NPASS Compound

Structure

NPC168153 OpenBabel07101718202D 28 30 0 0 1 0 0 0 0 0999 V2000 -5.0285 -2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8666 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9988 0.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1904 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0955 1.8058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0955 0.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0633 1.8058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0633 0.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0285 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6117 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5471 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 1.4516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 0.9677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1600 1.8058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5149 0.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 14 19 2 0 0 0 0 15 22 1 0 0 0 0 16 27 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 1 0 0 0 20 28 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.17
Volume:	397.255
LogP:	3.903
LogD:	3.096
LogS:	-3.972
# Rotatable Bonds:	5
TPSA:	88.02
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	3.612
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	8.459010132355615e-06
Pgp-inhibitor:	0.926
Pgp-substrate:	0.176
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.367
Plasma Protein Binding (PPB):	94.81195831298828%
Volume Distribution (VD):	1.019
Pgp-substrate:	5.691539287567139%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.367
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.712
CYP2D6-inhibitor:	0.406
CYP2D6-substrate:	0.636
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	1.834
Half-life (T1/2):	0.491

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.446
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.913
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.166

Download Data

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

Natural Product: NPC168153

Natural Product ID:	NPC168153
*Common Name:**	Peniprequinolone
IUPAC Name:	(3R,4R)-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)-1,3-dihydroquinolin-2-one
Synonyms:	Peniprequinolone
Standard InCHIKey:	ZRZQXSGEIJXJEO-RBBKRZOGSA-N
Standard InCHI:	InChI=1S/C22H25NO5/c1-13(2)5-6-14-7-12-17-18(19(14)24)22(26,20(28-4)21(25)23-17)15-8-10-16(27-3)11-9-15/h5,7-12,20,24,26H,6H2,1-4H3,(H,23,25)/t20-,22+/m0/s1
SMILES:	CC(=CCc1ccc2c(c1O)[C@](c1ccc(cc1)OC)([C@H](C(=N2)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516699
PubChem CID:	16681748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	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
Others	4
Potency	12

Activity Type	# Activity
Cell Line	4
Individual Protein	9
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	8.4	%	PMID[537020]
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	30.8	%	PMID[537020]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Activity	=	20.2	%	PMID[537020]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	4.0	%	PMID[537020]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	22387.2	nM	PMID[537021]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	251.2	nM	PMID[537021]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	12589.3	nM	PMID[537021]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[537021]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[537021]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	100.0	nM	PMID[537021]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[537021]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[537021]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[537021]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[537021]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[537021]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[537021]

☑ 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 NPC168153 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	346
0.1-0.2	1522
0.2-0.3	7006
0.3-0.4	10684
0.4-0.5	5529
0.5-0.6	13573
0.6-0.7	3896
0.7-0.8	118
0.8-0.85	16
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9299	High Similarity	NPC291359
0.925	High Similarity	NPC19555
0.9051	High Similarity	NPC10730
0.9051	High Similarity	NPC10875
0.9018	High Similarity	NPC257354
0.8981	High Similarity	NPC184161
0.8588	High Similarity	NPC472331
0.8588	High Similarity	NPC126515
0.8588	High Similarity	NPC274002
0.8061	Intermediate Similarity	NPC219383
0.8045	Intermediate Similarity	NPC180253
0.8045	Intermediate Similarity	NPC219170
0.8034	Intermediate Similarity	NPC28425
0.8023	Intermediate Similarity	NPC192939
0.8023	Intermediate Similarity	NPC215747
0.8	Intermediate Similarity	NPC22928
0.7978	Intermediate Similarity	NPC119579
0.7966	Intermediate Similarity	NPC260118
0.7933	Intermediate Similarity	NPC276060
0.7921	Intermediate Similarity	NPC311936
0.791	Intermediate Similarity	NPC265383
0.7819	Intermediate Similarity	NPC472329
0.7819	Intermediate Similarity	NPC472330
0.7778	Intermediate Similarity	NPC235628
0.7772	Intermediate Similarity	NPC294244
0.774	Intermediate Similarity	NPC231371
0.7663	Intermediate Similarity	NPC112676
0.7663	Intermediate Similarity	NPC296742
0.7614	Intermediate Similarity	NPC68328
0.7609	Intermediate Similarity	NPC224293
0.7594	Intermediate Similarity	NPC29472
0.7554	Intermediate Similarity	NPC69213
0.7552	Intermediate Similarity	NPC159101
0.7544	Intermediate Similarity	NPC275027
0.7532	Intermediate Similarity	NPC197680
0.7532	Intermediate Similarity	NPC259098
0.7528	Intermediate Similarity	NPC225381
0.75	Intermediate Similarity	NPC9475
0.7471	Intermediate Similarity	NPC306366
0.7443	Intermediate Similarity	NPC204179
0.7429	Intermediate Similarity	NPC329837
0.7374	Intermediate Similarity	NPC310894
0.7371	Intermediate Similarity	NPC206736
0.7371	Intermediate Similarity	NPC195766
0.7351	Intermediate Similarity	NPC313886
0.7349	Intermediate Similarity	NPC314113
0.733	Intermediate Similarity	NPC200888
0.7326	Intermediate Similarity	NPC320088
0.7297	Intermediate Similarity	NPC62069
0.7296	Intermediate Similarity	NPC476106
0.7268	Intermediate Similarity	NPC316161
0.725	Intermediate Similarity	NPC116178
0.7249	Intermediate Similarity	NPC28510
0.724	Intermediate Similarity	NPC70956
0.724	Intermediate Similarity	NPC243834
0.7236	Intermediate Similarity	NPC25961
0.7233	Intermediate Similarity	NPC325013
0.7231	Intermediate Similarity	NPC475085
0.7231	Intermediate Similarity	NPC291535
0.7231	Intermediate Similarity	NPC475112
0.7219	Intermediate Similarity	NPC33902
0.7219	Intermediate Similarity	NPC276674
0.7214	Intermediate Similarity	NPC217903
0.7213	Intermediate Similarity	NPC474051
0.7173	Intermediate Similarity	NPC279401
0.7173	Intermediate Similarity	NPC79293
0.7169	Intermediate Similarity	NPC166667
0.7157	Intermediate Similarity	NPC164374
0.7157	Intermediate Similarity	NPC137929
0.7152	Intermediate Similarity	NPC92805
0.7135	Intermediate Similarity	NPC72291
0.7129	Intermediate Similarity	NPC321166
0.7126	Intermediate Similarity	NPC262585
0.7126	Intermediate Similarity	NPC18189
0.7126	Intermediate Similarity	NPC20829
0.7108	Intermediate Similarity	NPC117048
0.7108	Intermediate Similarity	NPC124085
0.7097	Intermediate Similarity	NPC190461
0.7088	Intermediate Similarity	NPC474931
0.7088	Intermediate Similarity	NPC81218
0.7088	Intermediate Similarity	NPC117188
0.7088	Intermediate Similarity	NPC12053
0.7088	Intermediate Similarity	NPC306555
0.7088	Intermediate Similarity	NPC205421
0.7088	Intermediate Similarity	NPC158376
0.7088	Intermediate Similarity	NPC145832
0.7083	Intermediate Similarity	NPC78284
0.7073	Intermediate Similarity	NPC313466
0.7049	Intermediate Similarity	NPC182257
0.7048	Intermediate Similarity	NPC85435
0.7039	Intermediate Similarity	NPC57105
0.7033	Intermediate Similarity	NPC90984
0.7031	Intermediate Similarity	NPC114335
0.7031	Intermediate Similarity	NPC141915
0.7031	Intermediate Similarity	NPC280964
0.703	Intermediate Similarity	NPC103799
0.7029	Intermediate Similarity	NPC276665
0.7029	Intermediate Similarity	NPC265473
0.7027	Intermediate Similarity	NPC289743
0.7027	Intermediate Similarity	NPC110374
0.7026	Intermediate Similarity	NPC72211
0.7024	Intermediate Similarity	NPC3049
0.7017	Intermediate Similarity	NPC1229
0.7015	Intermediate Similarity	NPC168250
0.7	Intermediate Similarity	NPC193777
0.7	Intermediate Similarity	NPC198160
0.6995	Remote Similarity	NPC48353
0.6983	Remote Similarity	NPC231862
0.6983	Remote Similarity	NPC156348
0.6982	Remote Similarity	NPC299583
0.6982	Remote Similarity	NPC474687
0.6979	Remote Similarity	NPC475411
0.6979	Remote Similarity	NPC469390
0.6978	Remote Similarity	NPC253043
0.6978	Remote Similarity	NPC196447
0.6978	Remote Similarity	NPC136508
0.6978	Remote Similarity	NPC306843
0.6978	Remote Similarity	NPC96603
0.6978	Remote Similarity	NPC212794
0.6978	Remote Similarity	NPC13504
0.6978	Remote Similarity	NPC78222
0.6978	Remote Similarity	NPC477563
0.6973	Remote Similarity	NPC239775
0.6973	Remote Similarity	NPC477115
0.6971	Remote Similarity	NPC477532
0.6971	Remote Similarity	NPC329830
0.697	Remote Similarity	NPC66815
0.6966	Remote Similarity	NPC87363
0.6965	Remote Similarity	NPC470931
0.6964	Remote Similarity	NPC126637
0.6963	Remote Similarity	NPC477186
0.6961	Remote Similarity	NPC79402
0.6961	Remote Similarity	NPC80759
0.6957	Remote Similarity	NPC474160
0.6954	Remote Similarity	NPC115144
0.6954	Remote Similarity	NPC277857
0.6952	Remote Similarity	NPC115343
0.6952	Remote Similarity	NPC1291
0.6951	Remote Similarity	NPC222572
0.6951	Remote Similarity	NPC87224
0.6946	Remote Similarity	NPC218530
0.6944	Remote Similarity	NPC69360
0.6941	Remote Similarity	NPC475836
0.694	Remote Similarity	NPC264850
0.694	Remote Similarity	NPC13916
0.6936	Remote Similarity	NPC313414
0.6935	Remote Similarity	NPC228040
0.6935	Remote Similarity	NPC192135
0.6935	Remote Similarity	NPC477020
0.6935	Remote Similarity	NPC285941
0.6935	Remote Similarity	NPC66341
0.6935	Remote Similarity	NPC162484
0.6928	Remote Similarity	NPC93882
0.6928	Remote Similarity	NPC211413
0.6928	Remote Similarity	NPC118683
0.6928	Remote Similarity	NPC162801
0.6928	Remote Similarity	NPC164804
0.6928	Remote Similarity	NPC244888
0.6928	Remote Similarity	NPC130595
0.6928	Remote Similarity	NPC68205
0.6928	Remote Similarity	NPC293203
0.6923	Remote Similarity	NPC160607
0.6923	Remote Similarity	NPC41473
0.6923	Remote Similarity	NPC312770
0.6923	Remote Similarity	NPC324144
0.6923	Remote Similarity	NPC14600
0.6923	Remote Similarity	NPC70259
0.6923	Remote Similarity	NPC204848
0.6919	Remote Similarity	NPC168753
0.6919	Remote Similarity	NPC118274
0.6919	Remote Similarity	NPC178466
0.6919	Remote Similarity	NPC63628
0.6914	Remote Similarity	NPC95733
0.6914	Remote Similarity	NPC471032
0.6914	Remote Similarity	NPC470935
0.6914	Remote Similarity	NPC62101
0.6912	Remote Similarity	NPC203168
0.6911	Remote Similarity	NPC66083
0.6909	Remote Similarity	NPC134360
0.6906	Remote Similarity	NPC271388
0.6906	Remote Similarity	NPC205255
0.6906	Remote Similarity	NPC119649
0.6906	Remote Similarity	NPC230956
0.6906	Remote Similarity	NPC235143
0.6905	Remote Similarity	NPC115335
0.6905	Remote Similarity	NPC223008
0.6905	Remote Similarity	NPC97834
0.6905	Remote Similarity	NPC296915
0.6905	Remote Similarity	NPC198154
0.6905	Remote Similarity	NPC225696
0.6902	Remote Similarity	NPC304846
0.69	Remote Similarity	NPC313112
0.69	Remote Similarity	NPC301292
0.6897	Remote Similarity	NPC219664
0.6894	Remote Similarity	NPC471314
0.6894	Remote Similarity	NPC471315
0.6893	Remote Similarity	NPC52475
0.6888	Remote Similarity	NPC234318
0.6886	Remote Similarity	NPC285078
0.6886	Remote Similarity	NPC13005

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 NPC168153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	700
0.2-0.3	937
0.3-0.4	1938
0.4-0.5	2518
0.5-0.6	2263
0.6-0.7	539
0.7-0.8	26
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
0.8182	Intermediate Similarity	NPD5617	Suspended
0.7917	Intermediate Similarity	NPD3778	Approved
0.7796	Intermediate Similarity	NPD4605	Approved
0.7796	Intermediate Similarity	NPD4604	Approved
0.7771	Intermediate Similarity	NPD2215	Approved
0.7771	Intermediate Similarity	NPD2216	Approved
0.7647	Intermediate Similarity	NPD3296	Phase 1
0.7514	Intermediate Similarity	NPD6184	Discontinued
0.7427	Intermediate Similarity	NPD4003	Phase 3
0.7396	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3453	Discontinued
0.738	Intermediate Similarity	NPD2843	Phase 2
0.738	Intermediate Similarity	NPD2845	Phase 2
0.736	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3236	Phase 3
0.7299	Intermediate Similarity	NPD6072	Discontinued
0.7299	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5811	Approved
0.72	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6296	Discontinued
0.7172	Intermediate Similarity	NPD7263	Phase 2
0.7143	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3793	Phase 3
0.7068	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6331	Phase 2
0.7	Intermediate Similarity	NPD4951	Discontinued
0.7	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7125	Discontinued
0.6989	Remote Similarity	NPD7479	Phase 2
0.6989	Remote Similarity	NPD4005	Discontinued
0.6983	Remote Similarity	NPD3556	Approved
0.6983	Remote Similarity	NPD3557	Approved
0.6983	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3558	Approved
0.6983	Remote Similarity	NPD6063	Approved
0.6983	Remote Similarity	NPD3560	Approved
0.6966	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3634	Approved
0.6943	Remote Similarity	NPD3633	Approved
0.6935	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2883	Discontinued
0.6928	Remote Similarity	NPD2674	Phase 3
0.6928	Remote Similarity	NPD7477	Discontinued
0.6923	Remote Similarity	NPD1850	Phase 3
0.6923	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5984	Phase 2
0.6906	Remote Similarity	NPD4055	Discovery
0.6902	Remote Similarity	NPD4083	Discontinued
0.6898	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2821	Approved
0.6878	Remote Similarity	NPD4012	Approved
0.6872	Remote Similarity	NPD4771	Phase 2
0.6862	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD3119	Phase 1
0.6823	Remote Similarity	NPD3120	Approved
0.6821	Remote Similarity	NPD5150	Phase 2
0.6802	Remote Similarity	NPD5652	Approved
0.6802	Remote Similarity	NPD5650	Approved
0.6802	Remote Similarity	NPD5651	Approved
0.6791	Remote Similarity	NPD8067	Phase 3
0.6771	Remote Similarity	NPD5565	Discontinued
0.6769	Remote Similarity	NPD5937	Approved
0.6769	Remote Similarity	NPD3963	Phase 1
0.6769	Remote Similarity	NPD5587	Approved
0.6766	Remote Similarity	NPD3145	Approved
0.6766	Remote Similarity	NPD3144	Approved
0.6761	Remote Similarity	NPD4123	Phase 3
0.676	Remote Similarity	NPD4675	Approved
0.676	Remote Similarity	NPD4678	Approved
0.6755	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7546	Discontinued
0.6753	Remote Similarity	NPD3342	Phase 2
0.674	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3515	Approved
0.6716	Remote Similarity	NPD3516	Approved
0.6702	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2802	Phase 3
0.6701	Remote Similarity	NPD3398	Discontinued
0.6701	Remote Similarity	NPD4523	Approved
0.6686	Remote Similarity	NPD2238	Phase 2
0.6685	Remote Similarity	NPD4433	Discontinued
0.6684	Remote Similarity	NPD3823	Discontinued
0.6684	Remote Similarity	NPD4740	Approved
0.6684	Remote Similarity	NPD3601	Discontinued
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7628	Phase 3
0.6667	Remote Similarity	NPD7773	Phase 2
0.6667	Remote Similarity	NPD7630	Phase 3
0.6667	Remote Similarity	NPD5582	Discontinued
0.665	Remote Similarity	NPD7262	Phase 1
0.665	Remote Similarity	NPD6874	Approved
0.6649	Remote Similarity	NPD1411	Approved
0.6649	Remote Similarity	NPD1413	Approved
0.6649	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1414	Approved
0.6648	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1669	Approved
0.6633	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2789	Approved
0.663	Remote Similarity	NPD8070	Approved
0.6627	Remote Similarity	NPD839	Approved
0.6627	Remote Similarity	NPD840	Approved
0.6618	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3003	Approved
0.6617	Remote Similarity	NPD6612	Phase 2
0.6615	Remote Similarity	NPD7906	Approved
0.6615	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1898	Discontinued
0.6612	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6357	Discontinued
0.6609	Remote Similarity	NPD4598	Approved
0.6609	Remote Similarity	NPD4597	Approved
0.6608	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3027	Phase 3
0.6597	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7311	Approved
0.658	Remote Similarity	NPD7313	Approved
0.658	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7310	Approved
0.658	Remote Similarity	NPD7312	Approved
0.6579	Remote Similarity	NPD3965	Phase 1
0.6575	Remote Similarity	NPD6494	Phase 2
0.6567	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3037	Phase 1
0.6559	Remote Similarity	NPD3251	Approved
0.6557	Remote Similarity	NPD5773	Approved
0.6557	Remote Similarity	NPD5772	Approved
0.6557	Remote Similarity	NPD5929	Approved
0.6556	Remote Similarity	NPD814	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6034	Phase 2
0.6548	Remote Similarity	NPD5641	Discontinued
0.6548	Remote Similarity	NPD4908	Phase 1
0.6546	Remote Similarity	NPD8053	Approved
0.6546	Remote Similarity	NPD7309	Approved
0.6546	Remote Similarity	NPD8054	Approved
0.6545	Remote Similarity	NPD3920	Phase 2
0.6545	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2970	Approved
0.6543	Remote Similarity	NPD2388	Discontinued
0.6543	Remote Similarity	NPD2969	Approved
0.6541	Remote Similarity	NPD955	Approved
0.6538	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4502	Phase 2
0.6538	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2366	Approved
0.6536	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD52	Approved
0.6536	Remote Similarity	NPD7526	Approved
0.6536	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4108	Discontinued
0.6531	Remote Similarity	NPD3490	Discontinued
0.6531	Remote Similarity	NPD1339	Discontinued
0.6528	Remote Similarity	NPD7883	Discontinued
0.6528	Remote Similarity	NPD2166	Phase 3
0.6524	Remote Similarity	NPD5903	Approved
0.6524	Remote Similarity	NPD5902	Approved
0.6522	Remote Similarity	NPD2415	Discontinued
0.6522	Remote Similarity	NPD5599	Discontinued
0.6517	Remote Similarity	NPD7213	Phase 3
0.6517	Remote Similarity	NPD7212	Phase 2
0.6513	Remote Similarity	NPD6340	Approved
0.6513	Remote Similarity	NPD6339	Approved
0.6513	Remote Similarity	NPD4375	Approved
0.651	Remote Similarity	NPD7007	Discovery
0.651	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD27	Approved
0.6508	Remote Similarity	NPD2489	Approved
0.6508	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7584	Approved
0.6503	Remote Similarity	NPD2668	Approved
0.6503	Remote Similarity	NPD2667	Approved
0.65	Remote Similarity	NPD7558	Phase 2
0.6495	Remote Similarity	NPD4577	Approved
0.6495	Remote Similarity	NPD4578	Approved
0.6494	Remote Similarity	NPD2161	Phase 2
0.6491	Remote Similarity	NPD1613	Approved
0.6491	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3051	Approved
0.6486	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3538	Suspended

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