NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	466.9
Volume:	312.994
LogP:	3.821
LogD:	2.713
LogS:	-4.346
# Rotatable Bonds:	4
TPSA:	15.48
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	3.595
Fsp3:	0.5
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:	-4.667
MDCK Permeability:	1.9280956621514633e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.103

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	95.48711395263672%
Volume Distribution (VD):	1.496
Pgp-substrate:	6.678529262542725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.426
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	1.764
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.317
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.877
Maximum Recommended Daily Dose:	0.784
Skin Sensitization:	0.506
Carcinogencity:	0.226
Eye Corrosion:	0.014
Eye Irritation:	0.295
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC470247

Natural Product ID:	NPC470247
*Common Name:**	Convolutamine J
IUPAC Name:	1-methyl-3-[2-(2,4,6-tribromo-3-methoxyphenyl)ethyl]-5,6-dihydro-4H-pyrimidin-1-ium
Synonyms:	Convolutamine J
Standard InCHIKey:	SUDFBSPZLXGBCI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H18Br3N2O/c1-18-5-3-6-19(9-18)7-4-10-11(15)8-12(16)14(20-2)13(10)17/h8-9H,3-7H2,1-2H3/q+1
SMILES:	C[N+]1=CN(CCC1)CCC2=C(C(=C(C=C2Br)Br)OC)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915493
PubChem CID:	54764322
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
NPO32745	amathia tortusa	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21705225]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	13700.0	nM	PMID[487611]
NPT35	Others	n.a.		LogP	=	3.9	n.a.	PMID[487611]

☑ 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 NPC470247 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	416
0.1-0.2	3838
0.2-0.3	13972
0.3-0.4	8202
0.4-0.5	13764
0.5-0.6	2347
0.6-0.7	141
0.7-0.8	9
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8841	High Similarity	NPC235633
0.8511	High Similarity	NPC470248
0.8478	Intermediate Similarity	NPC135173
0.8392	Intermediate Similarity	NPC470250
0.8252	Intermediate Similarity	NPC470249
0.7552	Intermediate Similarity	NPC110131
0.7338	Intermediate Similarity	NPC79076
0.7115	Intermediate Similarity	NPC135349
0.7105	Intermediate Similarity	NPC470471
0.7022	Intermediate Similarity	NPC102245
0.7013	Intermediate Similarity	NPC470470
0.7007	Intermediate Similarity	NPC272463
0.6957	Remote Similarity	NPC258222
0.6923	Remote Similarity	NPC470709
0.6914	Remote Similarity	NPC47672
0.6899	Remote Similarity	NPC470472
0.6894	Remote Similarity	NPC76412
0.6893	Remote Similarity	NPC80337
0.6875	Remote Similarity	NPC296085
0.6875	Remote Similarity	NPC71629
0.6842	Remote Similarity	NPC476570
0.6821	Remote Similarity	NPC471306
0.6821	Remote Similarity	NPC471321
0.6816	Remote Similarity	NPC230539
0.6792	Remote Similarity	NPC78530
0.6788	Remote Similarity	NPC233926
0.6772	Remote Similarity	NPC474128
0.6752	Remote Similarity	NPC128877
0.6748	Remote Similarity	NPC109968
0.674	Remote Similarity	NPC64066
0.673	Remote Similarity	NPC308571
0.6705	Remote Similarity	NPC288747
0.6687	Remote Similarity	NPC156311
0.6646	Remote Similarity	NPC40321
0.6582	Remote Similarity	NPC474673
0.6561	Remote Similarity	NPC11147
0.6558	Remote Similarity	NPC160193
0.6536	Remote Similarity	NPC172403
0.6534	Remote Similarity	NPC143450
0.6533	Remote Similarity	NPC298486
0.6519	Remote Similarity	NPC249113
0.6503	Remote Similarity	NPC21890
0.6494	Remote Similarity	NPC191557
0.6478	Remote Similarity	NPC213471
0.6474	Remote Similarity	NPC158078
0.6474	Remote Similarity	NPC118419
0.6455	Remote Similarity	NPC98685
0.6443	Remote Similarity	NPC471308
0.6443	Remote Similarity	NPC289330
0.6443	Remote Similarity	NPC53596
0.6443	Remote Similarity	NPC17388
0.6443	Remote Similarity	NPC321133
0.6443	Remote Similarity	NPC160120
0.6424	Remote Similarity	NPC471315
0.6424	Remote Similarity	NPC471314
0.6415	Remote Similarity	NPC231884
0.6415	Remote Similarity	NPC42793
0.6415	Remote Similarity	NPC167944
0.6409	Remote Similarity	NPC129885
0.6407	Remote Similarity	NPC469711
0.6364	Remote Similarity	NPC301713
0.6364	Remote Similarity	NPC475361
0.6323	Remote Similarity	NPC280736
0.631	Remote Similarity	NPC13397
0.6289	Remote Similarity	NPC303993
0.6275	Remote Similarity	NPC217277
0.6273	Remote Similarity	NPC193528
0.6272	Remote Similarity	NPC476568
0.6271	Remote Similarity	NPC90245
0.6267	Remote Similarity	NPC43275
0.6264	Remote Similarity	NPC477254
0.6259	Remote Similarity	NPC115803
0.6243	Remote Similarity	NPC475396
0.6242	Remote Similarity	NPC195902
0.6242	Remote Similarity	NPC120075
0.6242	Remote Similarity	NPC262641
0.6226	Remote Similarity	NPC325568
0.6226	Remote Similarity	NPC160692
0.6224	Remote Similarity	NPC186469
0.6218	Remote Similarity	NPC153990
0.6211	Remote Similarity	NPC301050
0.6211	Remote Similarity	NPC7018
0.6211	Remote Similarity	NPC131204
0.6209	Remote Similarity	NPC116562
0.6203	Remote Similarity	NPC70485
0.6203	Remote Similarity	NPC475735
0.6197	Remote Similarity	NPC42383
0.6196	Remote Similarity	NPC314682
0.6181	Remote Similarity	NPC97811
0.6178	Remote Similarity	NPC281499
0.6173	Remote Similarity	NPC253429
0.6167	Remote Similarity	NPC475976
0.6167	Remote Similarity	NPC226001
0.6164	Remote Similarity	NPC214869
0.6159	Remote Similarity	NPC213206
0.6159	Remote Similarity	NPC470925
0.6159	Remote Similarity	NPC188163
0.6159	Remote Similarity	NPC323204
0.6159	Remote Similarity	NPC328750
0.6159	Remote Similarity	NPC474915
0.6149	Remote Similarity	NPC237227
0.6149	Remote Similarity	NPC475828
0.6144	Remote Similarity	NPC211992
0.6139	Remote Similarity	NPC474091
0.6133	Remote Similarity	NPC126128
0.6133	Remote Similarity	NPC473462
0.6133	Remote Similarity	NPC110454
0.6133	Remote Similarity	NPC298981
0.6133	Remote Similarity	NPC207819
0.6124	Remote Similarity	NPC477255
0.6121	Remote Similarity	NPC474850
0.6121	Remote Similarity	NPC474851
0.6118	Remote Similarity	NPC263835
0.6115	Remote Similarity	NPC251571
0.6115	Remote Similarity	NPC470161
0.6105	Remote Similarity	NPC292003
0.6101	Remote Similarity	NPC114102
0.6101	Remote Similarity	NPC473724
0.6084	Remote Similarity	NPC128019
0.6084	Remote Similarity	NPC476567
0.6084	Remote Similarity	NPC136860
0.6081	Remote Similarity	NPC26524
0.6077	Remote Similarity	NPC469979
0.6076	Remote Similarity	NPC155838
0.6076	Remote Similarity	NPC283079
0.6075	Remote Similarity	NPC473892
0.6075	Remote Similarity	NPC475658
0.6074	Remote Similarity	NPC197045
0.6069	Remote Similarity	NPC146530
0.6065	Remote Similarity	NPC211218
0.6062	Remote Similarity	NPC130595
0.6062	Remote Similarity	NPC93882
0.6057	Remote Similarity	NPC216816
0.6056	Remote Similarity	NPC319933
0.6054	Remote Similarity	NPC166837
0.6051	Remote Similarity	NPC218323
0.6043	Remote Similarity	NPC147847
0.6038	Remote Similarity	NPC99280
0.6038	Remote Similarity	NPC35961
0.6038	Remote Similarity	NPC195749
0.6038	Remote Similarity	NPC52029
0.6033	Remote Similarity	NPC74618
0.6033	Remote Similarity	NPC301941
0.6033	Remote Similarity	NPC214188
0.6031	Remote Similarity	NPC156055
0.6026	Remote Similarity	NPC62101
0.6026	Remote Similarity	NPC95733
0.6026	Remote Similarity	NPC236265
0.6026	Remote Similarity	NPC105513
0.6025	Remote Similarity	NPC285078
0.6025	Remote Similarity	NPC6854
0.6025	Remote Similarity	NPC313737
0.6022	Remote Similarity	NPC77435
0.6022	Remote Similarity	NPC225130
0.6022	Remote Similarity	NPC259071
0.6012	Remote Similarity	NPC185838
0.6012	Remote Similarity	NPC130926
0.6	Remote Similarity	NPC227953
0.6	Remote Similarity	NPC11449
0.5989	Remote Similarity	NPC471591
0.5989	Remote Similarity	NPC174607
0.5988	Remote Similarity	NPC218530
0.5987	Remote Similarity	NPC29477
0.5987	Remote Similarity	NPC124776
0.5979	Remote Similarity	NPC473450
0.5973	Remote Similarity	NPC76400
0.5973	Remote Similarity	NPC59387
0.5962	Remote Similarity	NPC13020
0.5962	Remote Similarity	NPC140359
0.5962	Remote Similarity	NPC328267
0.596	Remote Similarity	NPC258992
0.5957	Remote Similarity	NPC473409
0.5957	Remote Similarity	NPC82741
0.5957	Remote Similarity	NPC141405
0.5956	Remote Similarity	NPC475615
0.5954	Remote Similarity	NPC476580
0.5944	Remote Similarity	NPC85482
0.5944	Remote Similarity	NPC12870
0.5944	Remote Similarity	NPC24327
0.5941	Remote Similarity	NPC210437
0.5941	Remote Similarity	NPC106295
0.5941	Remote Similarity	NPC321505
0.5941	Remote Similarity	NPC191376
0.5941	Remote Similarity	NPC51957
0.5941	Remote Similarity	NPC16107
0.5941	Remote Similarity	NPC476144
0.5941	Remote Similarity	NPC179825
0.5941	Remote Similarity	NPC476151
0.5939	Remote Similarity	NPC231572
0.5939	Remote Similarity	NPC210086
0.5938	Remote Similarity	NPC85049
0.5933	Remote Similarity	NPC221301
0.5924	Remote Similarity	NPC290534
0.5921	Remote Similarity	NPC323948
0.592	Remote Similarity	NPC135103
0.5917	Remote Similarity	NPC9373
0.5917	Remote Similarity	NPC145304
0.5915	Remote Similarity	NPC416184
0.5912	Remote Similarity	NPC186898
0.5912	Remote Similarity	NPC291847

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 NPC470247 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	826
0.2-0.3	1281
0.3-0.4	3061
0.4-0.5	2811
0.5-0.6	858
0.6-0.7	79
0.7-0.8	0
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
0.725	Intermediate Similarity	NPD1009	Approved
0.68	Remote Similarity	NPD7905	Discontinued
0.6687	Remote Similarity	NPD2183	Approved
0.6687	Remote Similarity	NPD2184	Approved
0.6646	Remote Similarity	NPD3156	Discontinued
0.6628	Remote Similarity	NPD4010	Discontinued
0.6623	Remote Similarity	NPD1039	Discontinued
0.6623	Remote Similarity	NPD5718	Phase 2
0.6601	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9244	Approved
0.659	Remote Similarity	NPD6688	Approved
0.659	Remote Similarity	NPD6687	Approved
0.6474	Remote Similarity	NPD2245	Discovery
0.646	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2667	Approved
0.6443	Remote Similarity	NPD2668	Approved
0.6424	Remote Similarity	NPD2230	Approved
0.6424	Remote Similarity	NPD2233	Approved
0.6424	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2232	Approved
0.642	Remote Similarity	NPD6364	Approved
0.642	Remote Similarity	NPD44	Approved
0.6419	Remote Similarity	NPD2486	Discontinued
0.6415	Remote Similarity	NPD6895	Approved
0.6415	Remote Similarity	NPD6896	Approved
0.6407	Remote Similarity	NPD5267	Discontinued
0.6382	Remote Similarity	NPD1669	Approved
0.6382	Remote Similarity	NPD1421	Approved
0.6382	Remote Similarity	NPD1420	Approved
0.6375	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.637	Remote Similarity	NPD593	Approved
0.637	Remote Similarity	NPD595	Approved
0.6347	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2496	Approved
0.6345	Remote Similarity	NPD2497	Approved
0.6341	Remote Similarity	NPD3692	Discontinued
0.6299	Remote Similarity	NPD1318	Phase 2
0.6299	Remote Similarity	NPD4098	Discontinued
0.6296	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3294	Phase 2
0.629	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2594	Approved
0.6267	Remote Similarity	NPD2595	Approved
0.6235	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2238	Phase 2
0.6226	Remote Similarity	NPD3110	Approved
0.6226	Remote Similarity	NPD3109	Approved
0.6221	Remote Similarity	NPD6737	Phase 2
0.6221	Remote Similarity	NPD6738	Phase 2
0.6218	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8070	Approved
0.619	Remote Similarity	NPD1350	Approved
0.619	Remote Similarity	NPD1349	Approved
0.619	Remote Similarity	NPD1351	Approved
0.6174	Remote Similarity	NPD3596	Phase 2
0.6173	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3124	Discontinued
0.6164	Remote Similarity	NPD840	Approved
0.6164	Remote Similarity	NPD839	Approved
0.6164	Remote Similarity	NPD4475	Approved
0.6164	Remote Similarity	NPD4474	Approved
0.6163	Remote Similarity	NPD5720	Discontinued
0.6159	Remote Similarity	NPD3444	Approved
0.6159	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1391	Approved
0.6159	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3445	Approved
0.6159	Remote Similarity	NPD3443	Approved
0.6159	Remote Similarity	NPD6382	Discontinued
0.6149	Remote Similarity	NPD1793	Approved
0.6149	Remote Similarity	NPD1791	Approved
0.6139	Remote Similarity	NPD1024	Discontinued
0.6136	Remote Similarity	NPD1411	Approved
0.6129	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2922	Phase 1
0.6118	Remote Similarity	NPD2554	Approved
0.6118	Remote Similarity	NPD2556	Approved
0.6115	Remote Similarity	NPD455	Discontinued
0.6115	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7124	Phase 2
0.6107	Remote Similarity	NPD2557	Approved
0.6101	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3656	Approved
0.6094	Remote Similarity	NPD8095	Phase 1
0.6092	Remote Similarity	NPD5967	Approved
0.6087	Remote Similarity	NPD3337	Discontinued
0.6084	Remote Similarity	NPD5754	Discontinued
0.6074	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD2674	Phase 3
0.6062	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3049	Approved
0.605	Remote Similarity	NPD3336	Discovery
0.6049	Remote Similarity	NPD2986	Phase 2
0.6049	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD2989	Phase 2
0.6048	Remote Similarity	NPD5241	Discontinued
0.6047	Remote Similarity	NPD3679	Phase 2
0.6042	Remote Similarity	NPD1444	Approved
0.6042	Remote Similarity	NPD1445	Approved
0.6038	Remote Similarity	NPD5746	Approved
0.6036	Remote Similarity	NPD6419	Discontinued
0.6027	Remote Similarity	NPD1792	Phase 2
0.6024	Remote Similarity	NPD4162	Approved
0.6024	Remote Similarity	NPD3060	Approved
0.6013	Remote Similarity	NPD1712	Approved
0.6012	Remote Similarity	NPD6111	Discontinued
0.601	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5373	Approved
0.6	Remote Similarity	NPD709	Approved
0.6	Remote Similarity	NPD5374	Approved
0.5988	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD6331	Phase 2
0.5987	Remote Similarity	NPD6581	Approved
0.5987	Remote Similarity	NPD6580	Approved
0.5978	Remote Similarity	NPD6747	Phase 1
0.5976	Remote Similarity	NPD6380	Phase 1
0.5967	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3033	Phase 2
0.5963	Remote Similarity	NPD5745	Approved
0.5962	Remote Similarity	NPD2429	Approved
0.5962	Remote Similarity	NPD2428	Approved
0.5954	Remote Similarity	NPD6875	Approved
0.5954	Remote Similarity	NPD6876	Approved
0.5952	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD2653	Approved
0.5949	Remote Similarity	NPD6584	Phase 3
0.5949	Remote Similarity	NPD2987	Approved
0.5949	Remote Similarity	NPD7018	Phase 2
0.5949	Remote Similarity	NPD2990	Approved
0.5948	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3158	Phase 1
0.5941	Remote Similarity	NPD1424	Approved
0.5941	Remote Similarity	NPD3157	Approved
0.5941	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4584	Approved
0.5931	Remote Similarity	NPD810	Approved
0.5931	Remote Similarity	NPD811	Approved
0.5931	Remote Similarity	NPD812	Approved
0.5928	Remote Similarity	NPD5177	Phase 3
0.5926	Remote Similarity	NPD6225	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7110	Phase 1
0.592	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4993	Discontinued
0.5909	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD2376	Approved
0.5904	Remote Similarity	NPD2378	Approved
0.5904	Remote Similarity	NPD2377	Approved
0.5901	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD3145	Approved
0.5901	Remote Similarity	NPD3144	Approved
0.5897	Remote Similarity	NPD2235	Phase 2
0.5897	Remote Similarity	NPD2231	Phase 2
0.5893	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD316	Approved
0.5879	Remote Similarity	NPD1753	Discontinued
0.5879	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD596	Approved
0.5875	Remote Similarity	NPD600	Approved
0.5872	Remote Similarity	NPD3641	Approved
0.5872	Remote Similarity	NPD3639	Approved
0.5872	Remote Similarity	NPD3640	Phase 3
0.5868	Remote Similarity	NPD7153	Discontinued
0.586	Remote Similarity	NPD6539	Approved
0.586	Remote Similarity	NPD6540	Phase 3
0.586	Remote Similarity	NPD6543	Approved
0.586	Remote Similarity	NPD6542	Approved
0.5852	Remote Similarity	NPD5772	Approved
0.5852	Remote Similarity	NPD5773	Approved
0.5849	Remote Similarity	NPD558	Phase 2
0.5848	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD4123	Phase 3
0.5848	Remote Similarity	NPD7020	Approved
0.5848	Remote Similarity	NPD7019	Approved
0.5844	Remote Similarity	NPD4093	Discontinued
0.5843	Remote Similarity	NPD2161	Phase 2
0.5833	Remote Similarity	NPD2458	Approved
0.5833	Remote Similarity	NPD2459	Approved
0.5833	Remote Similarity	NPD4236	Phase 3
0.5833	Remote Similarity	NPD4237	Approved
0.5833	Remote Similarity	NPD2211	Approved
0.5833	Remote Similarity	NPD2460	Phase 3
0.5833	Remote Similarity	NPD2209	Approved
0.5829	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD3142	Approved
0.5828	Remote Similarity	NPD3140	Approved

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