NPASS Compound

Structure

NPC471540 OpenBabel07101718322D 45 48 0 0 1 0 0 0 0 0999 V2000 -1.6845 -11.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 -10.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -9.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -8.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -8.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -7.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -6.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -5.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 -0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2569 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 -0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 2.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 2.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 3.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9757 1.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 3.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 3.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 4.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.6527 0.4296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 33 1 0 0 0 0 17 33 1 0 0 0 0 18 19 1 0 0 0 0 18 33 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 21 34 1 0 0 0 0 22 39 2 0 0 0 0 23 13 1 1 0 0 0 23 44 1 0 0 0 0 24 43 1 6 0 0 0 25 26 2 0 0 0 0 25 27 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 29 2 0 0 0 0 27 35 1 0 0 0 0 28 30 2 0 0 0 0 28 36 1 0 0 0 0 29 30 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 0 0 0 0 31 40 2 0 0 0 0 31 41 1 0 0 0 0 32 42 2 0 0 0 0 32 43 1 0 0 0 0 33 45 1 0 0 0 0 34 19 1 1 0 0 0 34 44 1 0 0 0 0 34 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	877.97
Volume:	679.969
LogP:	8.886
LogD:	3.402
LogS:	-5.037
# Rotatable Bonds:	16
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	5.216
Fsp3:	0.618
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	3.8174872315721586e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	107.02982330322266%
Volume Distribution (VD):	2.307
Pgp-substrate:	1.1865557432174683%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.724
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.23
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	2.463
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.638
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.98
Carcinogencity:	0.513
Eye Corrosion:	0.004
Eye Irritation:	0.315
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471540

Natural Product ID:	NPC471540
*Common Name:**	3,4,5,6-Tetrabromo-Phthalic Acid Mono-((2R,4R,6R)-11-Oxo-2-Tridecyl-1,7-Dioxa-Dispiro[5.1.5.2]Pentadeca-9,12-Dien-4-Yl) Ester
IUPAC Name:	2,3,4,5-tetrabromo-6-[[(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl]oxycarbonyl]benzoic acid
Synonyms:
Standard InCHIKey:	LYZVRGOEGVAFTF-ZLEIESQFSA-N
Standard InCHI:	InChI=1S/C34H42Br4O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-23-20-24(21-34(44-23)19-18-33(45-34)16-14-22(39)15-17-33)43-32(42)26-25(31(40)41)27(35)29(37)30(38)28(26)36/h14-17,23-24H,2-13,18-21H2,1H3,(H,40,41)/t23-,24-,34-/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(CC2(O1)CCC3(O2)C=CC(=O)C=C3)OC(=O)C4=C(C(=C(C(=C4Br)Br)Br)Br)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255721
PubChem CID:	24853603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	10.3	uM	PMID[471337]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	5.1	uM	PMID[471337]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	4.7	uM	PMID[471337]

☑ 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 NPC471540 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	337
0.1-0.2	1383
0.2-0.3	2964
0.3-0.4	8868
0.4-0.5	15239
0.5-0.6	12614
0.6-0.7	1286
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8367	Intermediate Similarity	NPC473359
0.716	Intermediate Similarity	NPC473367
0.6943	Remote Similarity	NPC27712
0.6937	Remote Similarity	NPC473399
0.6937	Remote Similarity	NPC473216
0.6886	Remote Similarity	NPC97188
0.6882	Remote Similarity	NPC37642
0.6871	Remote Similarity	NPC475400
0.6842	Remote Similarity	NPC51198
0.6839	Remote Similarity	NPC246166
0.6829	Remote Similarity	NPC77493
0.6824	Remote Similarity	NPC153053
0.6824	Remote Similarity	NPC307651
0.6818	Remote Similarity	NPC223351
0.681	Remote Similarity	NPC475195
0.6803	Remote Similarity	NPC321852
0.677	Remote Similarity	NPC38420
0.677	Remote Similarity	NPC136608
0.6747	Remote Similarity	NPC153214
0.6747	Remote Similarity	NPC95449
0.6746	Remote Similarity	NPC469498
0.6735	Remote Similarity	NPC260818
0.673	Remote Similarity	NPC147561
0.6727	Remote Similarity	NPC16912
0.6726	Remote Similarity	NPC477737
0.6725	Remote Similarity	NPC35160
0.6725	Remote Similarity	NPC235033
0.6725	Remote Similarity	NPC73132
0.6725	Remote Similarity	NPC52931
0.6725	Remote Similarity	NPC162569
0.6725	Remote Similarity	NPC471235
0.671	Remote Similarity	NPC141970
0.671	Remote Similarity	NPC140561
0.6709	Remote Similarity	NPC148026
0.6706	Remote Similarity	NPC469448
0.6689	Remote Similarity	NPC82899
0.6689	Remote Similarity	NPC270699
0.6687	Remote Similarity	NPC472551
0.6687	Remote Similarity	NPC472374
0.6687	Remote Similarity	NPC469519
0.6687	Remote Similarity	NPC472372
0.6687	Remote Similarity	NPC472545
0.6686	Remote Similarity	NPC208293
0.6686	Remote Similarity	NPC471135
0.6667	Remote Similarity	NPC17600
0.6667	Remote Similarity	NPC183270
0.6667	Remote Similarity	NPC162613
0.6667	Remote Similarity	NPC472547
0.6667	Remote Similarity	NPC28836
0.6667	Remote Similarity	NPC21873
0.6667	Remote Similarity	NPC171207
0.6667	Remote Similarity	NPC97667
0.6667	Remote Similarity	NPC469415
0.6667	Remote Similarity	NPC228739
0.6667	Remote Similarity	NPC469417
0.6667	Remote Similarity	NPC251854
0.6667	Remote Similarity	NPC100913
0.6667	Remote Similarity	NPC87934
0.6667	Remote Similarity	NPC477904
0.6667	Remote Similarity	NPC301857
0.6667	Remote Similarity	NPC93084
0.6667	Remote Similarity	NPC90614
0.6667	Remote Similarity	NPC275592
0.6648	Remote Similarity	NPC29552
0.6647	Remote Similarity	NPC91703
0.6647	Remote Similarity	NPC469456
0.6647	Remote Similarity	NPC257003
0.6647	Remote Similarity	NPC11892
0.6647	Remote Similarity	NPC471444
0.6646	Remote Similarity	NPC233860
0.6646	Remote Similarity	NPC472394
0.6646	Remote Similarity	NPC114096
0.6646	Remote Similarity	NPC233692
0.6646	Remote Similarity	NPC169913
0.6646	Remote Similarity	NPC39549
0.6629	Remote Similarity	NPC471134
0.6628	Remote Similarity	NPC472548
0.6628	Remote Similarity	NPC116292
0.6628	Remote Similarity	NPC267469
0.6628	Remote Similarity	NPC179128
0.6628	Remote Similarity	NPC87630
0.6627	Remote Similarity	NPC118080
0.6627	Remote Similarity	NPC170668
0.6627	Remote Similarity	NPC291599
0.6627	Remote Similarity	NPC87448
0.6627	Remote Similarity	NPC41481
0.6627	Remote Similarity	NPC474935
0.6627	Remote Similarity	NPC295339
0.6627	Remote Similarity	NPC472576
0.6627	Remote Similarity	NPC27377
0.6627	Remote Similarity	NPC242355
0.6627	Remote Similarity	NPC266374
0.6627	Remote Similarity	NPC224491
0.6627	Remote Similarity	NPC469513
0.6627	Remote Similarity	NPC97947
0.6626	Remote Similarity	NPC477893
0.6626	Remote Similarity	NPC200154
0.6624	Remote Similarity	NPC295664
0.6623	Remote Similarity	NPC149691
0.6622	Remote Similarity	NPC305912
0.6622	Remote Similarity	NPC1082
0.661	Remote Similarity	NPC477188
0.661	Remote Similarity	NPC477190
0.661	Remote Similarity	NPC43304
0.6609	Remote Similarity	NPC475638
0.6609	Remote Similarity	NPC290683
0.6609	Remote Similarity	NPC326235
0.6609	Remote Similarity	NPC475548
0.6609	Remote Similarity	NPC323001
0.6608	Remote Similarity	NPC475561
0.6608	Remote Similarity	NPC475417
0.6608	Remote Similarity	NPC303429
0.6608	Remote Similarity	NPC222102
0.6607	Remote Similarity	NPC163719
0.6607	Remote Similarity	NPC472573
0.6607	Remote Similarity	NPC472570
0.6607	Remote Similarity	NPC11685
0.6607	Remote Similarity	NPC57628
0.6607	Remote Similarity	NPC478250
0.6607	Remote Similarity	NPC95810
0.6607	Remote Similarity	NPC476974
0.6607	Remote Similarity	NPC125106
0.6607	Remote Similarity	NPC475122
0.6607	Remote Similarity	NPC95265
0.6607	Remote Similarity	NPC25768
0.6607	Remote Similarity	NPC70716
0.6607	Remote Similarity	NPC472569
0.6607	Remote Similarity	NPC188865
0.6606	Remote Similarity	NPC473301
0.6606	Remote Similarity	NPC9905
0.6605	Remote Similarity	NPC472248
0.6604	Remote Similarity	NPC115797
0.6604	Remote Similarity	NPC51448
0.66	Remote Similarity	NPC237366
0.6599	Remote Similarity	NPC17417
0.6599	Remote Similarity	NPC83628
0.6599	Remote Similarity	NPC10251
0.6599	Remote Similarity	NPC265407
0.6599	Remote Similarity	NPC85493
0.659	Remote Similarity	NPC472658
0.659	Remote Similarity	NPC472657
0.659	Remote Similarity	NPC133430
0.659	Remote Similarity	NPC469477
0.6587	Remote Similarity	NPC472546
0.6587	Remote Similarity	NPC34012
0.6587	Remote Similarity	NPC192658
0.6585	Remote Similarity	NPC202729
0.6584	Remote Similarity	NPC475478
0.6582	Remote Similarity	NPC275576
0.6573	Remote Similarity	NPC66193
0.6573	Remote Similarity	NPC322420
0.6571	Remote Similarity	NPC477735
0.6571	Remote Similarity	NPC318447
0.6571	Remote Similarity	NPC322048
0.657	Remote Similarity	NPC51602
0.6568	Remote Similarity	NPC472568
0.6568	Remote Similarity	NPC70403
0.6568	Remote Similarity	NPC472556
0.6568	Remote Similarity	NPC476973
0.6568	Remote Similarity	NPC25043
0.6568	Remote Similarity	NPC134131
0.6568	Remote Similarity	NPC200471
0.6568	Remote Similarity	NPC271451
0.6568	Remote Similarity	NPC96903
0.6568	Remote Similarity	NPC470159
0.6568	Remote Similarity	NPC476473
0.6568	Remote Similarity	NPC174982
0.6568	Remote Similarity	NPC158663
0.6568	Remote Similarity	NPC472572
0.6568	Remote Similarity	NPC470157
0.6568	Remote Similarity	NPC171525
0.6568	Remote Similarity	NPC184817
0.6568	Remote Similarity	NPC177940
0.6568	Remote Similarity	NPC469349
0.6568	Remote Similarity	NPC473088
0.6568	Remote Similarity	NPC472571
0.6568	Remote Similarity	NPC472575
0.6568	Remote Similarity	NPC29704
0.6568	Remote Similarity	NPC471104
0.6566	Remote Similarity	NPC251294
0.6566	Remote Similarity	NPC81137
0.6566	Remote Similarity	NPC61590
0.6564	Remote Similarity	NPC298547
0.6564	Remote Similarity	NPC311492
0.6564	Remote Similarity	NPC474608
0.6564	Remote Similarity	NPC203486
0.6564	Remote Similarity	NPC134937
0.6564	Remote Similarity	NPC48929
0.6564	Remote Similarity	NPC324898
0.6561	Remote Similarity	NPC472704
0.6558	Remote Similarity	NPC476096
0.6556	Remote Similarity	NPC306740
0.6554	Remote Similarity	NPC214067
0.6554	Remote Similarity	NPC196246
0.6552	Remote Similarity	NPC21410
0.6552	Remote Similarity	NPC5115
0.6552	Remote Similarity	NPC475093
0.6552	Remote Similarity	NPC469422
0.6552	Remote Similarity	NPC472549
0.6552	Remote Similarity	NPC34066

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 NPC471540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	890
0.2-0.3	2057
0.3-0.4	3319
0.4-0.5	2053
0.5-0.6	524
0.6-0.7	18
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
0.6735	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2182	Approved
0.6508	Remote Similarity	NPD4287	Approved
0.6481	Remote Similarity	NPD3764	Approved
0.6441	Remote Similarity	NPD4288	Approved
0.6438	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD164	Approved
0.6279	Remote Similarity	NPD7236	Approved
0.627	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5125	Phase 3
0.6203	Remote Similarity	NPD5126	Approved
0.6167	Remote Similarity	NPD2296	Approved
0.6159	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8407	Phase 2
0.6121	Remote Similarity	NPD7008	Discontinued
0.6108	Remote Similarity	NPD4445	Approved
0.6102	Remote Similarity	NPD7239	Suspended
0.6101	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8368	Discontinued
0.6026	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2532	Approved
0.6023	Remote Similarity	NPD2534	Approved
0.6023	Remote Similarity	NPD2533	Approved
0.6022	Remote Similarity	NPD7819	Suspended
0.602	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.601	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.599	Remote Similarity	NPD8312	Approved
0.599	Remote Similarity	NPD8313	Approved
0.5979	Remote Similarity	NPD8434	Phase 2
0.5977	Remote Similarity	NPD3750	Approved
0.5975	Remote Similarity	NPD9545	Approved
0.5933	Remote Similarity	NPD6647	Phase 2
0.5932	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD5951	Approved
0.592	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8150	Discontinued
0.5896	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD2346	Discontinued
0.5889	Remote Similarity	NPD3226	Approved
0.5886	Remote Similarity	NPD4628	Phase 3
0.5885	Remote Similarity	NPD7685	Pre-registration
0.5875	Remote Similarity	NPD7741	Discontinued
0.5858	Remote Similarity	NPD7961	Discontinued
0.5839	Remote Similarity	NPD1238	Approved
0.5838	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD8360	Approved
0.5838	Remote Similarity	NPD3749	Approved
0.5838	Remote Similarity	NPD8361	Approved
0.5816	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD2067	Discontinued
0.5802	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD37	Approved
0.5789	Remote Similarity	NPD1237	Approved
0.5787	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4966	Approved
0.5784	Remote Similarity	NPD7058	Phase 2
0.5784	Remote Similarity	NPD4967	Phase 2
0.5784	Remote Similarity	NPD7057	Phase 3
0.5784	Remote Similarity	NPD4965	Approved
0.578	Remote Similarity	NPD3748	Approved
0.5769	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8435	Approved
0.5753	Remote Similarity	NPD7075	Discontinued
0.5753	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD6085	Phase 2
0.5739	Remote Similarity	NPD2800	Approved
0.5738	Remote Similarity	NPD7411	Suspended
0.5732	Remote Similarity	NPD969	Suspended
0.5732	Remote Similarity	NPD6287	Discontinued
0.5723	Remote Similarity	NPD2567	Approved
0.5723	Remote Similarity	NPD2569	Approved
0.5722	Remote Similarity	NPD6234	Discontinued
0.5722	Remote Similarity	NPD6559	Discontinued
0.5714	Remote Similarity	NPD7699	Phase 2
0.5714	Remote Similarity	NPD7458	Discontinued
0.5714	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6004	Phase 3
0.5714	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5711	Approved
0.5714	Remote Similarity	NPD5710	Approved
0.5714	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6005	Phase 3
0.5714	Remote Similarity	NPD7266	Discontinued
0.5714	Remote Similarity	NPD7700	Phase 2
0.5714	Remote Similarity	NPD6002	Phase 3
0.5706	Remote Similarity	NPD8166	Discontinued
0.5706	Remote Similarity	NPD2575	Approved
0.5706	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2313	Discontinued
0.57	Remote Similarity	NPD8319	Approved
0.57	Remote Similarity	NPD8320	Phase 1
0.5699	Remote Similarity	NPD7768	Phase 2
0.5698	Remote Similarity	NPD230	Phase 1
0.5691	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7033	Discontinued
0.5686	Remote Similarity	NPD5909	Discontinued
0.5682	Remote Similarity	NPD1549	Phase 2
0.5677	Remote Similarity	NPD7228	Approved
0.5677	Remote Similarity	NPD3751	Discontinued
0.5677	Remote Similarity	NPD3818	Discontinued
0.5676	Remote Similarity	NPD8455	Phase 2
0.5673	Remote Similarity	NPD7713	Phase 3
0.5659	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD2798	Approved
0.5652	Remote Similarity	NPD9493	Approved
0.5652	Remote Similarity	NPD7435	Discontinued
0.5649	Remote Similarity	NPD5048	Discontinued
0.5648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5844	Phase 1
0.5645	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6534	Approved
0.5644	Remote Similarity	NPD6535	Approved
0.5638	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6273	Approved
0.5632	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7097	Phase 1
0.5629	Remote Similarity	NPD2066	Phase 3
0.5625	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7473	Discontinued
0.5625	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2629	Approved
0.5622	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD6801	Discontinued
0.5621	Remote Similarity	NPD1929	Approved
0.5621	Remote Similarity	NPD1930	Approved
0.5621	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD3268	Approved
0.5613	Remote Similarity	NPD6685	Approved
0.5608	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5124	Phase 1
0.5604	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5403	Approved
0.5602	Remote Similarity	NPD6637	Approved
0.5602	Remote Similarity	NPD4878	Approved
0.56	Remote Similarity	NPD4308	Phase 3
0.56	Remote Similarity	NPD2799	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