NPASS Compound

Structure

CID143450 OpenBabel06191715502D 25 27 0 0 0 0 0 0 0 0999 V2000 -0.1522 2.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3726 -2.5365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3664 1.0663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5957 0.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0826 -0.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0524 -1.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7911 -0.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 -1.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8060 -1.4723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9258 -1.4982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6495 0.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5379 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5229 -0.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7435 -2.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6346 1.0404 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.4113 -1.9334 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7034 -1.7934 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5797 -3.0603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3814 0.0664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 23 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 24 2 0 0 0 0 17 20 2 3 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	465.96
Volume:	355.962
LogP:	3.52
LogD:	2.952
LogS:	-5.328
# Rotatable Bonds:	2
TPSA:	73.48
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	3.706
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.207
MDCK Permeability:	2.15198851947207e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.973
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	90.94561004638672%
Volume Distribution (VD):	0.811
Pgp-substrate:	14.48023509979248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.603
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	1.793
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.843
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.715
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC143450

Natural Product ID:	NPC143450
*Common Name:**	Ceratamine A
IUPAC Name:	4-[(3,5-dibromo-4-methoxyphenyl)methyl]-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5-one
Synonyms:
Standard InCHIKey:	HAIJSTYZBPUVSG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16Br2N4O2/c1-20-17-21-13-4-5-23(2)16(24)10(14(13)22-17)6-9-7-11(18)15(25-3)12(19)8-9/h4-5,7-8H,6H2,1-3H3,(H,20,22)
SMILES:	COc1c(Br)cc(cc1Br)Cc1c(=O)n(C)ccc2c1[nH]c(=NC)n2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1277687
PubChem CID:	11488186
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO31461	Pseudoceratina	Genus	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14627391]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18393464]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[20584605]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24964362]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[573135]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	54.0	%	PMID[573135]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	7800.0	nM	PMID[573137]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	12400.0	nM	PMID[573137]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	11200.0	nM	PMID[573137]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	26800.0	nM	PMID[573137]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	20000.0	nM	PMID[573137]

☑ 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 NPC143450 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	676
0.1-0.2	8554
0.2-0.3	9214
0.3-0.4	16614
0.4-0.5	4324
0.5-0.6	2744
0.6-0.7	555
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7833	Intermediate Similarity	NPC477254
0.7627	Intermediate Similarity	NPC477255
0.7289	Intermediate Similarity	NPC470470
0.7273	Intermediate Similarity	NPC470471
0.7268	Intermediate Similarity	NPC123140
0.7181	Intermediate Similarity	NPC8093
0.7181	Intermediate Similarity	NPC121571
0.7151	Intermediate Similarity	NPC71629
0.7151	Intermediate Similarity	NPC296085
0.71	Intermediate Similarity	NPC470746
0.71	Intermediate Similarity	NPC471336
0.7076	Intermediate Similarity	NPC470472
0.7069	Intermediate Similarity	NPC76412
0.7047	Intermediate Similarity	NPC474678
0.7047	Intermediate Similarity	NPC471338
0.701	Intermediate Similarity	NPC475843
0.7	Intermediate Similarity	NPC77435
0.7	Intermediate Similarity	NPC259071
0.6989	Remote Similarity	NPC47672
0.6977	Remote Similarity	NPC135349
0.6966	Remote Similarity	NPC233926
0.6966	Remote Similarity	NPC156311
0.6959	Remote Similarity	NPC227953
0.6941	Remote Similarity	NPC40321
0.6941	Remote Similarity	NPC128877
0.6932	Remote Similarity	NPC258222
0.6919	Remote Similarity	NPC471337
0.6919	Remote Similarity	NPC308571
0.6879	Remote Similarity	NPC78530
0.6847	Remote Similarity	NPC471339
0.6837	Remote Similarity	NPC202866
0.6829	Remote Similarity	NPC110131
0.6802	Remote Similarity	NPC470709
0.6784	Remote Similarity	NPC197045
0.6772	Remote Similarity	NPC181905
0.6763	Remote Similarity	NPC474128
0.6753	Remote Similarity	NPC246591
0.6742	Remote Similarity	NPC109968
0.6699	Remote Similarity	NPC471335
0.6686	Remote Similarity	NPC213471
0.6667	Remote Similarity	NPC473450
0.6667	Remote Similarity	NPC237227
0.6667	Remote Similarity	NPC147847
0.6615	Remote Similarity	NPC96275
0.6615	Remote Similarity	NPC28368
0.6615	Remote Similarity	NPC174607
0.6611	Remote Similarity	NPC469711
0.6611	Remote Similarity	NPC13397
0.661	Remote Similarity	NPC9373
0.6583	Remote Similarity	NPC80514
0.6566	Remote Similarity	NPC272463
0.655	Remote Similarity	NPC169766
0.6545	Remote Similarity	NPC116562
0.654	Remote Similarity	NPC67658
0.6534	Remote Similarity	NPC470247
0.6515	Remote Similarity	NPC248822
0.6512	Remote Similarity	NPC303993
0.6497	Remote Similarity	NPC473804
0.6461	Remote Similarity	NPC119569
0.6453	Remote Similarity	NPC266425
0.6444	Remote Similarity	NPC324081
0.6435	Remote Similarity	NPC175150
0.6435	Remote Similarity	NPC243633
0.64	Remote Similarity	NPC102245
0.6379	Remote Similarity	NPC235633
0.6378	Remote Similarity	NPC287757
0.6378	Remote Similarity	NPC319320
0.6337	Remote Similarity	NPC11449
0.6335	Remote Similarity	NPC115595
0.6322	Remote Similarity	NPC29650
0.6307	Remote Similarity	NPC474673
0.6286	Remote Similarity	NPC138365
0.6279	Remote Similarity	NPC135173
0.6279	Remote Similarity	NPC99280
0.6276	Remote Similarity	NPC475396
0.6264	Remote Similarity	NPC132308
0.6262	Remote Similarity	NPC50562
0.6243	Remote Similarity	NPC475735
0.6226	Remote Similarity	NPC113369
0.6221	Remote Similarity	NPC471321
0.6221	Remote Similarity	NPC471306
0.6216	Remote Similarity	NPC235033
0.6216	Remote Similarity	NPC473580
0.6216	Remote Similarity	NPC474852
0.6216	Remote Similarity	NPC471235
0.6216	Remote Similarity	NPC73132
0.6207	Remote Similarity	NPC470392
0.6207	Remote Similarity	NPC474753
0.6199	Remote Similarity	NPC218323
0.6193	Remote Similarity	NPC196708
0.6185	Remote Similarity	NPC474087
0.6185	Remote Similarity	NPC474091
0.6175	Remote Similarity	NPC20755
0.6171	Remote Similarity	NPC243404
0.6163	Remote Similarity	NPC122359
0.6163	Remote Similarity	NPC78061
0.6163	Remote Similarity	NPC159987
0.6158	Remote Similarity	NPC470249
0.6158	Remote Similarity	NPC64066
0.615	Remote Similarity	NPC292003
0.6146	Remote Similarity	NPC280022
0.6146	Remote Similarity	NPC129486
0.614	Remote Similarity	NPC124776
0.6134	Remote Similarity	NPC90245
0.6129	Remote Similarity	NPC470710
0.6126	Remote Similarity	NPC254700
0.6119	Remote Similarity	NPC80337
0.6098	Remote Similarity	NPC198401
0.6089	Remote Similarity	NPC470250
0.6085	Remote Similarity	NPC469243
0.6085	Remote Similarity	NPC475544
0.608	Remote Similarity	NPC74618
0.608	Remote Similarity	NPC301941
0.608	Remote Similarity	NPC214188
0.6073	Remote Similarity	NPC168209
0.6067	Remote Similarity	NPC307682
0.6067	Remote Similarity	NPC309667
0.6067	Remote Similarity	NPC470248
0.6066	Remote Similarity	NPC189908
0.6066	Remote Similarity	NPC81845
0.6062	Remote Similarity	NPC66490
0.6061	Remote Similarity	NPC303370
0.6059	Remote Similarity	NPC230539
0.6056	Remote Similarity	NPC81137
0.6056	Remote Similarity	NPC212850
0.6056	Remote Similarity	NPC189724
0.6056	Remote Similarity	NPC83289
0.6051	Remote Similarity	NPC475532
0.6043	Remote Similarity	NPC123011
0.6043	Remote Similarity	NPC256689
0.6034	Remote Similarity	NPC28641
0.6034	Remote Similarity	NPC48202
0.6034	Remote Similarity	NPC471316
0.6034	Remote Similarity	NPC283079
0.6034	Remote Similarity	NPC194359
0.6034	Remote Similarity	NPC225745
0.6031	Remote Similarity	NPC274198
0.6031	Remote Similarity	NPC276506
0.6031	Remote Similarity	NPC198254
0.603	Remote Similarity	NPC270301
0.6023	Remote Similarity	NPC274732
0.602	Remote Similarity	NPC235194
0.602	Remote Similarity	NPC17698
0.602	Remote Similarity	NPC165285
0.6012	Remote Similarity	NPC166837
0.6011	Remote Similarity	NPC80928
0.601	Remote Similarity	NPC475615
0.601	Remote Similarity	NPC473502
0.6	Remote Similarity	NPC191557
0.599	Remote Similarity	NPC472923
0.599	Remote Similarity	NPC223207
0.5989	Remote Similarity	NPC163810
0.5988	Remote Similarity	NPC213414
0.598	Remote Similarity	NPC290534
0.5976	Remote Similarity	NPC180207
0.5966	Remote Similarity	NPC473724
0.5961	Remote Similarity	NPC144823
0.596	Remote Similarity	NPC469979
0.5959	Remote Similarity	NPC247251
0.5959	Remote Similarity	NPC304074
0.5959	Remote Similarity	NPC290755
0.5959	Remote Similarity	NPC471771
0.5955	Remote Similarity	NPC120114
0.5955	Remote Similarity	NPC71888
0.5955	Remote Similarity	NPC473360
0.5954	Remote Similarity	NPC476249
0.5949	Remote Similarity	NPC196091
0.5947	Remote Similarity	NPC169742
0.5944	Remote Similarity	NPC252107
0.5942	Remote Similarity	NPC280638
0.5941	Remote Similarity	NPC299806
0.5941	Remote Similarity	NPC129885
0.5932	Remote Similarity	NPC328070
0.593	Remote Similarity	NPC473462
0.593	Remote Similarity	NPC105999
0.593	Remote Similarity	NPC126128
0.593	Remote Similarity	NPC110454
0.593	Remote Similarity	NPC298981
0.593	Remote Similarity	NPC207819
0.5928	Remote Similarity	NPC258992
0.5926	Remote Similarity	NPC295795
0.5924	Remote Similarity	NPC247298
0.5922	Remote Similarity	NPC180647
0.5917	Remote Similarity	NPC43275
0.5917	Remote Similarity	NPC256369
0.5912	Remote Similarity	NPC197766
0.5912	Remote Similarity	NPC231572
0.5912	Remote Similarity	NPC150712
0.5912	Remote Similarity	NPC471236
0.5911	Remote Similarity	NPC87391
0.5909	Remote Similarity	NPC195902
0.5909	Remote Similarity	NPC196243
0.5909	Remote Similarity	NPC120251
0.5904	Remote Similarity	NPC115803
0.5902	Remote Similarity	NPC174629
0.5893	Remote Similarity	NPC323948
0.5889	Remote Similarity	NPC475132
0.5889	Remote Similarity	NPC145446
0.5889	Remote Similarity	NPC137172
0.5889	Remote Similarity	NPC474587

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 NPC143450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	827
0.2-0.3	727
0.3-0.4	2217
0.4-0.5	2477
0.5-0.6	2036
0.6-0.7	496
0.7-0.8	10
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
0.7263	Intermediate Similarity	NPD5165	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD1009	Approved
0.6667	Remote Similarity	NPD5967	Approved
0.6629	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2186	Approved
0.6477	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2592	Discontinued
0.6354	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4157	Discontinued
0.6324	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2183	Approved
0.6319	Remote Similarity	NPD2184	Approved
0.6313	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5481	Discontinued
0.6296	Remote Similarity	NPD2190	Approved
0.6284	Remote Similarity	NPD7131	Phase 3
0.6281	Remote Similarity	NPD2942	Phase 2
0.6279	Remote Similarity	NPD9718	Approved
0.625	Remote Similarity	NPD5267	Discontinued
0.6238	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD3964	Approved
0.6203	Remote Similarity	NPD7317	Phase 3
0.6202	Remote Similarity	NPD6510	Phase 1
0.6202	Remote Similarity	NPD6511	Phase 1
0.6201	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD3802	Phase 3
0.6171	Remote Similarity	NPD3142	Approved
0.6171	Remote Similarity	NPD3140	Approved
0.6166	Remote Similarity	NPD644	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD743	Approved
0.6154	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6967	Phase 2
0.6141	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD1349	Approved
0.6141	Remote Similarity	NPD1350	Approved
0.6141	Remote Similarity	NPD1351	Approved
0.6138	Remote Similarity	NPD7318	Phase 3
0.6114	Remote Similarity	NPD5183	Approved
0.6114	Remote Similarity	NPD5186	Approved
0.6093	Remote Similarity	NPD3336	Discovery
0.6089	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD1725	Approved
0.6087	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD1039	Discontinued
0.6049	Remote Similarity	NPD3631	Phase 3
0.604	Remote Similarity	NPD4515	Suspended
0.6034	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3312	Phase 1
0.6032	Remote Similarity	NPD8019	Approved
0.6032	Remote Similarity	NPD3311	Phase 1
0.6032	Remote Similarity	NPD7495	Discontinued
0.6031	Remote Similarity	NPD7608	Discontinued
0.603	Remote Similarity	NPD1298	Discontinued
0.6023	Remote Similarity	NPD2245	Discovery
0.6022	Remote Similarity	NPD7523	Phase 3
0.6022	Remote Similarity	NPD1670	Discontinued
0.602	Remote Similarity	NPD5605	Phase 2
0.601	Remote Similarity	NPD5557	Phase 1
0.599	Remote Similarity	NPD1309	Phase 2
0.599	Remote Similarity	NPD1307	Phase 2
0.598	Remote Similarity	NPD4258	Approved
0.598	Remote Similarity	NPD4259	Approved
0.5968	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5515	Phase 2
0.5959	Remote Similarity	NPD8303	Discontinued
0.5959	Remote Similarity	NPD6862	Phase 2
0.5944	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD7032	Approved
0.5939	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD3873	Phase 3
0.5936	Remote Similarity	NPD3869	Phase 3
0.593	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1411	Approved
0.5926	Remote Similarity	NPD3679	Phase 2
0.5917	Remote Similarity	NPD4356	Discontinued
0.5914	Remote Similarity	NPD2335	Discontinued
0.5912	Remote Similarity	NPD2239	Approved
0.5912	Remote Similarity	NPD3156	Discontinued
0.5912	Remote Similarity	NPD2240	Approved
0.5907	Remote Similarity	NPD3368	Phase 2
0.5907	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD593	Approved
0.5904	Remote Similarity	NPD595	Approved
0.5902	Remote Similarity	NPD2654	Approved
0.5902	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7485	Phase 3
0.5897	Remote Similarity	NPD7484	Phase 3
0.5896	Remote Similarity	NPD196	Phase 1
0.5886	Remote Similarity	NPD4993	Discontinued
0.5882	Remote Similarity	NPD6390	Discontinued
0.5879	Remote Similarity	NPD3965	Phase 1
0.5877	Remote Similarity	NPD8106	Phase 2
0.5874	Remote Similarity	NPD7668	Phase 2
0.5872	Remote Similarity	NPD7225	Discontinued
0.5872	Remote Similarity	NPD6826	Discontinued
0.5867	Remote Similarity	NPD1161	Approved
0.5867	Remote Similarity	NPD6747	Phase 1
0.5862	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6380	Phase 1
0.5854	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.585	Remote Similarity	NPD2325	Approved
0.5848	Remote Similarity	NPD8311	Discontinued
0.5847	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD1391	Approved
0.5838	Remote Similarity	NPD1421	Approved
0.5838	Remote Similarity	NPD1420	Approved
0.5833	Remote Similarity	NPD2492	Phase 1
0.5833	Remote Similarity	NPD4154	Approved
0.5829	Remote Similarity	NPD3909	Discontinued
0.5829	Remote Similarity	NPD6419	Discontinued
0.5825	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7617	Discontinued
0.5822	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD8162	Phase 2
0.5821	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD5746	Approved
0.5819	Remote Similarity	NPD5163	Phase 2
0.5816	Remote Similarity	NPD2247	Approved
0.5816	Remote Similarity	NPD2249	Approved
0.5815	Remote Similarity	NPD44	Approved
0.5815	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD6364	Approved
0.5813	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7110	Phase 1
0.5812	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.581	Remote Similarity	NPD3463	Discontinued
0.5806	Remote Similarity	NPD2120	Phase 2
0.5805	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD2296	Approved
0.5802	Remote Similarity	NPD6612	Phase 2
0.5797	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5513	Phase 2
0.5792	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2668	Approved
0.5789	Remote Similarity	NPD2667	Approved
0.5789	Remote Similarity	NPD7669	Phase 3
0.5784	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD3489	Phase 3
0.5777	Remote Similarity	NPD3349	Phase 2
0.5777	Remote Similarity	NPD8025	Phase 2
0.5777	Remote Similarity	NPD7291	Discontinued
0.5773	Remote Similarity	NPD4377	Discontinued
0.5764	Remote Similarity	NPD2802	Phase 3
0.5763	Remote Similarity	NPD2614	Approved
0.5762	Remote Similarity	NPD3659	Discontinued
0.5761	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD6875	Approved
0.5759	Remote Similarity	NPD6876	Approved
0.5756	Remote Similarity	NPD3154	Approved
0.5756	Remote Similarity	NPD3153	Approved
0.5755	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD5745	Approved
0.5754	Remote Similarity	NPD1423	Approved
0.575	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6863	Phase 2
0.5747	Remote Similarity	NPD2428	Approved
0.5747	Remote Similarity	NPD5149	Phase 2
0.5747	Remote Similarity	NPD4129	Approved
0.5747	Remote Similarity	NPD2429	Approved
0.5747	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7498	Phase 1
0.5745	Remote Similarity	NPD7499	Phase 1
0.5744	Remote Similarity	NPD8031	Discontinued
0.5743	Remote Similarity	NPD2759	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD4539	Phase 1
0.5738	Remote Similarity	NPD4477	Approved
0.5738	Remote Similarity	NPD4476	Approved
0.5738	Remote Similarity	NPD7450	Phase 2
0.5737	Remote Similarity	NPD2883	Discontinued
0.5737	Remote Similarity	NPD950	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD2821	Approved
0.5736	Remote Similarity	NPD3286	Discontinued
0.5735	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD3591	Approved
0.5734	Remote Similarity	NPD3592	Approved
0.573	Remote Similarity	NPD2458	Approved
0.573	Remote Similarity	NPD2460	Phase 3
0.573	Remote Similarity	NPD2459	Approved
0.5729	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6894	Phase 1
0.5727	Remote Similarity	NPD5480	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD160	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD5014	Discontinued
0.5714	Remote Similarity	NPD4847	Phase 1
0.5714	Remote Similarity	NPD4413	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