NPASS Compound

Structure

NPC97106 OpenBabel07101719242D 21 23 0 0 0 0 0 0 0 0999 V2000 -3.9274 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9105 -2.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8887 -2.6806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 -1.8146 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 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2954 -3.5941 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.3832 -1.7100 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 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 -3.7195 -1.0714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 11 21 2 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.93
Volume:	285.752
LogP:	1.541
LogD:	2.129
LogS:	-3.406
# Rotatable Bonds:	2
TPSA:	97.74
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	3.706
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.399
MDCK Permeability:	3.4289150789845735e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.712
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	71.37358856201172%
Volume Distribution (VD):	1.001
Pgp-substrate:	30.035709381103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.601
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	3.36
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.571
Skin Sensitization:	0.252
Carcinogencity:	0.97
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC97106

Natural Product ID:	NPC97106
*Common Name:**	Agelanin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YHNMNTDKHSRLIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H11Br2N5O2/c1-18-6(4-5(13)9(18)14)11(21)19-3-2-7(20)8-10(19)17-12(15)16-8/h4,20H,2-3H2,1H3,(H2,15,16)
SMILES:	Cn1c(cc(c1Br)Br)C(=O)N1CCC(=C2C1=NC(=N)N2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599321
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000328] Imidazopyridines

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	98.9	%	PMID[456519]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	48000.0	nM	PMID[456519]

☑ 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 NPC97106 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	871
0.1-0.2	14884
0.2-0.3	18876
0.3-0.4	3252
0.4-0.5	3377
0.5-0.6	1248
0.6-0.7	137
0.7-0.8	33
0.8-0.85	15
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC476418
0.8855	High Similarity	NPC136441
0.8563	High Similarity	NPC226835
0.8485	Intermediate Similarity	NPC206148
0.8452	Intermediate Similarity	NPC28096
0.8452	Intermediate Similarity	NPC476421
0.8452	Intermediate Similarity	NPC227489
0.8448	Intermediate Similarity	NPC112489
0.8354	Intermediate Similarity	NPC27296
0.8343	Intermediate Similarity	NPC46022
0.8333	Intermediate Similarity	NPC469814
0.8315	Intermediate Similarity	NPC476413
0.8268	Intermediate Similarity	NPC476414
0.8235	Intermediate Similarity	NPC54214
0.8214	Intermediate Similarity	NPC474383
0.8187	Intermediate Similarity	NPC80528
0.8122	Intermediate Similarity	NPC46811
0.8121	Intermediate Similarity	NPC474236
0.7941	Intermediate Similarity	NPC306160
0.791	Intermediate Similarity	NPC184932
0.791	Intermediate Similarity	NPC472861
0.7836	Intermediate Similarity	NPC73687
0.7833	Intermediate Similarity	NPC63571
0.7833	Intermediate Similarity	NPC111566
0.7805	Intermediate Similarity	NPC260041
0.779	Intermediate Similarity	NPC310633
0.7766	Intermediate Similarity	NPC9635
0.7727	Intermediate Similarity	NPC37268
0.7676	Intermediate Similarity	NPC19342
0.7625	Intermediate Similarity	NPC150592
0.7616	Intermediate Similarity	NPC473706
0.7582	Intermediate Similarity	NPC476423
0.7571	Intermediate Similarity	NPC271927
0.7566	Intermediate Similarity	NPC19696
0.7566	Intermediate Similarity	NPC136957
0.7539	Intermediate Similarity	NPC469716
0.7514	Intermediate Similarity	NPC469976
0.746	Intermediate Similarity	NPC174281
0.746	Intermediate Similarity	NPC475286
0.7459	Intermediate Similarity	NPC40530
0.7459	Intermediate Similarity	NPC314281
0.7453	Intermediate Similarity	NPC20021
0.7407	Intermediate Similarity	NPC329765
0.7407	Intermediate Similarity	NPC476526
0.7407	Intermediate Similarity	NPC48117
0.7345	Intermediate Similarity	NPC474696
0.7259	Intermediate Similarity	NPC476524
0.7192	Intermediate Similarity	NPC469717
0.7191	Intermediate Similarity	NPC2414
0.7168	Intermediate Similarity	NPC109158
0.7085	Intermediate Similarity	NPC476525
0.7016	Intermediate Similarity	NPC210123
0.7005	Intermediate Similarity	NPC270834
0.6971	Remote Similarity	NPC472260
0.6895	Remote Similarity	NPC476527
0.6864	Remote Similarity	NPC472288
0.6818	Remote Similarity	NPC52110
0.6798	Remote Similarity	NPC298288
0.6684	Remote Similarity	NPC474180
0.6684	Remote Similarity	NPC188821
0.6633	Remote Similarity	NPC474389
0.6618	Remote Similarity	NPC469715
0.6596	Remote Similarity	NPC469529
0.6575	Remote Similarity	NPC142688
0.655	Remote Similarity	NPC291517
0.6548	Remote Similarity	NPC71236
0.6541	Remote Similarity	NPC233380
0.6517	Remote Similarity	NPC100726
0.6476	Remote Similarity	NPC50562
0.6462	Remote Similarity	NPC475736
0.6445	Remote Similarity	NPC67658
0.6429	Remote Similarity	NPC470703
0.6421	Remote Similarity	NPC186068
0.6404	Remote Similarity	NPC66642
0.6387	Remote Similarity	NPC476419
0.6381	Remote Similarity	NPC470702
0.6381	Remote Similarity	NPC473218
0.6368	Remote Similarity	NPC77061
0.6359	Remote Similarity	NPC21429
0.6358	Remote Similarity	NPC23215
0.6355	Remote Similarity	NPC477004
0.6354	Remote Similarity	NPC240088
0.6354	Remote Similarity	NPC473380
0.6321	Remote Similarity	NPC265710
0.6304	Remote Similarity	NPC74357
0.6289	Remote Similarity	NPC182940
0.6289	Remote Similarity	NPC16659
0.6267	Remote Similarity	NPC175150
0.6267	Remote Similarity	NPC243633
0.6264	Remote Similarity	NPC471655
0.6263	Remote Similarity	NPC473946
0.6257	Remote Similarity	NPC253687
0.625	Remote Similarity	NPC75135
0.625	Remote Similarity	NPC243716
0.6244	Remote Similarity	NPC474258
0.6229	Remote Similarity	NPC14448
0.6229	Remote Similarity	NPC64661
0.6229	Remote Similarity	NPC292434
0.6229	Remote Similarity	NPC98156
0.6229	Remote Similarity	NPC167200
0.6229	Remote Similarity	NPC138596
0.6229	Remote Similarity	NPC200397
0.6229	Remote Similarity	NPC195704
0.6226	Remote Similarity	NPC471194
0.6226	Remote Similarity	NPC471193
0.6204	Remote Similarity	NPC168209
0.6196	Remote Similarity	NPC281094
0.6175	Remote Similarity	NPC473878
0.6175	Remote Similarity	NPC474195
0.6172	Remote Similarity	NPC471191
0.6162	Remote Similarity	NPC33229
0.6162	Remote Similarity	NPC133003
0.6162	Remote Similarity	NPC209362
0.6154	Remote Similarity	NPC11126
0.615	Remote Similarity	NPC6865
0.615	Remote Similarity	NPC153980
0.6135	Remote Similarity	NPC471944
0.6133	Remote Similarity	NPC467188
0.6122	Remote Similarity	NPC91179
0.612	Remote Similarity	NPC102664
0.6111	Remote Similarity	NPC285923
0.6103	Remote Similarity	NPC72956
0.6094	Remote Similarity	NPC471943
0.6089	Remote Similarity	NPC59839
0.6089	Remote Similarity	NPC474357
0.6089	Remote Similarity	NPC302717
0.6089	Remote Similarity	NPC3698
0.6089	Remote Similarity	NPC205604
0.6089	Remote Similarity	NPC129753
0.6089	Remote Similarity	NPC12831
0.6089	Remote Similarity	NPC97230
0.6089	Remote Similarity	NPC244087
0.6089	Remote Similarity	NPC238499
0.6089	Remote Similarity	NPC209281
0.6089	Remote Similarity	NPC48171
0.6089	Remote Similarity	NPC74928
0.6089	Remote Similarity	NPC169308
0.6089	Remote Similarity	NPC77582
0.6089	Remote Similarity	NPC286529
0.6087	Remote Similarity	NPC269203
0.6087	Remote Similarity	NPC166209
0.6087	Remote Similarity	NPC77241
0.6087	Remote Similarity	NPC13456
0.6071	Remote Similarity	NPC470323
0.6066	Remote Similarity	NPC105811
0.6065	Remote Similarity	NPC177996
0.6065	Remote Similarity	NPC147983
0.6063	Remote Similarity	NPC474196
0.6056	Remote Similarity	NPC129412
0.6056	Remote Similarity	NPC114033
0.6056	Remote Similarity	NPC101130
0.6056	Remote Similarity	NPC58268
0.6054	Remote Similarity	NPC156003
0.6048	Remote Similarity	NPC473376
0.6044	Remote Similarity	NPC935
0.6044	Remote Similarity	NPC267078
0.6041	Remote Similarity	NPC234403
0.6041	Remote Similarity	NPC88110
0.604	Remote Similarity	NPC268966
0.604	Remote Similarity	NPC324091
0.6039	Remote Similarity	NPC268744
0.6039	Remote Similarity	NPC201266
0.6039	Remote Similarity	NPC237414
0.6039	Remote Similarity	NPC220797
0.6039	Remote Similarity	NPC475914
0.6039	Remote Similarity	NPC474318
0.6039	Remote Similarity	NPC153123
0.603	Remote Similarity	NPC477003
0.603	Remote Similarity	NPC228835
0.6029	Remote Similarity	NPC106757
0.6022	Remote Similarity	NPC251391
0.6022	Remote Similarity	NPC232798
0.6012	Remote Similarity	NPC313823
0.601	Remote Similarity	NPC65080
0.6	Remote Similarity	NPC93390
0.6	Remote Similarity	NPC476341
0.5991	Remote Similarity	NPC471192
0.598	Remote Similarity	NPC473342
0.598	Remote Similarity	NPC304187
0.598	Remote Similarity	NPC477166
0.598	Remote Similarity	NPC477167
0.5972	Remote Similarity	NPC88115
0.597	Remote Similarity	NPC17273
0.597	Remote Similarity	NPC135601
0.597	Remote Similarity	NPC141612
0.5969	Remote Similarity	NPC247987
0.5969	Remote Similarity	NPC151635
0.5968	Remote Similarity	NPC70406
0.5968	Remote Similarity	NPC217021
0.5968	Remote Similarity	NPC470679
0.5961	Remote Similarity	NPC475874
0.596	Remote Similarity	NPC79777
0.5949	Remote Similarity	NPC161861
0.5949	Remote Similarity	NPC288074
0.5947	Remote Similarity	NPC470680
0.5947	Remote Similarity	NPC100104
0.5946	Remote Similarity	NPC13432
0.5946	Remote Similarity	NPC123906
0.5942	Remote Similarity	NPC78767
0.5942	Remote Similarity	NPC473814

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 NPC97106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1049
0.2-0.3	1657
0.3-0.4	2272
0.4-0.5	2817
0.5-0.6	1067
0.6-0.7	38
0.7-0.8	3
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
0.715	Intermediate Similarity	NPD7459	Phase 2
0.7053	Intermediate Similarity	NPD5686	Approved
0.7053	Intermediate Similarity	NPD5685	Approved
0.7047	Intermediate Similarity	NPD2289	Phase 3
0.7047	Intermediate Similarity	NPD2290	Phase 3
0.659	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD460	Discontinued
0.6409	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD1600	Suspended
0.6364	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1952	Discontinued
0.631	Remote Similarity	NPD1631	Approved
0.6294	Remote Similarity	NPD1031	Discontinued
0.6293	Remote Similarity	NPD7817	Phase 1
0.6263	Remote Similarity	NPD1573	Approved
0.6263	Remote Similarity	NPD1575	Approved
0.6262	Remote Similarity	NPD5643	Phase 2
0.6256	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6210	Phase 3
0.625	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7568	Phase 1
0.6244	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3968	Approved
0.622	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4962	Approved
0.6214	Remote Similarity	NPD4963	Approved
0.6212	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD4988	Discontinued
0.6172	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD1658	Discontinued
0.6165	Remote Similarity	NPD4961	Approved
0.6161	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.615	Remote Similarity	NPD1630	Approved
0.6143	Remote Similarity	NPD3411	Phase 2
0.6143	Remote Similarity	NPD1506	Discontinued
0.6143	Remote Similarity	NPD3410	Approved
0.6135	Remote Similarity	NPD5017	Discontinued
0.6134	Remote Similarity	NPD2367	Phase 2
0.6131	Remote Similarity	NPD4940	Approved
0.6119	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2443	Approved
0.6114	Remote Similarity	NPD2442	Approved
0.6114	Remote Similarity	NPD4959	Approved
0.6114	Remote Similarity	NPD4960	Approved
0.6111	Remote Similarity	NPD1096	Discontinued
0.6111	Remote Similarity	NPD721	Approved
0.6108	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.61	Remote Similarity	NPD3246	Discontinued
0.6095	Remote Similarity	NPD3967	Approved
0.6089	Remote Similarity	NPD2222	Discontinued
0.608	Remote Similarity	NPD272	Approved
0.6075	Remote Similarity	NPD1003	Phase 2
0.607	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4415	Approved
0.6065	Remote Similarity	NPD3353	Approved
0.6058	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5198	Approved
0.6055	Remote Similarity	NPD5199	Approved
0.6053	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4299	Phase 1
0.6048	Remote Similarity	NPD8169	Discontinued
0.6044	Remote Similarity	NPD175	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD2405	Phase 3
0.6027	Remote Similarity	NPD6579	Phase 2
0.6009	Remote Similarity	NPD1623	Approved
0.6009	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5935	Discontinued
0.6	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5016	Approved
0.599	Remote Similarity	NPD1587	Approved
0.599	Remote Similarity	NPD438	Approved
0.599	Remote Similarity	NPD439	Approved
0.5981	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5974	Approved
0.598	Remote Similarity	NPD5973	Phase 2
0.5972	Remote Similarity	NPD2130	Discontinued
0.597	Remote Similarity	NPD7026	Phase 2
0.5968	Remote Similarity	NPD510	Phase 1
0.5964	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7232	Discontinued
0.5951	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7717	Approved
0.5946	Remote Similarity	NPD7716	Approved
0.5943	Remote Similarity	NPD2008	Discontinued
0.5936	Remote Similarity	NPD6470	Phase 3
0.5935	Remote Similarity	NPD2408	Discontinued
0.5935	Remote Similarity	NPD5510	Approved
0.5926	Remote Similarity	NPD7656	Approved
0.5926	Remote Similarity	NPD7657	Approved
0.5911	Remote Similarity	NPD1657	Approved
0.5905	Remote Similarity	NPD3891	Phase 2
0.5905	Remote Similarity	NPD3890	Phase 2
0.5902	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.59	Remote Similarity	NPD2137	Approved
0.59	Remote Similarity	NPD2138	Approved
0.5896	Remote Similarity	NPD5000	Phase 2
0.5896	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD3315	Phase 3
0.5891	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2128	Phase 1
0.5865	Remote Similarity	NPD1174	Phase 2
0.5864	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3041	Approved
0.5859	Remote Similarity	NPD4155	Approved
0.5857	Remote Similarity	NPD2911	Approved
0.5857	Remote Similarity	NPD2912	Approved
0.5856	Remote Similarity	NPD174	Discontinued
0.5851	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.585	Remote Similarity	NPD3178	Discontinued
0.5847	Remote Similarity	NPD4887	Discontinued
0.5847	Remote Similarity	NPD4047	Discontinued
0.5845	Remote Similarity	NPD953	Approved
0.5838	Remote Similarity	NPD1586	Approved
0.5837	Remote Similarity	NPD1982	Phase 1
0.5829	Remote Similarity	NPD7727	Phase 2
0.5829	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD2363	Discontinued
0.5825	Remote Similarity	NPD1896	Approved
0.5822	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD3379	Phase 2
0.5822	Remote Similarity	NPD8115	Approved
0.5822	Remote Similarity	NPD8114	Approved
0.5822	Remote Similarity	NPD3380	Phase 3
0.5821	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD1591	Approved
0.5817	Remote Similarity	NPD7027	Phase 3
0.5814	Remote Similarity	NPD6487	Approved
0.5814	Remote Similarity	NPD6486	Approved
0.5813	Remote Similarity	NPD5809	Phase 3
0.5813	Remote Similarity	NPD645	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5854	Approved
0.5806	Remote Similarity	NPD3915	Approved
0.5806	Remote Similarity	NPD4863	Approved
0.5804	Remote Similarity	NPD6752	Phase 1
0.5804	Remote Similarity	NPD6753	Phase 1
0.5802	Remote Similarity	NPD3774	Approved
0.5802	Remote Similarity	NPD3773	Approved
0.5802	Remote Similarity	NPD6802	Phase 3
0.5802	Remote Similarity	NPD3775	Approved
0.58	Remote Similarity	NPD3989	Phase 3
0.58	Remote Similarity	NPD1618	Phase 2
0.58	Remote Similarity	NPD1643	Phase 3
0.5799	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD7970	Approved
0.5799	Remote Similarity	NPD2547	Discontinued
0.5795	Remote Similarity	NPD9582	Phase 3
0.5794	Remote Similarity	NPD6271	Approved
0.5789	Remote Similarity	NPD2880	Discontinued
0.5787	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.578	Remote Similarity	NPD3917	Approved
0.578	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.578	Remote Similarity	NPD3918	Approved
0.578	Remote Similarity	NPD2411	Approved
0.5777	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD499	Phase 3
0.5771	Remote Similarity	NPD7888	Approved
0.5771	Remote Similarity	NPD3990	Phase 3
0.5771	Remote Similarity	NPD7887	Approved
0.5767	Remote Similarity	NPD180	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD9724	Phase 1
0.5758	Remote Similarity	NPD7297	Phase 2
0.5758	Remote Similarity	NPD4883	Approved
0.5758	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD4334	Discontinued
0.5756	Remote Similarity	NPD7175	Phase 1
0.5755	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD1016	Phase 2
0.5751	Remote Similarity	NPD1015	Phase 2
0.575	Remote Similarity	NPD3077	Approved
0.575	Remote Similarity	NPD3079	Approved
0.575	Remote Similarity	NPD3078	Approved
0.575	Remote Similarity	NPD3076	Approved
0.5747	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD2813	Phase 3
0.5746	Remote Similarity	NPD200	Phase 2
0.5746	Remote Similarity	NPD201	Phase 2
0.5745	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.5744	Remote Similarity	NPD1215	Discontinued
0.5744	Remote Similarity	NPD5611	Phase 2
0.5744	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD1871	Approved
0.5742	Remote Similarity	NPD4848	Phase 1
0.5738	Remote Similarity	NPD9599	Approved
0.5737	Remote Similarity	NPD2061	Approved
0.5735	Remote Similarity	NPD3425	Discontinued
0.5735	Remote Similarity	NPD2591	Phase 2
0.5733	Remote Similarity	NPD6850	Phase 2
0.5733	Remote Similarity	NPD6849	Phase 2
0.5733	Remote Similarity	NPD6173	Approved
0.573	Remote Similarity	NPD809	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data