NPASS Compound

Structure

NPC470889 OpenBabel07101718182D 29 32 0 0 0 0 0 0 0 0999 V2000 -6.8053 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 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 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 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 -5.9393 -1.3309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 3.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 9 1 0 0 0 0 5 14 2 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 24 2 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.12
Volume:	410.44
LogP:	4.858
LogD:	3.734
LogS:	-6.221
# Rotatable Bonds:	6
TPSA:	49.81
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	2.413
Fsp3:	0.174
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:	-4.883
MDCK Permeability:	1.0610407116473652e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	98.6118392944336%
Volume Distribution (VD):	0.476
Pgp-substrate:	1.3182737827301025%

ADMET: Metabolism

CYP1A2-inhibitor:	0.716
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.831
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.94
CYP3A4-inhibitor:	0.364
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	6.662
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.541
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.573
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.048
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC470889

Natural Product ID:	NPC470889
*Common Name:**	5,6-Dimethoxy-4,7-Bis(4-Methoxyphenyl)-1,3-Benzothiazole
IUPAC Name:	5,6-dimethoxy-4,7-bis(4-methoxyphenyl)-1,3-benzothiazole
Synonyms:
Standard InCHIKey:	HHZHOMXMQXTDKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H21NO4S/c1-25-16-9-5-14(6-10-16)18-20-23(29-13-24-20)19(22(28-4)21(18)27-3)15-7-11-17(26-2)12-8-15/h5-13H,1-4H3
SMILES:	COc1ccc(cc1)c1c(OC)c(OC)c(c2c1scn2)c1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2289485
PubChem CID:	76331182
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO33384	0cardiopsis gilva YIM 90087	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23441911]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	14.3	%	PMID[512493]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	28.4	%	PMID[512493]

☑ 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 NPC470889 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	864
0.1-0.2	6154
0.2-0.3	11704
0.3-0.4	11416
0.4-0.5	9542
0.5-0.6	2538
0.6-0.7	460
0.7-0.8	16
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.76	Intermediate Similarity	NPC235076
0.7577	Intermediate Similarity	NPC23614
0.7577	Intermediate Similarity	NPC100079
0.7467	Intermediate Similarity	NPC46451
0.7422	Intermediate Similarity	NPC188420
0.7401	Intermediate Similarity	NPC271215
0.7401	Intermediate Similarity	NPC149471
0.7371	Intermediate Similarity	NPC118121
0.7297	Intermediate Similarity	NPC31930
0.72	Intermediate Similarity	NPC36229
0.72	Intermediate Similarity	NPC16452
0.72	Intermediate Similarity	NPC476581
0.7198	Intermediate Similarity	NPC204446
0.7131	Intermediate Similarity	NPC153467
0.713	Intermediate Similarity	NPC296482
0.713	Intermediate Similarity	NPC53069
0.713	Intermediate Similarity	NPC202768
0.7091	Intermediate Similarity	NPC195268
0.7091	Intermediate Similarity	NPC133140
0.7056	Intermediate Similarity	NPC251160
0.7035	Intermediate Similarity	NPC199277
0.7035	Intermediate Similarity	NPC135887
0.7026	Intermediate Similarity	NPC266931
0.7022	Intermediate Similarity	NPC234197
0.6983	Remote Similarity	NPC96405
0.6983	Remote Similarity	NPC316981
0.6983	Remote Similarity	NPC171409
0.6983	Remote Similarity	NPC112206
0.6983	Remote Similarity	NPC202605
0.6978	Remote Similarity	NPC4071
0.6978	Remote Similarity	NPC476582
0.6978	Remote Similarity	NPC476578
0.6951	Remote Similarity	NPC131017
0.6941	Remote Similarity	NPC204385
0.693	Remote Similarity	NPC162484
0.6916	Remote Similarity	NPC312872
0.6913	Remote Similarity	NPC313189
0.6913	Remote Similarity	NPC193777
0.6872	Remote Similarity	NPC477019
0.6867	Remote Similarity	NPC208284
0.6853	Remote Similarity	NPC201697
0.6826	Remote Similarity	NPC285558
0.6824	Remote Similarity	NPC11464
0.6789	Remote Similarity	NPC277351
0.6777	Remote Similarity	NPC200888
0.6767	Remote Similarity	NPC135549
0.6766	Remote Similarity	NPC48353
0.6758	Remote Similarity	NPC206201
0.6752	Remote Similarity	NPC290689
0.6751	Remote Similarity	NPC170114
0.6737	Remote Similarity	NPC162530
0.6734	Remote Similarity	NPC473183
0.6724	Remote Similarity	NPC304183
0.6723	Remote Similarity	NPC473513
0.6722	Remote Similarity	NPC122463
0.6711	Remote Similarity	NPC72211
0.6709	Remote Similarity	NPC470549
0.6708	Remote Similarity	NPC214980
0.6708	Remote Similarity	NPC174049
0.6697	Remote Similarity	NPC179704
0.6693	Remote Similarity	NPC270515
0.6681	Remote Similarity	NPC470930
0.668	Remote Similarity	NPC473182
0.6667	Remote Similarity	NPC243834
0.6667	Remote Similarity	NPC70956
0.6653	Remote Similarity	NPC252251
0.6653	Remote Similarity	NPC473184
0.6653	Remote Similarity	NPC217554
0.6652	Remote Similarity	NPC11017
0.664	Remote Similarity	NPC284141
0.6639	Remote Similarity	NPC202503
0.6639	Remote Similarity	NPC477533
0.6639	Remote Similarity	NPC227908
0.6637	Remote Similarity	NPC141915
0.6637	Remote Similarity	NPC280964
0.6637	Remote Similarity	NPC114335
0.6627	Remote Similarity	NPC295228
0.6625	Remote Similarity	NPC473822
0.6625	Remote Similarity	NPC173080
0.6623	Remote Similarity	NPC70259
0.6623	Remote Similarity	NPC267423
0.6622	Remote Similarity	NPC76748
0.661	Remote Similarity	NPC123976
0.661	Remote Similarity	NPC167860
0.6608	Remote Similarity	NPC307963
0.6599	Remote Similarity	NPC477531
0.6597	Remote Similarity	NPC478074
0.6596	Remote Similarity	NPC470931
0.6595	Remote Similarity	NPC66815
0.6593	Remote Similarity	NPC92111
0.6585	Remote Similarity	NPC476997
0.6584	Remote Similarity	NPC280272
0.6584	Remote Similarity	NPC210434
0.658	Remote Similarity	NPC315957
0.6579	Remote Similarity	NPC205934
0.6579	Remote Similarity	NPC43787
0.6578	Remote Similarity	NPC296527
0.6574	Remote Similarity	NPC11408
0.657	Remote Similarity	NPC86078
0.6567	Remote Similarity	NPC223427
0.6561	Remote Similarity	NPC168486
0.6561	Remote Similarity	NPC222592
0.6561	Remote Similarity	NPC287588
0.6559	Remote Similarity	NPC24019
0.6559	Remote Similarity	NPC476998
0.6559	Remote Similarity	NPC476996
0.6559	Remote Similarity	NPC209174
0.6552	Remote Similarity	NPC232727
0.655	Remote Similarity	NPC13880
0.655	Remote Similarity	NPC251090
0.655	Remote Similarity	NPC194967
0.6547	Remote Similarity	NPC84478
0.6546	Remote Similarity	NPC255800
0.6546	Remote Similarity	NPC22481
0.6546	Remote Similarity	NPC96584
0.6545	Remote Similarity	NPC473185
0.6545	Remote Similarity	NPC285941
0.654	Remote Similarity	NPC219664
0.6532	Remote Similarity	NPC476999
0.6532	Remote Similarity	NPC201508
0.6529	Remote Similarity	NPC193267
0.6529	Remote Similarity	NPC213530
0.6527	Remote Similarity	NPC236668
0.6524	Remote Similarity	NPC291535
0.6524	Remote Similarity	NPC475112
0.6524	Remote Similarity	NPC475085
0.6522	Remote Similarity	NPC474188
0.6522	Remote Similarity	NPC153042
0.6518	Remote Similarity	NPC476994
0.6509	Remote Similarity	NPC176538
0.6509	Remote Similarity	NPC121772
0.6509	Remote Similarity	NPC329747
0.6502	Remote Similarity	NPC176127
0.65	Remote Similarity	NPC146976
0.6498	Remote Similarity	NPC174672
0.6498	Remote Similarity	NPC469589
0.6498	Remote Similarity	NPC209769
0.6498	Remote Similarity	NPC174758
0.6496	Remote Similarity	NPC475774
0.6494	Remote Similarity	NPC108342
0.6492	Remote Similarity	NPC278525
0.6485	Remote Similarity	NPC203168
0.6468	Remote Similarity	NPC182907
0.6468	Remote Similarity	NPC189903
0.6466	Remote Similarity	NPC475253
0.6463	Remote Similarity	NPC302001
0.6461	Remote Similarity	NPC148409
0.6461	Remote Similarity	NPC473179
0.6457	Remote Similarity	NPC190461
0.6456	Remote Similarity	NPC82548
0.6453	Remote Similarity	NPC132385
0.6444	Remote Similarity	NPC249405
0.6443	Remote Similarity	NPC166722
0.6441	Remote Similarity	NPC476106
0.6441	Remote Similarity	NPC472111
0.6432	Remote Similarity	NPC477186
0.6417	Remote Similarity	NPC473180
0.641	Remote Similarity	NPC476044
0.6408	Remote Similarity	NPC477532
0.6407	Remote Similarity	NPC472193
0.6404	Remote Similarity	NPC474904
0.6404	Remote Similarity	NPC312531
0.6402	Remote Similarity	NPC470020
0.6402	Remote Similarity	NPC26850
0.6402	Remote Similarity	NPC89549
0.6398	Remote Similarity	NPC164374
0.6398	Remote Similarity	NPC137929
0.6395	Remote Similarity	NPC287437
0.6389	Remote Similarity	NPC24802
0.6389	Remote Similarity	NPC90875
0.6383	Remote Similarity	NPC295898
0.6379	Remote Similarity	NPC314552
0.6375	Remote Similarity	NPC233334
0.6368	Remote Similarity	NPC329793
0.6364	Remote Similarity	NPC326634
0.636	Remote Similarity	NPC128751
0.6352	Remote Similarity	NPC193906
0.6352	Remote Similarity	NPC46561
0.6352	Remote Similarity	NPC23080
0.6349	Remote Similarity	NPC94157
0.6349	Remote Similarity	NPC26679
0.6348	Remote Similarity	NPC99666
0.6345	Remote Similarity	NPC110151
0.6344	Remote Similarity	NPC276674
0.6344	Remote Similarity	NPC33902
0.6341	Remote Similarity	NPC310118
0.6339	Remote Similarity	NPC476995
0.6337	Remote Similarity	NPC274982
0.6336	Remote Similarity	NPC162653
0.6333	Remote Similarity	NPC199667
0.6332	Remote Similarity	NPC469497
0.6332	Remote Similarity	NPC106833
0.6328	Remote Similarity	NPC210296
0.6325	Remote Similarity	NPC212163
0.6324	Remote Similarity	NPC253675
0.6322	Remote Similarity	NPC471080
0.6322	Remote Similarity	NPC469592
0.6322	Remote Similarity	NPC474594
0.6322	Remote Similarity	NPC473188
0.6318	Remote Similarity	NPC475910

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 NPC470889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	462
0.1-0.2	762
0.2-0.3	993
0.3-0.4	2405
0.4-0.5	3095
0.5-0.6	1248
0.6-0.7	181
0.7-0.8	4
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
0.7609	Intermediate Similarity	NPD7719	Discontinued
0.7467	Intermediate Similarity	NPD3763	Approved
0.7465	Intermediate Similarity	NPD2749	Discontinued
0.7257	Intermediate Similarity	NPD5658	Approved
0.713	Intermediate Similarity	NPD3816	Phase 1
0.713	Intermediate Similarity	NPD3815	Phase 1
0.7091	Intermediate Similarity	NPD3921	Approved
0.7091	Intermediate Similarity	NPD3924	Approved
0.7091	Intermediate Similarity	NPD3922	Approved
0.7091	Intermediate Similarity	NPD3923	Approved
0.708	Intermediate Similarity	NPD6324	Phase 1
0.6976	Remote Similarity	NPD6230	Discontinued
0.6971	Remote Similarity	NPD7567	Approved
0.6953	Remote Similarity	NPD4331	Approved
0.6929	Remote Similarity	NPD7555	Discontinued
0.6923	Remote Similarity	NPD5903	Approved
0.6923	Remote Similarity	NPD5902	Approved
0.6898	Remote Similarity	NPD3920	Phase 2
0.6885	Remote Similarity	NPD6494	Phase 2
0.6875	Remote Similarity	NPD6246	Approved
0.6875	Remote Similarity	NPD4418	Discontinued
0.6849	Remote Similarity	NPD5930	Phase 3
0.6835	Remote Similarity	NPD3354	Phase 2
0.682	Remote Similarity	NPD4439	Discontinued
0.6812	Remote Similarity	NPD1897	Discontinued
0.6808	Remote Similarity	NPD8284	Discontinued
0.6793	Remote Similarity	NPD5453	Phase 2
0.6767	Remote Similarity	NPD7453	Approved
0.6767	Remote Similarity	NPD7222	Phase 2
0.6767	Remote Similarity	NPD7452	Approved
0.6766	Remote Similarity	NPD5452	Phase 2
0.6765	Remote Similarity	NPD2021	Discontinued
0.6746	Remote Similarity	NPD8100	Phase 3
0.6721	Remote Similarity	NPD6963	Approved
0.6721	Remote Similarity	NPD6964	Approved
0.6706	Remote Similarity	NPD3756	Phase 1
0.6681	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4795	Phase 2
0.6667	Remote Similarity	NPD4996	Approved
0.6667	Remote Similarity	NPD4995	Approved
0.6667	Remote Similarity	NPD8101	Phase 3
0.6654	Remote Similarity	NPD3328	Phase 2
0.6639	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6755	Phase 2
0.6626	Remote Similarity	NPD4925	Approved
0.6613	Remote Similarity	NPD7558	Phase 2
0.6611	Remote Similarity	NPD5612	Discontinued
0.6608	Remote Similarity	NPD1038	Approved
0.6608	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6276	Discontinued
0.6584	Remote Similarity	NPD1954	Phase 1
0.6581	Remote Similarity	NPD3003	Approved
0.658	Remote Similarity	NPD1739	Approved
0.658	Remote Similarity	NPD1740	Approved
0.655	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5905	Phase 1
0.6538	Remote Similarity	NPD3397	Phase 2
0.6533	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD5530	Phase 1
0.6508	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4876	Phase 3
0.6496	Remote Similarity	NPD4875	Phase 3
0.6489	Remote Similarity	NPD9542	Approved
0.6486	Remote Similarity	NPD6743	Phase 2
0.6486	Remote Similarity	NPD6742	Phase 2
0.6478	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6243	Phase 3
0.6473	Remote Similarity	NPD6244	Phase 3
0.6466	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6558	Phase 1
0.6464	Remote Similarity	NPD6228	Discontinued
0.6459	Remote Similarity	NPD7214	Phase 3
0.6452	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1218	Approved
0.645	Remote Similarity	NPD1219	Approved
0.6446	Remote Similarity	NPD1976	Approved
0.6444	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7691	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD5833	Phase 1
0.6426	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4850	Phase 1
0.6414	Remote Similarity	NPD1392	Approved
0.6409	Remote Similarity	NPD7215	Phase 2
0.6395	Remote Similarity	NPD6205	Discontinued
0.6388	Remote Similarity	NPD8091	Phase 3
0.6384	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5164	Discontinued
0.6379	Remote Similarity	NPD6988	Phase 1
0.6364	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3395	Approved
0.6364	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3396	Approved
0.636	Remote Similarity	NPD7859	Phase 2
0.6352	Remote Similarity	NPD6985	Discontinued
0.6352	Remote Similarity	NPD1788	Approved
0.6352	Remote Similarity	NPD1789	Approved
0.6346	Remote Similarity	NPD7873	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8108	Approved
0.6336	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7194	Discontinued
0.6326	Remote Similarity	NPD6207	Discovery
0.6325	Remote Similarity	NPD1768	Approved
0.6316	Remote Similarity	NPD3611	Phase 3
0.631	Remote Similarity	NPD4885	Approved
0.6309	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7403	Phase 1
0.6301	Remote Similarity	NPD6242	Discontinued
0.6291	Remote Similarity	NPD8107	Approved
0.6289	Remote Similarity	NPD6134	Phase 2
0.6289	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4044	Discontinued
0.6286	Remote Similarity	NPD4994	Phase 2
0.6281	Remote Similarity	NPD7069	Discontinued
0.6279	Remote Similarity	NPD7620	Phase 2
0.6265	Remote Similarity	NPD7417	Discontinued
0.6261	Remote Similarity	NPD5628	Clinical (unspecified phase)
0.626	Remote Similarity	NPD3838	Phase 3
0.6255	Remote Similarity	NPD5945	Phase 1
0.6255	Remote Similarity	NPD3825	Phase 3
0.6255	Remote Similarity	NPD5944	Phase 1
0.625	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2189	Approved
0.625	Remote Similarity	NPD2187	Approved
0.6245	Remote Similarity	NPD3886	Phase 1
0.6245	Remote Similarity	NPD6975	Discontinued
0.624	Remote Similarity	NPD7426	Phase 1
0.624	Remote Similarity	NPD7674	Phase 3
0.624	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5066	Phase 2
0.624	Remote Similarity	NPD7675	Phase 3
0.624	Remote Similarity	NPD5051	Phase 1
0.624	Remote Similarity	NPD5067	Phase 2
0.6239	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5488	Discontinued
0.623	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD6219	Discontinued
0.6228	Remote Similarity	NPD4889	Approved
0.6226	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8016	Phase 3
0.6224	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6590	Discontinued
0.6221	Remote Similarity	NPD6972	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5144	Discontinued
0.6217	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6450	Phase 2
0.6204	Remote Similarity	NPD5101	Discontinued
0.6204	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6790	Phase 1
0.6198	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD4033	Approved
0.6192	Remote Similarity	NPD4034	Approved
0.6192	Remote Similarity	NPD4038	Approved
0.6192	Remote Similarity	NPD31	Approved
0.6192	Remote Similarity	NPD4122	Approved
0.6192	Remote Similarity	NPD4035	Approved
0.6192	Remote Similarity	NPD32	Approved
0.6192	Remote Similarity	NPD4037	Approved
0.6192	Remote Similarity	NPD4036	Approved
0.6192	Remote Similarity	NPD4039	Approved
0.619	Remote Similarity	NPD7227	Phase 3
0.619	Remote Similarity	NPD7226	Phase 3
0.6189	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8102	Discontinued
0.618	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7956	Approved
0.618	Remote Similarity	NPD802	Phase 2
0.618	Remote Similarity	NPD7955	Approved
0.6179	Remote Similarity	NPD5059	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6517	Phase 3
0.6175	Remote Similarity	NPD7002	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4502	Phase 2
0.617	Remote Similarity	NPD2474	Discontinued
0.617	Remote Similarity	NPD7948	Phase 1
0.6166	Remote Similarity	NPD4952	Phase 3
0.6166	Remote Similarity	NPD8512	Phase 3
0.6161	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6475	Phase 2
0.6157	Remote Similarity	NPD2472	Approved
0.6157	Remote Similarity	NPD2471	Approved
0.6154	Remote Similarity	NPD5632	Approved
0.6151	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD8358	Approved
0.6142	Remote Similarity	NPD6962	Phase 2
0.6137	Remote Similarity	NPD6569	Phase 2
0.6134	Remote Similarity	NPD5259	Phase 3
0.6133	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5007	Approved
0.6119	Remote Similarity	NPD8489	Phase 1
0.6118	Remote Similarity	NPD5828	Phase 2
0.6114	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD5857	Phase 3
0.6107	Remote Similarity	NPD5817	Discontinued
0.6104	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4899	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