NPASS Compound

Structure

NPC474877 OpenBabel07101718202D 34 40 0 0 1 0 0 0 0 0999 V2000 -2.5372 0.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0445 -1.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6824 -3.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6289 -0.5343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4866 -3.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1272 -1.1108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8781 -3.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2961 0.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4866 -2.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9760 1.0164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3743 1.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 -0.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8781 -2.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9274 0.0890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3788 0.4780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6824 -2.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7356 -1.8371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5657 -1.0857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1244 0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7329 -0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9287 0.9287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1880 -1.9341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9287 -0.9287 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8731 1.2568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4893 -1.1828 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7329 0.4643 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -0.4643 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3027 1.7649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3570 -2.5272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6798 0.9287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5372 -0.9287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2720 0.6567 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.2720 -0.6567 0.0000 S 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 26 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 19 30 2 0 0 0 0 20 26 1 0 0 0 0 20 31 2 0 0 0 0 21 11 1 1 0 0 0 21 26 1 0 0 0 0 21 32 1 0 0 0 0 22 14 1 6 0 0 0 23 20 1 1 0 0 0 23 27 1 0 0 0 0 23 33 1 0 0 0 0 32 34 1 0 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.06
Volume:	457.416
LogP:	2.788
LogD:	2.074
LogS:	-3.74
# Rotatable Bonds:	2
TPSA:	108.9
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	6.128
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.549
MDCK Permeability:	7.414728315779939e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.366
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	75.0057144165039%
Volume Distribution (VD):	0.7
Pgp-substrate:	22.161808013916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.175
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.985
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.98
CYP2C9-substrate:	0.572
CYP2D6-inhibitor:	0.815
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.971

ADMET: Excretion

Clearance (CL):	8.698
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.867
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC474877

Natural Product ID:	NPC474877
*Common Name:**	LNPYPYPXOCKQQO-HMKLVTIHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LNPYPYPXOCKQQO-HMKLVTIHSA-N
Standard InCHI:	InChI=1S/C23H20N4O4S3/c1-26-20(31)23-17(29)22(14-10-24-15-8-4-2-6-12(14)15)13-7-3-5-9-16(13)25-18(22)27(23)19(30)21(26,11-28)32-34-33-23/h2-10,17-18,24-25,28-29H,11H2,1H3/t17-,18+,21+,22+,23-/m0/s1
SMILES:	CN1C(=O)C23C(C4(C(N2C(=O)C1(SSS3)CO)NC5=CC=CC=C54)C6=CNC7=CC=CC=C76)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486014
PubChem CID:	44559599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO33289	tilachlidium sp.	Species	Tilachlidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620259]
NPO5778	Oidiodendron truncatum	Species	Myxotrichaceae	Eukaryota	n.a.	Antarctic	n.a.	PMID[22583079]
NPO32990	acrostalagmus luteoalbus scsio f457	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23079524]
NPO5778	Oidiodendron truncatum	Species	Myxotrichaceae	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
IC50	9
Others	1

Activity Type	# Activity
Cell Line	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ID50	=	0.25	uM	PMID[511492]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1180.0	nM	PMID[511493]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	750.0	nM	PMID[511493]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	1460.0	nM	PMID[511493]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1530.0	nM	PMID[511493]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	420.0	nM	PMID[511493]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3520.0	nM	PMID[511494]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	5600.0	nM	PMID[511494]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	910.0	nM	PMID[511494]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	1040.0	nM	PMID[511494]

☑ 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 NPC474877 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	372
0.1-0.2	2302
0.2-0.3	16620
0.3-0.4	16365
0.4-0.5	2542
0.5-0.6	2774
0.6-0.7	1404
0.7-0.8	295
0.8-0.85	9
0.85-0.9	1
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9951	High Similarity	NPC470729
0.9951	High Similarity	NPC477176
0.971	High Similarity	NPC475969
0.971	High Similarity	NPC475859
0.9662	High Similarity	NPC477175
0.9662	High Similarity	NPC470730
0.9617	High Similarity	NPC63279
0.9615	High Similarity	NPC477177
0.9571	High Similarity	NPC297642
0.9569	High Similarity	NPC165743
0.9363	High Similarity	NPC470732
0.9082	High Similarity	NPC470731
0.8698	High Similarity	NPC40455
0.8479	Intermediate Similarity	NPC312942
0.8479	Intermediate Similarity	NPC327095
0.8436	Intermediate Similarity	NPC162860
0.8402	Intermediate Similarity	NPC19170
0.8341	Intermediate Similarity	NPC54420
0.8303	Intermediate Similarity	NPC272174
0.8288	Intermediate Similarity	NPC297862
0.8273	Intermediate Similarity	NPC476817
0.8182	Intermediate Similarity	NPC474896
0.8178	Intermediate Similarity	NPC107077
0.8178	Intermediate Similarity	NPC223791
0.8157	Intermediate Similarity	NPC478157
0.8145	Intermediate Similarity	NPC31097
0.8104	Intermediate Similarity	NPC475506
0.8093	Intermediate Similarity	NPC478158
0.8066	Intermediate Similarity	NPC155143
0.8063	Intermediate Similarity	NPC253987
0.8048	Intermediate Similarity	NPC171317
0.8045	Intermediate Similarity	NPC477714
0.8045	Intermediate Similarity	NPC281049
0.8043	Intermediate Similarity	NPC14812
0.8	Intermediate Similarity	NPC477715
0.7991	Intermediate Similarity	NPC478028
0.7962	Intermediate Similarity	NPC473640
0.7953	Intermediate Similarity	NPC477173
0.7945	Intermediate Similarity	NPC54744
0.7936	Intermediate Similarity	NPC320968
0.7922	Intermediate Similarity	NPC478029
0.7917	Intermediate Similarity	NPC470488
0.7907	Intermediate Similarity	NPC473376
0.79	Intermediate Similarity	NPC75634
0.7874	Intermediate Similarity	NPC17059
0.7837	Intermediate Similarity	NPC213629
0.7826	Intermediate Similarity	NPC94752
0.7804	Intermediate Similarity	NPC470497
0.7803	Intermediate Similarity	NPC475736
0.7788	Intermediate Similarity	NPC64216
0.7783	Intermediate Similarity	NPC89987
0.7778	Intermediate Similarity	NPC477179
0.7757	Intermediate Similarity	NPC100321
0.7742	Intermediate Similarity	NPC477181
0.7742	Intermediate Similarity	NPC477180
0.7742	Intermediate Similarity	NPC477178
0.7742	Intermediate Similarity	NPC254850
0.7738	Intermediate Similarity	NPC31385
0.7738	Intermediate Similarity	NPC75726
0.7738	Intermediate Similarity	NPC110602
0.7736	Intermediate Similarity	NPC294693
0.7729	Intermediate Similarity	NPC56109
0.7729	Intermediate Similarity	NPC191382
0.7706	Intermediate Similarity	NPC470490
0.7706	Intermediate Similarity	NPC477174
0.7696	Intermediate Similarity	NPC69843
0.7683	Intermediate Similarity	NPC125181
0.7683	Intermediate Similarity	NPC242872
0.7683	Intermediate Similarity	NPC263117
0.7675	Intermediate Similarity	NPC474196
0.7674	Intermediate Similarity	NPC293917
0.7665	Intermediate Similarity	NPC155444
0.7661	Intermediate Similarity	NPC470489
0.7655	Intermediate Similarity	NPC474195
0.7644	Intermediate Similarity	NPC228835
0.7639	Intermediate Similarity	NPC325976
0.7636	Intermediate Similarity	NPC471945
0.7636	Intermediate Similarity	NPC471950
0.7636	Intermediate Similarity	NPC470491
0.7636	Intermediate Similarity	NPC475259
0.761	Intermediate Similarity	NPC321939
0.7602	Intermediate Similarity	NPC471946
0.7602	Intermediate Similarity	NPC471951
0.76	Intermediate Similarity	NPC472285
0.7583	Intermediate Similarity	NPC321708
0.7569	Intermediate Similarity	NPC476874
0.7568	Intermediate Similarity	NPC475359
0.7568	Intermediate Similarity	NPC191817
0.7565	Intermediate Similarity	NPC24370
0.7565	Intermediate Similarity	NPC319232
0.7546	Intermediate Similarity	NPC131887
0.7543	Intermediate Similarity	NPC326363
0.754	Intermediate Similarity	NPC314056
0.7536	Intermediate Similarity	NPC11126
0.7531	Intermediate Similarity	NPC314882
0.7524	Intermediate Similarity	NPC15102
0.7523	Intermediate Similarity	NPC300183
0.7522	Intermediate Similarity	NPC238945
0.7512	Intermediate Similarity	NPC473763
0.7512	Intermediate Similarity	NPC117244
0.75	Intermediate Similarity	NPC28945
0.75	Intermediate Similarity	NPC91179
0.7489	Intermediate Similarity	NPC193761
0.7489	Intermediate Similarity	NPC476073
0.748	Intermediate Similarity	NPC478006
0.7479	Intermediate Similarity	NPC63031
0.7477	Intermediate Similarity	NPC252338
0.747	Intermediate Similarity	NPC478011
0.747	Intermediate Similarity	NPC478012
0.7467	Intermediate Similarity	NPC229348
0.7465	Intermediate Similarity	NPC470499
0.7455	Intermediate Similarity	NPC54981
0.7455	Intermediate Similarity	NPC82370
0.745	Intermediate Similarity	NPC478013
0.7448	Intermediate Similarity	NPC17487
0.7448	Intermediate Similarity	NPC201831
0.7444	Intermediate Similarity	NPC469743
0.7441	Intermediate Similarity	NPC314176
0.744	Intermediate Similarity	NPC315467
0.7432	Intermediate Similarity	NPC323927
0.7422	Intermediate Similarity	NPC475778
0.7419	Intermediate Similarity	NPC227582
0.7417	Intermediate Similarity	NPC477108
0.7417	Intermediate Similarity	NPC477109
0.7417	Intermediate Similarity	NPC477107
0.7411	Intermediate Similarity	NPC234999
0.741	Intermediate Similarity	NPC478009
0.741	Intermediate Similarity	NPC478010
0.7409	Intermediate Similarity	NPC260900
0.7406	Intermediate Similarity	NPC315555
0.7401	Intermediate Similarity	NPC471192
0.7387	Intermediate Similarity	NPC277350
0.7383	Intermediate Similarity	NPC95783
0.7382	Intermediate Similarity	NPC476491
0.7373	Intermediate Similarity	NPC323752
0.7373	Intermediate Similarity	NPC220852
0.7368	Intermediate Similarity	NPC126709
0.7368	Intermediate Similarity	NPC248041
0.7368	Intermediate Similarity	NPC248462
0.7368	Intermediate Similarity	NPC283219
0.7357	Intermediate Similarity	NPC474412
0.7353	Intermediate Similarity	NPC285343
0.7353	Intermediate Similarity	NPC184225
0.7345	Intermediate Similarity	NPC471194
0.7345	Intermediate Similarity	NPC471193
0.7345	Intermediate Similarity	NPC6865
0.7345	Intermediate Similarity	NPC153980
0.7336	Intermediate Similarity	NPC473310
0.7336	Intermediate Similarity	NPC175474
0.7325	Intermediate Similarity	NPC36405
0.7324	Intermediate Similarity	NPC235684
0.7324	Intermediate Similarity	NPC62749
0.7322	Intermediate Similarity	NPC470784
0.7321	Intermediate Similarity	NPC314957
0.7321	Intermediate Similarity	NPC64436
0.7321	Intermediate Similarity	NPC71238
0.7321	Intermediate Similarity	NPC145885
0.7321	Intermediate Similarity	NPC84827
0.7321	Intermediate Similarity	NPC14113
0.7316	Intermediate Similarity	NPC471506
0.7306	Intermediate Similarity	NPC52557
0.7301	Intermediate Similarity	NPC72956
0.73	Intermediate Similarity	NPC70155
0.7297	Intermediate Similarity	NPC98715
0.7297	Intermediate Similarity	NPC317701
0.7293	Intermediate Similarity	NPC79386
0.7286	Intermediate Similarity	NPC219336
0.728	Intermediate Similarity	NPC184680
0.7277	Intermediate Similarity	NPC99939
0.7277	Intermediate Similarity	NPC225821
0.7277	Intermediate Similarity	NPC308931
0.7277	Intermediate Similarity	NPC46225
0.7276	Intermediate Similarity	NPC153400
0.7273	Intermediate Similarity	NPC267885
0.7273	Intermediate Similarity	NPC74413
0.7269	Intermediate Similarity	NPC87856
0.7269	Intermediate Similarity	NPC151976
0.726	Intermediate Similarity	NPC161861
0.7253	Intermediate Similarity	NPC229893
0.7251	Intermediate Similarity	NPC16659
0.725	Intermediate Similarity	NPC470785
0.7249	Intermediate Similarity	NPC204491
0.7249	Intermediate Similarity	NPC203614
0.7244	Intermediate Similarity	NPC127677
0.7244	Intermediate Similarity	NPC258062
0.724	Intermediate Similarity	NPC79129
0.724	Intermediate Similarity	NPC81654
0.724	Intermediate Similarity	NPC313985
0.724	Intermediate Similarity	NPC214428
0.724	Intermediate Similarity	NPC49196
0.724	Intermediate Similarity	NPC249150
0.724	Intermediate Similarity	NPC195461
0.7238	Intermediate Similarity	NPC111275
0.7238	Intermediate Similarity	NPC15573
0.7238	Intermediate Similarity	NPC217372
0.7238	Intermediate Similarity	NPC183662
0.7238	Intermediate Similarity	NPC59269
0.7237	Intermediate Similarity	NPC475602
0.7237	Intermediate Similarity	NPC267965
0.7234	Intermediate Similarity	NPC475258

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 NPC474877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	552
0.2-0.3	963
0.3-0.4	2065
0.4-0.5	2406
0.5-0.6	2215
0.6-0.7	694
0.7-0.8	63
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
0.8056	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD7970	Approved
0.7773	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD7470	Discontinued
0.7773	Intermediate Similarity	NPD7824	Approved
0.7749	Intermediate Similarity	NPD7789	Approved
0.7749	Intermediate Similarity	NPD7951	Approved
0.7749	Intermediate Similarity	NPD7952	Approved
0.7749	Intermediate Similarity	NPD7790	Approved
0.7749	Intermediate Similarity	NPD7953	Approved
0.7749	Intermediate Similarity	NPD7950	Approved
0.7749	Intermediate Similarity	NPD7791	Approved
0.7742	Intermediate Similarity	NPD5426	Phase 3
0.7736	Intermediate Similarity	NPD7618	Phase 3
0.7736	Intermediate Similarity	NPD7619	Phase 3
0.7729	Intermediate Similarity	NPD7780	Approved
0.7729	Intermediate Similarity	NPD7781	Approved
0.7686	Intermediate Similarity	NPD7730	Approved
0.7686	Intermediate Similarity	NPD7731	Approved
0.7675	Intermediate Similarity	NPD7271	Approved
0.7674	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8272	Phase 2
0.7653	Intermediate Similarity	NPD7944	Discontinued
0.7604	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7001	Phase 3
0.7532	Intermediate Similarity	NPD6164	Phase 2
0.7532	Intermediate Similarity	NPD6165	Phase 2
0.7511	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD8322	Phase 2
0.7489	Intermediate Similarity	NPD7711	Discontinued
0.7489	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6999	Discontinued
0.7416	Intermediate Similarity	NPD6595	Phase 3
0.7414	Intermediate Similarity	NPD7603	Discontinued
0.7389	Intermediate Similarity	NPD8094	Discontinued
0.7387	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2094	Phase 2
0.7346	Intermediate Similarity	NPD2092	Phase 2
0.7346	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2095	Phase 2
0.7345	Intermediate Similarity	NPD8093	Discontinued
0.7342	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7665	Phase 2
0.7321	Intermediate Similarity	NPD7666	Phase 3
0.7313	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2091	Phase 2
0.7311	Intermediate Similarity	NPD2096	Phase 2
0.729	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4600	Approved
0.724	Intermediate Similarity	NPD4601	Approved
0.7225	Intermediate Similarity	NPD482	Approved
0.7217	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7817	Phase 1
0.7191	Intermediate Similarity	NPD8289	Discontinued
0.7188	Intermediate Similarity	NPD8169	Discontinued
0.7179	Intermediate Similarity	NPD6173	Approved
0.7176	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4499	Approved
0.7143	Intermediate Similarity	NPD8072	Approved
0.7143	Intermediate Similarity	NPD8271	Discontinued
0.7136	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8115	Approved
0.7111	Intermediate Similarity	NPD8114	Approved
0.7104	Intermediate Similarity	NPD6664	Approved
0.7098	Intermediate Similarity	NPD8073	Approved
0.7095	Intermediate Similarity	NPD750	Phase 2
0.7093	Intermediate Similarity	NPD2509	Approved
0.7093	Intermediate Similarity	NPD2510	Approved
0.7089	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7026	Phase 2
0.708	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7957	Phase 1
0.708	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6665	Discontinued
0.7075	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5065	Approved
0.7054	Intermediate Similarity	NPD7727	Phase 2
0.7048	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2511	Approved
0.7035	Intermediate Similarity	NPD5901	Discontinued
0.7034	Intermediate Similarity	NPD7717	Approved
0.7034	Intermediate Similarity	NPD7716	Approved
0.7027	Intermediate Similarity	NPD2880	Discontinued
0.7026	Intermediate Similarity	NPD7543	Phase 2
0.7018	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7415	Suspended
0.7005	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5017	Discontinued
0.6972	Remote Similarity	NPD3961	Discontinued
0.6971	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4076	Approved
0.6963	Remote Similarity	NPD4079	Approved
0.6955	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8240	Discontinued
0.6951	Remote Similarity	NPD5003	Discontinued
0.6948	Remote Similarity	NPD4558	Phase 2
0.6947	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2443	Approved
0.6943	Remote Similarity	NPD2442	Approved
0.6937	Remote Similarity	NPD4602	Approved
0.6936	Remote Similarity	NPD5199	Approved
0.6936	Remote Similarity	NPD5198	Approved
0.6936	Remote Similarity	NPD7168	Phase 3
0.6927	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8256	Approved
0.6923	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8257	Approved
0.692	Remote Similarity	NPD4397	Phase 1
0.692	Remote Similarity	NPD6995	Phase 1
0.6916	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3505	Approved
0.6916	Remote Similarity	NPD6176	Phase 1
0.6916	Remote Similarity	NPD3506	Approved
0.6914	Remote Similarity	NPD6970	Phase 2
0.6901	Remote Similarity	NPD8119	Discontinued
0.6897	Remote Similarity	NPD4852	Phase 2
0.6895	Remote Similarity	NPD8431	Approved
0.6872	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6268	Phase 1
0.6872	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8284	Discontinued
0.6858	Remote Similarity	NPD484	Approved
0.6852	Remote Similarity	NPD8349	Phase 1
0.6851	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5818	Discontinued
0.6849	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8250	Phase 2
0.684	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3321	Discontinued
0.6815	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3393	Approved
0.6809	Remote Similarity	NPD3389	Approved
0.6809	Remote Similarity	NPD3394	Approved
0.6808	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6978	Phase 2
0.6802	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7948	Phase 1
0.6795	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7688	Phase 1
0.679	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5596	Phase 2
0.6784	Remote Similarity	NPD5043	Discontinued
0.6784	Remote Similarity	NPD4501	Approved
0.6784	Remote Similarity	NPD4500	Approved
0.6777	Remote Similarity	NPD5559	Phase 2
0.6769	Remote Similarity	NPD4310	Phase 3
0.6769	Remote Similarity	NPD5487	Phase 1
0.6767	Remote Similarity	NPD2408	Discontinued
0.6765	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8075	Discontinued
0.6762	Remote Similarity	NPD4885	Approved
0.6762	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7921	Approved
0.676	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2144	Approved
0.6758	Remote Similarity	NPD1096	Discontinued
0.675	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD8246	Approved
0.6745	Remote Similarity	NPD8247	Approved
0.6745	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6987	Phase 1
0.6736	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8016	Phase 3
0.6734	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8386	Phase 2
0.6726	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4612	Discontinued
0.6723	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4075	Phase 2
0.6713	Remote Similarity	NPD6044	Discontinued
0.6712	Remote Similarity	NPD4334	Discontinued
0.6711	Remote Similarity	NPD6479	Discontinued
0.671	Remote Similarity	NPD2008	Discontinued
0.671	Remote Similarity	NPD4901	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