NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	217.04
Volume:	209.402
LogP:	0.948
LogD:	0.883
LogS:	-2.889
# Rotatable Bonds:	2
TPSA:	73.33
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.394
Fsp3:	0.091
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:	-4.56
MDCK Permeability:	2.3487831640522927e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.727
Plasma Protein Binding (PPB):	89.64527130126953%
Volume Distribution (VD):	0.575
Pgp-substrate:	3.458167552947998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.462
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.355
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	6.543
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.645
Drug-inuced Liver Injury (DILI):	0.719
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.381
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.778
Carcinogencity:	0.888
Eye Corrosion:	0.01
Eye Irritation:	0.963
Respiratory Toxicity:	0.413

Download Data

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

Natural Product: NPC470894

Natural Product ID:	NPC470894
*Common Name:**	Methyl 5,8-Dioxoquinoline-2-Carboxylate
IUPAC Name:	methyl 5,8-dioxoquinoline-2-carboxylate
Synonyms:
Standard InCHIKey:	ZHWHKWXPBQONKT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H7NO4/c1-16-11(15)7-3-2-6-8(13)4-5-9(14)10(6)12-7/h2-5H,1H3
SMILES:	COC(=O)c1ccc2c(n1)C(=O)C=CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229640
PubChem CID:	9859230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002570] Quinoline 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
NPO32570	aplidium sp.	Species	Polyclinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[17497807]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4110.0	nM	PMID[546443]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4000.0	nM	PMID[546444]
NPT2	Others	Unspecified		IC50	=	1750.0	nM	PMID[546443]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1740.0	nM	PMID[546444]

☑ 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 NPC470894 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	312
0.1-0.2	2565
0.2-0.3	10241
0.3-0.4	11035
0.4-0.5	14131
0.5-0.6	3019
0.6-0.7	1226
0.7-0.8	157
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8713	High Similarity	NPC469489
0.8398	Intermediate Similarity	NPC473239
0.8232	Intermediate Similarity	NPC322644
0.8202	Intermediate Similarity	NPC135950
0.8122	Intermediate Similarity	NPC103361
0.8098	Intermediate Similarity	NPC132539
0.8056	Intermediate Similarity	NPC109922
0.8036	Intermediate Similarity	NPC41717
0.8025	Intermediate Similarity	NPC85443
0.7967	Intermediate Similarity	NPC248782
0.7953	Intermediate Similarity	NPC191310
0.7944	Intermediate Similarity	NPC230403
0.7923	Intermediate Similarity	NPC123395
0.7861	Intermediate Similarity	NPC84347
0.7838	Intermediate Similarity	NPC98864
0.7791	Intermediate Similarity	NPC273532
0.7697	Intermediate Similarity	NPC207851
0.7688	Intermediate Similarity	NPC249614
0.766	Intermediate Similarity	NPC317572
0.7541	Intermediate Similarity	NPC114974
0.7538	Intermediate Similarity	NPC477979
0.75	Intermediate Similarity	NPC266249
0.75	Intermediate Similarity	NPC470280
0.7487	Intermediate Similarity	NPC89508
0.7486	Intermediate Similarity	NPC144381
0.7473	Intermediate Similarity	NPC206186
0.747	Intermediate Similarity	NPC112741
0.7423	Intermediate Similarity	NPC123839
0.7418	Intermediate Similarity	NPC160381
0.7396	Intermediate Similarity	NPC107287
0.7374	Intermediate Similarity	NPC312645
0.7363	Intermediate Similarity	NPC282103
0.7358	Intermediate Similarity	NPC314297
0.7358	Intermediate Similarity	NPC315545
0.7347	Intermediate Similarity	NPC118940
0.734	Intermediate Similarity	NPC141454
0.7322	Intermediate Similarity	NPC194040
0.731	Intermediate Similarity	NPC232225
0.7306	Intermediate Similarity	NPC313796
0.7306	Intermediate Similarity	NPC315638
0.7306	Intermediate Similarity	NPC313345
0.7306	Intermediate Similarity	NPC314855
0.7305	Intermediate Similarity	NPC302159
0.7296	Intermediate Similarity	NPC220337
0.7294	Intermediate Similarity	NPC312860
0.7292	Intermediate Similarity	NPC165599
0.7278	Intermediate Similarity	NPC256268
0.7268	Intermediate Similarity	NPC321428
0.7253	Intermediate Similarity	NPC243058
0.7245	Intermediate Similarity	NPC314834
0.7235	Intermediate Similarity	NPC70406
0.7228	Intermediate Similarity	NPC90415
0.7222	Intermediate Similarity	NPC219848
0.7213	Intermediate Similarity	NPC203635
0.7196	Intermediate Similarity	NPC472116
0.7193	Intermediate Similarity	NPC251391
0.7179	Intermediate Similarity	NPC244741
0.7176	Intermediate Similarity	NPC313889
0.7175	Intermediate Similarity	NPC70949
0.7173	Intermediate Similarity	NPC280714
0.7168	Intermediate Similarity	NPC116573
0.7166	Intermediate Similarity	NPC138370
0.7165	Intermediate Similarity	NPC314648
0.7159	Intermediate Similarity	NPC115232
0.7151	Intermediate Similarity	NPC221873
0.715	Intermediate Similarity	NPC57398
0.7129	Intermediate Similarity	NPC288987
0.7128	Intermediate Similarity	NPC472287
0.7128	Intermediate Similarity	NPC472286
0.712	Intermediate Similarity	NPC285923
0.712	Intermediate Similarity	NPC320394
0.712	Intermediate Similarity	NPC46895
0.7118	Intermediate Similarity	NPC123906
0.7111	Intermediate Similarity	NPC303225
0.7105	Intermediate Similarity	NPC102592
0.7105	Intermediate Similarity	NPC79356
0.7083	Intermediate Similarity	NPC159630
0.7083	Intermediate Similarity	NPC230085
0.7079	Intermediate Similarity	NPC174576
0.7065	Intermediate Similarity	NPC36405
0.7059	Intermediate Similarity	NPC105811
0.7052	Intermediate Similarity	NPC298288
0.7052	Intermediate Similarity	NPC263455
0.7052	Intermediate Similarity	NPC209362
0.7041	Intermediate Similarity	NPC467188
0.7035	Intermediate Similarity	NPC146418
0.7016	Intermediate Similarity	NPC472293
0.7011	Intermediate Similarity	NPC142688
0.7	Intermediate Similarity	NPC247735
0.7	Intermediate Similarity	NPC472295
0.7	Intermediate Similarity	NPC318299
0.7	Intermediate Similarity	NPC81802
0.7	Intermediate Similarity	NPC192306
0.7	Intermediate Similarity	NPC472210
0.7	Intermediate Similarity	NPC269886
0.6995	Remote Similarity	NPC67659
0.699	Remote Similarity	NPC94842
0.6989	Remote Similarity	NPC241025
0.6971	Remote Similarity	NPC213914
0.6968	Remote Similarity	NPC44354
0.6965	Remote Similarity	NPC317752
0.6965	Remote Similarity	NPC39500
0.6957	Remote Similarity	NPC61011
0.6947	Remote Similarity	NPC471546
0.6941	Remote Similarity	NPC167400
0.6935	Remote Similarity	NPC472752
0.6919	Remote Similarity	NPC243850
0.691	Remote Similarity	NPC118511
0.6907	Remote Similarity	NPC472297
0.6907	Remote Similarity	NPC472296
0.6904	Remote Similarity	NPC327592
0.6891	Remote Similarity	NPC90229
0.6885	Remote Similarity	NPC151635
0.6884	Remote Similarity	NPC470190
0.6872	Remote Similarity	NPC260434
0.6869	Remote Similarity	NPC317373
0.6869	Remote Similarity	NPC300156
0.6865	Remote Similarity	NPC469896
0.6862	Remote Similarity	NPC118084
0.686	Remote Similarity	NPC477788
0.686	Remote Similarity	NPC257142
0.6859	Remote Similarity	NPC472292
0.6857	Remote Similarity	NPC229055
0.6856	Remote Similarity	NPC472284
0.6848	Remote Similarity	NPC83774
0.6847	Remote Similarity	NPC118228
0.6839	Remote Similarity	NPC284348
0.6837	Remote Similarity	NPC471944
0.6836	Remote Similarity	NPC80681
0.6834	Remote Similarity	NPC4687
0.6834	Remote Similarity	NPC193238
0.6832	Remote Similarity	NPC280473
0.6832	Remote Similarity	NPC323551
0.6832	Remote Similarity	NPC244856
0.6829	Remote Similarity	NPC184408
0.6827	Remote Similarity	NPC250807
0.6827	Remote Similarity	NPC229893
0.6827	Remote Similarity	NPC57797
0.6821	Remote Similarity	NPC81535
0.6821	Remote Similarity	NPC13432
0.6818	Remote Similarity	NPC289086
0.6818	Remote Similarity	NPC74357
0.6814	Remote Similarity	NPC62844
0.6814	Remote Similarity	NPC193361
0.68	Remote Similarity	NPC63041
0.68	Remote Similarity	NPC39679
0.6798	Remote Similarity	NPC41724
0.6798	Remote Similarity	NPC236668
0.6798	Remote Similarity	NPC306644
0.6798	Remote Similarity	NPC236424
0.6798	Remote Similarity	NPC51008
0.6794	Remote Similarity	NPC473850
0.6786	Remote Similarity	NPC470279
0.6782	Remote Similarity	NPC470189
0.6782	Remote Similarity	NPC187501
0.6782	Remote Similarity	NPC40919
0.6779	Remote Similarity	NPC216612
0.6776	Remote Similarity	NPC182222
0.6776	Remote Similarity	NPC252572
0.6774	Remote Similarity	NPC73994
0.6766	Remote Similarity	NPC304179
0.6766	Remote Similarity	NPC48042
0.6766	Remote Similarity	NPC472550
0.6765	Remote Similarity	NPC274842
0.6765	Remote Similarity	NPC264674
0.6765	Remote Similarity	NPC146976
0.6763	Remote Similarity	NPC323969
0.6749	Remote Similarity	NPC476467
0.6749	Remote Similarity	NPC473493
0.6747	Remote Similarity	NPC173295
0.6746	Remote Similarity	NPC314633
0.6746	Remote Similarity	NPC76565
0.6743	Remote Similarity	NPC470679
0.6743	Remote Similarity	NPC217021
0.6737	Remote Similarity	NPC278434
0.6736	Remote Similarity	NPC103230
0.6732	Remote Similarity	NPC42678
0.6732	Remote Similarity	NPC477907
0.6732	Remote Similarity	NPC207531
0.6732	Remote Similarity	NPC477909
0.673	Remote Similarity	NPC146824
0.673	Remote Similarity	NPC228377
0.673	Remote Similarity	NPC477787
0.673	Remote Similarity	NPC328186
0.673	Remote Similarity	NPC122968
0.6722	Remote Similarity	NPC265100
0.672	Remote Similarity	NPC164340
0.6718	Remote Similarity	NPC106824
0.6716	Remote Similarity	NPC472291
0.6714	Remote Similarity	NPC475137
0.6714	Remote Similarity	NPC475498
0.6712	Remote Similarity	NPC165964
0.6705	Remote Similarity	NPC26872
0.6703	Remote Similarity	NPC286195
0.6702	Remote Similarity	NPC159125
0.6702	Remote Similarity	NPC143533
0.6702	Remote Similarity	NPC183805
0.6701	Remote Similarity	NPC214428
0.67	Remote Similarity	NPC87413
0.67	Remote Similarity	NPC82053

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 NPC470894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	662
0.2-0.3	899
0.3-0.4	1366
0.4-0.5	3380
0.5-0.6	2119
0.6-0.7	483
0.7-0.8	32
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
0.7738	Intermediate Similarity	NPD1630	Approved
0.7602	Intermediate Similarity	NPD1631	Approved
0.7571	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD9271	Approved
0.7401	Intermediate Similarity	NPD1586	Approved
0.733	Intermediate Similarity	NPD1575	Approved
0.733	Intermediate Similarity	NPD1573	Approved
0.7278	Intermediate Similarity	NPD1587	Approved
0.7267	Intermediate Similarity	NPD820	Phase 3
0.7254	Intermediate Similarity	NPD3947	Discontinued
0.7211	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5416	Discontinued
0.7202	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4506	Discontinued
0.7193	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2778	Approved
0.7172	Intermediate Similarity	NPD5866	Approved
0.7129	Intermediate Similarity	NPD6770	Approved
0.712	Intermediate Similarity	NPD721	Approved
0.7108	Intermediate Similarity	NPD107	Approved
0.7104	Intermediate Similarity	NPD3178	Discontinued
0.7102	Intermediate Similarity	NPD5088	Discontinued
0.71	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2779	Approved
0.7053	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1643	Phase 3
0.7035	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5512	Phase 3
0.7	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4429	Discontinued
0.698	Remote Similarity	NPD3389	Approved
0.698	Remote Similarity	NPD3394	Approved
0.698	Remote Similarity	NPD3393	Approved
0.6971	Remote Similarity	NPD2582	Approved
0.6971	Remote Similarity	NPD2581	Approved
0.697	Remote Similarity	NPD2510	Approved
0.697	Remote Similarity	NPD2509	Approved
0.6952	Remote Similarity	NPD3315	Phase 3
0.695	Remote Similarity	NPD5475	Discontinued
0.6941	Remote Similarity	NPD9075	Approved
0.6941	Remote Similarity	NPD9074	Approved
0.6935	Remote Similarity	NPD1096	Discontinued
0.6923	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5003	Discontinued
0.6878	Remote Similarity	NPD6974	Phase 3
0.686	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6641	Approved
0.6848	Remote Similarity	NPD6642	Approved
0.6847	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1996	Discontinued
0.6842	Remote Similarity	NPD2564	Approved
0.6842	Remote Similarity	NPD2565	Phase 2
0.6829	Remote Similarity	NPD7395	Discontinued
0.6827	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3525	Discontinued
0.6818	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3259	Approved
0.6798	Remote Similarity	NPD3794	Approved
0.6798	Remote Similarity	NPD3795	Approved
0.6788	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7010	Phase 3
0.6782	Remote Similarity	NPD4417	Approved
0.6778	Remote Similarity	NPD2915	Discontinued
0.6765	Remote Similarity	NPD1638	Discovery
0.6761	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6550	Discontinued
0.675	Remote Similarity	NPD5429	Discontinued
0.6744	Remote Similarity	NPD7853	Phase 2
0.674	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4948	Discontinued
0.673	Remote Similarity	NPD7994	Phase 2
0.6719	Remote Similarity	NPD2336	Approved
0.6716	Remote Similarity	NPD3945	Discontinued
0.6715	Remote Similarity	NPD7404	Approved
0.6714	Remote Similarity	NPD1867	Approved
0.67	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4524	Discontinued
0.6685	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3257	Approved
0.6683	Remote Similarity	NPD7180	Phase 3
0.6682	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5022	Discontinued
0.6667	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1270	Approved
0.6649	Remote Similarity	NPD4526	Approved
0.6649	Remote Similarity	NPD4528	Approved
0.6649	Remote Similarity	NPD4529	Approved
0.6648	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1466	Phase 3
0.6636	Remote Similarity	NPD1467	Approved
0.6635	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3925	Approved
0.663	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1801	Approved
0.6609	Remote Similarity	NPD1802	Approved
0.6603	Remote Similarity	NPD3280	Approved
0.66	Remote Similarity	NPD6176	Phase 1
0.6599	Remote Similarity	NPD772	Phase 3
0.6595	Remote Similarity	NPD2076	Approved
0.6595	Remote Similarity	NPD2077	Approved
0.6587	Remote Similarity	NPD1623	Approved
0.6584	Remote Similarity	NPD3371	Approved
0.6582	Remote Similarity	NPD2307	Discontinued
0.6575	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5020	Approved
0.657	Remote Similarity	NPD8160	Phase 2
0.6568	Remote Similarity	NPD2670	Approved
0.6567	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4368	Phase 2
0.6558	Remote Similarity	NPD7688	Phase 1
0.6557	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2214	Approved
0.6556	Remote Similarity	NPD2213	Approved
0.6555	Remote Similarity	NPD3258	Approved
0.6545	Remote Similarity	NPD4889	Approved
0.6538	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1626	Approved
0.6526	Remote Similarity	NPD3263	Phase 3
0.6524	Remote Similarity	NPD5104	Approved
0.6524	Remote Similarity	NPD5850	Phase 3
0.6522	Remote Similarity	NPD2844	Phase 3
0.6517	Remote Similarity	NPD5513	Phase 2
0.6512	Remote Similarity	NPD4952	Phase 3
0.6507	Remote Similarity	NPD5632	Approved
0.65	Remote Similarity	NPD7727	Phase 2
0.6495	Remote Similarity	NPD8063	Discontinued
0.6492	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3392	Approved
0.6488	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3243	Approved
0.6465	Remote Similarity	NPD6988	Phase 1
0.6462	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8356	Approved
0.6459	Remote Similarity	NPD1591	Approved
0.6453	Remote Similarity	NPD3507	Phase 2
0.6453	Remote Similarity	NPD4804	Approved
0.6453	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7031	Phase 1
0.6449	Remote Similarity	NPD8289	Discontinued
0.6447	Remote Similarity	NPD4602	Approved
0.6443	Remote Similarity	NPD2792	Approved
0.6439	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5891	Approved
0.6436	Remote Similarity	NPD3238	Discontinued
0.6436	Remote Similarity	NPD2920	Discontinued
0.6435	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1109	Approved
0.6433	Remote Similarity	NPD1110	Approved
0.6429	Remote Similarity	NPD1527	Phase 2
0.6429	Remote Similarity	NPD6665	Discontinued
0.6429	Remote Similarity	NPD4376	Phase 3
0.6425	Remote Similarity	NPD8097	Phase 3
0.6425	Remote Similarity	NPD8096	Phase 3
0.6422	Remote Similarity	NPD4373	Phase 2
0.6419	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5482	Discontinued
0.6416	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4301	Approved
0.641	Remote Similarity	NPD4499	Approved
0.6406	Remote Similarity	NPD6962	Phase 2
0.6404	Remote Similarity	NPD6987	Phase 1
0.6404	Remote Similarity	NPD2831	Approved
0.6402	Remote Similarity	NPD7869	Discontinued
0.6402	Remote Similarity	NPD2753	Discontinued
0.6402	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6790	Phase 1
0.6395	Remote Similarity	NPD2896	Discontinued
0.6394	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7467	Discontinued
0.6384	Remote Similarity	NPD7528	Approved
0.6379	Remote Similarity	NPD4805	Approved
0.6379	Remote Similarity	NPD1625	Approved
0.6377	Remote Similarity	NPD7470	Discontinued
0.6377	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5255	Approved
0.6373	Remote Similarity	NPD5075	Discontinued
0.6368	Remote Similarity	NPD8479	Phase 2
0.6364	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD553	Approved
0.6364	Remote Similarity	NPD3006	Discontinued
0.6364	Remote Similarity	NPD9567	Approved
0.6364	Remote Similarity	NPD552	Approved
0.6364	Remote Similarity	NPD5293	Phase 2
0.6359	Remote Similarity	NPD5479	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