NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	251.07
Volume:	245.953
LogP:	1.226
LogD:	1.454
LogS:	-2.881
# Rotatable Bonds:	1
TPSA:	56.49
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	2.807
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.734
MDCK Permeability:	2.4183713321690448e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	76.45174407958984%
Volume Distribution (VD):	1.156
Pgp-substrate:	16.86693572998047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.693
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.76
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	6.287
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.93
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.086
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC17565

Natural Product ID:	NPC17565
*Common Name:**	LMHRIBSXZWWDSE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LMHRIBSXZWWDSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H9N3O2/c1-19-10-6-8-2-4-15-9-3-5-17-11(18)7-16-13(10)14(17)12(8)9/h2-7H,1H3
SMILES:	COc1cc2ccnc3c2c2c1ncc(=O)n2cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337112
PubChem CID:	71524397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0001857] Naphthyridines

*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
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20451377]
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[23282083]
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	0.0	%	PMID[570160]

☑ 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 NPC17565 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	1038
0.1-0.2	8265
0.2-0.3	9796
0.3-0.4	16249
0.4-0.5	3575
0.5-0.6	2666
0.6-0.7	972
0.7-0.8	133
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC65277
0.8592	High Similarity	NPC162530
0.8486	Intermediate Similarity	NPC472061
0.8469	Intermediate Similarity	NPC473513
0.8429	Intermediate Similarity	NPC173080
0.8364	Intermediate Similarity	NPC30540
0.8309	Intermediate Similarity	NPC174758
0.8075	Intermediate Similarity	NPC274982
0.8048	Intermediate Similarity	NPC174672
0.801	Intermediate Similarity	NPC315957
0.8	Intermediate Similarity	NPC82548
0.7933	Intermediate Similarity	NPC295898
0.7915	Intermediate Similarity	NPC287208
0.783	Intermediate Similarity	NPC18348
0.7828	Intermediate Similarity	NPC470018
0.7793	Intermediate Similarity	NPC74575
0.7714	Intermediate Similarity	NPC232727
0.7703	Intermediate Similarity	NPC287437
0.7689	Intermediate Similarity	NPC285558
0.7655	Intermediate Similarity	NPC49547
0.7642	Intermediate Similarity	NPC476138
0.7642	Intermediate Similarity	NPC245816
0.7642	Intermediate Similarity	NPC53144
0.7606	Intermediate Similarity	NPC36229
0.7606	Intermediate Similarity	NPC476581
0.7606	Intermediate Similarity	NPC16452
0.7593	Intermediate Similarity	NPC167860
0.7593	Intermediate Similarity	NPC123976
0.7585	Intermediate Similarity	NPC133140
0.7585	Intermediate Similarity	NPC195268
0.7574	Intermediate Similarity	NPC26543
0.757	Intermediate Similarity	NPC470164
0.757	Intermediate Similarity	NPC323345
0.7555	Intermediate Similarity	NPC470017
0.7548	Intermediate Similarity	NPC198673
0.7547	Intermediate Similarity	NPC470586
0.7546	Intermediate Similarity	NPC185782
0.7543	Intermediate Similarity	NPC72905
0.7542	Intermediate Similarity	NPC137353
0.7536	Intermediate Similarity	NPC4071
0.7536	Intermediate Similarity	NPC476582
0.7536	Intermediate Similarity	NPC476578
0.7532	Intermediate Similarity	NPC270515
0.7524	Intermediate Similarity	NPC267928
0.7522	Intermediate Similarity	NPC470022
0.7512	Intermediate Similarity	NPC470020
0.75	Intermediate Similarity	NPC234197
0.75	Intermediate Similarity	NPC322482
0.7489	Intermediate Similarity	NPC476287
0.7467	Intermediate Similarity	NPC141053
0.7465	Intermediate Similarity	NPC31930
0.7443	Intermediate Similarity	NPC26679
0.7431	Intermediate Similarity	NPC85273
0.7418	Intermediate Similarity	NPC176538
0.7418	Intermediate Similarity	NPC121772
0.7418	Intermediate Similarity	NPC477019
0.7406	Intermediate Similarity	NPC239954
0.7406	Intermediate Similarity	NPC168911
0.7399	Intermediate Similarity	NPC213530
0.7399	Intermediate Similarity	NPC193267
0.7397	Intermediate Similarity	NPC208284
0.7395	Intermediate Similarity	NPC200836
0.7395	Intermediate Similarity	NPC475774
0.7393	Intermediate Similarity	NPC194967
0.7382	Intermediate Similarity	NPC41501
0.7364	Intermediate Similarity	NPC112206
0.7364	Intermediate Similarity	NPC264176
0.7364	Intermediate Similarity	NPC53069
0.7364	Intermediate Similarity	NPC202768
0.7364	Intermediate Similarity	NPC296482
0.7364	Intermediate Similarity	NPC202605
0.7362	Intermediate Similarity	NPC142385
0.7358	Intermediate Similarity	NPC224928
0.735	Intermediate Similarity	NPC99891
0.7349	Intermediate Similarity	NPC211813
0.7342	Intermediate Similarity	NPC470799
0.7342	Intermediate Similarity	NPC8022
0.7336	Intermediate Similarity	NPC19872
0.7333	Intermediate Similarity	NPC60621
0.7331	Intermediate Similarity	NPC208522
0.733	Intermediate Similarity	NPC84478
0.7323	Intermediate Similarity	NPC118511
0.7309	Intermediate Similarity	NPC305984
0.7297	Intermediate Similarity	NPC235076
0.7294	Intermediate Similarity	NPC313189
0.7293	Intermediate Similarity	NPC471762
0.7289	Intermediate Similarity	NPC128115
0.7285	Intermediate Similarity	NPC96405
0.7285	Intermediate Similarity	NPC171409
0.7285	Intermediate Similarity	NPC251160
0.728	Intermediate Similarity	NPC472066
0.728	Intermediate Similarity	NPC472067
0.728	Intermediate Similarity	NPC472031
0.7277	Intermediate Similarity	NPC23614
0.7277	Intermediate Similarity	NPC303658
0.7277	Intermediate Similarity	NPC100079
0.7273	Intermediate Similarity	NPC290689
0.7273	Intermediate Similarity	NPC469554
0.7273	Intermediate Similarity	NPC188420
0.7269	Intermediate Similarity	NPC122436
0.7269	Intermediate Similarity	NPC472068
0.7256	Intermediate Similarity	NPC329747
0.7252	Intermediate Similarity	NPC271215
0.7252	Intermediate Similarity	NPC149471
0.7244	Intermediate Similarity	NPC46451
0.7229	Intermediate Similarity	NPC260434
0.7227	Intermediate Similarity	NPC469589
0.7225	Intermediate Similarity	NPC216612
0.7215	Intermediate Similarity	NPC135549
0.7212	Intermediate Similarity	NPC42591
0.7204	Intermediate Similarity	NPC92111
0.7202	Intermediate Similarity	NPC329708
0.7202	Intermediate Similarity	NPC47059
0.7202	Intermediate Similarity	NPC165349
0.7202	Intermediate Similarity	NPC264166
0.7202	Intermediate Similarity	NPC274291
0.7202	Intermediate Similarity	NPC118832
0.7198	Intermediate Similarity	NPC101543
0.719	Intermediate Similarity	NPC296527
0.7186	Intermediate Similarity	NPC177404
0.7167	Intermediate Similarity	NPC172222
0.7166	Intermediate Similarity	NPC132385
0.7163	Intermediate Similarity	NPC284559
0.7163	Intermediate Similarity	NPC212213
0.7156	Intermediate Similarity	NPC76748
0.715	Intermediate Similarity	NPC13880
0.7149	Intermediate Similarity	NPC210434
0.7149	Intermediate Similarity	NPC201697
0.7143	Intermediate Similarity	NPC314954
0.7143	Intermediate Similarity	NPC66777
0.7136	Intermediate Similarity	NPC307963
0.7129	Intermediate Similarity	NPC1527
0.7117	Intermediate Similarity	NPC199667
0.7104	Intermediate Similarity	NPC475910
0.71	Intermediate Similarity	NPC257851
0.71	Intermediate Similarity	NPC473185
0.7098	Intermediate Similarity	NPC236668
0.7095	Intermediate Similarity	NPC314573
0.7094	Intermediate Similarity	NPC476518
0.7093	Intermediate Similarity	NPC292958
0.7091	Intermediate Similarity	NPC472111
0.7082	Intermediate Similarity	NPC475253
0.7074	Intermediate Similarity	NPC118121
0.7072	Intermediate Similarity	NPC473181
0.707	Intermediate Similarity	NPC251090
0.7067	Intermediate Similarity	NPC118776
0.7067	Intermediate Similarity	NPC146976
0.7064	Intermediate Similarity	NPC253675
0.7059	Intermediate Similarity	NPC14651
0.7059	Intermediate Similarity	NPC121658
0.7056	Intermediate Similarity	NPC329541
0.7056	Intermediate Similarity	NPC26872
0.7054	Intermediate Similarity	NPC316981
0.7054	Intermediate Similarity	NPC94157
0.7048	Intermediate Similarity	NPC204446
0.7045	Intermediate Similarity	NPC470930
0.7035	Intermediate Similarity	NPC477110
0.7035	Intermediate Similarity	NPC26850
0.7034	Intermediate Similarity	NPC295228
0.7033	Intermediate Similarity	NPC176127
0.7031	Intermediate Similarity	NPC310118
0.7027	Intermediate Similarity	NPC477111
0.7026	Intermediate Similarity	NPC157931
0.7023	Intermediate Similarity	NPC131017
0.7022	Intermediate Similarity	NPC471080
0.7022	Intermediate Similarity	NPC469592
0.7018	Intermediate Similarity	NPC11017
0.701	Intermediate Similarity	NPC314940
0.701	Intermediate Similarity	NPC473764
0.7004	Intermediate Similarity	NPC235685
0.7	Intermediate Similarity	NPC122463
0.7	Intermediate Similarity	NPC62069
0.6996	Remote Similarity	NPC194740
0.699	Remote Similarity	NPC312872
0.6983	Remote Similarity	NPC200888
0.6983	Remote Similarity	NPC227908
0.6982	Remote Similarity	NPC193777
0.6978	Remote Similarity	NPC472098
0.6975	Remote Similarity	NPC101350
0.6974	Remote Similarity	NPC473822
0.6974	Remote Similarity	NPC473041
0.6972	Remote Similarity	NPC476167
0.6967	Remote Similarity	NPC133609
0.6967	Remote Similarity	NPC20249
0.6966	Remote Similarity	NPC24019
0.696	Remote Similarity	NPC170114
0.6955	Remote Similarity	NPC470678
0.6951	Remote Similarity	NPC470931
0.6948	Remote Similarity	NPC242928
0.6943	Remote Similarity	NPC473179
0.6942	Remote Similarity	NPC111624
0.6941	Remote Similarity	NPC329793
0.694	Remote Similarity	NPC21638
0.694	Remote Similarity	NPC473449
0.6937	Remote Similarity	NPC477113
0.6934	Remote Similarity	NPC61350
0.6933	Remote Similarity	NPC184680
0.693	Remote Similarity	NPC280964
0.693	Remote Similarity	NPC114335
0.693	Remote Similarity	NPC141915

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 NPC17565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	752
0.2-0.3	951
0.3-0.4	2183
0.4-0.5	2423
0.5-0.6	1696
0.6-0.7	636
0.7-0.8	33
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
0.8029	Intermediate Similarity	NPD4795	Phase 2
0.801	Intermediate Similarity	NPD1739	Approved
0.801	Intermediate Similarity	NPD1740	Approved
0.7756	Intermediate Similarity	NPD4372	Phase 1
0.7736	Intermediate Similarity	NPD5530	Phase 1
0.7585	Intermediate Similarity	NPD3924	Approved
0.7585	Intermediate Similarity	NPD3921	Approved
0.7585	Intermediate Similarity	NPD3923	Approved
0.7585	Intermediate Similarity	NPD3922	Approved
0.757	Intermediate Similarity	NPD5601	Phase 2
0.7534	Intermediate Similarity	NPD1856	Discontinued
0.7489	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7426	Phase 1
0.7432	Intermediate Similarity	NPD6568	Discontinued
0.7419	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6961	Discontinued
0.7416	Intermediate Similarity	NPD6569	Phase 2
0.7387	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5999	Phase 2
0.7368	Intermediate Similarity	NPD5559	Phase 2
0.7364	Intermediate Similarity	NPD3815	Phase 1
0.7364	Intermediate Similarity	NPD3816	Phase 1
0.7346	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6964	Approved
0.7284	Intermediate Similarity	NPD6963	Approved
0.7261	Intermediate Similarity	NPD6968	Phase 2
0.7261	Intermediate Similarity	NPD6969	Phase 2
0.726	Intermediate Similarity	NPD5658	Approved
0.7257	Intermediate Similarity	NPD6230	Discontinued
0.7244	Intermediate Similarity	NPD3763	Approved
0.7241	Intermediate Similarity	NPD6494	Phase 2
0.7222	Intermediate Similarity	NPD112	Approved
0.7222	Intermediate Similarity	NPD9705	Discontinued
0.722	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4551	Phase 2
0.7215	Intermediate Similarity	NPD7067	Approved
0.7215	Intermediate Similarity	NPD7068	Approved
0.7212	Intermediate Similarity	NPD4889	Approved
0.7209	Intermediate Similarity	NPD4548	Discontinued
0.7203	Intermediate Similarity	NPD6790	Phase 1
0.7202	Intermediate Similarity	NPD4035	Approved
0.7202	Intermediate Similarity	NPD32	Approved
0.7202	Intermediate Similarity	NPD31	Approved
0.7202	Intermediate Similarity	NPD4033	Approved
0.7202	Intermediate Similarity	NPD4122	Approved
0.7202	Intermediate Similarity	NPD4037	Approved
0.7202	Intermediate Similarity	NPD4036	Approved
0.7202	Intermediate Similarity	NPD4034	Approved
0.7202	Intermediate Similarity	NPD4039	Approved
0.7202	Intermediate Similarity	NPD4038	Approved
0.72	Intermediate Similarity	NPD4429	Discontinued
0.7172	Intermediate Similarity	NPD8091	Phase 3
0.7162	Intermediate Similarity	NPD4502	Phase 2
0.7161	Intermediate Similarity	NPD7117	Phase 2
0.715	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3477	Phase 2
0.715	Intermediate Similarity	NPD3386	Phase 2
0.7149	Intermediate Similarity	NPD7924	Phase 2
0.7149	Intermediate Similarity	NPD7925	Phase 2
0.7143	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3920	Phase 2
0.7136	Intermediate Similarity	NPD7222	Phase 2
0.7136	Intermediate Similarity	NPD1038	Approved
0.713	Intermediate Similarity	NPD7675	Phase 3
0.713	Intermediate Similarity	NPD7674	Phase 3
0.713	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7069	Discontinued
0.7129	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5948	Phase 2
0.7116	Intermediate Similarity	NPD1622	Discontinued
0.7094	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8016	Phase 3
0.7089	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5513	Phase 2
0.7071	Intermediate Similarity	NPD7413	Phase 3
0.7061	Intermediate Similarity	NPD5930	Phase 3
0.7031	Intermediate Similarity	NPD5147	Discontinued
0.7031	Intermediate Similarity	NPD5506	Approved
0.7031	Intermediate Similarity	NPD5507	Approved
0.7031	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6366	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4418	Discontinued
0.7023	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5488	Discontinued
0.7008	Intermediate Similarity	NPD7859	Phase 2
0.699	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4204	Approved
0.6986	Remote Similarity	NPD4203	Approved
0.6983	Remote Similarity	NPD7897	Phase 3
0.6983	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2952	Discontinued
0.6951	Remote Similarity	NPD5529	Phase 1
0.6951	Remote Similarity	NPD7467	Discontinued
0.6951	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3395	Approved
0.6944	Remote Similarity	NPD3396	Approved
0.6943	Remote Similarity	NPD6500	Approved
0.6943	Remote Similarity	NPD6501	Approved
0.6941	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD2600	Approved
0.6938	Remote Similarity	NPD2599	Approved
0.6938	Remote Similarity	NPD2601	Approved
0.6933	Remote Similarity	NPD3570	Phase 2
0.6929	Remote Similarity	NPD7620	Phase 2
0.6926	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4437	Phase 3
0.692	Remote Similarity	NPD2757	Phase 2
0.6917	Remote Similarity	NPD6848	Phase 1
0.6916	Remote Similarity	NPD4897	Phase 2
0.6913	Remote Similarity	NPD6242	Discontinued
0.6911	Remote Similarity	NPD7405	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7453	Approved
0.6906	Remote Similarity	NPD1392	Approved
0.6906	Remote Similarity	NPD7452	Approved
0.6901	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1034	Phase 3
0.6901	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5022	Discontinued
0.6892	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6716	Phase 1
0.6888	Remote Similarity	NPD5874	Phase 3
0.6888	Remote Similarity	NPD5873	Phase 3
0.6884	Remote Similarity	NPD2334	Discontinued
0.6883	Remote Similarity	NPD6298	Discontinued
0.6881	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5945	Phase 1
0.6872	Remote Similarity	NPD5944	Phase 1
0.6867	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4131	Phase 3
0.6856	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7758	Approved
0.6854	Remote Similarity	NPD7757	Approved
0.6853	Remote Similarity	NPD1954	Phase 1
0.6838	Remote Similarity	NPD7603	Discontinued
0.6837	Remote Similarity	NPD6281	Approved
0.6837	Remote Similarity	NPD3321	Discontinued
0.6835	Remote Similarity	NPD4885	Approved
0.6835	Remote Similarity	NPD7797	Approved
0.6835	Remote Similarity	NPD7796	Approved
0.6833	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9690	Approved
0.6824	Remote Similarity	NPD6306	Phase 2
0.6822	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.682	Remote Similarity	NPD9695	Approved
0.6818	Remote Similarity	NPD2177	Approved
0.6818	Remote Similarity	NPD2176	Approved
0.6818	Remote Similarity	NPD2175	Phase 3
0.6814	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7558	Phase 2
0.6797	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4995	Approved
0.6793	Remote Similarity	NPD4996	Approved
0.6789	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2581	Approved
0.6782	Remote Similarity	NPD2582	Approved
0.678	Remote Similarity	NPD2782	Approved
0.678	Remote Similarity	NPD2780	Approved
0.6776	Remote Similarity	NPD2917	Approved
0.677	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD1032	Phase 2
0.6762	Remote Similarity	NPD4071	Approved
0.6762	Remote Similarity	NPD7967	Discontinued
0.6762	Remote Similarity	NPD4072	Approved
0.6761	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6550	Discontinued
0.6757	Remote Similarity	NPD5437	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5429	Discontinued
0.6751	Remote Similarity	NPD4925	Approved
0.6748	Remote Similarity	NPD4558	Phase 2
0.6747	Remote Similarity	NPD8246	Approved
0.6747	Remote Similarity	NPD8247	Approved
0.6741	Remote Similarity	NPD3397	Phase 2
0.6739	Remote Similarity	NPD5612	Discontinued
0.6739	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4890	Phase 2
0.6721	Remote Similarity	NPD4440	Clinical (unspecified phase)

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