NPASS Compound

Structure

NPC292361 OpenBabel07101718222D 23 26 0 0 1 0 0 0 0 0999 V2000 -3.9927 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8587 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7298 0.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1266 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9927 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9644 1.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1266 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1756 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2727 0.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8587 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 -0.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8598 2.2293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4299 1.3457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 0 0 0 0 2 16 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 6 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 19 2 0 0 0 0 9 5 1 6 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 2 0 0 0 0 13 14 1 0 0 0 0 13 21 1 1 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 17 1 6 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.1
Volume:	295.323
LogP:	-0.241
LogD:	0.124
LogS:	-1.516
# Rotatable Bonds:	2
TPSA:	127.67
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	4.47
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.497
MDCK Permeability:	3.3178143894474488e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.955
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	78.08447265625%
Volume Distribution (VD):	1.011
Pgp-substrate:	21.71799659729004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	9.05
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.896
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.877
Carcinogencity:	0.885
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.248

Download Data

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

Natural Product: NPC292361

Natural Product ID:	NPC292361
*Common Name:**	PYFBXVNGGWCUQY-SEWBAHNZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PYFBXVNGGWCUQY-SEWBAHNZSA-N
Standard InCHI:	InChI=1S/C15H16N2O6/c18-5-9-13(21)14(22)15(23-9)17-4-6-1-2-16-7-3-8(19)12(20)11(17)10(6)7/h3-4,9,13-16,18,21-22H,1-2,5H2/t9-,13-,14-,15-/m1/s1
SMILES:	C1CNC2=CC(=O)C(=O)c3c2c1cn3[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516924
PubChem CID:	44575357
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	South African	n.a.	PMID[15844938]
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38000.0	nM	PMID[478486]

☑ 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 NPC292361 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	266
0.1-0.2	1588
0.2-0.3	11729
0.3-0.4	20958
0.4-0.5	3979
0.5-0.6	2889
0.6-0.7	1209
0.7-0.8	76
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8865	High Similarity	NPC474767
0.8125	Intermediate Similarity	NPC474492
0.8085	Intermediate Similarity	NPC75544
0.8079	Intermediate Similarity	NPC470680
0.8079	Intermediate Similarity	NPC100104
0.8046	Intermediate Similarity	NPC217021
0.8046	Intermediate Similarity	NPC470679
0.7886	Intermediate Similarity	NPC473878
0.7755	Intermediate Similarity	NPC149708
0.7692	Intermediate Similarity	NPC274981
0.7617	Intermediate Similarity	NPC209917
0.7548	Intermediate Similarity	NPC472285
0.7524	Intermediate Similarity	NPC469544
0.7473	Intermediate Similarity	NPC213914
0.7472	Intermediate Similarity	NPC100726
0.7435	Intermediate Similarity	NPC317010
0.7389	Intermediate Similarity	NPC471655
0.7363	Intermediate Similarity	NPC209362
0.7353	Intermediate Similarity	NPC469563
0.7343	Intermediate Similarity	NPC469562
0.7343	Intermediate Similarity	NPC220594
0.7333	Intermediate Similarity	NPC123906
0.733	Intermediate Similarity	NPC469578
0.7308	Intermediate Similarity	NPC251391
0.7259	Intermediate Similarity	NPC473628
0.7238	Intermediate Similarity	NPC229348
0.7238	Intermediate Similarity	NPC102664
0.7228	Intermediate Similarity	NPC477044
0.7228	Intermediate Similarity	NPC477041
0.7222	Intermediate Similarity	NPC154339
0.7222	Intermediate Similarity	NPC475874
0.7211	Intermediate Similarity	NPC262338
0.72	Intermediate Similarity	NPC267343
0.7194	Intermediate Similarity	NPC311282
0.7194	Intermediate Similarity	NPC62510
0.7165	Intermediate Similarity	NPC182940
0.7163	Intermediate Similarity	NPC143075
0.7136	Intermediate Similarity	NPC477416
0.712	Intermediate Similarity	NPC302647
0.7115	Intermediate Similarity	NPC475410
0.7115	Intermediate Similarity	NPC469577
0.7113	Intermediate Similarity	NPC475094
0.7108	Intermediate Similarity	NPC477045
0.7108	Intermediate Similarity	NPC103361
0.7101	Intermediate Similarity	NPC477043
0.7097	Intermediate Similarity	NPC138018
0.7094	Intermediate Similarity	NPC473814
0.7094	Intermediate Similarity	NPC78767
0.7087	Intermediate Similarity	NPC476874
0.7074	Intermediate Similarity	NPC71079
0.7056	Intermediate Similarity	NPC207851
0.7042	Intermediate Similarity	NPC313640
0.7037	Intermediate Similarity	NPC469813
0.7037	Intermediate Similarity	NPC476446
0.7037	Intermediate Similarity	NPC474217
0.7037	Intermediate Similarity	NPC78375
0.7028	Intermediate Similarity	NPC111732
0.7023	Intermediate Similarity	NPC281049
0.7011	Intermediate Similarity	NPC313889
0.7005	Intermediate Similarity	NPC328318
0.7005	Intermediate Similarity	NPC328596
0.6996	Remote Similarity	NPC70155
0.6995	Remote Similarity	NPC93390
0.6995	Remote Similarity	NPC105811
0.699	Remote Similarity	NPC61011
0.699	Remote Similarity	NPC477042
0.699	Remote Similarity	NPC79777
0.699	Remote Similarity	NPC234403
0.6985	Remote Similarity	NPC469359
0.6978	Remote Similarity	NPC467188
0.6974	Remote Similarity	NPC284775
0.6973	Remote Similarity	NPC70406
0.697	Remote Similarity	NPC46895
0.697	Remote Similarity	NPC477003
0.6967	Remote Similarity	NPC478158
0.6965	Remote Similarity	NPC268966
0.6963	Remote Similarity	NPC278366
0.6963	Remote Similarity	NPC127730
0.6951	Remote Similarity	NPC89987
0.695	Remote Similarity	NPC477415
0.695	Remote Similarity	NPC23476
0.695	Remote Similarity	NPC474259
0.695	Remote Similarity	NPC17059
0.6942	Remote Similarity	NPC123395
0.6939	Remote Similarity	NPC283219
0.6938	Remote Similarity	NPC25442
0.6938	Remote Similarity	NPC12944
0.6931	Remote Similarity	NPC476460
0.6927	Remote Similarity	NPC74153
0.6927	Remote Similarity	NPC167710
0.6927	Remote Similarity	NPC227582
0.6916	Remote Similarity	NPC472291
0.6912	Remote Similarity	NPC135950
0.6911	Remote Similarity	NPC85918
0.6909	Remote Similarity	NPC475498
0.6909	Remote Similarity	NPC475137
0.6905	Remote Similarity	NPC317373
0.69	Remote Similarity	NPC315555
0.6893	Remote Similarity	NPC317672
0.6893	Remote Similarity	NPC59033
0.6893	Remote Similarity	NPC476143
0.6888	Remote Similarity	NPC83774
0.6887	Remote Similarity	NPC472070
0.6887	Remote Similarity	NPC472752
0.6887	Remote Similarity	NPC162860
0.6881	Remote Similarity	NPC14686
0.6881	Remote Similarity	NPC469489
0.6878	Remote Similarity	NPC473506
0.6872	Remote Similarity	NPC156044
0.6872	Remote Similarity	NPC46225
0.6869	Remote Similarity	NPC110182
0.6869	Remote Similarity	NPC151976
0.6869	Remote Similarity	NPC191415
0.6864	Remote Similarity	NPC76565
0.6864	Remote Similarity	NPC64216
0.6864	Remote Similarity	NPC229893
0.6863	Remote Similarity	NPC304203
0.6863	Remote Similarity	NPC326422
0.686	Remote Similarity	NPC74413
0.6857	Remote Similarity	NPC88115
0.6857	Remote Similarity	NPC327592
0.6853	Remote Similarity	NPC126709
0.6853	Remote Similarity	NPC248041
0.6853	Remote Similarity	NPC141377
0.6847	Remote Similarity	NPC114974
0.6842	Remote Similarity	NPC472207
0.684	Remote Similarity	NPC127677
0.6839	Remote Similarity	NPC319456
0.6837	Remote Similarity	NPC317752
0.6835	Remote Similarity	NPC269270
0.6834	Remote Similarity	NPC159125
0.6834	Remote Similarity	NPC102755
0.6829	Remote Similarity	NPC20593
0.6827	Remote Similarity	NPC252338
0.6827	Remote Similarity	NPC79223
0.6825	Remote Similarity	NPC472065
0.6818	Remote Similarity	NPC73994
0.6816	Remote Similarity	NPC470486
0.6816	Remote Similarity	NPC471977
0.6816	Remote Similarity	NPC235684
0.6816	Remote Similarity	NPC475644
0.6816	Remote Similarity	NPC471190
0.6814	Remote Similarity	NPC170751
0.6812	Remote Similarity	NPC472284
0.6806	Remote Similarity	NPC478157
0.6802	Remote Similarity	NPC84827
0.6802	Remote Similarity	NPC14113
0.6802	Remote Similarity	NPC145885
0.6796	Remote Similarity	NPC77061
0.6794	Remote Similarity	NPC328559
0.6794	Remote Similarity	NPC32451
0.6792	Remote Similarity	NPC54420
0.6791	Remote Similarity	NPC318299
0.6786	Remote Similarity	NPC203468
0.6786	Remote Similarity	NPC110500
0.6786	Remote Similarity	NPC149155
0.6784	Remote Similarity	NPC71037
0.678	Remote Similarity	NPC477414
0.678	Remote Similarity	NPC472210
0.678	Remote Similarity	NPC225622
0.678	Remote Similarity	NPC473821
0.678	Remote Similarity	NPC472295
0.678	Remote Similarity	NPC221726
0.678	Remote Similarity	NPC269886
0.678	Remote Similarity	NPC247735
0.678	Remote Similarity	NPC81802
0.6779	Remote Similarity	NPC81535
0.6779	Remote Similarity	NPC284338
0.6771	Remote Similarity	NPC476110
0.6771	Remote Similarity	NPC475600
0.6771	Remote Similarity	NPC87152
0.6771	Remote Similarity	NPC475631
0.6769	Remote Similarity	NPC273532
0.6768	Remote Similarity	NPC55772
0.6763	Remote Similarity	NPC329024
0.6762	Remote Similarity	NPC472063
0.6762	Remote Similarity	NPC260900
0.6762	Remote Similarity	NPC155143
0.6762	Remote Similarity	NPC472062
0.6762	Remote Similarity	NPC106757
0.6762	Remote Similarity	NPC472069
0.6759	Remote Similarity	NPC54744
0.6757	Remote Similarity	NPC473850
0.6751	Remote Similarity	NPC267885
0.675	Remote Similarity	NPC469358
0.6749	Remote Similarity	NPC321708
0.6748	Remote Similarity	NPC202812
0.6745	Remote Similarity	NPC472287
0.6745	Remote Similarity	NPC472064
0.6745	Remote Similarity	NPC472286
0.6745	Remote Similarity	NPC313280
0.6744	Remote Similarity	NPC82370
0.6743	Remote Similarity	NPC249428
0.6741	Remote Similarity	NPC475362
0.6736	Remote Similarity	NPC233380
0.6736	Remote Similarity	NPC42372
0.6735	Remote Similarity	NPC477976
0.6731	Remote Similarity	NPC320748
0.6731	Remote Similarity	NPC324245
0.673	Remote Similarity	NPC317701

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 NPC292361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	471
0.2-0.3	864
0.3-0.4	2246
0.4-0.5	3057
0.5-0.6	1963
0.6-0.7	374
0.7-0.8	12
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
0.7233	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1643	Phase 3
0.7143	Intermediate Similarity	NPD1096	Discontinued
0.7128	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2510	Approved
0.7081	Intermediate Similarity	NPD2509	Approved
0.7059	Intermediate Similarity	NPD2214	Approved
0.7059	Intermediate Similarity	NPD2213	Approved
0.7056	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3178	Discontinued
0.7	Intermediate Similarity	NPD6068	Discontinued
0.6986	Remote Similarity	NPD7001	Phase 3
0.6979	Remote Similarity	NPD1573	Approved
0.6979	Remote Similarity	NPD1575	Approved
0.697	Remote Similarity	NPD2096	Phase 2
0.697	Remote Similarity	NPD2091	Phase 2
0.6957	Remote Similarity	NPD5017	Discontinued
0.6952	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD3947	Discontinued
0.693	Remote Similarity	NPD3389	Approved
0.693	Remote Similarity	NPD3393	Approved
0.693	Remote Similarity	NPD3394	Approved
0.6923	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2094	Phase 2
0.6919	Remote Similarity	NPD2092	Phase 2
0.6919	Remote Similarity	NPD2095	Phase 2
0.6916	Remote Similarity	NPD3795	Approved
0.6916	Remote Similarity	NPD5888	Phase 2
0.6916	Remote Similarity	NPD3794	Approved
0.6907	Remote Similarity	NPD750	Phase 2
0.6854	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5486	Discontinued
0.6827	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1618	Phase 2
0.6786	Remote Similarity	NPD482	Approved
0.6751	Remote Similarity	NPD749	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD5458	Discontinued
0.6744	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1996	Discontinued
0.6726	Remote Similarity	NPD8289	Discontinued
0.6714	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5426	Phase 3
0.6698	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4051	Discontinued
0.6684	Remote Similarity	NPD1631	Approved
0.6683	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7470	Discontinued
0.6667	Remote Similarity	NPD8250	Phase 2
0.6667	Remote Similarity	NPD7944	Discontinued
0.6667	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4427	Phase 2
0.6652	Remote Similarity	NPD3280	Approved
0.665	Remote Similarity	NPD6665	Discontinued
0.665	Remote Similarity	NPD4524	Discontinued
0.6637	Remote Similarity	NPD6173	Approved
0.6635	Remote Similarity	NPD7817	Phase 1
0.6635	Remote Similarity	NPD7727	Phase 2
0.6635	Remote Similarity	NPD4848	Phase 1
0.6622	Remote Similarity	NPD4086	Phase 1
0.662	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8114	Approved
0.662	Remote Similarity	NPD8115	Approved
0.6619	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6999	Discontinued
0.6616	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD510	Phase 1
0.659	Remote Similarity	NPD5475	Discontinued
0.6589	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1343	Approved
0.6567	Remote Similarity	NPD2481	Approved
0.6567	Remote Similarity	NPD2479	Phase 3
0.6561	Remote Similarity	NPD7878	Phase 2
0.6556	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD2290	Phase 3
0.6555	Remote Similarity	NPD2289	Phase 3
0.6553	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1270	Approved
0.6542	Remote Similarity	NPD8169	Discontinued
0.6542	Remote Similarity	NPD6987	Phase 1
0.654	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1630	Approved
0.6522	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2876	Phase 3
0.6507	Remote Similarity	NPD4602	Approved
0.6507	Remote Similarity	NPD7619	Phase 3
0.6507	Remote Similarity	NPD7618	Phase 3
0.6505	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD3968	Approved
0.6495	Remote Similarity	NPD2511	Approved
0.6494	Remote Similarity	NPD3006	Discontinued
0.6491	Remote Similarity	NPD5022	Discontinued
0.6485	Remote Similarity	NPD9510	Approved
0.6484	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD8468	Phase 2
0.6481	Remote Similarity	NPD3410	Approved
0.6481	Remote Similarity	NPD3411	Phase 2
0.6471	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7396	Approved
0.6465	Remote Similarity	NPD5901	Discontinued
0.6459	Remote Similarity	NPD460	Discontinued
0.6456	Remote Similarity	NPD4988	Discontinued
0.6452	Remote Similarity	NPD7665	Phase 2
0.6452	Remote Similarity	NPD2824	Phase 2
0.6452	Remote Similarity	NPD7666	Phase 3
0.6447	Remote Similarity	NPD7781	Approved
0.6447	Remote Similarity	NPD7780	Approved
0.6442	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2336	Approved
0.6441	Remote Similarity	NPD8326	Phase 3
0.6441	Remote Similarity	NPD8325	Phase 3
0.6441	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5088	Discontinued
0.6425	Remote Similarity	NPD7970	Approved
0.6425	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5510	Approved
0.6422	Remote Similarity	NPD6529	Discontinued
0.6422	Remote Similarity	NPD5596	Phase 2
0.6415	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6595	Phase 3
0.6395	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD820	Phase 3
0.639	Remote Similarity	NPD7482	Phase 2
0.639	Remote Similarity	NPD7483	Phase 2
0.6389	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8272	Phase 2
0.6385	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6770	Approved
0.6382	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4948	Discontinued
0.6373	Remote Similarity	NPD2061	Approved
0.6372	Remote Similarity	NPD6995	Phase 1
0.6368	Remote Similarity	NPD4702	Approved
0.6368	Remote Similarity	NPD4703	Approved
0.6364	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3915	Approved
0.6359	Remote Similarity	NPD2008	Discontinued
0.6359	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3967	Approved
0.6359	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1587	Approved
0.6351	Remote Similarity	NPD5293	Phase 2
0.6351	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD1600	Suspended
0.6346	Remote Similarity	NPD7233	Approved
0.6346	Remote Similarity	NPD7234	Approved
0.6343	Remote Similarity	NPD5487	Phase 1
0.6343	Remote Similarity	NPD8072	Approved
0.634	Remote Similarity	NPD2893	Phase 3
0.634	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7952	Approved
0.6336	Remote Similarity	NPD7791	Approved
0.6336	Remote Similarity	NPD7789	Approved
0.6336	Remote Similarity	NPD7951	Approved
0.6336	Remote Similarity	NPD7950	Approved
0.6336	Remote Similarity	NPD7790	Approved
0.6336	Remote Similarity	NPD7953	Approved
0.6335	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3918	Approved
0.6335	Remote Similarity	NPD4852	Phase 2
0.6335	Remote Similarity	NPD3917	Approved
0.6333	Remote Similarity	NPD4922	Phase 2
0.6333	Remote Similarity	NPD4376	Phase 3
0.6332	Remote Similarity	NPD7731	Approved
0.6332	Remote Similarity	NPD7730	Approved
0.6332	Remote Similarity	NPD4845	Discontinued
0.6332	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3839	Phase 2
0.633	Remote Similarity	NPD3840	Phase 2
0.633	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD201	Phase 2
0.6324	Remote Similarity	NPD5473	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