NPASS Compound

Structure

NPC470089 OpenBabel07101718272D 27 28 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 7 1 0 0 0 0 4 14 2 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	383.672
LogP:	3.449
LogD:	2.754
LogS:	-3.857
# Rotatable Bonds:	8
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	3.23
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.755
MDCK Permeability:	1.1310009540466126e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	99.8907699584961%
Volume Distribution (VD):	0.334
Pgp-substrate:	0.7751771211624146%

ADMET: Metabolism

CYP1A2-inhibitor:	0.793
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.366
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	11.294
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.793
Rat Oral Acute Toxicity:	0.693
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.923
Carcinogencity:	0.854
Eye Corrosion:	0.003
Eye Irritation:	0.536
Respiratory Toxicity:	0.806

Download Data

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

Natural Product: NPC470089

Natural Product ID:	NPC470089
*Common Name:**	Sid85272349
IUPAC Name:	(E)-1-[3-(2-hydroperoxy-3-methylbut-3-enyl)-2-hydroxy-4-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	AJERVVHSERWGFL-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-13(2)20(27-25)12-17-19(26-3)11-9-16(21(17)24)18(23)10-6-14-4-7-15(22)8-5-14/h4-11,20,22,24-25H,1,12H2,2-3H3/b10-6+
SMILES:	OOC(C(=C)C)Cc1c(OC)ccc(c1O)C(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1718454
PubChem CID:	10022050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

*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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	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
IC50	3
Ki	2
Others	1
Potency	20

Activity Type	# Activity
Cell Line	1
Individual Protein	19
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[521344]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[521344]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[521344]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[521344]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[521344]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[521344]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[521344]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[521344]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[521344]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[521344]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[521344]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[521344]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[521344]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[521344]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[521344]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[521344]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	1.43	ug.mL-1	PMID[521345]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	99.37	%	PMID[521345]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[521344]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[521344]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[521344]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[521344]
NPT2	Others	Unspecified		IC50	=	7100.0	nM	PMID[521346]
NPT2	Others	Unspecified		Ki	=	16100.0	nM	PMID[521346]
NPT2	Others	Unspecified		IC50	=	1200.0	nM	PMID[521346]
NPT2	Others	Unspecified		Ki	=	1200.0	nM	PMID[521346]

☑ 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 NPC470089 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	354
0.1-0.2	1451
0.2-0.3	3641
0.3-0.4	9257
0.4-0.5	9310
0.5-0.6	3486
0.6-0.7	5687
0.7-0.8	5773
0.8-0.85	2156
0.85-0.9	1075
0.9-0.95	471
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC470087
0.9853	High Similarity	NPC321980
0.971	High Similarity	NPC245482
0.971	High Similarity	NPC301751
0.971	High Similarity	NPC476178
0.971	High Similarity	NPC51887
0.971	High Similarity	NPC117836
0.971	High Similarity	NPC475705
0.9708	High Similarity	NPC469404
0.9706	High Similarity	NPC470211
0.9638	High Similarity	NPC148545
0.9635	High Similarity	NPC326109
0.9635	High Similarity	NPC48624
0.9635	High Similarity	NPC259166
0.9635	High Similarity	NPC144118
0.9635	High Similarity	NPC219917
0.9635	High Similarity	NPC215311
0.9635	High Similarity	NPC204985
0.9635	High Similarity	NPC213659
0.9635	High Similarity	NPC80962
0.9635	High Similarity	NPC172250
0.9632	High Similarity	NPC21350
0.963	High Similarity	NPC477242
0.963	High Similarity	NPC168105
0.963	High Similarity	NPC66349
0.963	High Similarity	NPC477243
0.963	High Similarity	NPC249606
0.963	High Similarity	NPC25287
0.963	High Similarity	NPC186838
0.963	High Similarity	NPC98115
0.963	High Similarity	NPC150399
0.963	High Similarity	NPC477244
0.963	High Similarity	NPC12165
0.963	High Similarity	NPC1486
0.963	High Similarity	NPC41461
0.963	High Similarity	NPC274109
0.9571	High Similarity	NPC316769
0.9565	High Similarity	NPC55832
0.9565	High Similarity	NPC26051
0.9565	High Similarity	NPC268204
0.9565	High Similarity	NPC52789
0.9562	High Similarity	NPC283429
0.9562	High Similarity	NPC477956
0.9562	High Similarity	NPC295384
0.9559	High Similarity	NPC472419
0.9559	High Similarity	NPC317119
0.9559	High Similarity	NPC153979
0.9556	High Similarity	NPC156092
0.9556	High Similarity	NPC13575
0.9556	High Similarity	NPC131039
0.9504	High Similarity	NPC222298
0.9504	High Similarity	NPC51070
0.9493	High Similarity	NPC101366
0.9493	High Similarity	NPC11056
0.9493	High Similarity	NPC253822
0.9489	High Similarity	NPC471620
0.9481	High Similarity	NPC103842
0.9481	High Similarity	NPC286336
0.9437	High Similarity	NPC168085
0.9433	High Similarity	NPC472629
0.9429	High Similarity	NPC175504
0.9429	High Similarity	NPC149026
0.9429	High Similarity	NPC143896
0.9429	High Similarity	NPC91560
0.9429	High Similarity	NPC75049
0.9429	High Similarity	NPC39329
0.9429	High Similarity	NPC310130
0.9429	High Similarity	NPC164980
0.9429	High Similarity	NPC169591
0.9429	High Similarity	NPC257097
0.9429	High Similarity	NPC68104
0.9429	High Similarity	NPC150408
0.9429	High Similarity	NPC221432
0.942	High Similarity	NPC472366
0.9416	High Similarity	NPC181124
0.9416	High Similarity	NPC162680
0.9416	High Similarity	NPC209560
0.9416	High Similarity	NPC294409
0.9416	High Similarity	NPC7013
0.9416	High Similarity	NPC303644
0.9416	High Similarity	NPC116632
0.9412	High Similarity	NPC84699
0.9407	High Similarity	NPC312318
0.9407	High Similarity	NPC159623
0.9407	High Similarity	NPC337373
0.9407	High Similarity	NPC144051
0.9407	High Similarity	NPC82225
0.9407	High Similarity	NPC28753
0.9407	High Similarity	NPC263670
0.9407	High Similarity	NPC175098
0.9407	High Similarity	NPC56031
0.9407	High Similarity	NPC18877
0.9407	High Similarity	NPC188646
0.9407	High Similarity	NPC204960
0.9407	High Similarity	NPC20560
0.9407	High Similarity	NPC472365
0.9407	High Similarity	NPC139813
0.9407	High Similarity	NPC294593
0.9407	High Similarity	NPC192304
0.9407	High Similarity	NPC242294
0.9407	High Similarity	NPC27643
0.9371	High Similarity	NPC317492
0.9371	High Similarity	NPC89442
0.9362	High Similarity	NPC236766
0.9362	High Similarity	NPC476055
0.9362	High Similarity	NPC470890
0.9362	High Similarity	NPC224714
0.9362	High Similarity	NPC197252
0.9362	High Similarity	NPC209040
0.9362	High Similarity	NPC473013
0.9362	High Similarity	NPC87486
0.9362	High Similarity	NPC473015
0.9362	High Similarity	NPC124780
0.9362	High Similarity	NPC328623
0.9357	High Similarity	NPC182852
0.9357	High Similarity	NPC64915
0.9357	High Similarity	NPC37496
0.9357	High Similarity	NPC10937
0.9357	High Similarity	NPC40833
0.9357	High Similarity	NPC167624
0.9357	High Similarity	NPC107572
0.9357	High Similarity	NPC227579
0.9357	High Similarity	NPC76338
0.9357	High Similarity	NPC125855
0.9357	High Similarity	NPC223500
0.9357	High Similarity	NPC1089
0.9357	High Similarity	NPC265040
0.9357	High Similarity	NPC78
0.9357	High Similarity	NPC166482
0.9357	High Similarity	NPC76372
0.9357	High Similarity	NPC32739
0.9357	High Similarity	NPC324436
0.9357	High Similarity	NPC161506
0.9357	High Similarity	NPC177354
0.9357	High Similarity	NPC328164
0.9357	High Similarity	NPC66515
0.9357	High Similarity	NPC306829
0.9357	High Similarity	NPC194432
0.9357	High Similarity	NPC148757
0.9357	High Similarity	NPC296917
0.9357	High Similarity	NPC324134
0.9357	High Similarity	NPC166934
0.9357	High Similarity	NPC228504
0.9357	High Similarity	NPC220998
0.9348	High Similarity	NPC278323
0.9348	High Similarity	NPC90665
0.9348	High Similarity	NPC12175
0.9348	High Similarity	NPC251681
0.9348	High Similarity	NPC55162
0.9348	High Similarity	NPC309154
0.9348	High Similarity	NPC243528
0.9348	High Similarity	NPC279668
0.9348	High Similarity	NPC124269
0.9343	High Similarity	NPC213603
0.9343	High Similarity	NPC472364
0.9343	High Similarity	NPC24394
0.9343	High Similarity	NPC473391
0.9338	High Similarity	NPC164136
0.9333	High Similarity	NPC129132
0.9333	High Similarity	NPC87231
0.9333	High Similarity	NPC257756
0.9333	High Similarity	NPC212631
0.9333	High Similarity	NPC205468
0.9306	High Similarity	NPC61258
0.9306	High Similarity	NPC472421
0.9301	High Similarity	NPC39195
0.9296	High Similarity	NPC24136
0.9296	High Similarity	NPC290133
0.9296	High Similarity	NPC187282
0.9291	High Similarity	NPC278249
0.9291	High Similarity	NPC316816
0.9291	High Similarity	NPC214166
0.9291	High Similarity	NPC166138
0.9291	High Similarity	NPC185276
0.9291	High Similarity	NPC81697
0.9291	High Similarity	NPC107177
0.9291	High Similarity	NPC478086
0.9291	High Similarity	NPC106985
0.9291	High Similarity	NPC77794
0.9291	High Similarity	NPC125894
0.9291	High Similarity	NPC18585
0.9291	High Similarity	NPC223812
0.9291	High Similarity	NPC85162
0.9286	High Similarity	NPC166689
0.9286	High Similarity	NPC4743
0.9286	High Similarity	NPC324386
0.9286	High Similarity	NPC279650
0.9286	High Similarity	NPC17170
0.9286	High Similarity	NPC3188
0.9286	High Similarity	NPC258630
0.9286	High Similarity	NPC110038
0.9286	High Similarity	NPC213322
0.9286	High Similarity	NPC156190
0.9286	High Similarity	NPC248372
0.9286	High Similarity	NPC110969
0.9286	High Similarity	NPC96408
0.9286	High Similarity	NPC312391
0.9275	High Similarity	NPC188879
0.9275	High Similarity	NPC23870
0.927	High Similarity	NPC39426

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 NPC470089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	921
0.2-0.3	1517
0.3-0.4	2570
0.4-0.5	1971
0.5-0.6	1184
0.6-0.7	475
0.7-0.8	150
0.8-0.85	34
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.927	High Similarity	NPD1510	Phase 2
0.9259	High Similarity	NPD1240	Approved
0.9225	High Similarity	NPD4378	Clinical (unspecified phase)
0.9172	High Similarity	NPD4380	Phase 2
0.9124	High Similarity	NPD1607	Approved
0.9071	High Similarity	NPD1549	Phase 2
0.9	High Similarity	NPD1550	Clinical (unspecified phase)
0.9	High Similarity	NPD1552	Clinical (unspecified phase)
0.8986	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD2796	Approved
0.8828	High Similarity	NPD7410	Clinical (unspecified phase)
0.8808	High Similarity	NPD7075	Discontinued
0.88	High Similarity	NPD8443	Clinical (unspecified phase)
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8725	High Similarity	NPD7411	Suspended
0.8667	High Similarity	NPD1934	Approved
0.8662	High Similarity	NPD2935	Discontinued
0.8609	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD6801	Discontinued
0.8503	High Similarity	NPD6799	Approved
0.8451	Intermediate Similarity	NPD6651	Approved
0.8397	Intermediate Similarity	NPD6959	Discontinued
0.8378	Intermediate Similarity	NPD1511	Approved
0.8377	Intermediate Similarity	NPD7768	Phase 2
0.8377	Intermediate Similarity	NPD3882	Suspended
0.8366	Intermediate Similarity	NPD2801	Approved
0.8356	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2800	Approved
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.8288	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1551	Phase 2
0.8267	Intermediate Similarity	NPD1512	Approved
0.8239	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD5494	Approved
0.8212	Intermediate Similarity	NPD920	Approved
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD3750	Approved
0.8169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8108	Intermediate Similarity	NPD1243	Approved
0.8098	Intermediate Similarity	NPD5953	Discontinued
0.8086	Intermediate Similarity	NPD7286	Phase 2
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3817	Phase 2
0.8067	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD943	Approved
0.8049	Intermediate Similarity	NPD6559	Discontinued
0.8037	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD5403	Approved
0.7973	Intermediate Similarity	NPD2344	Approved
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7927	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD2313	Discontinued
0.7895	Intermediate Similarity	NPD7390	Discontinued
0.7892	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD2798	Approved
0.7879	Intermediate Similarity	NPD6797	Phase 2
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7848	Intermediate Similarity	NPD5402	Approved
0.7843	Intermediate Similarity	NPD5401	Approved
0.7838	Intermediate Similarity	NPD3748	Approved
0.7831	Intermediate Similarity	NPD7251	Discontinued
0.7817	Intermediate Similarity	NPD1203	Approved
0.7793	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD6832	Phase 2
0.7763	Intermediate Similarity	NPD2309	Approved
0.7756	Intermediate Similarity	NPD3226	Approved
0.7748	Intermediate Similarity	NPD2654	Approved
0.773	Intermediate Similarity	NPD3972	Approved
0.7716	Intermediate Similarity	NPD1247	Approved
0.7702	Intermediate Similarity	NPD919	Approved
0.7679	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7644	Intermediate Similarity	NPD4360	Phase 2
0.7644	Intermediate Similarity	NPD4363	Phase 3
0.7643	Intermediate Similarity	NPD7458	Discontinued
0.7635	Intermediate Similarity	NPD230	Phase 1
0.7628	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.7609	Intermediate Similarity	NPD9493	Approved
0.7606	Intermediate Similarity	NPD9717	Approved
0.7603	Intermediate Similarity	NPD3027	Phase 3
0.76	Intermediate Similarity	NPD7033	Discontinued
0.7569	Intermediate Similarity	NPD1164	Approved
0.756	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1610	Phase 2
0.7529	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1470	Approved
0.7434	Intermediate Similarity	NPD5406	Approved
0.7434	Intermediate Similarity	NPD5408	Approved
0.7434	Intermediate Similarity	NPD5404	Approved
0.7434	Intermediate Similarity	NPD5405	Approved
0.7432	Intermediate Similarity	NPD3268	Approved
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7413	Intermediate Similarity	NPD1201	Approved
0.7401	Intermediate Similarity	NPD4361	Phase 2
0.7401	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5124	Phase 1
0.7386	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1876	Approved
0.7368	Intermediate Similarity	NPD4308	Phase 3
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3764	Approved
0.7314	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD37	Approved
0.7283	Intermediate Similarity	NPD7584	Approved
0.7279	Intermediate Similarity	NPD1019	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1241	Discontinued
0.7248	Intermediate Similarity	NPD4625	Phase 3
0.7246	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD1608	Approved
0.7238	Intermediate Similarity	NPD6782	Approved
0.7238	Intermediate Similarity	NPD6776	Approved
0.7238	Intermediate Similarity	NPD6781	Approved
0.7238	Intermediate Similarity	NPD6777	Approved
0.7238	Intermediate Similarity	NPD6780	Approved
0.7238	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6778	Approved
0.7238	Intermediate Similarity	NPD6779	Approved
0.723	Intermediate Similarity	NPD9494	Approved
0.7226	Intermediate Similarity	NPD2424	Discontinued
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7203	Intermediate Similarity	NPD1651	Approved
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD6798	Discontinued
0.7195	Intermediate Similarity	NPD2296	Approved
0.7195	Intermediate Similarity	NPD4288	Approved
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6844	Discontinued
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD1933	Approved
0.717	Intermediate Similarity	NPD4662	Approved
0.717	Intermediate Similarity	NPD4661	Approved
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7161	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6005	Phase 3
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD1471	Phase 3
0.7161	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD5761	Phase 2
0.7134	Intermediate Similarity	NPD5760	Phase 2
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7117	Intermediate Similarity	NPD5890	Approved
0.7117	Intermediate Similarity	NPD5889	Approved
0.7114	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2861	Phase 2

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