NPASS Compound

Structure

NPC10875 OpenBabel07101718322D 21 23 0 0 1 0 0 0 0 0999 V2000 6.9659 -0.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7593 0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1889 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6850 0.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1146 -0.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5112 -0.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3626 0.0338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8299 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -0.9583 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 2.4898 0.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5348 -1.9085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2883 0.2818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 12 2 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 10 2 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 1 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.1
Volume:	287.325
LogP:	1.894
LogD:	1.78
LogS:	-3.384
# Rotatable Bonds:	2
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.776
Synthetic Accessibility Score:	3.079
Fsp3:	0.188
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:	-4.983
MDCK Permeability:	1.0205849321209826e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.549
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.244
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	79.45328521728516%
Volume Distribution (VD):	0.71
Pgp-substrate:	18.506267547607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.311
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.707
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.755

ADMET: Excretion

Clearance (CL):	1.244
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.652
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.111
Skin Sensitization:	0.367
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC10875

Natural Product ID:	NPC10875
*Common Name:**	3S,4R-Dihydroxy-4-(4'-Methoxyphenyl)-3,4-Dihydro-2(1H)-Quinolinone
IUPAC Name:	(3S,4R)-3,4-dihydroxy-4-(4-methoxyphenyl)-1,3-dihydroquinolin-2-one
Synonyms:
Standard InCHIKey:	VJLVPUFVTPJHDI-GDBMZVCRSA-N
Standard InCHI:	InChI=1S/C16H15NO4/c1-21-11-8-6-10(7-9-11)16(20)12-4-2-3-5-13(12)17-15(19)14(16)18/h2-9,14,18,20H,1H3,(H,17,19)/t14-,16-/m1/s1
SMILES:	COc1ccc(cc1)[C@]1(c2ccccc2N=C([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465969
PubChem CID:	11536531
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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	52.9	%	PMID[467943]
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	50.6	%	PMID[467943]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Activity	=	44.6	%	PMID[467943]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	58.8	%	PMID[467943]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	56.3	%	PMID[467943]
NPT308	Cell Line	CAKI-1	Homo sapiens	Activity	=	80.3	%	PMID[467943]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	Activity	=	55.2	%	PMID[467943]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	52.4	%	PMID[467943]

☑ 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 NPC10875 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	269
0.1-0.2	1392
0.2-0.3	6228
0.3-0.4	11088
0.4-0.5	5605
0.5-0.6	14120
0.6-0.7	3828
0.7-0.8	155
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10730
0.9051	High Similarity	NPC168153
0.8627	High Similarity	NPC184161
0.8354	Intermediate Similarity	NPC291359
0.8333	Intermediate Similarity	NPC197680
0.8333	Intermediate Similarity	NPC259098
0.8323	Intermediate Similarity	NPC19555
0.8221	Intermediate Similarity	NPC257354
0.8075	Intermediate Similarity	NPC235628
0.7925	Intermediate Similarity	NPC219383
0.7755	Intermediate Similarity	NPC325013
0.7742	Intermediate Similarity	NPC314113
0.7733	Intermediate Similarity	NPC260118
0.7719	Intermediate Similarity	NPC126515
0.7719	Intermediate Similarity	NPC274002
0.7719	Intermediate Similarity	NPC472331
0.7719	Intermediate Similarity	NPC316161
0.7701	Intermediate Similarity	NPC28425
0.7697	Intermediate Similarity	NPC57105
0.7688	Intermediate Similarity	NPC215747
0.7688	Intermediate Similarity	NPC192939
0.7674	Intermediate Similarity	NPC265383
0.7644	Intermediate Similarity	NPC119579
0.7636	Intermediate Similarity	NPC231862
0.7614	Intermediate Similarity	NPC219170
0.7614	Intermediate Similarity	NPC180253
0.76	Intermediate Similarity	NPC313886
0.76	Intermediate Similarity	NPC276060
0.7586	Intermediate Similarity	NPC311936
0.7571	Intermediate Similarity	NPC22928
0.7566	Intermediate Similarity	NPC313466
0.7517	Intermediate Similarity	NPC95733
0.7517	Intermediate Similarity	NPC62101
0.7467	Intermediate Similarity	NPC29477
0.743	Intermediate Similarity	NPC296742
0.7425	Intermediate Similarity	NPC306366
0.7391	Intermediate Similarity	NPC313414
0.7383	Intermediate Similarity	NPC471314
0.7383	Intermediate Similarity	NPC471315
0.7381	Intermediate Similarity	NPC69360
0.7381	Intermediate Similarity	NPC329837
0.7374	Intermediate Similarity	NPC224293
0.7356	Intermediate Similarity	NPC9475
0.7348	Intermediate Similarity	NPC294244
0.7345	Intermediate Similarity	NPC62069
0.7333	Intermediate Similarity	NPC112676
0.7333	Intermediate Similarity	NPC211218
0.7326	Intermediate Similarity	NPC159101
0.7318	Intermediate Similarity	NPC69213
0.7308	Intermediate Similarity	NPC79293
0.7308	Intermediate Similarity	NPC279401
0.7299	Intermediate Similarity	NPC231371
0.7294	Intermediate Similarity	NPC204179
0.7289	Intermediate Similarity	NPC275027
0.7278	Intermediate Similarity	NPC312770
0.7278	Intermediate Similarity	NPC14600
0.7278	Intermediate Similarity	NPC204848
0.7278	Intermediate Similarity	NPC160607
0.7278	Intermediate Similarity	NPC41473
0.7268	Intermediate Similarity	NPC29472
0.7267	Intermediate Similarity	NPC63628
0.7267	Intermediate Similarity	NPC68328
0.7267	Intermediate Similarity	NPC178466
0.7251	Intermediate Similarity	NPC314861
0.7233	Intermediate Similarity	NPC299583
0.7225	Intermediate Similarity	NPC310894
0.7215	Intermediate Similarity	NPC126637
0.7209	Intermediate Similarity	NPC54125
0.7209	Intermediate Similarity	NPC89199
0.7197	Intermediate Similarity	NPC218530
0.7179	Intermediate Similarity	NPC93882
0.7179	Intermediate Similarity	NPC130595
0.7152	Intermediate Similarity	NPC470935
0.7152	Intermediate Similarity	NPC471032
0.7134	Intermediate Similarity	NPC313737
0.7134	Intermediate Similarity	NPC6854
0.7134	Intermediate Similarity	NPC285078
0.7126	Intermediate Similarity	NPC304846
0.7118	Intermediate Similarity	NPC206736
0.7118	Intermediate Similarity	NPC195766
0.7115	Intermediate Similarity	NPC114102
0.7114	Intermediate Similarity	NPC43275
0.7104	Intermediate Similarity	NPC28510
0.7102	Intermediate Similarity	NPC477115
0.7091	Intermediate Similarity	NPC115144
0.7091	Intermediate Similarity	NPC277857
0.709	Intermediate Similarity	NPC311357
0.7086	Intermediate Similarity	NPC225381
0.7086	Intermediate Similarity	NPC182257
0.7073	Intermediate Similarity	NPC473769
0.707	Intermediate Similarity	NPC214869
0.7069	Intermediate Similarity	NPC477888
0.7067	Intermediate Similarity	NPC160120
0.7067	Intermediate Similarity	NPC471308
0.7067	Intermediate Similarity	NPC41801
0.7067	Intermediate Similarity	NPC289330
0.7067	Intermediate Similarity	NPC17388
0.7067	Intermediate Similarity	NPC53596
0.7055	Intermediate Similarity	NPC264782
0.7045	Intermediate Similarity	NPC474953
0.7041	Intermediate Similarity	NPC112766
0.7037	Intermediate Similarity	NPC472330
0.7037	Intermediate Similarity	NPC472329
0.7033	Intermediate Similarity	NPC66083
0.7032	Intermediate Similarity	NPC251571
0.703	Intermediate Similarity	NPC245974
0.702	Intermediate Similarity	NPC83279
0.7019	Intermediate Similarity	NPC296898
0.7018	Intermediate Similarity	NPC156348
0.7016	Intermediate Similarity	NPC164374
0.7016	Intermediate Similarity	NPC137929
0.7011	Intermediate Similarity	NPC469390
0.7006	Intermediate Similarity	NPC288943
0.7006	Intermediate Similarity	NPC255550
0.7006	Intermediate Similarity	NPC308885
0.7	Intermediate Similarity	NPC70549
0.7	Intermediate Similarity	NPC87363
0.7	Intermediate Similarity	NPC166667
0.7	Intermediate Similarity	NPC474077
0.6995	Remote Similarity	NPC320088
0.6995	Remote Similarity	NPC217294
0.6994	Remote Similarity	NPC70172
0.6993	Remote Similarity	NPC474160
0.6993	Remote Similarity	NPC315632
0.698	Remote Similarity	NPC323948
0.6977	Remote Similarity	NPC92191
0.6977	Remote Similarity	NPC72291
0.6977	Remote Similarity	NPC59028
0.6975	Remote Similarity	NPC212850
0.6975	Remote Similarity	NPC189724
0.6975	Remote Similarity	NPC83289
0.697	Remote Similarity	NPC5462
0.6968	Remote Similarity	NPC301713
0.6966	Remote Similarity	NPC110374
0.6966	Remote Similarity	NPC289743
0.6966	Remote Similarity	NPC283152
0.6964	Remote Similarity	NPC276665
0.6964	Remote Similarity	NPC265473
0.6962	Remote Similarity	NPC471953
0.6961	Remote Similarity	NPC474607
0.6954	Remote Similarity	NPC263835
0.6954	Remote Similarity	NPC321133
0.6954	Remote Similarity	NPC127362
0.6946	Remote Similarity	NPC135538
0.6946	Remote Similarity	NPC24233
0.6946	Remote Similarity	NPC428
0.6946	Remote Similarity	NPC147390
0.6946	Remote Similarity	NPC246587
0.6946	Remote Similarity	NPC476571
0.6943	Remote Similarity	NPC52029
0.6943	Remote Similarity	NPC195749
0.6943	Remote Similarity	NPC35961
0.6937	Remote Similarity	NPC64205
0.6936	Remote Similarity	NPC205167
0.6936	Remote Similarity	NPC249274
0.6935	Remote Similarity	NPC469594
0.6933	Remote Similarity	NPC195814
0.6923	Remote Similarity	NPC474650
0.6923	Remote Similarity	NPC127402
0.6923	Remote Similarity	NPC52475
0.6923	Remote Similarity	NPC5428
0.6923	Remote Similarity	NPC165045
0.6923	Remote Similarity	NPC118533
0.6914	Remote Similarity	NPC36434
0.6913	Remote Similarity	NPC258992
0.6909	Remote Similarity	NPC247298
0.6905	Remote Similarity	NPC114659
0.6905	Remote Similarity	NPC139699
0.6903	Remote Similarity	NPC148627
0.6902	Remote Similarity	NPC477186
0.6901	Remote Similarity	NPC26850
0.6897	Remote Similarity	NPC24954
0.6897	Remote Similarity	NPC474272
0.6893	Remote Similarity	NPC66573
0.6891	Remote Similarity	NPC476106
0.6889	Remote Similarity	NPC1291
0.6889	Remote Similarity	NPC115343
0.6886	Remote Similarity	NPC191376
0.6886	Remote Similarity	NPC179825
0.6886	Remote Similarity	NPC321505
0.6885	Remote Similarity	NPC61350
0.6885	Remote Similarity	NPC276674
0.6885	Remote Similarity	NPC33902
0.6883	Remote Similarity	NPC471693
0.6882	Remote Similarity	NPC18614
0.6879	Remote Similarity	NPC245826
0.6879	Remote Similarity	NPC155838
0.6879	Remote Similarity	NPC470084
0.6879	Remote Similarity	NPC252307
0.6879	Remote Similarity	NPC474178
0.6875	Remote Similarity	NPC264850
0.6875	Remote Similarity	NPC251306
0.6875	Remote Similarity	NPC13916
0.6872	Remote Similarity	NPC228040
0.6872	Remote Similarity	NPC469589
0.6872	Remote Similarity	NPC315631
0.6872	Remote Similarity	NPC474051
0.6871	Remote Similarity	NPC298821
0.6867	Remote Similarity	NPC185838
0.6864	Remote Similarity	NPC274026

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 NPC10875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	668
0.2-0.3	915
0.3-0.4	1578
0.4-0.5	2562
0.5-0.6	2452
0.6-0.7	733
0.7-0.8	50
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
0.8344	Intermediate Similarity	NPD3778	Approved
0.7826	Intermediate Similarity	NPD5617	Suspended
0.7764	Intermediate Similarity	NPD5811	Approved
0.7738	Intermediate Similarity	NPD2216	Approved
0.7738	Intermediate Similarity	NPD2215	Approved
0.7673	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4003	Phase 3
0.7561	Intermediate Similarity	NPD3236	Phase 3
0.7561	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3296	Phase 1
0.7473	Intermediate Similarity	NPD4605	Approved
0.7473	Intermediate Similarity	NPD4604	Approved
0.7455	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3556	Approved
0.7425	Intermediate Similarity	NPD3560	Approved
0.7425	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3558	Approved
0.7425	Intermediate Similarity	NPD3557	Approved
0.7378	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4005	Discontinued
0.7273	Intermediate Similarity	NPD6184	Discontinued
0.7235	Intermediate Similarity	NPD3453	Discontinued
0.7225	Intermediate Similarity	NPD4083	Discontinued
0.7219	Intermediate Similarity	NPD6063	Approved
0.7209	Intermediate Similarity	NPD2821	Approved
0.7209	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2674	Phase 3
0.717	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6331	Phase 2
0.7151	Intermediate Similarity	NPD1850	Phase 3
0.7151	Intermediate Similarity	NPD7546	Discontinued
0.7143	Intermediate Similarity	NPD2845	Phase 2
0.7143	Intermediate Similarity	NPD2843	Phase 2
0.7143	Intermediate Similarity	NPD6072	Discontinued
0.712	Intermediate Similarity	NPD6296	Discontinued
0.712	Intermediate Similarity	NPD7263	Phase 2
0.7073	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7477	Discontinued
0.7066	Intermediate Similarity	NPD2883	Discontinued
0.7056	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6793	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4951	Discontinued
0.7025	Intermediate Similarity	NPD2238	Phase 2
0.7006	Intermediate Similarity	NPD3144	Approved
0.7006	Intermediate Similarity	NPD3145	Approved
0.7	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4123	Phase 3
0.6988	Remote Similarity	NPD681	Clinical (unspecified phase)
0.698	Remote Similarity	NPD254	Approved
0.6973	Remote Similarity	NPD3634	Approved
0.6973	Remote Similarity	NPD3633	Approved
0.6961	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2668	Approved
0.6954	Remote Similarity	NPD2667	Approved
0.6936	Remote Similarity	NPD4055	Discovery
0.6935	Remote Similarity	NPD5150	Phase 2
0.6927	Remote Similarity	NPD7479	Phase 2
0.6919	Remote Similarity	NPD5641	Discontinued
0.6918	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4502	Phase 2
0.6883	Remote Similarity	NPD1669	Approved
0.6883	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4678	Approved
0.6882	Remote Similarity	NPD5587	Approved
0.6882	Remote Similarity	NPD4675	Approved
0.6872	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5582	Discontinued
0.686	Remote Similarity	NPD6738	Phase 2
0.686	Remote Similarity	NPD6737	Phase 2
0.686	Remote Similarity	NPD5773	Approved
0.686	Remote Similarity	NPD5772	Approved
0.6854	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3037	Phase 1
0.6845	Remote Similarity	NPD52	Approved
0.6845	Remote Similarity	NPD7125	Discontinued
0.6845	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7526	Approved
0.6833	Remote Similarity	NPD3920	Phase 2
0.6833	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6357	Discontinued
0.6821	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4993	Discontinued
0.6811	Remote Similarity	NPD1898	Discontinued
0.681	Remote Similarity	NPD2161	Phase 2
0.6809	Remote Similarity	NPD6590	Discontinued
0.6798	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7773	Phase 2
0.6778	Remote Similarity	NPD3965	Phase 1
0.6778	Remote Similarity	NPD3793	Phase 3
0.6776	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3342	Phase 2
0.6772	Remote Similarity	NPD6550	Discontinued
0.6763	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4203	Approved
0.6758	Remote Similarity	NPD4204	Approved
0.6754	Remote Similarity	NPD6874	Approved
0.675	Remote Similarity	NPD839	Approved
0.675	Remote Similarity	NPD840	Approved
0.6748	Remote Similarity	NPD4108	Discontinued
0.6744	Remote Similarity	NPD2789	Approved
0.6744	Remote Similarity	NPD2366	Approved
0.6738	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3027	Phase 3
0.6728	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7153	Discontinued
0.6727	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4597	Approved
0.6727	Remote Similarity	NPD4598	Approved
0.6723	Remote Similarity	NPD3983	Phase 3
0.6723	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7883	Discontinued
0.6721	Remote Similarity	NPD2802	Phase 3
0.6707	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3301	Approved
0.6707	Remote Similarity	NPD5241	Discontinued
0.6703	Remote Similarity	NPD7007	Discovery
0.6702	Remote Similarity	NPD3963	Phase 1
0.6688	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4103	Phase 2
0.6687	Remote Similarity	NPD3060	Approved
0.6687	Remote Similarity	NPD696	Discontinued
0.6685	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD32	Approved
0.6667	Remote Similarity	NPD31	Approved
0.6667	Remote Similarity	NPD4122	Approved
0.6667	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6283	Phase 2
0.6667	Remote Similarity	NPD4036	Approved
0.6667	Remote Similarity	NPD4033	Approved
0.6667	Remote Similarity	NPD4038	Approved
0.6667	Remote Similarity	NPD5938	Phase 3
0.6667	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4035	Approved
0.6667	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4034	Approved
0.6667	Remote Similarity	NPD4037	Approved
0.6667	Remote Similarity	NPD4039	Approved
0.6649	Remote Similarity	NPD6034	Phase 2
0.6648	Remote Similarity	NPD8070	Approved
0.6647	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7256	Discontinued
0.6631	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5599	Discontinued
0.6629	Remote Similarity	NPD2563	Approved
0.6629	Remote Similarity	NPD2560	Approved
0.6628	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3052	Approved
0.6626	Remote Similarity	NPD3054	Approved
0.6612	Remote Similarity	NPD3823	Discontinued
0.6611	Remote Similarity	NPD3952	Approved
0.6611	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3951	Phase 3
0.6609	Remote Similarity	NPD4433	Discontinued
0.6608	Remote Similarity	NPD6030	Approved
0.6608	Remote Similarity	NPD6031	Approved
0.6606	Remote Similarity	NPD1422	Approved
0.6603	Remote Similarity	NPD2233	Approved
0.6603	Remote Similarity	NPD2232	Approved
0.6603	Remote Similarity	NPD2230	Approved
0.6599	Remote Similarity	NPD7453	Approved
0.6599	Remote Similarity	NPD7222	Phase 2
0.6599	Remote Similarity	NPD7452	Approved
0.6597	Remote Similarity	NPD5512	Phase 3
0.659	Remote Similarity	NPD3538	Suspended
0.659	Remote Similarity	NPD6502	Phase 2
0.6588	Remote Similarity	NPD4584	Approved
0.6588	Remote Similarity	NPD2874	Phase 2
0.6587	Remote Similarity	NPD2460	Phase 3
0.6587	Remote Similarity	NPD4237	Approved
0.6587	Remote Similarity	NPD2458	Approved
0.6587	Remote Similarity	NPD4236	Phase 3
0.6587	Remote Similarity	NPD2459	Approved
0.6584	Remote Similarity	NPD2322	Discovery
0.6582	Remote Similarity	NPD3567	Approved
0.6582	Remote Similarity	NPD3568	Approved
0.6579	Remote Similarity	NPD5984	Phase 2
0.6576	Remote Similarity	NPD3386	Phase 2
0.6576	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3251	Approved
0.6571	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6667	Approved
0.6568	Remote Similarity	NPD6666	Approved
0.6566	Remote Similarity	NPD1375	Discontinued
0.6566	Remote Similarity	NPD3656	Approved
0.6564	Remote Similarity	NPD654	Phase 3
0.6562	Remote Similarity	NPD5872	Discontinued

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