NPASS Compound

Structure

NPC207866 OpenBabel07101718282D 25 29 0 0 0 0 0 0 0 0999 V2000 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5154 -1.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6494 0.2707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3815 -0.7293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5154 0.7707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6950 1.7374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4951 1.5922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6789 -2.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6494 -0.7293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3815 0.2707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7834 -1.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8698 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7007 -2.4317 0.0000 N 0 0 0 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 -2.8804 0.8762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2475 0.7707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5534 -2.1009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8794 0.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 13 2 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	279.09
Volume:	284.638
LogP:	3.564
LogD:	2.686
LogS:	-5.744
# Rotatable Bonds:	1
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	2.445
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	2.8883097911602817e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.218
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.293
Plasma Protein Binding (PPB):	90.869873046875%
Volume Distribution (VD):	0.896
Pgp-substrate:	8.726910591125488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.381
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.567
CYP3A4-inhibitor:	0.346
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	0.56
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.733
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.493
Skin Sensitization:	0.863
Carcinogencity:	0.907
Eye Corrosion:	0.01
Eye Irritation:	0.693
Respiratory Toxicity:	0.602

Download Data

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

Natural Product: NPC207866

Natural Product ID:	NPC207866
*Common Name:**	XWBZGMXEEBRBEB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XWBZGMXEEBRBEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15N3O3/c1-21-9-11-6-7-22(25)17-14(11)18(21)19(24)16-15(17)13(8-20-16)10-2-4-12(23)5-3-10/h2-5,8-9,20,23H,6-7H2,1H3
SMILES:	Oc1ccc(cc1)c1c[nH]c2c1C1=N(=O)CCc3c1c(C2=O)n(c3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2448602
PubChem CID:	n.a.
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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	16541.0	nM	PMID[505339]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	Activity	=	26.0	%	PMID[505339]
NPT2	Others	Unspecified		Ks	=	30.0	uM	PMID[505339]

☑ 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 NPC207866 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	416
0.1-0.2	3000
0.2-0.3	13453
0.3-0.4	6370
0.4-0.5	14467
0.5-0.6	2917
0.6-0.7	1885
0.7-0.8	177
0.8-0.85	1
0.85-0.9	6
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9788	High Similarity	NPC61038
0.963	High Similarity	NPC175602
0.9137	High Similarity	NPC110182
0.901	High Similarity	NPC14686
0.896	High Similarity	NPC269270
0.8653	High Similarity	NPC473821
0.8615	High Similarity	NPC78767
0.8615	High Similarity	NPC473814
0.8615	High Similarity	NPC74153
0.8608	High Similarity	NPC93390
0.8057	Intermediate Similarity	NPC27041
0.7944	Intermediate Similarity	NPC276657
0.7934	Intermediate Similarity	NPC264285
0.7828	Intermediate Similarity	NPC207686
0.7716	Intermediate Similarity	NPC271792
0.7706	Intermediate Similarity	NPC16352
0.7689	Intermediate Similarity	NPC15801
0.7674	Intermediate Similarity	NPC322064
0.7653	Intermediate Similarity	NPC82370
0.765	Intermediate Similarity	NPC295158
0.7628	Intermediate Similarity	NPC237740
0.7621	Intermediate Similarity	NPC227582
0.7589	Intermediate Similarity	NPC200553
0.7589	Intermediate Similarity	NPC279189
0.7543	Intermediate Similarity	NPC91868
0.7543	Intermediate Similarity	NPC63971
0.7533	Intermediate Similarity	NPC235685
0.7533	Intermediate Similarity	NPC184225
0.7532	Intermediate Similarity	NPC178858
0.7512	Intermediate Similarity	NPC45459
0.7512	Intermediate Similarity	NPC324149
0.7512	Intermediate Similarity	NPC252338
0.7512	Intermediate Similarity	NPC315491
0.7512	Intermediate Similarity	NPC99666
0.7511	Intermediate Similarity	NPC229893
0.75	Intermediate Similarity	NPC101350
0.75	Intermediate Similarity	NPC326363
0.7489	Intermediate Similarity	NPC162002
0.7477	Intermediate Similarity	NPC476818
0.7477	Intermediate Similarity	NPC472285
0.7465	Intermediate Similarity	NPC183777
0.7445	Intermediate Similarity	NPC325976
0.7445	Intermediate Similarity	NPC475635
0.7445	Intermediate Similarity	NPC174489
0.7429	Intermediate Similarity	NPC213308
0.7416	Intermediate Similarity	NPC131887
0.7412	Intermediate Similarity	NPC477549
0.7383	Intermediate Similarity	NPC270918
0.738	Intermediate Similarity	NPC26641
0.7378	Intermediate Similarity	NPC194740
0.7373	Intermediate Similarity	NPC219087
0.7368	Intermediate Similarity	NPC77555
0.7361	Intermediate Similarity	NPC85273
0.7354	Intermediate Similarity	NPC122436
0.7349	Intermediate Similarity	NPC171787
0.7343	Intermediate Similarity	NPC471448
0.7333	Intermediate Similarity	NPC306376
0.733	Intermediate Similarity	NPC48317
0.7323	Intermediate Similarity	NPC262338
0.7322	Intermediate Similarity	NPC63109
0.7317	Intermediate Similarity	NPC46580
0.7316	Intermediate Similarity	NPC37152
0.7311	Intermediate Similarity	NPC471944
0.7304	Intermediate Similarity	NPC314002
0.7299	Intermediate Similarity	NPC74413
0.7289	Intermediate Similarity	NPC319232
0.7289	Intermediate Similarity	NPC24370
0.7273	Intermediate Similarity	NPC36405
0.7273	Intermediate Similarity	NPC330009
0.7269	Intermediate Similarity	NPC39679
0.7268	Intermediate Similarity	NPC171171
0.7265	Intermediate Similarity	NPC473317
0.7264	Intermediate Similarity	NPC284775
0.726	Intermediate Similarity	NPC56170
0.7255	Intermediate Similarity	NPC204717
0.7248	Intermediate Similarity	NPC23294
0.7246	Intermediate Similarity	NPC475874
0.7246	Intermediate Similarity	NPC83111
0.7243	Intermediate Similarity	NPC53144
0.724	Intermediate Similarity	NPC469727
0.7217	Intermediate Similarity	NPC182222
0.7217	Intermediate Similarity	NPC97902
0.7209	Intermediate Similarity	NPC475070
0.7209	Intermediate Similarity	NPC472259
0.7209	Intermediate Similarity	NPC470500
0.7206	Intermediate Similarity	NPC220765
0.7204	Intermediate Similarity	NPC156704
0.7202	Intermediate Similarity	NPC303951
0.7198	Intermediate Similarity	NPC321708
0.7198	Intermediate Similarity	NPC41679
0.7198	Intermediate Similarity	NPC473628
0.7196	Intermediate Similarity	NPC470678
0.7196	Intermediate Similarity	NPC260900
0.7196	Intermediate Similarity	NPC57398
0.7191	Intermediate Similarity	NPC78609
0.7189	Intermediate Similarity	NPC86834
0.7189	Intermediate Similarity	NPC210828
0.7189	Intermediate Similarity	NPC143075
0.7175	Intermediate Similarity	NPC74360
0.717	Intermediate Similarity	NPC477041
0.717	Intermediate Similarity	NPC477044
0.7168	Intermediate Similarity	NPC125597
0.7163	Intermediate Similarity	NPC134848
0.7156	Intermediate Similarity	NPC220851
0.715	Intermediate Similarity	NPC302647
0.715	Intermediate Similarity	NPC278434
0.7149	Intermediate Similarity	NPC74619
0.7143	Intermediate Similarity	NPC323969
0.7143	Intermediate Similarity	NPC470680
0.7143	Intermediate Similarity	NPC100104
0.7143	Intermediate Similarity	NPC88008
0.7143	Intermediate Similarity	NPC304203
0.7136	Intermediate Similarity	NPC241025
0.713	Intermediate Similarity	NPC196718
0.713	Intermediate Similarity	NPC477043
0.7129	Intermediate Similarity	NPC476460
0.7125	Intermediate Similarity	NPC314882
0.7123	Intermediate Similarity	NPC11464
0.7123	Intermediate Similarity	NPC124086
0.7117	Intermediate Similarity	NPC469928
0.7116	Intermediate Similarity	NPC211813
0.7116	Intermediate Similarity	NPC328318
0.7116	Intermediate Similarity	NPC328596
0.7115	Intermediate Similarity	NPC32771
0.7109	Intermediate Similarity	NPC276517
0.7108	Intermediate Similarity	NPC79777
0.7107	Intermediate Similarity	NPC475746
0.7106	Intermediate Similarity	NPC473312
0.71	Intermediate Similarity	NPC323752
0.7091	Intermediate Similarity	NPC9894
0.7091	Intermediate Similarity	NPC87413
0.7089	Intermediate Similarity	NPC474916
0.7089	Intermediate Similarity	NPC67288
0.7087	Intermediate Similarity	NPC477112
0.7087	Intermediate Similarity	NPC260434
0.7085	Intermediate Similarity	NPC246658
0.7085	Intermediate Similarity	NPC293151
0.7083	Intermediate Similarity	NPC476098
0.708	Intermediate Similarity	NPC216612
0.7067	Intermediate Similarity	NPC23476
0.7067	Intermediate Similarity	NPC474259
0.7067	Intermediate Similarity	NPC477415
0.7067	Intermediate Similarity	NPC206186
0.7064	Intermediate Similarity	NPC283117
0.7062	Intermediate Similarity	NPC326422
0.7059	Intermediate Similarity	NPC72980
0.7059	Intermediate Similarity	NPC67659
0.7056	Intermediate Similarity	NPC132329
0.7056	Intermediate Similarity	NPC102593
0.7056	Intermediate Similarity	NPC477045
0.7056	Intermediate Similarity	NPC473186
0.7054	Intermediate Similarity	NPC303658
0.7048	Intermediate Similarity	NPC322482
0.7047	Intermediate Similarity	NPC471655
0.7045	Intermediate Similarity	NPC309845
0.7042	Intermediate Similarity	NPC167710
0.704	Intermediate Similarity	NPC3207
0.7035	Intermediate Similarity	NPC60621
0.7034	Intermediate Similarity	NPC171393
0.7034	Intermediate Similarity	NPC295452
0.7033	Intermediate Similarity	NPC209917
0.7028	Intermediate Similarity	NPC202812
0.7027	Intermediate Similarity	NPC477610
0.7026	Intermediate Similarity	NPC70155
0.7024	Intermediate Similarity	NPC234403
0.7024	Intermediate Similarity	NPC182940
0.7018	Intermediate Similarity	NPC317373
0.7017	Intermediate Similarity	NPC469734
0.7014	Intermediate Similarity	NPC47190
0.7013	Intermediate Similarity	NPC315062
0.701	Intermediate Similarity	NPC184964
0.701	Intermediate Similarity	NPC96890
0.701	Intermediate Similarity	NPC59269
0.7009	Intermediate Similarity	NPC476041
0.7009	Intermediate Similarity	NPC28945
0.7009	Intermediate Similarity	NPC472284
0.7009	Intermediate Similarity	NPC304926
0.7005	Intermediate Similarity	NPC200836
0.7005	Intermediate Similarity	NPC317701
0.7005	Intermediate Similarity	NPC474492
0.6996	Remote Similarity	NPC39370
0.6996	Remote Similarity	NPC190401
0.6996	Remote Similarity	NPC239763
0.6996	Remote Similarity	NPC208898
0.6995	Remote Similarity	NPC139763
0.6995	Remote Similarity	NPC242209
0.6991	Remote Similarity	NPC150239
0.6991	Remote Similarity	NPC300183
0.6986	Remote Similarity	NPC17059
0.6982	Remote Similarity	NPC471194
0.6982	Remote Similarity	NPC471193
0.6978	Remote Similarity	NPC247803
0.6977	Remote Similarity	NPC81535
0.6977	Remote Similarity	NPC476167
0.6976	Remote Similarity	NPC213468
0.6976	Remote Similarity	NPC248041
0.6976	Remote Similarity	NPC126709
0.6972	Remote Similarity	NPC285558
0.6972	Remote Similarity	NPC327592
0.6968	Remote Similarity	NPC470020

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 NPC207866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	657
0.2-0.3	826
0.3-0.4	1232
0.4-0.5	3046
0.5-0.6	2383
0.6-0.7	747
0.7-0.8	21
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
0.7788	Intermediate Similarity	NPD5901	Discontinued
0.7762	Intermediate Similarity	NPD6376	Discontinued
0.7647	Intermediate Similarity	NPD4845	Discontinued
0.7634	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6242	Discontinued
0.7512	Intermediate Similarity	NPD484	Approved
0.7452	Intermediate Similarity	NPD7948	Phase 1
0.7366	Intermediate Similarity	NPD7603	Discontinued
0.7311	Intermediate Similarity	NPD4511	Phase 1
0.7241	Intermediate Similarity	NPD3178	Discontinued
0.7215	Intermediate Similarity	NPD4852	Phase 2
0.7209	Intermediate Similarity	NPD5426	Phase 3
0.7179	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5065	Approved
0.7143	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6999	Discontinued
0.7136	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7470	Discontinued
0.7067	Intermediate Similarity	NPD4948	Discontinued
0.7056	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2510	Approved
0.7032	Intermediate Similarity	NPD2509	Approved
0.7005	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6530	Approved
0.698	Remote Similarity	NPD6531	Approved
0.6971	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6975	Discontinued
0.6955	Remote Similarity	NPD7666	Phase 3
0.6955	Remote Similarity	NPD7665	Phase 2
0.6941	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7001	Phase 3
0.692	Remote Similarity	NPD6790	Phase 1
0.6912	Remote Similarity	NPD482	Approved
0.691	Remote Similarity	NPD3746	Discontinued
0.6906	Remote Similarity	NPD8093	Discontinued
0.6904	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4429	Discontinued
0.6898	Remote Similarity	NPD3814	Phase 1
0.6894	Remote Similarity	NPD3006	Discontinued
0.6889	Remote Similarity	NPD3393	Approved
0.6889	Remote Similarity	NPD3394	Approved
0.6889	Remote Similarity	NPD3389	Approved
0.6886	Remote Similarity	NPD4923	Phase 1
0.6878	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8094	Discontinued
0.6864	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD750	Phase 2
0.6858	Remote Similarity	NPD2813	Phase 3
0.6858	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1573	Approved
0.6847	Remote Similarity	NPD1575	Approved
0.6835	Remote Similarity	NPD5017	Discontinued
0.683	Remote Similarity	NPD5866	Approved
0.683	Remote Similarity	NPD3330	Phase 1
0.6822	Remote Similarity	NPD1038	Approved
0.6822	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6987	Phase 1
0.6818	Remote Similarity	NPD3947	Discontinued
0.6818	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5612	Discontinued
0.6802	Remote Similarity	NPD2916	Discontinued
0.6798	Remote Similarity	NPD2781	Approved
0.6797	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2092	Phase 2
0.6794	Remote Similarity	NPD2094	Phase 2
0.6794	Remote Similarity	NPD2095	Phase 2
0.6793	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5482	Discontinued
0.6786	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6995	Phase 1
0.6782	Remote Similarity	NPD2780	Approved
0.6782	Remote Similarity	NPD2782	Approved
0.6779	Remote Similarity	NPD6595	Phase 3
0.6776	Remote Similarity	NPD5937	Approved
0.6773	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1996	Discontinued
0.6763	Remote Similarity	NPD3962	Phase 2
0.6763	Remote Similarity	NPD3959	Phase 2
0.6762	Remote Similarity	NPD2091	Phase 2
0.6762	Remote Similarity	NPD2096	Phase 2
0.6759	Remote Similarity	NPD4848	Phase 1
0.6753	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5022	Discontinued
0.6749	Remote Similarity	NPD4558	Phase 2
0.6746	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD802	Phase 2
0.6738	Remote Similarity	NPD6164	Phase 2
0.6738	Remote Similarity	NPD7994	Phase 2
0.6738	Remote Similarity	NPD6165	Phase 2
0.6733	Remote Similarity	NPD1631	Approved
0.6731	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8349	Phase 1
0.6726	Remote Similarity	NPD3243	Approved
0.6724	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8356	Approved
0.67	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3263	Phase 3
0.6683	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3918	Approved
0.6681	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3917	Approved
0.668	Remote Similarity	NPD7925	Phase 2
0.668	Remote Similarity	NPD7924	Phase 2
0.6667	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8430	Approved
0.6667	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8395	Approved
0.6667	Remote Similarity	NPD8396	Approved
0.6653	Remote Similarity	NPD3809	Discontinued
0.6651	Remote Similarity	NPD4079	Approved
0.6651	Remote Similarity	NPD4076	Approved
0.6651	Remote Similarity	NPD2336	Approved
0.6651	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4989	Phase 2
0.6638	Remote Similarity	NPD6710	Phase 3
0.6637	Remote Similarity	NPD3915	Approved
0.6637	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7618	Phase 3
0.6636	Remote Similarity	NPD7619	Phase 3
0.6636	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6456	Discontinued
0.6622	Remote Similarity	NPD1600	Suspended
0.662	Remote Similarity	NPD4922	Phase 2
0.662	Remote Similarity	NPD6569	Phase 2
0.6619	Remote Similarity	NPD5473	Discontinued
0.6611	Remote Similarity	NPD7853	Phase 2
0.661	Remote Similarity	NPD5479	Discontinued
0.6608	Remote Similarity	NPD2411	Approved
0.6608	Remote Similarity	NPD7069	Discontinued
0.6603	Remote Similarity	NPD3506	Approved
0.6603	Remote Similarity	NPD3505	Approved
0.6602	Remote Similarity	NPD1326	Approved
0.6602	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1325	Approved
0.6596	Remote Similarity	NPD3259	Approved
0.6594	Remote Similarity	NPD6733	Discontinued
0.6592	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3825	Phase 3
0.6589	Remote Similarity	NPD3961	Discontinued
0.6585	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1630	Approved
0.6581	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6974	Phase 3
0.6578	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4889	Approved
0.6567	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5067	Phase 2
0.6564	Remote Similarity	NPD5066	Phase 2
0.6564	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6282	Discontinued
0.6562	Remote Similarity	NPD2008	Discontinued
0.6562	Remote Similarity	NPD7010	Phase 3
0.6562	Remote Similarity	NPD7568	Phase 1
0.6562	Remote Similarity	NPD8403	Phase 1
0.6557	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5471	Phase 3
0.6555	Remote Similarity	NPD4885	Approved
0.6555	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4075	Phase 2
0.6553	Remote Similarity	NPD8289	Discontinued
0.6553	Remote Similarity	NPD2844	Phase 3
0.655	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5513	Phase 2
0.6544	Remote Similarity	NPD3404	Approved
0.6542	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD925	Approved
0.6537	Remote Similarity	NPD7689	Approved
0.6537	Remote Similarity	NPD926	Approved
0.6537	Remote Similarity	NPD3354	Phase 2
0.6534	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5552	Discontinued
0.653	Remote Similarity	NPD2307	Discontinued
0.6528	Remote Similarity	NPD4499	Approved
0.6528	Remote Similarity	NPD1213	Phase 3
0.6525	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD9695	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