NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	400.95
Volume:	273.678
LogP:	1.833
LogD:	1.576
LogS:	-3.016
# Rotatable Bonds:	0
TPSA:	66.86
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	5.017
Fsp3:	0.5
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:	-4.954
MDCK Permeability:	2.413527727185283e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.456
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	72.615234375%
Volume Distribution (VD):	0.839
Pgp-substrate:	34.808387756347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.253
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.753
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.569
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	4.469
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.228
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.776
Carcinogencity:	0.984
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC226835

Natural Product ID:	NPC226835
*Common Name:**	YPAFHZXYEACLQB-CMPLNLGQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YPAFHZXYEACLQB-CMPLNLGQSA-N
Standard InCHI:	InChI=1S/C12H13Br2N5O/c1-17-10-12(16-11(17)15)3-2-4-18(12)9(20)7-5-6(13)8(14)19(7)10/h5,10H,2-4H2,1H3,(H2,15,16)/t10-,12+/m0/s1
SMILES:	N=C1N[C@]23[C@@H](N1C)n1c(Br)c(cc1C(=O)N3CCC2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505073
PubChem CID:	11211821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO32878	Agelas	Genus	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332838]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	=	10700.0	nM	PMID[503016]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	=	48000.0	nM	PMID[503016]

☑ 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 NPC226835 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	1743
0.1-0.2	18212
0.2-0.3	15697
0.3-0.4	2936
0.4-0.5	2930
0.5-0.6	985
0.6-0.7	122
0.7-0.8	54
0.8-0.85	10
0.85-0.9	2
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC476421
0.9871	High Similarity	NPC227489
0.9871	High Similarity	NPC28096
0.9317	High Similarity	NPC136441
0.9212	High Similarity	NPC469814
0.8589	High Similarity	NPC206148
0.8589	High Similarity	NPC476418
0.8563	High Similarity	NPC97106
0.8333	Intermediate Similarity	NPC54214
0.8221	Intermediate Similarity	NPC474236
0.8125	Intermediate Similarity	NPC111566
0.8125	Intermediate Similarity	NPC63571
0.8121	Intermediate Similarity	NPC27296
0.8095	Intermediate Similarity	NPC474383
0.8079	Intermediate Similarity	NPC310633
0.8023	Intermediate Similarity	NPC112489
0.8	Intermediate Similarity	NPC476413
0.7956	Intermediate Similarity	NPC476414
0.7956	Intermediate Similarity	NPC19342
0.7929	Intermediate Similarity	NPC306160
0.7929	Intermediate Similarity	NPC73687
0.7921	Intermediate Similarity	NPC46022
0.7901	Intermediate Similarity	NPC260041
0.7838	Intermediate Similarity	NPC19696
0.7838	Intermediate Similarity	NPC136957
0.7834	Intermediate Similarity	NPC150592
0.773	Intermediate Similarity	NPC475286
0.773	Intermediate Similarity	NPC174281
0.7717	Intermediate Similarity	NPC46811
0.7713	Intermediate Similarity	NPC469716
0.7706	Intermediate Similarity	NPC473706
0.7676	Intermediate Similarity	NPC329765
0.7676	Intermediate Similarity	NPC48117
0.7676	Intermediate Similarity	NPC476526
0.7658	Intermediate Similarity	NPC20021
0.7657	Intermediate Similarity	NPC80528
0.76	Intermediate Similarity	NPC469976
0.7598	Intermediate Similarity	NPC184932
0.7598	Intermediate Similarity	NPC472861
0.7566	Intermediate Similarity	NPC9635
0.7444	Intermediate Similarity	NPC40530
0.7444	Intermediate Similarity	NPC314281
0.7353	Intermediate Similarity	NPC472260
0.7333	Intermediate Similarity	NPC476525
0.7318	Intermediate Similarity	NPC37268
0.7283	Intermediate Similarity	NPC476423
0.7268	Intermediate Similarity	NPC270834
0.7263	Intermediate Similarity	NPC271927
0.7245	Intermediate Similarity	NPC476524
0.7196	Intermediate Similarity	NPC188821
0.7196	Intermediate Similarity	NPC474180
0.7181	Intermediate Similarity	NPC210123
0.7178	Intermediate Similarity	NPC469717
0.7175	Intermediate Similarity	NPC2414
0.7151	Intermediate Similarity	NPC476527
0.7135	Intermediate Similarity	NPC474389
0.7039	Intermediate Similarity	NPC474696
0.7015	Intermediate Similarity	NPC469715
0.6966	Remote Similarity	NPC253687
0.6865	Remote Similarity	NPC240088
0.6865	Remote Similarity	NPC473380
0.6857	Remote Similarity	NPC109158
0.678	Remote Similarity	NPC298288
0.6738	Remote Similarity	NPC265710
0.6702	Remote Similarity	NPC16659
0.6648	Remote Similarity	NPC142688
0.6647	Remote Similarity	NPC472288
0.6627	Remote Similarity	NPC71236
0.6627	Remote Similarity	NPC291517
0.661	Remote Similarity	NPC52110
0.6533	Remote Similarity	NPC66642
0.6529	Remote Similarity	NPC23215
0.6528	Remote Similarity	NPC135601
0.6528	Remote Similarity	NPC141612
0.6528	Remote Similarity	NPC17273
0.6524	Remote Similarity	NPC475736
0.6522	Remote Similarity	NPC233380
0.6514	Remote Similarity	NPC474357
0.6498	Remote Similarity	NPC470323
0.6468	Remote Similarity	NPC935
0.6468	Remote Similarity	NPC267078
0.6462	Remote Similarity	NPC474195
0.6411	Remote Similarity	NPC470703
0.6395	Remote Similarity	NPC200397
0.6395	Remote Similarity	NPC167200
0.6395	Remote Similarity	NPC98156
0.6395	Remote Similarity	NPC14448
0.6395	Remote Similarity	NPC195704
0.6395	Remote Similarity	NPC64661
0.6395	Remote Similarity	NPC292434
0.6395	Remote Similarity	NPC138596
0.6392	Remote Similarity	NPC133003
0.6374	Remote Similarity	NPC74357
0.6364	Remote Similarity	NPC473218
0.6364	Remote Similarity	NPC470702
0.6349	Remote Similarity	NPC161861
0.6343	Remote Similarity	NPC474196
0.634	Remote Similarity	NPC21429
0.6337	Remote Similarity	NPC477004
0.6333	Remote Similarity	NPC473878
0.6329	Remote Similarity	NPC116555
0.6313	Remote Similarity	NPC100726
0.6303	Remote Similarity	NPC50562
0.6292	Remote Similarity	NPC467188
0.629	Remote Similarity	NPC247987
0.6289	Remote Similarity	NPC470205
0.6274	Remote Similarity	NPC67658
0.6272	Remote Similarity	NPC313823
0.6256	Remote Similarity	NPC237414
0.625	Remote Similarity	NPC169308
0.625	Remote Similarity	NPC3698
0.625	Remote Similarity	NPC129753
0.625	Remote Similarity	NPC302717
0.625	Remote Similarity	NPC12831
0.625	Remote Similarity	NPC97230
0.625	Remote Similarity	NPC205604
0.625	Remote Similarity	NPC286529
0.625	Remote Similarity	NPC48171
0.625	Remote Similarity	NPC74928
0.625	Remote Similarity	NPC244087
0.625	Remote Similarity	NPC59839
0.625	Remote Similarity	NPC209281
0.625	Remote Similarity	NPC77582
0.623	Remote Similarity	NPC186068
0.6225	Remote Similarity	NPC13456
0.6225	Remote Similarity	NPC166209
0.6225	Remote Similarity	NPC269203
0.6225	Remote Similarity	NPC77241
0.6215	Remote Similarity	NPC114033
0.6215	Remote Similarity	NPC58268
0.6215	Remote Similarity	NPC101130
0.6215	Remote Similarity	NPC129412
0.6214	Remote Similarity	NPC317701
0.6201	Remote Similarity	NPC470440
0.6188	Remote Similarity	NPC77061
0.6181	Remote Similarity	NPC324091
0.6176	Remote Similarity	NPC268744
0.6176	Remote Similarity	NPC475914
0.6176	Remote Similarity	NPC220797
0.6176	Remote Similarity	NPC201266
0.6176	Remote Similarity	NPC474318
0.6176	Remote Similarity	NPC153123
0.6168	Remote Similarity	NPC267811
0.6157	Remote Similarity	NPC272174
0.6146	Remote Similarity	NPC469529
0.6133	Remote Similarity	NPC105811
0.6129	Remote Similarity	NPC474896
0.6121	Remote Similarity	NPC470732
0.6121	Remote Similarity	NPC470731
0.6114	Remote Similarity	NPC476419
0.6114	Remote Similarity	NPC151635
0.6103	Remote Similarity	NPC182940
0.6101	Remote Similarity	NPC175150
0.6101	Remote Similarity	NPC31097
0.6101	Remote Similarity	NPC243633
0.6095	Remote Similarity	NPC71238
0.6087	Remote Similarity	NPC251391
0.6073	Remote Similarity	NPC471943
0.6073	Remote Similarity	NPC476817
0.6066	Remote Similarity	NPC471655
0.6054	Remote Similarity	NPC75135
0.6054	Remote Similarity	NPC209362
0.6037	Remote Similarity	NPC168209
0.6036	Remote Similarity	NPC156003
0.6033	Remote Similarity	NPC217021
0.6033	Remote Similarity	NPC70406
0.6033	Remote Similarity	NPC470679
0.6032	Remote Similarity	NPC274981
0.6029	Remote Similarity	NPC473376
0.6027	Remote Similarity	NPC312942
0.6027	Remote Similarity	NPC327095
0.6011	Remote Similarity	NPC123906
0.6011	Remote Similarity	NPC100104
0.6011	Remote Similarity	NPC470680
0.601	Remote Similarity	NPC108011
0.601	Remote Similarity	NPC477003
0.6009	Remote Similarity	NPC54981
0.6	Remote Similarity	NPC2165
0.6	Remote Similarity	NPC40455
0.6	Remote Similarity	NPC232798
0.6	Remote Similarity	NPC195507
0.599	Remote Similarity	NPC307191
0.599	Remote Similarity	NPC243716
0.599	Remote Similarity	NPC191415
0.599	Remote Similarity	NPC476460
0.5989	Remote Similarity	NPC65408
0.5973	Remote Similarity	NPC19170
0.5971	Remote Similarity	NPC171317
0.5968	Remote Similarity	NPC33229
0.5957	Remote Similarity	NPC474492
0.5952	Remote Similarity	NPC88115
0.5951	Remote Similarity	NPC102592
0.5951	Remote Similarity	NPC79356
0.5939	Remote Similarity	NPC91179
0.5934	Remote Similarity	NPC204141
0.5933	Remote Similarity	NPC106757
0.5931	Remote Similarity	NPC326422
0.593	Remote Similarity	NPC110158
0.5928	Remote Similarity	NPC252572
0.5924	Remote Similarity	NPC102664

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 NPC226835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	1197
0.2-0.3	1865
0.3-0.4	2317
0.4-0.5	2514
0.5-0.6	866
0.6-0.7	42
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD7459	Phase 2
0.7128	Intermediate Similarity	NPD5686	Approved
0.7128	Intermediate Similarity	NPD5685	Approved
0.6839	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2289	Phase 3
0.6684	Remote Similarity	NPD2290	Phase 3
0.665	Remote Similarity	NPD2443	Approved
0.665	Remote Similarity	NPD2442	Approved
0.6635	Remote Similarity	NPD5643	Phase 2
0.6566	Remote Similarity	NPD1031	Discontinued
0.6537	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1658	Discontinued
0.6456	Remote Similarity	NPD2408	Discontinued
0.6443	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1506	Discontinued
0.6437	Remote Similarity	NPD2222	Discontinued
0.6414	Remote Similarity	NPD460	Discontinued
0.6379	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1600	Suspended
0.6368	Remote Similarity	NPD6470	Phase 3
0.6337	Remote Similarity	NPD2405	Phase 3
0.6337	Remote Similarity	NPD272	Approved
0.6333	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD1952	Discontinued
0.6318	Remote Similarity	NPD2880	Discontinued
0.6302	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD2367	Phase 2
0.628	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5199	Approved
0.6262	Remote Similarity	NPD5198	Approved
0.6233	Remote Similarity	NPD6210	Phase 3
0.6232	Remote Similarity	NPD2008	Discontinued
0.6223	Remote Similarity	NPD439	Approved
0.6223	Remote Similarity	NPD438	Approved
0.6195	Remote Similarity	NPD5017	Discontinued
0.6166	Remote Similarity	NPD3041	Approved
0.6164	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD809	Discontinued
0.6157	Remote Similarity	NPD6579	Phase 2
0.6154	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1623	Approved
0.6127	Remote Similarity	NPD1982	Phase 1
0.612	Remote Similarity	NPD2128	Phase 1
0.6111	Remote Similarity	NPD645	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD174	Discontinued
0.6098	Remote Similarity	NPD5854	Approved
0.6091	Remote Similarity	NPD1096	Discontinued
0.608	Remote Similarity	NPD3246	Discontinued
0.608	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5446	Phase 2
0.6077	Remote Similarity	NPD6271	Approved
0.6067	Remote Similarity	NPD9599	Approved
0.6065	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1015	Phase 2
0.6064	Remote Similarity	NPD1016	Phase 2
0.6056	Remote Similarity	NPD2411	Approved
0.6051	Remote Similarity	NPD3078	Approved
0.6051	Remote Similarity	NPD3079	Approved
0.6051	Remote Similarity	NPD3077	Approved
0.6051	Remote Similarity	NPD3076	Approved
0.6049	Remote Similarity	NPD465	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5974	Approved
0.604	Remote Similarity	NPD5973	Phase 2
0.604	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD7817	Phase 1
0.6029	Remote Similarity	NPD7208	Approved
0.6029	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7209	Approved
0.6029	Remote Similarity	NPD2130	Discontinued
0.6029	Remote Similarity	NPD7207	Approved
0.6028	Remote Similarity	NPD2363	Discontinued
0.6022	Remote Similarity	NPD2150	Discontinued
0.6	Remote Similarity	NPD7717	Approved
0.6	Remote Similarity	NPD7716	Approved
0.6	Remote Similarity	NPD3967	Approved
0.6	Remote Similarity	NPD2547	Discontinued
0.6	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7568	Phase 1
0.6	Remote Similarity	NPD1174	Phase 2
0.6	Remote Similarity	NPD1333	Phase 3
0.599	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.599	Remote Similarity	NPD1575	Approved
0.599	Remote Similarity	NPD1573	Approved
0.5989	Remote Similarity	NPD200	Phase 2
0.5989	Remote Similarity	NPD201	Phase 2
0.5981	Remote Similarity	NPD7657	Approved
0.5981	Remote Similarity	NPD7656	Approved
0.598	Remote Similarity	NPD5855	Phase 3
0.598	Remote Similarity	NPD5853	Phase 3
0.598	Remote Similarity	NPD7406	Phase 2
0.5979	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5016	Approved
0.597	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.597	Remote Similarity	NPD7175	Phase 1
0.5968	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD7887	Approved
0.5964	Remote Similarity	NPD7888	Approved
0.5962	Remote Similarity	NPD3891	Phase 2
0.5962	Remote Similarity	NPD3890	Phase 2
0.5957	Remote Similarity	NPD1630	Approved
0.5952	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4299	Phase 1
0.5949	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD6986	Phase 1
0.5943	Remote Similarity	NPD6459	Phase 2
0.5939	Remote Similarity	NPD5508	Phase 1
0.5939	Remote Similarity	NPD3927	Phase 2
0.5938	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD2927	Phase 3
0.5935	Remote Similarity	NPD4863	Approved
0.5933	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD6268	Phase 1
0.5933	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.592	Remote Similarity	NPD4988	Discontinued
0.5918	Remote Similarity	NPD4155	Approved
0.5916	Remote Similarity	NPD509	Phase 3
0.5915	Remote Similarity	NPD3968	Approved
0.5897	Remote Similarity	NPD7297	Phase 2
0.5896	Remote Similarity	NPD3905	Phase 3
0.5886	Remote Similarity	NPD803	Phase 1
0.5885	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1003	Phase 2
0.5882	Remote Similarity	NPD3430	Approved
0.5882	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3431	Approved
0.588	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD7027	Phase 3
0.5874	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8256	Approved
0.5872	Remote Similarity	NPD8257	Approved
0.5871	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7026	Phase 2
0.5871	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1631	Approved
0.586	Remote Similarity	NPD2660	Approved
0.586	Remote Similarity	NPD3248	Phase 1
0.586	Remote Similarity	NPD2662	Approved
0.5858	Remote Similarity	NPD9598	Discontinued
0.5857	Remote Similarity	NPD2881	Approved
0.5857	Remote Similarity	NPD2879	Approved
0.5854	Remote Similarity	NPD3460	Discontinued
0.5852	Remote Similarity	NPD9100	Approved
0.5833	Remote Similarity	NPD1313	Approved
0.5833	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD180	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD2402	Approved
0.5826	Remote Similarity	NPD2401	Approved
0.5826	Remote Similarity	NPD3353	Approved
0.5824	Remote Similarity	NPD5787	Discontinued
0.5822	Remote Similarity	NPD3411	Phase 2
0.5822	Remote Similarity	NPD3410	Approved
0.5821	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4883	Approved
0.5812	Remote Similarity	NPD6771	Discontinued
0.5808	Remote Similarity	NPD9396	Approved
0.5808	Remote Similarity	NPD9392	Approved
0.5803	Remote Similarity	NPD1215	Discontinued
0.5803	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD5611	Phase 2
0.5802	Remote Similarity	NPD5000	Phase 2
0.5802	Remote Similarity	NPD6229	Phase 2
0.58	Remote Similarity	NPD3320	Approved
0.58	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3318	Approved
0.58	Remote Similarity	NPD3319	Phase 1
0.5799	Remote Similarity	NPD4811	Discontinued
0.5799	Remote Similarity	NPD1591	Approved
0.5795	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD5809	Phase 3
0.5792	Remote Similarity	NPD4940	Approved
0.5782	Remote Similarity	NPD6802	Phase 3
0.578	Remote Similarity	NPD4395	Phase 1
0.5779	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD5962	Phase 2
0.5777	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD5491	Phase 3
0.5775	Remote Similarity	NPD5489	Phase 1
0.5771	Remote Similarity	NPD7564	Discontinued
0.5771	Remote Similarity	NPD721	Approved
0.5765	Remote Similarity	NPD4524	Discontinued
0.5764	Remote Similarity	NPD6465	Phase 2
0.5759	Remote Similarity	NPD5986	Approved
0.5759	Remote Similarity	NPD5987	Approved
0.5756	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD206	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD953	Approved
0.5742	Remote Similarity	NPD4364	Phase 1
0.5742	Remote Similarity	NPD7204	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