NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.05
Volume:	220.399
LogP:	0.111
LogD:	0.619
LogS:	-2.502
# Rotatable Bonds:	2
TPSA:	97.18
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	2.986
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.801
MDCK Permeability:	1.4131723219179548e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	68.96065521240234%
Volume Distribution (VD):	0.89
Pgp-substrate:	50.44499588012695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	2.678
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.418
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.389
Carcinogencity:	0.055
Eye Corrosion:	0.004
Eye Irritation:	0.443
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC469489

Natural Product ID:	NPC469489
*Common Name:**	Mansouramycin C
IUPAC Name:	methyl 7-amino-5,8-dioxoisoquinoline-3-carboxylate
Synonyms:	Mansouramycin C
Standard InCHIKey:	TVLMCSGOOOIIKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8N2O4/c1-17-11(16)8-2-5-6(4-13-8)10(15)7(12)3-9(5)14/h2-4H,12H2,1H3
SMILES:	COC(=O)C1=NC=C2C(=C1)C(=O)C=C(C2=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080354
PubChem CID:	46879289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002567] Isoquinoline quinones

*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
NPO33479	Streptomycete	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15043417]
NPO33479	Streptomycete	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19921834]

☑ 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	36

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	8.0	nM	PMID[551758]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	114.0	nM	PMID[551758]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	146.0	nM	PMID[551758]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	134.0	nM	PMID[551758]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12.0	nM	PMID[551758]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	12.0	nM	PMID[551758]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	549.0	nM	PMID[551758]
NPT1629	Cell Line	CWR22R	Homo sapiens	IC50	=	671.0	nM	PMID[551758]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	992.0	nM	PMID[551758]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	1431.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	134.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	130.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	167.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	146.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	150.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	110.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	89.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	195.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	106.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	179.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	61.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	215.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	114.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	122.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1646.0	nM	PMID[551758]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20.0	nM	PMID[551758]

☑ 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 NPC469489 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	316
0.1-0.2	3347
0.2-0.3	12354
0.3-0.4	14213
0.4-0.5	8289
0.5-0.6	2748
0.6-0.7	1269
0.7-0.8	145
0.8-0.85	11
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8994	High Similarity	NPC135950
0.8901	High Similarity	NPC103361
0.8713	High Similarity	NPC470894
0.8533	High Similarity	NPC109922
0.8298	Intermediate Similarity	NPC123395
0.8295	Intermediate Similarity	NPC249614
0.8129	Intermediate Similarity	NPC251391
0.8125	Intermediate Similarity	NPC41717
0.8083	Intermediate Similarity	NPC473239
0.8059	Intermediate Similarity	NPC123906
0.8021	Intermediate Similarity	NPC114974
0.8012	Intermediate Similarity	NPC313889
0.7965	Intermediate Similarity	NPC70406
0.7959	Intermediate Similarity	NPC266249
0.7889	Intermediate Similarity	NPC273532
0.7879	Intermediate Similarity	NPC123839
0.78	Intermediate Similarity	NPC118940
0.7796	Intermediate Similarity	NPC207851
0.7791	Intermediate Similarity	NPC105811
0.7684	Intermediate Similarity	NPC213914
0.768	Intermediate Similarity	NPC248782
0.7674	Intermediate Similarity	NPC467188
0.767	Intermediate Similarity	NPC209362
0.766	Intermediate Similarity	NPC282103
0.7644	Intermediate Similarity	NPC138370
0.7626	Intermediate Similarity	NPC132539
0.7614	Intermediate Similarity	NPC107287
0.7586	Intermediate Similarity	NPC112741
0.7563	Intermediate Similarity	NPC98864
0.7512	Intermediate Similarity	NPC36405
0.7474	Intermediate Similarity	NPC311282
0.7472	Intermediate Similarity	NPC229055
0.7463	Intermediate Similarity	NPC477979
0.7459	Intermediate Similarity	NPC191310
0.7437	Intermediate Similarity	NPC57398
0.743	Intermediate Similarity	NPC74357
0.7429	Intermediate Similarity	NPC302159
0.7421	Intermediate Similarity	NPC46895
0.7416	Intermediate Similarity	NPC312860
0.7391	Intermediate Similarity	NPC70949
0.7366	Intermediate Similarity	NPC318299
0.736	Intermediate Similarity	NPC470679
0.736	Intermediate Similarity	NPC106824
0.736	Intermediate Similarity	NPC217021
0.7346	Intermediate Similarity	NPC229893
0.7344	Intermediate Similarity	NPC118084
0.733	Intermediate Similarity	NPC317752
0.7308	Intermediate Similarity	NPC470680
0.7308	Intermediate Similarity	NPC100104
0.7304	Intermediate Similarity	NPC472070
0.7303	Intermediate Similarity	NPC473878
0.7302	Intermediate Similarity	NPC260434
0.7286	Intermediate Similarity	NPC284338
0.7281	Intermediate Similarity	NPC182222
0.7278	Intermediate Similarity	NPC263455
0.7277	Intermediate Similarity	NPC327592
0.7268	Intermediate Similarity	NPC44354
0.7263	Intermediate Similarity	NPC61011
0.7253	Intermediate Similarity	NPC474492
0.7241	Intermediate Similarity	NPC317373
0.7222	Intermediate Similarity	NPC472293
0.7222	Intermediate Similarity	NPC77061
0.7217	Intermediate Similarity	NPC216612
0.7216	Intermediate Similarity	NPC230085
0.7216	Intermediate Similarity	NPC159630
0.7213	Intermediate Similarity	NPC322644
0.7206	Intermediate Similarity	NPC193238
0.7196	Intermediate Similarity	NPC84347
0.7191	Intermediate Similarity	NPC100726
0.7178	Intermediate Similarity	NPC472063
0.7178	Intermediate Similarity	NPC472062
0.7178	Intermediate Similarity	NPC472069
0.7171	Intermediate Similarity	NPC470190
0.7158	Intermediate Similarity	NPC83774
0.7157	Intermediate Similarity	NPC82053
0.7157	Intermediate Similarity	NPC472065
0.7136	Intermediate Similarity	NPC472752
0.7128	Intermediate Similarity	NPC278434
0.7128	Intermediate Similarity	NPC302647
0.7123	Intermediate Similarity	NPC475426
0.7121	Intermediate Similarity	NPC247735
0.7121	Intermediate Similarity	NPC472210
0.7121	Intermediate Similarity	NPC81802
0.7121	Intermediate Similarity	NPC230403
0.7121	Intermediate Similarity	NPC269886
0.7121	Intermediate Similarity	NPC472295
0.7117	Intermediate Similarity	NPC148889
0.7114	Intermediate Similarity	NPC472296
0.7114	Intermediate Similarity	NPC81535
0.7114	Intermediate Similarity	NPC472297
0.7108	Intermediate Similarity	NPC289086
0.7095	Intermediate Similarity	NPC193361
0.7095	Intermediate Similarity	NPC62844
0.7095	Intermediate Similarity	NPC207531
0.7086	Intermediate Similarity	NPC85443
0.7083	Intermediate Similarity	NPC73994
0.7081	Intermediate Similarity	NPC89508
0.7081	Intermediate Similarity	NPC236668
0.7079	Intermediate Similarity	NPC167400
0.7079	Intermediate Similarity	NPC470279
0.7073	Intermediate Similarity	NPC472064
0.7071	Intermediate Similarity	NPC472292
0.7067	Intermediate Similarity	NPC82370
0.7067	Intermediate Similarity	NPC40919
0.7067	Intermediate Similarity	NPC470189
0.7065	Intermediate Similarity	NPC80681
0.7064	Intermediate Similarity	NPC267853
0.7056	Intermediate Similarity	NPC477788
0.705	Intermediate Similarity	NPC472116
0.705	Intermediate Similarity	NPC79356
0.705	Intermediate Similarity	NPC102592
0.7048	Intermediate Similarity	NPC146976
0.7043	Intermediate Similarity	NPC265100
0.7033	Intermediate Similarity	NPC280473
0.7033	Intermediate Similarity	NPC323551
0.7032	Intermediate Similarity	NPC244897
0.7028	Intermediate Similarity	NPC319556
0.7023	Intermediate Similarity	NPC250807
0.7023	Intermediate Similarity	NPC76565
0.7023	Intermediate Similarity	NPC57797
0.7023	Intermediate Similarity	NPC122436
0.7019	Intermediate Similarity	NPC309845
0.7017	Intermediate Similarity	NPC471655
0.701	Intermediate Similarity	NPC328596
0.701	Intermediate Similarity	NPC328318
0.701	Intermediate Similarity	NPC143977
0.7005	Intermediate Similarity	NPC192712
0.7005	Intermediate Similarity	NPC63041
0.7005	Intermediate Similarity	NPC74575
0.7	Intermediate Similarity	NPC51008
0.7	Intermediate Similarity	NPC202812
0.7	Intermediate Similarity	NPC93390
0.7	Intermediate Similarity	NPC41724
0.6995	Remote Similarity	NPC288987
0.6995	Remote Similarity	NPC74360
0.6995	Remote Similarity	NPC471997
0.6995	Remote Similarity	NPC121327
0.6991	Remote Similarity	NPC475498
0.6991	Remote Similarity	NPC473850
0.6991	Remote Similarity	NPC475137
0.6982	Remote Similarity	NPC15801
0.6981	Remote Similarity	NPC312645
0.698	Remote Similarity	NPC474916
0.6976	Remote Similarity	NPC317572
0.6974	Remote Similarity	NPC284559
0.6971	Remote Similarity	NPC472550
0.6971	Remote Similarity	NPC304179
0.6971	Remote Similarity	NPC48042
0.6968	Remote Similarity	NPC316411
0.6967	Remote Similarity	NPC264674
0.6959	Remote Similarity	NPC473506
0.6959	Remote Similarity	NPC470018
0.6955	Remote Similarity	NPC49547
0.6954	Remote Similarity	NPC206186
0.6952	Remote Similarity	NPC476467
0.695	Remote Similarity	NPC103230
0.695	Remote Similarity	NPC473821
0.6948	Remote Similarity	NPC187494
0.6946	Remote Similarity	NPC474767
0.6943	Remote Similarity	NPC164340
0.6934	Remote Similarity	NPC477909
0.6934	Remote Similarity	NPC477907
0.6934	Remote Similarity	NPC42678
0.6931	Remote Similarity	NPC141454
0.6931	Remote Similarity	NPC473814
0.6931	Remote Similarity	NPC78767
0.6931	Remote Similarity	NPC90229
0.6927	Remote Similarity	NPC122968
0.6927	Remote Similarity	NPC476110
0.6927	Remote Similarity	NPC475600
0.6927	Remote Similarity	NPC228377
0.6927	Remote Similarity	NPC87152
0.6927	Remote Similarity	NPC328186
0.6927	Remote Similarity	NPC146824
0.6927	Remote Similarity	NPC477787
0.6927	Remote Similarity	NPC476419
0.6927	Remote Similarity	NPC475631
0.6919	Remote Similarity	NPC165837
0.6915	Remote Similarity	NPC233380
0.6914	Remote Similarity	NPC328029
0.6911	Remote Similarity	NPC477976
0.6909	Remote Similarity	NPC315062
0.6907	Remote Similarity	NPC317010
0.6904	Remote Similarity	NPC160381
0.6895	Remote Similarity	NPC471977
0.6895	Remote Similarity	NPC471190
0.6895	Remote Similarity	NPC475644
0.6895	Remote Similarity	NPC475362
0.6895	Remote Similarity	NPC470486
0.6893	Remote Similarity	NPC165599
0.6892	Remote Similarity	NPC35208
0.6887	Remote Similarity	NPC4421
0.6887	Remote Similarity	NPC228331
0.6884	Remote Similarity	NPC477901
0.6881	Remote Similarity	NPC292361
0.6875	Remote Similarity	NPC139763
0.6875	Remote Similarity	NPC156044
0.6875	Remote Similarity	NPC114310
0.6875	Remote Similarity	NPC314297
0.6875	Remote Similarity	NPC315545

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 NPC469489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	615
0.2-0.3	923
0.3-0.4	1658
0.4-0.5	3034
0.5-0.6	2049
0.6-0.7	648
0.7-0.8	36
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
0.7755	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3947	Discontinued
0.7692	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD9271	Approved
0.7513	Intermediate Similarity	NPD1096	Discontinued
0.7512	Intermediate Similarity	NPD2509	Approved
0.7512	Intermediate Similarity	NPD3389	Approved
0.7512	Intermediate Similarity	NPD2510	Approved
0.7512	Intermediate Similarity	NPD3394	Approved
0.7512	Intermediate Similarity	NPD3393	Approved
0.75	Intermediate Similarity	NPD3178	Discontinued
0.7486	Intermediate Similarity	NPD820	Phase 3
0.7416	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1996	Discontinued
0.7356	Intermediate Similarity	NPD4429	Discontinued
0.7317	Intermediate Similarity	NPD5475	Discontinued
0.7316	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2581	Approved
0.7293	Intermediate Similarity	NPD2582	Approved
0.7259	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7010	Phase 3
0.7241	Intermediate Similarity	NPD107	Approved
0.7228	Intermediate Similarity	NPD5088	Discontinued
0.7173	Intermediate Similarity	NPD1643	Phase 3
0.7163	Intermediate Similarity	NPD3795	Approved
0.7163	Intermediate Similarity	NPD3794	Approved
0.7158	Intermediate Similarity	NPD1630	Approved
0.7156	Intermediate Similarity	NPD6770	Approved
0.7095	Intermediate Similarity	NPD1270	Approved
0.7079	Intermediate Similarity	NPD9075	Approved
0.7079	Intermediate Similarity	NPD9074	Approved
0.7075	Intermediate Similarity	NPD7404	Approved
0.7071	Intermediate Similarity	NPD6665	Discontinued
0.7065	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1631	Approved
0.7039	Intermediate Similarity	NPD3371	Approved
0.702	Intermediate Similarity	NPD2336	Approved
0.7018	Intermediate Similarity	NPD1659	Phase 1
0.7018	Intermediate Similarity	NPD5022	Discontinued
0.6996	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4417	Approved
0.6984	Remote Similarity	NPD1573	Approved
0.6984	Remote Similarity	NPD1575	Approved
0.6982	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4506	Discontinued
0.6971	Remote Similarity	NPD6529	Discontinued
0.6968	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3280	Approved
0.695	Remote Similarity	NPD4526	Approved
0.695	Remote Similarity	NPD4528	Approved
0.695	Remote Similarity	NPD4529	Approved
0.6947	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3006	Discontinued
0.6936	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4376	Phase 3
0.6881	Remote Similarity	NPD2307	Discontinued
0.6881	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1586	Approved
0.6872	Remote Similarity	NPD5866	Approved
0.6872	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD1623	Approved
0.6852	Remote Similarity	NPD4301	Approved
0.683	Remote Similarity	NPD946	Discontinued
0.6826	Remote Similarity	NPD5482	Discontinued
0.6825	Remote Similarity	NPD7470	Discontinued
0.6823	Remote Similarity	NPD4524	Discontinued
0.6823	Remote Similarity	NPD2076	Approved
0.6823	Remote Similarity	NPD2077	Approved
0.6822	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2479	Phase 3
0.6821	Remote Similarity	NPD2481	Approved
0.6804	Remote Similarity	NPD8289	Discontinued
0.6802	Remote Similarity	NPD721	Approved
0.6782	Remote Similarity	NPD1173	Approved
0.6779	Remote Similarity	NPD5901	Discontinued
0.6774	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1587	Approved
0.6768	Remote Similarity	NPD4889	Approved
0.6746	Remote Similarity	NPD3967	Approved
0.6745	Remote Similarity	NPD5416	Discontinued
0.674	Remote Similarity	NPD6790	Phase 1
0.674	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD750	Phase 2
0.6735	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5513	Phase 2
0.6718	Remote Similarity	NPD2753	Discontinued
0.6716	Remote Similarity	NPD8063	Discontinued
0.6713	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6173	Approved
0.6712	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5891	Approved
0.6711	Remote Similarity	NPD1483	Discontinued
0.6704	Remote Similarity	NPD4804	Approved
0.6702	Remote Similarity	NPD2213	Approved
0.6702	Remote Similarity	NPD2214	Approved
0.6702	Remote Similarity	NPD5255	Approved
0.6701	Remote Similarity	NPD9362	Approved
0.6701	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4948	Discontinued
0.6699	Remote Similarity	NPD6987	Phase 1
0.6697	Remote Similarity	NPD7994	Phase 2
0.6685	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7467	Discontinued
0.6667	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3238	Discontinued
0.6667	Remote Similarity	NPD6479	Discontinued
0.6667	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8356	Approved
0.6667	Remote Similarity	NPD272	Approved
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6242	Discontinued
0.6651	Remote Similarity	NPD3968	Approved
0.665	Remote Similarity	NPD3315	Phase 3
0.665	Remote Similarity	NPD9510	Approved
0.6649	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4952	Phase 3
0.6636	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6753	Phase 1
0.6636	Remote Similarity	NPD6752	Phase 1
0.6635	Remote Similarity	NPD3411	Phase 2
0.6635	Remote Similarity	NPD3410	Approved
0.6634	Remote Similarity	NPD6226	Phase 3
0.6633	Remote Similarity	NPD3569	Discontinued
0.6633	Remote Similarity	NPD2096	Phase 2
0.6633	Remote Similarity	NPD2091	Phase 2
0.6631	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4805	Approved
0.6623	Remote Similarity	NPD8468	Phase 2
0.6622	Remote Similarity	NPD3259	Approved
0.662	Remote Similarity	NPD3353	Approved
0.662	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2831	Approved
0.6619	Remote Similarity	NPD7396	Approved
0.6616	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD482	Approved
0.6607	Remote Similarity	NPD7688	Phase 1
0.659	Remote Similarity	NPD1591	Approved
0.6589	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2092	Phase 2
0.6583	Remote Similarity	NPD2095	Phase 2
0.6583	Remote Similarity	NPD2094	Phase 2
0.658	Remote Similarity	NPD1343	Approved
0.6579	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD1802	Approved
0.6576	Remote Similarity	NPD1801	Approved
0.6575	Remote Similarity	NPD8479	Phase 2
0.6571	Remote Similarity	NPD6176	Phase 1
0.6564	Remote Similarity	NPD7853	Phase 2
0.6556	Remote Similarity	NPD2896	Discontinued
0.6552	Remote Similarity	NPD3321	Discontinued
0.655	Remote Similarity	NPD7885	Phase 2
0.655	Remote Similarity	NPD7886	Phase 2
0.6549	Remote Similarity	NPD4373	Phase 2
0.6547	Remote Similarity	NPD4845	Discontinued
0.6547	Remote Similarity	NPD8430	Approved
0.654	Remote Similarity	NPD944	Approved
0.6538	Remote Similarity	NPD2778	Approved
0.6535	Remote Similarity	NPD9364	Phase 2
0.6535	Remote Similarity	NPD9363	Approved
0.6528	Remote Similarity	NPD3945	Discontinued
0.6528	Remote Similarity	NPD5888	Phase 2
0.6528	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5003	Discontinued
0.6516	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3915	Approved
0.6509	Remote Similarity	NPD7001	Phase 3
0.6507	Remote Similarity	NPD484	Approved
0.6507	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5640	Discontinued
0.6502	Remote Similarity	NPD7233	Approved
0.6502	Remote Similarity	NPD7234	Approved
0.6498	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD2511	Approved
0.6488	Remote Similarity	NPD5450	Discontinued
0.6484	Remote Similarity	NPD6568	Discontinued
0.6484	Remote Similarity	NPD7395	Discontinued
0.6481	Remote Similarity	NPD3917	Approved
0.6481	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7069	Discontinued
0.6481	Remote Similarity	NPD3918	Approved
0.6479	Remote Similarity	NPD3840	Phase 2
0.6479	Remote Similarity	NPD3839	Phase 2
0.6477	Remote Similarity	NPD2915	Discontinued
0.6476	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5017	Discontinued
0.6473	Remote Similarity	NPD4848	Phase 1
0.6471	Remote Similarity	NPD2565	Phase 2
0.6471	Remote Similarity	NPD2564	Approved
0.6468	Remote Similarity	NPD8160	Phase 2

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