NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	243.1
Volume:	248.407
LogP:	3.028
LogD:	3.457
LogS:	-4.403
# Rotatable Bonds:	4
TPSA:	56.6
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	2.546
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.513
MDCK Permeability:	1.7463285985286348e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	87.19489288330078%
Volume Distribution (VD):	0.73
Pgp-substrate:	8.997106552124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.383
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	2.608
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.601
Skin Sensitization:	0.147
Carcinogencity:	0.041
Eye Corrosion:	0.006
Eye Irritation:	0.707
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC476518

Natural Product ID:	NPC476518
*Common Name:**	(E)-N-methoxy-1-(4-methoxy-6-pyridin-2-ylpyridin-2-yl)methanimine
IUPAC Name:	(E)-N-methoxy-1-(4-methoxy-6-pyridin-2-ylpyridin-2-yl)methanimine
Synonyms:
Standard InCHIKey:	WOCWELSPPBUMDA-OQLLNIDSSA-N
Standard InCHI:	InChI=1S/C13H13N3O2/c1-17-11-7-10(9-15-18-2)16-13(8-11)12-5-3-4-6-14-12/h3-9H,1-2H3/b15-9+
SMILES:	COC1=CC(=NC(=C1)C2=CC=CC=N2)/C=N/OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16128661
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	isolated from marine sediments	the seashore of Weihai, China	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4
MIC	4

Activity Type	# Activity
Cell Line	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000	nM	PMID[21770434]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000	nM	PMID[21770434]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	31800	nM	PMID[21770434]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000	nM	PMID[21770434]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>=	100000	nM	PMID[21770434]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	100000	nM	PMID[21770434]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>=	100000	nM	PMID[21770434]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	41100	nM	PMID[21770434]

☑ 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 NPC476518 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	608
0.1-0.2	11433
0.2-0.3	6862
0.3-0.4	15679
0.4-0.5	4536
0.5-0.6	2717
0.6-0.7	754
0.7-0.8	91
0.8-0.85	2
0.85-0.9	4
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC121658
0.9935	High Similarity	NPC14651
0.9503	High Similarity	NPC266551
0.9494	High Similarity	NPC111624
0.9329	High Similarity	NPC20249
0.9264	High Similarity	NPC161887
0.9264	High Similarity	NPC219963
0.9217	High Similarity	NPC206251
0.9217	High Similarity	NPC74382
0.9051	High Similarity	NPC48192
0.8987	High Similarity	NPC25899
0.8824	High Similarity	NPC224327
0.8772	High Similarity	NPC134079
0.8728	High Similarity	NPC226202
0.858	High Similarity	NPC267928
0.8466	Intermediate Similarity	NPC177404
0.8132	Intermediate Similarity	NPC19872
0.8072	Intermediate Similarity	NPC285635
0.8	Intermediate Similarity	NPC84853
0.7989	Intermediate Similarity	NPC232727
0.7935	Intermediate Similarity	NPC315957
0.7935	Intermediate Similarity	NPC176538
0.7926	Intermediate Similarity	NPC287208
0.7886	Intermediate Similarity	NPC222592
0.7886	Intermediate Similarity	NPC168486
0.7884	Intermediate Similarity	NPC174672
0.788	Intermediate Similarity	NPC187558
0.7879	Intermediate Similarity	NPC26872
0.7849	Intermediate Similarity	NPC258773
0.7842	Intermediate Similarity	NPC123976
0.7842	Intermediate Similarity	NPC167860
0.7789	Intermediate Similarity	NPC174758
0.7738	Intermediate Similarity	NPC26850
0.7737	Intermediate Similarity	NPC82548
0.7733	Intermediate Similarity	NPC1527
0.7732	Intermediate Similarity	NPC274982
0.7725	Intermediate Similarity	NPC323345
0.7725	Intermediate Similarity	NPC470164
0.7713	Intermediate Similarity	NPC476138
0.7713	Intermediate Similarity	NPC245816
0.7704	Intermediate Similarity	NPC193267
0.7704	Intermediate Similarity	NPC213530
0.7696	Intermediate Similarity	NPC185782
0.7688	Intermediate Similarity	NPC287437
0.7647	Intermediate Similarity	NPC121772
0.7579	Intermediate Similarity	NPC476581
0.7579	Intermediate Similarity	NPC36229
0.7579	Intermediate Similarity	NPC16452
0.7577	Intermediate Similarity	NPC26679
0.75	Intermediate Similarity	NPC476582
0.75	Intermediate Similarity	NPC476578
0.75	Intermediate Similarity	NPC4071
0.7487	Intermediate Similarity	NPC274291
0.7487	Intermediate Similarity	NPC264166
0.7487	Intermediate Similarity	NPC329708
0.7487	Intermediate Similarity	NPC118832
0.7487	Intermediate Similarity	NPC47059
0.7487	Intermediate Similarity	NPC165349
0.7486	Intermediate Similarity	NPC296527
0.7462	Intermediate Similarity	NPC8022
0.7462	Intermediate Similarity	NPC470799
0.7459	Intermediate Similarity	NPC195268
0.7459	Intermediate Similarity	NPC284559
0.7459	Intermediate Similarity	NPC133140
0.745	Intermediate Similarity	NPC60621
0.745	Intermediate Similarity	NPC310118
0.7446	Intermediate Similarity	NPC76748
0.7444	Intermediate Similarity	NPC118776
0.7433	Intermediate Similarity	NPC13880
0.7421	Intermediate Similarity	NPC31930
0.7419	Intermediate Similarity	NPC307963
0.7419	Intermediate Similarity	NPC198673
0.7405	Intermediate Similarity	NPC92111
0.7402	Intermediate Similarity	NPC314954
0.7396	Intermediate Similarity	NPC285558
0.7363	Intermediate Similarity	NPC284678
0.736	Intermediate Similarity	NPC476287
0.7356	Intermediate Similarity	NPC118511
0.7348	Intermediate Similarity	NPC470474
0.7314	Intermediate Similarity	NPC471178
0.731	Intermediate Similarity	NPC112206
0.731	Intermediate Similarity	NPC202605
0.731	Intermediate Similarity	NPC296482
0.731	Intermediate Similarity	NPC202768
0.731	Intermediate Similarity	NPC53069
0.7299	Intermediate Similarity	NPC59779
0.7299	Intermediate Similarity	NPC124542
0.7299	Intermediate Similarity	NPC471177
0.7295	Intermediate Similarity	NPC469554
0.7295	Intermediate Similarity	NPC101543
0.7291	Intermediate Similarity	NPC122436
0.7277	Intermediate Similarity	NPC234197
0.7268	Intermediate Similarity	NPC110151
0.7263	Intermediate Similarity	NPC168911
0.7263	Intermediate Similarity	NPC239954
0.7262	Intermediate Similarity	NPC220523
0.726	Intermediate Similarity	NPC141053
0.7251	Intermediate Similarity	NPC36168
0.7249	Intermediate Similarity	NPC251090
0.7231	Intermediate Similarity	NPC313189
0.7222	Intermediate Similarity	NPC96405
0.7222	Intermediate Similarity	NPC171409
0.7211	Intermediate Similarity	NPC224928
0.7208	Intermediate Similarity	NPC290689
0.7204	Intermediate Similarity	NPC110741
0.7188	Intermediate Similarity	NPC477019
0.7182	Intermediate Similarity	NPC283152
0.7181	Intermediate Similarity	NPC324149
0.7179	Intermediate Similarity	NPC472111
0.7167	Intermediate Similarity	NPC312872
0.7165	Intermediate Similarity	NPC475774
0.7165	Intermediate Similarity	NPC200836
0.7157	Intermediate Similarity	NPC469589
0.7143	Intermediate Similarity	NPC135549
0.7143	Intermediate Similarity	NPC193238
0.7127	Intermediate Similarity	NPC288943
0.71	Intermediate Similarity	NPC162530
0.7095	Intermediate Similarity	NPC473764
0.7095	Intermediate Similarity	NPC314940
0.7094	Intermediate Similarity	NPC17565
0.7094	Intermediate Similarity	NPC292958
0.7085	Intermediate Similarity	NPC208284
0.7081	Intermediate Similarity	NPC260434
0.7081	Intermediate Similarity	NPC84478
0.7081	Intermediate Similarity	NPC62069
0.7077	Intermediate Similarity	NPC53144
0.7062	Intermediate Similarity	NPC473057
0.7062	Intermediate Similarity	NPC97367
0.7059	Intermediate Similarity	NPC66083
0.7053	Intermediate Similarity	NPC289786
0.7047	Intermediate Similarity	NPC476167
0.7047	Intermediate Similarity	NPC18487
0.7043	Intermediate Similarity	NPC42591
0.7041	Intermediate Similarity	NPC470500
0.7041	Intermediate Similarity	NPC471323
0.7039	Intermediate Similarity	NPC322482
0.7035	Intermediate Similarity	NPC85273
0.703	Intermediate Similarity	NPC170114
0.7028	Intermediate Similarity	NPC295228
0.7027	Intermediate Similarity	NPC176127
0.7026	Intermediate Similarity	NPC211813
0.7006	Intermediate Similarity	NPC79911
0.7005	Intermediate Similarity	NPC204385
0.6995	Remote Similarity	NPC212213
0.6995	Remote Similarity	NPC192315
0.6995	Remote Similarity	NPC473513
0.699	Remote Similarity	NPC223427
0.699	Remote Similarity	NPC216612
0.6982	Remote Similarity	NPC470394
0.6982	Remote Similarity	NPC470404
0.6982	Remote Similarity	NPC470403
0.698	Remote Similarity	NPC470549
0.6979	Remote Similarity	NPC194967
0.6965	Remote Similarity	NPC264176
0.6965	Remote Similarity	NPC472098
0.6963	Remote Similarity	NPC329541
0.6961	Remote Similarity	NPC252590
0.6961	Remote Similarity	NPC197141
0.6961	Remote Similarity	NPC173080
0.6957	Remote Similarity	NPC472168
0.6957	Remote Similarity	NPC65277
0.6954	Remote Similarity	NPC475070
0.695	Remote Similarity	NPC470020
0.695	Remote Similarity	NPC5145
0.6949	Remote Similarity	NPC120798
0.694	Remote Similarity	NPC224764
0.6939	Remote Similarity	NPC295898
0.6937	Remote Similarity	NPC151489
0.6935	Remote Similarity	NPC48938
0.6931	Remote Similarity	NPC469592
0.6931	Remote Similarity	NPC471080
0.6928	Remote Similarity	NPC328029
0.6923	Remote Similarity	NPC329793
0.6916	Remote Similarity	NPC235685
0.6901	Remote Similarity	NPC470395
0.6893	Remote Similarity	NPC84508
0.689	Remote Similarity	NPC174421
0.6888	Remote Similarity	NPC470586
0.6885	Remote Similarity	NPC95898
0.6884	Remote Similarity	NPC101350
0.6882	Remote Similarity	NPC206201
0.6881	Remote Similarity	NPC316981
0.6878	Remote Similarity	NPC46580
0.6872	Remote Similarity	NPC263439
0.6866	Remote Similarity	NPC11464
0.6865	Remote Similarity	NPC42979
0.6863	Remote Similarity	NPC152768
0.6863	Remote Similarity	NPC148183
0.6862	Remote Similarity	NPC314002
0.685	Remote Similarity	NPC476465
0.685	Remote Similarity	NPC475910
0.6848	Remote Similarity	NPC203754
0.6848	Remote Similarity	NPC150048
0.6847	Remote Similarity	NPC266931
0.6842	Remote Similarity	NPC472289
0.6837	Remote Similarity	NPC329747
0.6834	Remote Similarity	NPC476124
0.6834	Remote Similarity	NPC476121
0.6821	Remote Similarity	NPC470111
0.682	Remote Similarity	NPC99891

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 NPC476518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	1035
0.2-0.3	573
0.3-0.4	1895
0.4-0.5	2748
0.5-0.6	1954
0.6-0.7	581
0.7-0.8	77
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
0.7941	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1740	Approved
0.7935	Intermediate Similarity	NPD1739	Approved
0.7845	Intermediate Similarity	NPD4372	Phase 1
0.7772	Intermediate Similarity	NPD1622	Discontinued
0.7766	Intermediate Similarity	NPD4795	Phase 2
0.7722	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1034	Phase 3
0.7717	Intermediate Similarity	NPD3477	Phase 2
0.7717	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2334	Discontinued
0.765	Intermediate Similarity	NPD6569	Phase 2
0.764	Intermediate Similarity	NPD3386	Phase 2
0.7637	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5319	Approved
0.7586	Intermediate Similarity	NPD5320	Approved
0.7586	Intermediate Similarity	NPD565	Phase 2
0.7514	Intermediate Similarity	NPD4889	Approved
0.75	Intermediate Similarity	NPD9596	Approved
0.75	Intermediate Similarity	NPD9595	Approved
0.7487	Intermediate Similarity	NPD32	Approved
0.7487	Intermediate Similarity	NPD4039	Approved
0.7487	Intermediate Similarity	NPD4033	Approved
0.7487	Intermediate Similarity	NPD4035	Approved
0.7487	Intermediate Similarity	NPD4122	Approved
0.7487	Intermediate Similarity	NPD4037	Approved
0.7487	Intermediate Similarity	NPD4038	Approved
0.7487	Intermediate Similarity	NPD4034	Approved
0.7487	Intermediate Similarity	NPD31	Approved
0.7487	Intermediate Similarity	NPD4036	Approved
0.7473	Intermediate Similarity	NPD1602	Discontinued
0.7473	Intermediate Similarity	NPD4375	Approved
0.7473	Intermediate Similarity	NPD3396	Approved
0.7473	Intermediate Similarity	NPD3395	Approved
0.746	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3922	Approved
0.7459	Intermediate Similarity	NPD3923	Approved
0.7459	Intermediate Similarity	NPD3924	Approved
0.7459	Intermediate Similarity	NPD3921	Approved
0.7458	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4204	Approved
0.7444	Intermediate Similarity	NPD4203	Approved
0.743	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1038	Approved
0.7389	Intermediate Similarity	NPD2599	Approved
0.7389	Intermediate Similarity	NPD2600	Approved
0.7389	Intermediate Similarity	NPD2601	Approved
0.7384	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4071	Approved
0.7374	Intermediate Similarity	NPD4072	Approved
0.7371	Intermediate Similarity	NPD424	Approved
0.7371	Intermediate Similarity	NPD425	Approved
0.7358	Intermediate Similarity	NPD715	Phase 3
0.7341	Intermediate Similarity	NPD112	Approved
0.7341	Intermediate Similarity	NPD9705	Discontinued
0.7327	Intermediate Similarity	NPD1856	Discontinued
0.7326	Intermediate Similarity	NPD2581	Approved
0.7326	Intermediate Similarity	NPD2582	Approved
0.7326	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3816	Phase 1
0.731	Intermediate Similarity	NPD3815	Phase 1
0.7302	Intermediate Similarity	NPD2952	Discontinued
0.7283	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1032	Phase 2
0.725	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2958	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4548	Discontinued
0.722	Intermediate Similarity	NPD1603	Discontinued
0.7216	Intermediate Similarity	NPD925	Approved
0.7216	Intermediate Similarity	NPD2782	Approved
0.7216	Intermediate Similarity	NPD2780	Approved
0.7216	Intermediate Similarity	NPD926	Approved
0.7211	Intermediate Similarity	NPD2959	Phase 3
0.7211	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5601	Phase 2
0.7179	Intermediate Similarity	NPD5530	Phase 1
0.7151	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1621	Discontinued
0.7143	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4551	Phase 2
0.7143	Intermediate Similarity	NPD1392	Approved
0.7135	Intermediate Similarity	NPD5999	Phase 2
0.7135	Intermediate Similarity	NPD2781	Approved
0.712	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4021	Phase 2
0.7107	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1951	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5255	Approved
0.7085	Intermediate Similarity	NPD4131	Phase 3
0.7085	Intermediate Similarity	NPD3570	Phase 2
0.7081	Intermediate Similarity	NPD3569	Discontinued
0.7077	Intermediate Similarity	NPD5513	Phase 2
0.7066	Intermediate Similarity	NPD1649	Discontinued
0.7065	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7069	Discontinued
0.7047	Intermediate Similarity	NPD3825	Phase 3
0.7045	Intermediate Similarity	NPD1418	Phase 2
0.7041	Intermediate Similarity	NPD3397	Phase 2
0.7039	Intermediate Similarity	NPD6306	Phase 2
0.7037	Intermediate Similarity	NPD4148	Approved
0.7026	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2816	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6366	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5529	Phase 1
0.701	Intermediate Similarity	NPD6500	Approved
0.701	Intermediate Similarity	NPD6501	Approved
0.7005	Intermediate Similarity	NPD7758	Approved
0.7005	Intermediate Similarity	NPD7757	Approved
0.7	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2062	Phase 2
0.6989	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2757	Phase 2
0.6976	Remote Similarity	NPD8479	Phase 2
0.6976	Remote Similarity	NPD6856	Discontinued
0.6974	Remote Similarity	NPD5259	Phase 3
0.6971	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7674	Phase 3
0.6971	Remote Similarity	NPD7675	Phase 3
0.6971	Remote Similarity	NPD7426	Phase 1
0.6965	Remote Similarity	NPD2848	Discontinued
0.6961	Remote Similarity	NPD6568	Discontinued
0.6961	Remote Similarity	NPD9548	Phase 2
0.6957	Remote Similarity	NPD3920	Phase 2
0.6947	Remote Similarity	NPD1286	Suspended
0.6941	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5658	Approved
0.693	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2077	Approved
0.6923	Remote Similarity	NPD2076	Approved
0.6923	Remote Similarity	NPD1258	Discontinued
0.6915	Remote Similarity	NPD4919	Phase 3
0.6915	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5067	Phase 2
0.6915	Remote Similarity	NPD3939	Suspended
0.6915	Remote Similarity	NPD5066	Phase 2
0.6915	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4921	Phase 3
0.6915	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8063	Discontinued
0.6885	Remote Similarity	NPD9690	Approved
0.6875	Remote Similarity	NPD9695	Approved
0.6875	Remote Similarity	NPD6361	Phase 2
0.6875	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6969	Phase 2
0.6872	Remote Similarity	NPD6968	Phase 2
0.6869	Remote Similarity	NPD1259	Discontinued
0.6863	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4673	Phase 2
0.6854	Remote Similarity	NPD2472	Approved
0.6854	Remote Similarity	NPD2471	Approved
0.6852	Remote Similarity	NPD1927	Discontinued
0.685	Remote Similarity	NPD2187	Approved
0.685	Remote Similarity	NPD2189	Approved
0.6845	Remote Similarity	NPD3402	Phase 1
0.6842	Remote Similarity	NPD3938	Phase 1
0.6839	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5256	Discontinued
0.6821	Remote Similarity	NPD4703	Approved
0.6821	Remote Similarity	NPD1661	Suspended
0.6821	Remote Similarity	NPD4702	Approved
0.681	Remote Similarity	NPD5640	Discontinued
0.6806	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2410	Phase 2
0.6804	Remote Similarity	NPD6550	Discontinued
0.6804	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2440	Phase 3
0.6796	Remote Similarity	NPD4429	Discontinued
0.6796	Remote Similarity	NPD2441	Approved
0.6794	Remote Similarity	NPD5045	Phase 2
0.6792	Remote Similarity	NPD8512	Phase 3
0.6788	Remote Similarity	NPD802	Phase 2
0.6786	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1768	Approved
0.6784	Remote Similarity	NPD3717	Discontinued
0.6779	Remote Similarity	NPD6298	Discontinued
0.6778	Remote Similarity	NPD863	Approved
0.6778	Remote Similarity	NPD862	Approved
0.6778	Remote Similarity	NPD861	Approved
0.6776	Remote Similarity	NPD4306	Phase 1
0.6772	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2894	Phase 2
0.6761	Remote Similarity	NPD6131	Phase 1
0.6753	Remote Similarity	NPD4418	Discontinued
0.6751	Remote Similarity	NPD6219	Discontinued
0.6749	Remote Similarity	NPD949	Phase 1

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