NPASS Compound

Structure

NPC254088 OpenBabel07101719252D 40 41 0 0 1 0 0 0 0 0999 V2000 -8.8637 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2979 -5.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8637 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5658 -4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8637 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2979 -4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8338 3.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6998 4.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8338 2.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5658 3.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6998 2.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4319 2.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3637 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4319 -3.7979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5658 2.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4319 1.0658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3637 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4319 -2.7979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3978 0.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1049 -1.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4659 -2.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7588 0.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4659 0.8070 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1049 0.0999 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3978 -2.5391 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7588 -1.8320 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8978 1.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9709 -2.3320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9659 -3.4051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8928 0.5999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 6 1 0 0 0 0 2 7 1 0 0 0 0 5 17 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 40 1 0 0 0 0 15 3 1 6 0 0 0 16 4 1 1 0 0 0 17 19 1 0 0 0 0 17 32 2 0 0 0 0 19 14 1 6 0 0 0 20 13 1 6 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 15 1 6 0 0 0 21 25 1 0 0 0 0 21 29 1 0 0 0 0 22 16 1 6 0 0 0 22 26 1 0 0 0 0 22 30 1 0 0 0 0 23 19 1 6 0 0 0 23 27 1 0 0 0 0 23 31 1 0 0 0 0 24 29 2 3 0 0 0 24 33 1 0 0 0 0 25 30 2 3 0 0 0 25 34 1 0 0 0 0 26 31 2 3 0 0 0 26 35 1 0 0 0 0 27 28 2 3 0 0 0 27 36 1 0 0 0 0 37 40 1 0 0 0 0 38 40 2 0 0 0 0 39 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.26
Volume:	570.161
LogP:	0.197
LogD:	1.144
LogS:	-1.739
# Rotatable Bonds:	10
TPSA:	187.84
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.939
Fsp3:	0.593
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.884
MDCK Permeability:	1.9691384295583703e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	84.81497955322266%
Volume Distribution (VD):	0.387
Pgp-substrate:	6.672075271606445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	3.69
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.465
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.139
Carcinogencity:	0.313
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.201

Download Data

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

Natural Product: NPC254088

Natural Product ID:	NPC254088
*Common Name:**	(S)-2-((2S,5S,8S,11S)-5-Benzyl-8,11-Di-Sec-Butyl-3,6,9,12-Tetraoxo-1,4,7,10-Tetraazacyclododecan-2-Yl)-3-Oxobutane-1-Sulfonic Acid
IUPAC Name:	(2S)-2-[(2S,5S,8S,11S)-5-benzyl-8,11-bis[(2S)-butan-2-yl]-3,6,9,12-tetraoxo-1,4,7,10-tetrazacyclododec-2-yl]-3-oxobutane-1-sulfonic acid
Synonyms:
Standard InCHIKey:	YWMWRRNNRCIAAJ-WGPXQLEISA-N
Standard InCHI:	InChI=1S/C27H40N4O8S/c1-6-15(3)21-25(34)30-22(16(4)7-2)26(35)31-23(19(17(5)32)14-40(37,38)39)27(36)28-20(24(33)29-21)13-18-11-9-8-10-12-18/h8-12,15-16,19-23H,6-7,13-14H2,1-5H3,(H,28,36)(H,29,33)(H,30,34)(H,31,35)(H,37,38,39)/t15-,16-,19+,20-,21-,22-,23-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=N[C@@H]([C@@H](C)CC)C(=N[C@@H]([C@H](CS(=O)(=O)O)C(=O)C)C(=N[C@@H](Cc2ccccc2)C(=N1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475845
PubChem CID:	24886452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO33240	nonomuraea sp. ta-0426	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19013063]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1125	Cell Line	T98G	Homo sapiens	IC50	=	12.5	nM	PMID[502217]
NPT6623	Individual Protein	Galanin receptor 1	Rattus norvegicus	IC50	=	20.4	nM	PMID[502217]
NPT6505	Individual Protein	Galanin receptor 2	Rattus norvegicus	IC50	=	2260.0	nM	PMID[502217]

☑ 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 NPC254088 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	96
0.1-0.2	846
0.2-0.3	6195
0.3-0.4	21570
0.4-0.5	11882
0.5-0.6	1649
0.6-0.7	358
0.7-0.8	97
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8165	Intermediate Similarity	NPC25565
0.8091	Intermediate Similarity	NPC473501
0.8091	Intermediate Similarity	NPC475439
0.7826	Intermediate Similarity	NPC224610
0.7826	Intermediate Similarity	NPC88267
0.7826	Intermediate Similarity	NPC194390
0.7826	Intermediate Similarity	NPC113326
0.775	Intermediate Similarity	NPC474584
0.7589	Intermediate Similarity	NPC161972
0.7589	Intermediate Similarity	NPC303045
0.7586	Intermediate Similarity	NPC471317
0.7581	Intermediate Similarity	NPC169328
0.7557	Intermediate Similarity	NPC300315
0.7542	Intermediate Similarity	NPC327481
0.754	Intermediate Similarity	NPC478014
0.754	Intermediate Similarity	NPC478015
0.754	Intermediate Similarity	NPC478016
0.7536	Intermediate Similarity	NPC322878
0.752	Intermediate Similarity	NPC310467
0.752	Intermediate Similarity	NPC237420
0.7519	Intermediate Similarity	NPC47667
0.75	Intermediate Similarity	NPC470544
0.744	Intermediate Similarity	NPC470545
0.7436	Intermediate Similarity	NPC202613
0.7402	Intermediate Similarity	NPC45777
0.7402	Intermediate Similarity	NPC477061
0.7381	Intermediate Similarity	NPC470546
0.7377	Intermediate Similarity	NPC329011
0.7328	Intermediate Similarity	NPC12730
0.7321	Intermediate Similarity	NPC226438
0.7304	Intermediate Similarity	NPC311242
0.7292	Intermediate Similarity	NPC286551
0.7281	Intermediate Similarity	NPC58674
0.728	Intermediate Similarity	NPC197470
0.7258	Intermediate Similarity	NPC276949
0.7258	Intermediate Similarity	NPC35850
0.7244	Intermediate Similarity	NPC314992
0.7232	Intermediate Similarity	NPC78041
0.7232	Intermediate Similarity	NPC141139
0.7232	Intermediate Similarity	NPC121872
0.7232	Intermediate Similarity	NPC471307
0.7232	Intermediate Similarity	NPC74936
0.7232	Intermediate Similarity	NPC159178
0.7232	Intermediate Similarity	NPC209764
0.7222	Intermediate Similarity	NPC2265
0.72	Intermediate Similarity	NPC33742
0.7177	Intermediate Similarity	NPC273814
0.7154	Intermediate Similarity	NPC319579
0.7143	Intermediate Similarity	NPC319766
0.7143	Intermediate Similarity	NPC164859
0.7143	Intermediate Similarity	NPC470877
0.7143	Intermediate Similarity	NPC317254
0.7099	Intermediate Similarity	NPC6975
0.7077	Intermediate Similarity	NPC202521
0.7043	Intermediate Similarity	NPC471309
0.7023	Intermediate Similarity	NPC252878
0.7014	Intermediate Similarity	NPC105717
0.7008	Intermediate Similarity	NPC188010
0.7	Intermediate Similarity	NPC200964
0.7	Intermediate Similarity	NPC476990
0.7	Intermediate Similarity	NPC190663
0.6992	Remote Similarity	NPC101719
0.697	Remote Similarity	NPC46427
0.697	Remote Similarity	NPC35996
0.6964	Remote Similarity	NPC471638
0.6953	Remote Similarity	NPC239357
0.6947	Remote Similarity	NPC71684
0.694	Remote Similarity	NPC477937
0.693	Remote Similarity	NPC172128
0.693	Remote Similarity	NPC316108
0.6929	Remote Similarity	NPC471318
0.6923	Remote Similarity	NPC283760
0.6917	Remote Similarity	NPC222466
0.6917	Remote Similarity	NPC22746
0.6903	Remote Similarity	NPC325441
0.6901	Remote Similarity	NPC316202
0.6894	Remote Similarity	NPC160493
0.6884	Remote Similarity	NPC287401
0.6879	Remote Similarity	NPC476259
0.687	Remote Similarity	NPC80150
0.6861	Remote Similarity	NPC130309
0.6861	Remote Similarity	NPC255447
0.6842	Remote Similarity	NPC472415
0.6838	Remote Similarity	NPC473322
0.6831	Remote Similarity	NPC168113
0.6812	Remote Similarity	NPC326966
0.6809	Remote Similarity	NPC89489
0.6806	Remote Similarity	NPC314287
0.6791	Remote Similarity	NPC476241
0.6791	Remote Similarity	NPC476260
0.6783	Remote Similarity	NPC258627
0.6783	Remote Similarity	NPC176226
0.6783	Remote Similarity	NPC197682
0.6767	Remote Similarity	NPC474862
0.6754	Remote Similarity	NPC12429
0.6744	Remote Similarity	NPC235421
0.6742	Remote Similarity	NPC476183
0.6741	Remote Similarity	NPC476179
0.6741	Remote Similarity	NPC476125
0.6741	Remote Similarity	NPC472414
0.6738	Remote Similarity	NPC68865
0.6738	Remote Similarity	NPC6570
0.6738	Remote Similarity	NPC471265
0.6738	Remote Similarity	NPC471264
0.6724	Remote Similarity	NPC245259
0.6715	Remote Similarity	NPC111428
0.6715	Remote Similarity	NPC472413
0.6714	Remote Similarity	NPC248283
0.6694	Remote Similarity	NPC191215
0.6694	Remote Similarity	NPC274089
0.6692	Remote Similarity	NPC476184
0.6692	Remote Similarity	NPC476281
0.6667	Remote Similarity	NPC468984
0.6667	Remote Similarity	NPC139326
0.6667	Remote Similarity	NPC118202
0.6667	Remote Similarity	NPC478147
0.6643	Remote Similarity	NPC239762
0.6643	Remote Similarity	NPC163392
0.662	Remote Similarity	NPC127741
0.6619	Remote Similarity	NPC183722
0.6618	Remote Similarity	NPC4974
0.6614	Remote Similarity	NPC474149
0.6613	Remote Similarity	NPC211551
0.6597	Remote Similarity	NPC469427
0.6597	Remote Similarity	NPC269398
0.6597	Remote Similarity	NPC469426
0.6597	Remote Similarity	NPC197921
0.6597	Remote Similarity	NPC263493
0.6594	Remote Similarity	NPC71271
0.6594	Remote Similarity	NPC296712
0.6593	Remote Similarity	NPC476278
0.6585	Remote Similarity	NPC471310
0.6583	Remote Similarity	NPC122493
0.6583	Remote Similarity	NPC10781
0.6583	Remote Similarity	NPC293628
0.6575	Remote Similarity	NPC478040
0.6573	Remote Similarity	NPC132636
0.6571	Remote Similarity	NPC246913
0.6552	Remote Similarity	NPC469360
0.6552	Remote Similarity	NPC91953
0.6549	Remote Similarity	NPC314835
0.6547	Remote Similarity	NPC200589
0.6541	Remote Similarity	NPC319950
0.6535	Remote Similarity	NPC258056
0.6529	Remote Similarity	NPC322598
0.6525	Remote Similarity	NPC244866
0.6515	Remote Similarity	NPC38458
0.6515	Remote Similarity	NPC311737
0.651	Remote Similarity	NPC283783
0.6507	Remote Similarity	NPC476978
0.6491	Remote Similarity	NPC3210
0.648	Remote Similarity	NPC67043
0.6475	Remote Similarity	NPC116057
0.6463	Remote Similarity	NPC209509
0.6463	Remote Similarity	NPC5620
0.6462	Remote Similarity	NPC474544
0.6462	Remote Similarity	NPC1986
0.6458	Remote Similarity	NPC476133
0.6458	Remote Similarity	NPC178662
0.6458	Remote Similarity	NPC92784
0.6458	Remote Similarity	NPC98424
0.6458	Remote Similarity	NPC470884
0.6454	Remote Similarity	NPC246079
0.6454	Remote Similarity	NPC194857
0.6454	Remote Similarity	NPC32858
0.6454	Remote Similarity	NPC42423
0.6446	Remote Similarity	NPC33168
0.6446	Remote Similarity	NPC324569
0.6439	Remote Similarity	NPC285926
0.6439	Remote Similarity	NPC315276
0.6439	Remote Similarity	NPC14672
0.6439	Remote Similarity	NPC82963
0.6438	Remote Similarity	NPC161069
0.6429	Remote Similarity	NPC325651
0.6429	Remote Similarity	NPC323336
0.6429	Remote Similarity	NPC326349
0.6429	Remote Similarity	NPC231705
0.6423	Remote Similarity	NPC469457
0.6414	Remote Similarity	NPC307357
0.6414	Remote Similarity	NPC268841
0.6414	Remote Similarity	NPC46098
0.6397	Remote Similarity	NPC27581
0.6389	Remote Similarity	NPC208725
0.6389	Remote Similarity	NPC43755
0.6387	Remote Similarity	NPC323164
0.6379	Remote Similarity	NPC473031
0.6378	Remote Similarity	NPC142297
0.6372	Remote Similarity	NPC14326
0.6364	Remote Similarity	NPC141050
0.6364	Remote Similarity	NPC228511
0.6357	Remote Similarity	NPC469666
0.6351	Remote Similarity	NPC316008
0.6351	Remote Similarity	NPC313867
0.6351	Remote Similarity	NPC315266
0.6346	Remote Similarity	NPC471527
0.6345	Remote Similarity	NPC477557
0.6319	Remote Similarity	NPC279045
0.6319	Remote Similarity	NPC113325
0.6316	Remote Similarity	NPC300443
0.6309	Remote Similarity	NPC314358

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 NPC254088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	86
0.1-0.2	482
0.2-0.3	862
0.3-0.4	3047
0.4-0.5	3292
0.5-0.6	1175
0.6-0.7	187
0.7-0.8	18
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
0.8031	Intermediate Similarity	NPD7828	Discontinued
0.7565	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5367	Discontinued
0.7478	Intermediate Similarity	NPD1067	Discontinued
0.744	Intermediate Similarity	NPD6360	Discontinued
0.7411	Intermediate Similarity	NPD6690	Approved
0.7381	Intermediate Similarity	NPD6093	Discontinued
0.7313	Intermediate Similarity	NPD7908	Discontinued
0.7295	Intermediate Similarity	NPD3643	Approved
0.7295	Intermediate Similarity	NPD3644	Approved
0.7295	Intermediate Similarity	NPD3642	Approved
0.728	Intermediate Similarity	NPD1348	Approved
0.7257	Intermediate Similarity	NPD1814	Approved
0.7257	Intermediate Similarity	NPD1812	Approved
0.7244	Intermediate Similarity	NPD2217	Approved
0.7244	Intermediate Similarity	NPD2218	Phase 2
0.7188	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4125	Approved
0.7132	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6325	Discontinued
0.7092	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1040	Phase 2
0.7015	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4814	Discontinued
0.697	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5323	Approved
0.6929	Remote Similarity	NPD2635	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5981	Approved
0.6923	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1409	Phase 3
0.6885	Remote Similarity	NPD999	Phase 2
0.687	Remote Similarity	NPD7342	Discontinued
0.6849	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6624	Discontinued
0.6835	Remote Similarity	NPD8416	Discontinued
0.6835	Remote Similarity	NPD8265	Approved
0.6818	Remote Similarity	NPD4651	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5299	Approved
0.6786	Remote Similarity	NPD8643	Discontinued
0.6783	Remote Similarity	NPD2022	Approved
0.6774	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6864	Phase 2
0.6761	Remote Similarity	NPD6865	Phase 2
0.6752	Remote Similarity	NPD1080	Approved
0.6739	Remote Similarity	NPD2046	Approved
0.6739	Remote Similarity	NPD21	Approved
0.6739	Remote Similarity	NPD2044	Approved
0.6739	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2051	Approved
0.6739	Remote Similarity	NPD2043	Approved
0.6739	Remote Similarity	NPD2047	Approved
0.6739	Remote Similarity	NPD2048	Approved
0.6739	Remote Similarity	NPD2045	Approved
0.6736	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2087	Approved
0.6667	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2088	Approved
0.6667	Remote Similarity	NPD8076	Discontinued
0.6645	Remote Similarity	NPD6679	Phase 3
0.6645	Remote Similarity	NPD6678	Phase 3
0.6645	Remote Similarity	NPD6680	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7303	Discontinued
0.6643	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7522	Discontinued
0.662	Remote Similarity	NPD8172	Phase 2
0.662	Remote Similarity	NPD8173	Phase 2
0.6619	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD4738	Phase 2
0.6619	Remote Similarity	NPD3136	Phase 2
0.6617	Remote Similarity	NPD1727	Approved
0.661	Remote Similarity	NPD1066	Discontinued
0.6594	Remote Similarity	NPD767	Phase 1
0.6583	Remote Similarity	NPD9566	Approved
0.6565	Remote Similarity	NPD3123	Discovery
0.6562	Remote Similarity	NPD3651	Discontinued
0.6558	Remote Similarity	NPD4566	Approved
0.6558	Remote Similarity	NPD4567	Approved
0.6555	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5780	Phase 2
0.6547	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6390	Discontinued
0.6528	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4480	Approved
0.651	Remote Similarity	NPD5613	Approved
0.651	Remote Similarity	NPD3987	Approved
0.651	Remote Similarity	NPD5614	Approved
0.651	Remote Similarity	NPD3988	Approved
0.6508	Remote Similarity	NPD6406	Approved
0.65	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8124	Phase 3
0.6489	Remote Similarity	NPD7508	Discontinued
0.648	Remote Similarity	NPD5717	Approved
0.648	Remote Similarity	NPD1018	Approved
0.6471	Remote Similarity	NPD2584	Suspended
0.6458	Remote Similarity	NPD6901	Phase 3
0.6458	Remote Similarity	NPD6852	Discontinued
0.6454	Remote Similarity	NPD6076	Approved
0.6454	Remote Similarity	NPD6075	Approved
0.6446	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD530	Approved
0.6438	Remote Similarity	NPD7978	Discontinued
0.6423	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6304	Approved
0.6415	Remote Similarity	NPD6303	Approved
0.6414	Remote Similarity	NPD3480	Approved
0.6403	Remote Similarity	NPD7451	Discontinued
0.6395	Remote Similarity	NPD2437	Approved
0.6395	Remote Similarity	NPD6681	Discovery
0.6395	Remote Similarity	NPD2436	Approved
0.6382	Remote Similarity	NPD7523	Phase 3
0.6379	Remote Similarity	NPD9538	Approved
0.6376	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7450	Phase 2
0.6364	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2895	Discontinued
0.6357	Remote Similarity	NPD3626	Phase 3
0.6343	Remote Similarity	NPD4479	Discontinued
0.6341	Remote Similarity	NPD4737	Phase 2
0.6325	Remote Similarity	NPD1101	Approved
0.6319	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5230	Approved
0.6316	Remote Similarity	NPD5229	Approved
0.6312	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7965	Phase 2
0.6294	Remote Similarity	NPD8118	Discontinued
0.6291	Remote Similarity	NPD2013	Approved
0.6291	Remote Similarity	NPD2014	Approved
0.6291	Remote Similarity	NPD2016	Approved
0.629	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.627	Remote Similarity	NPD3407	Phase 3
0.6267	Remote Similarity	NPD8323	Discontinued
0.626	Remote Similarity	NPD3066	Phase 2
0.626	Remote Similarity	NPD4165	Phase 2
0.626	Remote Similarity	NPD253	Approved
0.6259	Remote Similarity	NPD3098	Discontinued
0.6258	Remote Similarity	NPD7822	Phase 1
0.6258	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.625	Remote Similarity	NPD752	Approved
0.625	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5272	Discontinued
0.625	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4006	Discontinued
0.624	Remote Similarity	NPD854	Approved
0.624	Remote Similarity	NPD4119	Approved
0.624	Remote Similarity	NPD5716	Approved
0.624	Remote Similarity	NPD855	Approved
0.6234	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4646	Approved
0.6234	Remote Similarity	NPD4647	Approved
0.6234	Remote Similarity	NPD4648	Approved
0.6233	Remote Similarity	NPD4214	Discontinued
0.623	Remote Similarity	NPD838	Approved
0.6218	Remote Similarity	NPD7438	Suspended
0.6212	Remote Similarity	NPD3150	Approved
0.6212	Remote Similarity	NPD7076	Approved
0.6212	Remote Similarity	NPD2658	Approved
0.6212	Remote Similarity	NPD3147	Approved
0.6212	Remote Similarity	NPD7077	Approved
0.6212	Remote Similarity	NPD3148	Approved
0.6212	Remote Similarity	NPD3149	Approved
0.6212	Remote Similarity	NPD1682	Approved
0.6212	Remote Similarity	NPD1681	Approved
0.6212	Remote Similarity	NPD1680	Approved
0.6212	Remote Similarity	NPD2659	Approved
0.6204	Remote Similarity	NPD5770	Phase 3
0.6202	Remote Similarity	NPD2679	Approved
0.6202	Remote Similarity	NPD2678	Approved
0.6202	Remote Similarity	NPD7156	Discontinued
0.6198	Remote Similarity	NPD3719	Approved
0.6198	Remote Similarity	NPD3718	Approved
0.6198	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD719	Approved
0.6198	Remote Similarity	NPD720	Approved
0.619	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1542	Approved
0.6178	Remote Similarity	NPD5355	Approved
0.6178	Remote Similarity	NPD5356	Approved
0.6176	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD1711	Phase 2
0.6165	Remote Similarity	NPD475	Phase 2
0.6159	Remote Similarity	NPD5618	Discontinued
0.6154	Remote Similarity	NPD1317	Discontinued
0.6149	Remote Similarity	NPD4508	Discontinued
0.6148	Remote Similarity	NPD1758	Phase 1
0.6144	Remote Similarity	NPD4432	Discontinued
0.6144	Remote Similarity	NPD4739	Approved
0.6143	Remote Similarity	NPD5578	Approved

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