NPASS Compound

Structure

NPC473359 OpenBabel07101719512D 39 42 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 4.3776 3.4067 0.0000 C 0 0 0 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 5.2437 3.9067 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 -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 4.3776 2.4067 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 -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 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 3.9067 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 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 1 0 0 0 0 14 26 2 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 27 2 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 28 1 0 0 0 0 20 32 1 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 25 33 1 0 0 0 0 26 31 1 0 0 0 0 27 34 1 0 0 0 0 28 35 2 0 0 0 0 29 13 1 1 0 0 0 29 38 1 0 0 0 0 30 37 1 6 0 0 0 31 36 2 0 0 0 0 31 37 1 0 0 0 0 32 39 1 0 0 0 0 33 23 1 1 0 0 0 33 38 1 0 0 0 0 33 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.25
Volume:	589.878
LogP:	8.331
LogD:	4.388
LogS:	-7.002
# Rotatable Bonds:	15
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	4.727
Fsp3:	0.636
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	4.1068982682190835e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.769
30% Bioavailability (F30%):	0.397

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	101.7073745727539%
Volume Distribution (VD):	2.137
Pgp-substrate:	0.5533604621887207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.73
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.451
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	6.09
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.669
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.353
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.985
Carcinogencity:	0.652
Eye Corrosion:	0.009
Eye Irritation:	0.473
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473359

Natural Product ID:	NPC473359
*Common Name:**	[(2R,4R,6R)-11-Oxo-4-Tridecyl-5,7-Dioxadispiro[5.1.5^{8}.2^{6}]Pentadeca-9,12-Dien-2-Yl] 4-Bromobenzoate
IUPAC Name:	[(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl] 4-bromobenzoate
Synonyms:
Standard InCHIKey:	UWIBWIWTOSSJGT-ZAPWPRAASA-N
Standard InCHI:	InChI=1S/C33H45BrO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-29-24-30(37-31(36)26-14-16-27(34)17-15-26)25-33(38-29)23-22-32(39-33)20-18-28(35)19-21-32/h14-21,29-30H,2-13,22-25H2,1H3/t29-,30-,33-/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(CC2(O1)CCC3(O2)C=CC(=O)C=C3)OC(=O)C4=CC=C(C=C4)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402863
PubChem CID:	24853604
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	=	1.3	uM	PMID[470557]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.8	uM	PMID[470557]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	0.7	uM	PMID[470557]

☑ 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 NPC473359 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	309
0.1-0.2	1238
0.2-0.3	2436
0.3-0.4	7321
0.4-0.5	14004
0.5-0.6	13103
0.6-0.7	3885
0.7-0.8	396
0.8-0.85	4
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	NPC471540
0.7943	Intermediate Similarity	NPC473216
0.7943	Intermediate Similarity	NPC473399
0.7724	Intermediate Similarity	NPC475400
0.7714	Intermediate Similarity	NPC147561
0.766	Intermediate Similarity	NPC469519
0.766	Intermediate Similarity	NPC475478
0.7656	Intermediate Similarity	NPC469636
0.7634	Intermediate Similarity	NPC307651
0.7622	Intermediate Similarity	NPC324898
0.7622	Intermediate Similarity	NPC298547
0.7622	Intermediate Similarity	NPC134937
0.7589	Intermediate Similarity	NPC475508
0.7586	Intermediate Similarity	NPC327511
0.7586	Intermediate Similarity	NPC205305
0.7571	Intermediate Similarity	NPC148026
0.7569	Intermediate Similarity	NPC149401
0.7569	Intermediate Similarity	NPC279637
0.7557	Intermediate Similarity	NPC474176
0.7556	Intermediate Similarity	NPC476096
0.754	Intermediate Similarity	NPC301943
0.754	Intermediate Similarity	NPC474365
0.7534	Intermediate Similarity	NPC121268
0.7534	Intermediate Similarity	NPC53361
0.7518	Intermediate Similarity	NPC301857
0.75	Intermediate Similarity	NPC114096
0.75	Intermediate Similarity	NPC474608
0.75	Intermediate Similarity	NPC153617
0.7483	Intermediate Similarity	NPC183270
0.7483	Intermediate Similarity	NPC472394
0.7483	Intermediate Similarity	NPC475569
0.7483	Intermediate Similarity	NPC477904
0.7483	Intermediate Similarity	NPC251294
0.7448	Intermediate Similarity	NPC472577
0.7448	Intermediate Similarity	NPC195647
0.7448	Intermediate Similarity	NPC291638
0.7448	Intermediate Similarity	NPC66761
0.7448	Intermediate Similarity	NPC17877
0.7445	Intermediate Similarity	NPC50872
0.7432	Intermediate Similarity	NPC77493
0.7432	Intermediate Similarity	NPC187566
0.7417	Intermediate Similarity	NPC477737
0.7415	Intermediate Similarity	NPC475652
0.7415	Intermediate Similarity	NPC214550
0.7415	Intermediate Similarity	NPC210591
0.7415	Intermediate Similarity	NPC475195
0.7388	Intermediate Similarity	NPC149691
0.7385	Intermediate Similarity	NPC265407
0.7385	Intermediate Similarity	NPC83628
0.7379	Intermediate Similarity	NPC472250
0.7379	Intermediate Similarity	NPC38420
0.7379	Intermediate Similarity	NPC136608
0.7365	Intermediate Similarity	NPC184747
0.7365	Intermediate Similarity	NPC200592
0.7365	Intermediate Similarity	NPC211137
0.7365	Intermediate Similarity	NPC48017
0.7365	Intermediate Similarity	NPC476094
0.7365	Intermediate Similarity	NPC473613
0.7365	Intermediate Similarity	NPC473060
0.7365	Intermediate Similarity	NPC473081
0.7365	Intermediate Similarity	NPC473758
0.7365	Intermediate Similarity	NPC147880
0.7365	Intermediate Similarity	NPC473085
0.7365	Intermediate Similarity	NPC473109
0.7365	Intermediate Similarity	NPC4341
0.7365	Intermediate Similarity	NPC473112
0.7365	Intermediate Similarity	NPC43241
0.7361	Intermediate Similarity	NPC238370
0.7361	Intermediate Similarity	NPC233860
0.7361	Intermediate Similarity	NPC471880
0.7357	Intermediate Similarity	NPC57607
0.7348	Intermediate Similarity	NPC270699
0.7348	Intermediate Similarity	NPC82899
0.7347	Intermediate Similarity	NPC183122
0.7347	Intermediate Similarity	NPC283375
0.7343	Intermediate Similarity	NPC27712
0.7338	Intermediate Similarity	NPC141970
0.7338	Intermediate Similarity	NPC140561
0.7333	Intermediate Similarity	NPC153214
0.7329	Intermediate Similarity	NPC270364
0.7329	Intermediate Similarity	NPC475262
0.7329	Intermediate Similarity	NPC290833
0.7329	Intermediate Similarity	NPC265459
0.7329	Intermediate Similarity	NPC79699
0.7329	Intermediate Similarity	NPC472206
0.7329	Intermediate Similarity	NPC200154
0.7328	Intermediate Similarity	NPC251854
0.7328	Intermediate Similarity	NPC93084
0.7319	Intermediate Similarity	NPC229600
0.7315	Intermediate Similarity	NPC16912
0.731	Intermediate Similarity	NPC472248
0.7305	Intermediate Similarity	NPC470818
0.7305	Intermediate Similarity	NPC476599
0.7302	Intermediate Similarity	NPC325497
0.7297	Intermediate Similarity	NPC276652
0.7293	Intermediate Similarity	NPC128368
0.7286	Intermediate Similarity	NPC473881
0.7286	Intermediate Similarity	NPC472704
0.7285	Intermediate Similarity	NPC470231
0.7285	Intermediate Similarity	NPC478250
0.7279	Intermediate Similarity	NPC285221
0.7279	Intermediate Similarity	NPC472545
0.7279	Intermediate Similarity	NPC469574
0.7279	Intermediate Similarity	NPC194769
0.7279	Intermediate Similarity	NPC472551
0.7273	Intermediate Similarity	NPC469448
0.7273	Intermediate Similarity	NPC474157
0.7273	Intermediate Similarity	NPC305912
0.7273	Intermediate Similarity	NPC210089
0.7273	Intermediate Similarity	NPC1082
0.726	Intermediate Similarity	NPC28836
0.7255	Intermediate Similarity	NPC97188
0.7252	Intermediate Similarity	NPC17417
0.7252	Intermediate Similarity	NPC474364
0.7252	Intermediate Similarity	NPC10251
0.7248	Intermediate Similarity	NPC275592
0.7248	Intermediate Similarity	NPC90614
0.7248	Intermediate Similarity	NPC97667
0.7248	Intermediate Similarity	NPC100913
0.7248	Intermediate Similarity	NPC472547
0.7248	Intermediate Similarity	NPC171207
0.7248	Intermediate Similarity	NPC475660
0.7246	Intermediate Similarity	NPC473243
0.7244	Intermediate Similarity	NPC37642
0.7244	Intermediate Similarity	NPC471135
0.7241	Intermediate Similarity	NPC239358
0.7241	Intermediate Similarity	NPC233692
0.7241	Intermediate Similarity	NPC475493
0.7234	Intermediate Similarity	NPC246166
0.7234	Intermediate Similarity	NPC244454
0.7234	Intermediate Similarity	NPC125053
0.723	Intermediate Similarity	NPC86772
0.723	Intermediate Similarity	NPC39549
0.723	Intermediate Similarity	NPC475373
0.7226	Intermediate Similarity	NPC469415
0.7222	Intermediate Similarity	NPC11025
0.7222	Intermediate Similarity	NPC35448
0.7222	Intermediate Similarity	NPC78701
0.7219	Intermediate Similarity	NPC177340
0.7219	Intermediate Similarity	NPC147217
0.7219	Intermediate Similarity	NPC246480
0.7219	Intermediate Similarity	NPC270498
0.7219	Intermediate Similarity	NPC475429
0.7219	Intermediate Similarity	NPC191082
0.7219	Intermediate Similarity	NPC473673
0.7219	Intermediate Similarity	NPC139067
0.7215	Intermediate Similarity	NPC477735
0.7214	Intermediate Similarity	NPC472703
0.7214	Intermediate Similarity	NPC223351
0.72	Intermediate Similarity	NPC291599
0.72	Intermediate Similarity	NPC242355
0.72	Intermediate Similarity	NPC472576
0.72	Intermediate Similarity	NPC266374
0.72	Intermediate Similarity	NPC224491
0.72	Intermediate Similarity	NPC97947
0.72	Intermediate Similarity	NPC27377
0.72	Intermediate Similarity	NPC473654
0.72	Intermediate Similarity	NPC118080
0.72	Intermediate Similarity	NPC41481
0.72	Intermediate Similarity	NPC87448
0.7197	Intermediate Similarity	NPC196246
0.7197	Intermediate Similarity	NPC214067
0.7197	Intermediate Similarity	NPC51198
0.719	Intermediate Similarity	NPC170668
0.719	Intermediate Similarity	NPC474935
0.7185	Intermediate Similarity	NPC474095
0.7183	Intermediate Similarity	NPC121272
0.7181	Intermediate Similarity	NPC472371
0.7181	Intermediate Similarity	NPC473301
0.7181	Intermediate Similarity	NPC272523
0.7181	Intermediate Similarity	NPC325805
0.7181	Intermediate Similarity	NPC472395
0.7179	Intermediate Similarity	NPC162569
0.7179	Intermediate Similarity	NPC35160
0.7176	Intermediate Similarity	NPC56493
0.7172	Intermediate Similarity	NPC60825
0.7172	Intermediate Similarity	NPC291419
0.7171	Intermediate Similarity	NPC472573
0.7171	Intermediate Similarity	NPC472569
0.7171	Intermediate Similarity	NPC95810
0.7171	Intermediate Similarity	NPC125106
0.7171	Intermediate Similarity	NPC476974
0.7171	Intermediate Similarity	NPC163719
0.7171	Intermediate Similarity	NPC472570
0.7171	Intermediate Similarity	NPC188865
0.7171	Intermediate Similarity	NPC25768
0.7171	Intermediate Similarity	NPC95265
0.7171	Intermediate Similarity	NPC57628
0.7171	Intermediate Similarity	NPC475122
0.7171	Intermediate Similarity	NPC51314
0.7171	Intermediate Similarity	NPC67777
0.7171	Intermediate Similarity	NPC11685
0.7171	Intermediate Similarity	NPC70716
0.717	Intermediate Similarity	NPC477736
0.7165	Intermediate Similarity	NPC146351
0.7164	Intermediate Similarity	NPC161611
0.7163	Intermediate Similarity	NPC138798
0.7162	Intermediate Similarity	NPC472372
0.7162	Intermediate Similarity	NPC472374
0.7162	Intermediate Similarity	NPC202729

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 NPC473359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	802
0.2-0.3	1417
0.3-0.4	3105
0.4-0.5	2546
0.5-0.6	860
0.6-0.7	160
0.7-0.8	5
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
0.7538	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2182	Approved
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1238	Approved
0.7014	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD164	Approved
0.6838	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2067	Discontinued
0.6795	Remote Similarity	NPD7236	Approved
0.6783	Remote Similarity	NPD6287	Discontinued
0.6746	Remote Similarity	NPD7799	Discontinued
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3764	Approved
0.6711	Remote Similarity	NPD2567	Approved
0.6711	Remote Similarity	NPD2569	Approved
0.6691	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5125	Phase 3
0.6643	Remote Similarity	NPD5126	Approved
0.6625	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4445	Approved
0.662	Remote Similarity	NPD9545	Approved
0.6604	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7239	Suspended
0.6577	Remote Similarity	NPD6832	Phase 2
0.6556	Remote Similarity	NPD7713	Phase 3
0.6547	Remote Similarity	NPD2497	Approved
0.6547	Remote Similarity	NPD2496	Approved
0.6545	Remote Similarity	NPD4288	Approved
0.6533	Remote Similarity	NPD6039	Approved
0.6522	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1202	Approved
0.6497	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6647	Phase 2
0.6477	Remote Similarity	NPD8407	Phase 2
0.6475	Remote Similarity	NPD969	Suspended
0.6471	Remote Similarity	NPD1933	Approved
0.6456	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3748	Approved
0.6444	Remote Similarity	NPD1237	Approved
0.6442	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7008	Discontinued
0.6419	Remote Similarity	NPD2199	Approved
0.6419	Remote Similarity	NPD5667	Approved
0.6419	Remote Similarity	NPD2198	Approved
0.641	Remote Similarity	NPD2796	Approved
0.64	Remote Similarity	NPD8368	Discontinued
0.6391	Remote Similarity	NPD7798	Approved
0.6386	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7819	Suspended
0.6383	Remote Similarity	NPD1241	Discontinued
0.6352	Remote Similarity	NPD4628	Phase 3
0.6349	Remote Similarity	NPD9259	Approved
0.6349	Remote Similarity	NPD9257	Approved
0.6335	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2798	Approved
0.6324	Remote Similarity	NPD5909	Discontinued
0.6312	Remote Similarity	NPD6858	Approved
0.6312	Remote Similarity	NPD7094	Approved
0.6299	Remote Similarity	NPD4307	Phase 2
0.6288	Remote Similarity	NPD1989	Approved
0.6284	Remote Similarity	NPD6637	Approved
0.6277	Remote Similarity	NPD5048	Discontinued
0.6276	Remote Similarity	NPD7741	Discontinued
0.6275	Remote Similarity	NPD2313	Discontinued
0.6272	Remote Similarity	NPD7075	Discontinued
0.6272	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2066	Phase 3
0.6266	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD7266	Discontinued
0.6266	Remote Similarity	NPD7611	Approved
0.6265	Remote Similarity	NPD7411	Suspended
0.626	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9493	Approved
0.625	Remote Similarity	NPD1930	Approved
0.625	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1929	Approved
0.625	Remote Similarity	NPD3750	Approved
0.6242	Remote Similarity	NPD7033	Discontinued
0.6235	Remote Similarity	NPD6799	Approved
0.6232	Remote Similarity	NPD6685	Approved
0.6226	Remote Similarity	NPD1549	Phase 2
0.6225	Remote Similarity	NPD1019	Discontinued
0.6224	Remote Similarity	NPD5951	Approved
0.6224	Remote Similarity	NPD2629	Approved
0.622	Remote Similarity	NPD920	Approved
0.622	Remote Similarity	NPD5403	Approved
0.6215	Remote Similarity	NPD7685	Pre-registration
0.6215	Remote Similarity	NPD6559	Discontinued
0.6213	Remote Similarity	NPD7058	Phase 2
0.6213	Remote Similarity	NPD7057	Phase 3
0.6211	Remote Similarity	NPD3887	Approved
0.6196	Remote Similarity	NPD5401	Approved
0.619	Remote Similarity	NPD8455	Phase 2
0.6181	Remote Similarity	NPD4198	Discontinued
0.6178	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD3972	Approved
0.617	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6002	Phase 3
0.6164	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6004	Phase 3
0.6164	Remote Similarity	NPD6005	Phase 3
0.6164	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2346	Discontinued
0.6159	Remote Similarity	NPD3267	Approved
0.6159	Remote Similarity	NPD3266	Approved
0.6154	Remote Similarity	NPD9256	Approved
0.6154	Remote Similarity	NPD6010	Discontinued
0.6154	Remote Similarity	NPD230	Phase 1
0.6154	Remote Similarity	NPD4287	Approved
0.6154	Remote Similarity	NPD9258	Approved
0.6154	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2575	Approved
0.6145	Remote Similarity	NPD8312	Approved
0.6145	Remote Similarity	NPD7458	Discontinued
0.6145	Remote Similarity	NPD8313	Approved
0.6144	Remote Similarity	NPD2613	Approved
0.6139	Remote Similarity	NPD4308	Phase 3
0.6136	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8434	Phase 2
0.6133	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5157	Phase 1
0.6133	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5159	Phase 2
0.6131	Remote Similarity	NPD6801	Discontinued
0.6129	Remote Similarity	NPD7961	Discontinued
0.6125	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6085	Phase 2
0.6118	Remote Similarity	NPD7768	Phase 2
0.6115	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6599	Discontinued
0.6108	Remote Similarity	NPD4380	Phase 2
0.6105	Remote Similarity	NPD5494	Approved
0.6101	Remote Similarity	NPD2935	Discontinued
0.6098	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD2347	Approved
0.6093	Remote Similarity	NPD1876	Approved
0.609	Remote Similarity	NPD3373	Approved
0.6087	Remote Similarity	NPD1243	Approved
0.6087	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD17	Approved
0.6081	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.608	Remote Similarity	NPD3818	Discontinued
0.6076	Remote Similarity	NPD7097	Phase 1
0.6074	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD9495	Approved
0.6067	Remote Similarity	NPD9717	Approved
0.6066	Remote Similarity	NPD8361	Approved
0.6066	Remote Similarity	NPD8435	Approved
0.6066	Remote Similarity	NPD8360	Approved
0.6065	Remote Similarity	NPD3268	Approved
0.6059	Remote Similarity	NPD5402	Approved
0.6059	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2201	Approved
0.6053	Remote Similarity	NPD2797	Approved
0.6053	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD8166	Discontinued
0.6047	Remote Similarity	NPD1282	Approved
0.6044	Remote Similarity	NPD8150	Discontinued
0.6038	Remote Similarity	NPD2799	Discontinued
0.6038	Remote Similarity	NPD1510	Phase 2
0.6031	Remote Similarity	NPD3672	Approved
0.6031	Remote Similarity	NPD3673	Approved
0.6026	Remote Similarity	NPD3090	Approved
0.6026	Remote Similarity	NPD4745	Approved
0.6026	Remote Similarity	NPD3088	Approved
0.6026	Remote Similarity	NPD3614	Approved
0.6026	Remote Similarity	NPD3087	Approved
0.6026	Remote Similarity	NPD2566	Approved
0.6026	Remote Similarity	NPD2573	Approved
0.6026	Remote Similarity	NPD3615	Approved
0.6026	Remote Similarity	NPD6233	Phase 2
0.6026	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3089	Approved
0.6026	Remote Similarity	NPD3616	Approved
0.6026	Remote Similarity	NPD2574	Discontinued
0.6026	Remote Similarity	NPD4746	Phase 3
0.6026	Remote Similarity	NPD2570	Approved
0.6026	Remote Similarity	NPD2571	Approved
0.6023	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD5765	Approved
0.6014	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2788	Approved
0.6012	Remote Similarity	NPD6190	Approved
0.6011	Remote Similarity	NPD7074	Phase 3
0.6	Remote Similarity	NPD2533	Approved
0.6	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2534	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data