPC170812
0.7355	Intermediate Similarity	NPC83535
0.7342	Intermediate Similarity	NPC211110
0.7338	Intermediate Similarity	NPC267336
0.7338	Intermediate Similarity	NPC272650
0.7338	Intermediate Similarity	NPC29734
0.7338	Intermediate Similarity	NPC250727
0.7329	Intermediate Similarity	NPC471824
0.7308	Intermediate Similarity	NPC92830
0.7296	Intermediate Similarity	NPC71903
0.7296	Intermediate Similarity	NPC312881
0.729	Intermediate Similarity	NPC19157
0.729	Intermediate Similarity	NPC281558
0.729	Intermediate Similarity	NPC307289
0.729	Intermediate Similarity	NPC14248
0.729	Intermediate Similarity	NPC175159
0.7284	Intermediate Similarity	NPC101255
0.7284	Intermediate Similarity	NPC475719
0.7284	Intermediate Similarity	NPC43716
0.7284	Intermediate Similarity	NPC295696
0.7284	Intermediate Similarity	NPC71739
0.7278	Intermediate Similarity	NPC474886
0.7273	Intermediate Similarity	NPC314025
0.7267	Intermediate Similarity	NPC50720
0.7267	Intermediate Similarity	NPC236419
0.7267	Intermediate Similarity	NPC229916
0.726	Intermediate Similarity	NPC263754
0.726	Intermediate Similarity	NPC183154
0.725	Intermediate Similarity	NPC287286
0.7244	Intermediate Similarity	NPC55147
0.7244	Intermediate Similarity	NPC1220
0.7244	Intermediate Similarity	NPC167111
0.7244	Intermediate Similarity	NPC241165
0.7244	Intermediate Similarity	NPC2363
0.7244	Intermediate Similarity	NPC142563
0.7244	Intermediate Similarity	NPC469449
0.7244	Intermediate Similarity	NPC472524
0.7244	Intermediate Similarity	NPC318400
0.7244	Intermediate Similarity	NPC141822
0.7244	Intermediate Similarity	NPC291551
0.7244	Intermediate Similarity	NPC7526
0.7244	Intermediate Similarity	NPC471910
0.7244	Intermediate Similarity	NPC205797
0.7244	Intermediate Similarity	NPC222036
0.7244	Intermediate Similarity	NPC296624
0.7244	Intermediate Similarity	NPC133956
0.7244	Intermediate Similarity	NPC207002
0.7244	Intermediate Similarity	NPC277021
0.7233	Intermediate Similarity	NPC148738
0.7233	Intermediate Similarity	NPC144512
0.7233	Intermediate Similarity	NPC319870
0.7233	Intermediate Similarity	NPC35501
0.7233	Intermediate Similarity	NPC278600
0.7233	Intermediate Similarity	NPC327612
0.7233	Intermediate Similarity	NPC47040
0.7233	Intermediate Similarity	NPC37428
0.7233	Intermediate Similarity	NPC137262
0.7233	Intermediate Similarity	NPC73078
0.7226	Intermediate Similarity	NPC472517
0.7226	Intermediate Similarity	NPC73738
0.7222	Intermediate Similarity	NPC471763
0.7215	Intermediate Similarity	NPC151113
0.7215	Intermediate Similarity	NPC223616
0.72	Intermediate Similarity	NPC150214
0.7197	Intermediate Similarity	NPC307412
0.7197	Intermediate Similarity	NPC166672
0.7197	Intermediate Similarity	NPC100986
0.7197	Intermediate Similarity	NPC84894
0.7197	Intermediate Similarity	NPC18804
0.7197	Intermediate Similarity	NPC74655
0.7197	Intermediate Similarity	NPC47163
0.7197	Intermediate Similarity	NPC319859
0.7197	Intermediate Similarity	NPC287182
0.7197	Intermediate Similarity	NPC164269
0.7197	Intermediate Similarity	NPC260265
0.7197	Intermediate Similarity	NPC127888
0.7197	Intermediate Similarity	NPC55149
0.7197	Intermediate Similarity	NPC195343
0.7197	Intermediate Similarity	NPC198381
0.7197	Intermediate Similarity	NPC267412
0.7179	Intermediate Similarity	NPC137949
0.7178	Intermediate Similarity	NPC86069
0.7178	Intermediate Similarity	NPC469701
0.717	Intermediate Similarity	NPC52086
0.717	Intermediate Similarity	NPC139548
0.717	Intermediate Similarity	NPC148835
0.717	Intermediate Similarity	NPC20511
0.717	Intermediate Similarity	NPC76336
0.717	Intermediate Similarity	NPC38874
0.717	Intermediate Similarity	NPC471069
0.717	Intermediate Similarity	NPC131198
0.717	Intermediate Similarity	NPC95162
0.717	Intermediate Similarity	NPC471068
0.7152	Intermediate Similarity	NPC471909
0.7152	Intermediate Similarity	NPC281241
0.7152	Intermediate Similarity	NPC143725
0.7152	Intermediate Similarity	NPC469675
0.7152	Intermediate Similarity	NPC472424
0.7152	Intermediate Similarity	NPC471625
0.7152	Intermediate Similarity	NPC86892
0.7143	Intermediate Similarity	NPC219923
0.7143	Intermediate Similarity	NPC155552

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 NPC473778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	895
0.2-0.3	1395
0.3-0.4	2704
0.4-0.5	2608
0.5-0.6	1049
0.6-0.7	216
0.7-0.8	47
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7972	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD1296	Phase 2
0.7255	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.6994	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3750	Approved
0.6966	Remote Similarity	NPD1729	Discontinued
0.6948	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1610	Phase 2
0.6875	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2797	Approved
0.6835	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1243	Approved
0.6788	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD9697	Approved
0.6782	Remote Similarity	NPD6971	Discontinued
0.6774	Remote Similarity	NPD3225	Approved
0.6763	Remote Similarity	NPD2415	Discontinued
0.675	Remote Similarity	NPD1240	Approved
0.6726	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4908	Phase 1
0.6707	Remote Similarity	NPD6666	Approved
0.6707	Remote Similarity	NPD6667	Approved
0.6689	Remote Similarity	NPD821	Approved
0.6687	Remote Similarity	NPD3748	Approved
0.6686	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1558	Phase 1
0.6646	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD9717	Approved
0.6629	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1048	Approved
0.6625	Remote Similarity	NPD3268	Approved
0.6624	Remote Similarity	NPD1203	Approved
0.6612	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1653	Approved
0.6607	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4749	Approved
0.6591	Remote Similarity	NPD7075	Discontinued
0.659	Remote Similarity	NPD6072	Discontinued
0.6585	Remote Similarity	NPD1510	Phase 2
0.6582	Remote Similarity	NPD3691	Phase 2
0.6582	Remote Similarity	NPD3690	Phase 2
0.6564	Remote Similarity	NPD4097	Suspended
0.6562	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4626	Approved
0.6552	Remote Similarity	NPD6801	Discontinued
0.655	Remote Similarity	NPD920	Approved
0.6543	Remote Similarity	NPD468	Phase 1
0.6541	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7773	Phase 2
0.6532	Remote Similarity	NPD6502	Phase 2
0.6529	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7819	Suspended
0.6514	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1898	Discontinued
0.6488	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4308	Phase 3
0.6481	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7213	Phase 3
0.6471	Remote Similarity	NPD6799	Approved
0.6471	Remote Similarity	NPD7212	Phase 2
0.6467	Remote Similarity	NPD5535	Approved
0.6458	Remote Similarity	NPD940	Approved
0.6458	Remote Similarity	NPD846	Approved
0.6446	Remote Similarity	NPD2796	Approved
0.6446	Remote Similarity	NPD2935	Discontinued
0.6442	Remote Similarity	NPD1613	Approved
0.6442	Remote Similarity	NPD4060	Phase 1
0.6442	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3070	Discontinued
0.6433	Remote Similarity	NPD7447	Phase 1
0.642	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3567	Approved
0.6415	Remote Similarity	NPD3266	Approved
0.6415	Remote Similarity	NPD3267	Approved
0.6415	Remote Similarity	NPD3568	Approved
0.6404	Remote Similarity	NPD3749	Approved
0.6402	Remote Similarity	NPD3490	Discontinued
0.6402	Remote Similarity	NPD4340	Discontinued
0.64	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2614	Approved
0.6395	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2186	Approved
0.6387	Remote Similarity	NPD5691	Approved
0.6386	Remote Similarity	NPD2799	Discontinued
0.638	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5953	Discontinued
0.6374	Remote Similarity	NPD4357	Discontinued
0.6374	Remote Similarity	NPD1511	Approved
0.6374	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2424	Discontinued
0.6359	Remote Similarity	NPD7286	Phase 2
0.6358	Remote Similarity	NPD5163	Phase 2
0.6347	Remote Similarity	NPD4477	Approved
0.6347	Remote Similarity	NPD4476	Approved
0.6343	Remote Similarity	NPD4380	Phase 2
0.6343	Remote Similarity	NPD6599	Discontinued
0.6341	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1555	Discontinued
0.6341	Remote Similarity	NPD2203	Discontinued
0.6333	Remote Similarity	NPD6746	Phase 2
0.6331	Remote Similarity	NPD2800	Approved
0.6329	Remote Similarity	NPD1608	Approved
0.6328	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD9545	Approved
0.6319	Remote Similarity	NPD2313	Discontinued
0.6312	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7549	Discontinued
0.6306	Remote Similarity	NPD3496	Discontinued
0.6306	Remote Similarity	NPD3847	Discontinued
0.6304	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1512	Approved
0.6292	Remote Similarity	NPD4288	Approved
0.6292	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.629	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4129	Approved
0.6287	Remote Similarity	NPD7033	Discontinued
0.6284	Remote Similarity	NPD3134	Approved
0.628	Remote Similarity	NPD1423	Approved
0.6279	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD919	Approved
0.6278	Remote Similarity	NPD5709	Phase 3
0.6272	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5844	Phase 1
0.6269	Remote Similarity	NPD7585	Approved
0.6266	Remote Similarity	NPD1611	Approved
0.6266	Remote Similarity	NPD1535	Discovery
0.6265	Remote Similarity	NPD2157	Approved
0.6264	Remote Similarity	NPD5403	Approved
0.6257	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1519	Approved
0.625	Remote Similarity	NPD6100	Approved
0.625	Remote Similarity	NPD1537	Approved
0.625	Remote Similarity	NPD6099	Approved
0.625	Remote Similarity	NPD1538	Phase 1
0.625	Remote Similarity	NPD9273	Approved
0.6243	Remote Similarity	NPD4666	Phase 3
0.6243	Remote Similarity	NPD2534	Approved
0.6243	Remote Similarity	NPD2532	Approved
0.6243	Remote Similarity	NPD5401	Approved
0.6243	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3536	Discontinued
0.6243	Remote Similarity	NPD2533	Approved
0.6242	Remote Similarity	NPD1778	Approved
0.6242	Remote Similarity	NPD4307	Phase 2
0.6242	Remote Similarity	NPD1358	Approved
0.6236	Remote Similarity	NPD1465	Phase 2
0.6234	Remote Similarity	NPD6671	Approved
0.6229	Remote Similarity	NPD4003	Phase 3
0.6228	Remote Similarity	NPD3555	Approved
0.6228	Remote Similarity	NPD696	Discontinued
0.6228	Remote Similarity	NPD3552	Approved
0.6228	Remote Similarity	NPD3553	Approved
0.6228	Remote Similarity	NPD3554	Approved
0.6226	Remote Similarity	NPD1481	Phase 2
0.6223	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.622	Remote Similarity	NPD411	Approved
0.6219	Remote Similarity	NPD7583	Approved
0.6216	Remote Similarity	NPD3909	Discontinued
0.6215	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD5090	Approved
0.6215	Remote Similarity	NPD5089	Approved
0.6209	Remote Similarity	NPD594	Approved
0.6209	Remote Similarity	NPD1241	Discontinued
0.6209	Remote Similarity	NPD592	Approved
0.6207	Remote Similarity	NPD1349	Approved
0.6207	Remote Similarity	NPD1350	Approved
0.6207	Remote Similarity	NPD1351	Approved
0.6207	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD447	Suspended
0.6205	Remote Similarity	NPD654	Phase 3
0.6199	Remote Similarity	NPD4628	Phase 3
0.6196	Remote Similarity	NPD6832	Phase 2
0.6196	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4377	Discontinued
0.6194	Remote Similarity	NPD9493	Approved
0.6193	Remote Similarity	NPD3226	Approved
0.6188	Remote Similarity	NPD6583	Phase 3

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