NPASS Compound

Structure

CID105213 OpenBabel06191715452D 26 27 0 0 0 0 0 0 0 0999 V2000 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 5.1962 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 0.8660 -1.5000 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 1.7321 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 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 11 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 14 21 2 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	374.882
LogP:	4.234
LogD:	3.37
LogS:	-3.504
# Rotatable Bonds:	6
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	2.643
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	1.7487634977442212e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	99.37321472167969%
Volume Distribution (VD):	0.581
Pgp-substrate:	1.8145792484283447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.897
CYP2D6-substrate:	0.799
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	13.944
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.426
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.472
Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.949
Carcinogencity:	0.652
Eye Corrosion:	0.003
Eye Irritation:	0.919
Respiratory Toxicity:	0.814

Download Data

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

Natural Product: NPC105213

Natural Product ID:	NPC105213
*Common Name:**	Licoagrochalcone C
IUPAC Name:	(E)-1-(3,4-dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
Synonyms:
Standard InCHIKey:	RDYZHQQZLIBKBP-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-13(2)4-8-16-18(23)10-6-14(21(16)26-3)5-9-17(22)15-7-11-19(24)20(25)12-15/h4-7,9-12,23-25H,8H2,1-3H3/b9-5+
SMILES:	CC(=CCc1c(ccc(/C=C/C(=O)c2ccc(c(c2)O)O)c1OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437370
PubChem CID:	5318990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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
Others	10

Activity Type	# Activity
Cell Line	6
CELL-LINE	1
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	59500.0	nM	PMID[507353]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	21.0	%	PMID[507354]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	21.0	%	PMID[507354]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	5.0	%	PMID[507354]
NPT2615	Cell Line	HEK-293T	Homo sapiens	GI	=	28.0	%	PMID[507354]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9350.0	nM	PMID[507354]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	85.0	%	PMID[507354]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	75.0	%	PMID[507354]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	2.07	n.a.	PMID[507355]
NPT21742	CELL-LINE	L02	Homo sapiens	GI	=	9.0	%	PMID[507354]
NPT2	Others	Unspecified		Inhibition	=	80.0	%	PMID[507354]
NPT2	Others	Unspecified		IC50	=	2440.0	nM	PMID[507354]
NPT2	Others	Unspecified		Inhibition	=	11.0	%	PMID[507354]

☑ 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 NPC105213 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	381
0.1-0.2	1577
0.2-0.3	4051
0.3-0.4	10665
0.4-0.5	7425
0.5-0.6	3251
0.6-0.7	5101
0.7-0.8	6668
0.8-0.85	2449
0.85-0.9	1018
0.9-0.95	104
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC157133
0.9712	High Similarity	NPC207732
0.958	High Similarity	NPC472279
0.9568	High Similarity	NPC312256
0.951	High Similarity	NPC38545
0.951	High Similarity	NPC171916
0.95	High Similarity	NPC471417
0.95	High Similarity	NPC287722
0.9496	High Similarity	NPC110419
0.9441	High Similarity	NPC203077
0.9441	High Similarity	NPC166036
0.9441	High Similarity	NPC238279
0.9437	High Similarity	NPC165389
0.9429	High Similarity	NPC301178
0.9429	High Similarity	NPC284556
0.9379	High Similarity	NPC256406
0.932	High Similarity	NPC57674
0.932	High Similarity	NPC230149
0.932	High Similarity	NPC168247
0.932	High Similarity	NPC117992
0.932	High Similarity	NPC152951
0.9315	High Similarity	NPC324233
0.9315	High Similarity	NPC323626
0.9296	High Similarity	NPC142165
0.927	High Similarity	NPC27643
0.9257	High Similarity	NPC472455
0.9252	High Similarity	NPC49402
0.9252	High Similarity	NPC70433
0.9252	High Similarity	NPC273462
0.9252	High Similarity	NPC33051
0.9252	High Similarity	NPC227337
0.9247	High Similarity	NPC78505
0.9247	High Similarity	NPC154345
0.9241	High Similarity	NPC264289
0.9241	High Similarity	NPC200060
0.9241	High Similarity	NPC40290
0.9241	High Similarity	NPC102003
0.9241	High Similarity	NPC139293
0.9241	High Similarity	NPC92722
0.9241	High Similarity	NPC264550
0.9241	High Similarity	NPC333691
0.9241	High Similarity	NPC69430
0.9241	High Similarity	NPC142876
0.9241	High Similarity	NPC195763
0.9225	High Similarity	NPC254659
0.9225	High Similarity	NPC50954
0.9225	High Similarity	NPC119663
0.9225	High Similarity	NPC16353
0.9209	High Similarity	NPC24394
0.9189	High Similarity	NPC472280
0.9189	High Similarity	NPC134287
0.9189	High Similarity	NPC113906
0.9189	High Similarity	NPC130589
0.9189	High Similarity	NPC234255
0.9189	High Similarity	NPC256925
0.9189	High Similarity	NPC39184
0.9178	High Similarity	NPC85131
0.9178	High Similarity	NPC10467
0.9178	High Similarity	NPC3825
0.9178	High Similarity	NPC88804
0.9172	High Similarity	NPC194653
0.9172	High Similarity	NPC15329
0.9172	High Similarity	NPC139364
0.9172	High Similarity	NPC80710
0.9172	High Similarity	NPC203747
0.9172	High Similarity	NPC254702
0.9172	High Similarity	NPC131451
0.9172	High Similarity	NPC474903
0.9172	High Similarity	NPC287395
0.9172	High Similarity	NPC183655
0.9161	High Similarity	NPC38065
0.9161	High Similarity	NPC242893
0.9149	High Similarity	NPC477956
0.9143	High Similarity	NPC23870
0.9143	High Similarity	NPC472419
0.9133	High Similarity	NPC204879
0.9128	High Similarity	NPC282307
0.9128	High Similarity	NPC170026
0.9124	High Similarity	NPC66384
0.9124	High Similarity	NPC189106
0.9124	High Similarity	NPC128348
0.9124	High Similarity	NPC112192
0.9124	High Similarity	NPC309717
0.9124	High Similarity	NPC164236
0.9122	High Similarity	NPC124714
0.9122	High Similarity	NPC93552
0.9122	High Similarity	NPC189130
0.9122	High Similarity	NPC192083
0.9122	High Similarity	NPC213896
0.9122	High Similarity	NPC107109
0.9116	High Similarity	NPC272566
0.9103	High Similarity	NPC188074
0.9103	High Similarity	NPC125449
0.9103	High Similarity	NPC93034
0.9103	High Similarity	NPC119660
0.9078	High Similarity	NPC21350
0.9073	High Similarity	NPC476980
0.9071	High Similarity	NPC98115
0.9071	High Similarity	NPC41461
0.9071	High Similarity	NPC25287
0.9071	High Similarity	NPC150399
0.9071	High Similarity	NPC477243
0.9071	High Similarity	NPC477244
0.9071	High Similarity	NPC477242
0.9071	High Similarity	NPC1486
0.9071	High Similarity	NPC66349
0.9071	High Similarity	NPC186838
0.9071	High Similarity	NPC168105
0.9071	High Similarity	NPC472364
0.9071	High Similarity	NPC274109
0.9071	High Similarity	NPC473391
0.9071	High Similarity	NPC12165
0.9071	High Similarity	NPC249606
0.9067	High Similarity	NPC187745
0.9067	High Similarity	NPC161960
0.9067	High Similarity	NPC304008
0.9067	High Similarity	NPC180011
0.9067	High Similarity	NPC199463
0.9067	High Similarity	NPC78103
0.9067	High Similarity	NPC291508
0.9067	High Similarity	NPC36852
0.9067	High Similarity	NPC37543
0.9067	High Similarity	NPC262286
0.9067	High Similarity	NPC218313
0.9067	High Similarity	NPC78225
0.9067	High Similarity	NPC178976
0.9067	High Similarity	NPC474681
0.9067	High Similarity	NPC219867
0.9065	High Similarity	NPC208760
0.906	High Similarity	NPC133392
0.906	High Similarity	NPC321779
0.9054	High Similarity	NPC291802
0.9054	High Similarity	NPC157784
0.9054	High Similarity	NPC100263
0.9054	High Similarity	NPC37684
0.9054	High Similarity	NPC63187
0.9054	High Similarity	NPC106976
0.9054	High Similarity	NPC209487
0.9054	High Similarity	NPC237994
0.9054	High Similarity	NPC131266
0.9054	High Similarity	NPC471982
0.9054	High Similarity	NPC257648
0.9054	High Similarity	NPC245382
0.9054	High Similarity	NPC39732
0.9054	High Similarity	NPC35763
0.9054	High Similarity	NPC121522
0.9054	High Similarity	NPC181209
0.9054	High Similarity	NPC216769
0.9054	High Similarity	NPC100971
0.9054	High Similarity	NPC60972
0.9054	High Similarity	NPC477231
0.9054	High Similarity	NPC269451
0.9048	High Similarity	NPC29231
0.9041	High Similarity	NPC107636
0.9041	High Similarity	NPC218490
0.9034	High Similarity	NPC12377
0.9021	High Similarity	NPC26051
0.9021	High Similarity	NPC268204
0.9021	High Similarity	NPC55832
0.9021	High Similarity	NPC49108
0.9021	High Similarity	NPC52789
0.9014	High Similarity	NPC19158
0.9014	High Similarity	NPC50823
0.9013	High Similarity	NPC258331
0.9013	High Similarity	NPC472275
0.9007	High Similarity	NPC172770
0.9007	High Similarity	NPC245891
0.9007	High Similarity	NPC185258
0.9007	High Similarity	NPC74178
0.9007	High Similarity	NPC184755
0.9007	High Similarity	NPC153979
0.9007	High Similarity	NPC317119
0.9007	High Similarity	NPC104876
0.9	High Similarity	NPC195796
0.9	High Similarity	NPC131039
0.9	High Similarity	NPC35038
0.9	High Similarity	NPC156092
0.9	High Similarity	NPC77807
0.9	High Similarity	NPC138243
0.9	High Similarity	NPC470600
0.9	High Similarity	NPC191146
0.9	High Similarity	NPC6633
0.9	High Similarity	NPC14561
0.9	High Similarity	NPC13575
0.9	High Similarity	NPC65005
0.9	High Similarity	NPC5379
0.9	High Similarity	NPC264112
0.9	High Similarity	NPC194764
0.9	High Similarity	NPC291878
0.9	High Similarity	NPC278778
0.9	High Similarity	NPC68093
0.9	High Similarity	NPC115853
0.9	High Similarity	NPC5322
0.9	High Similarity	NPC133970
0.8993	High Similarity	NPC74924
0.8993	High Similarity	NPC170492
0.8993	High Similarity	NPC298692
0.8993	High Similarity	NPC250557
0.8986	High Similarity	NPC31363
0.8986	High Similarity	NPC45291

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 NPC105213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	962
0.2-0.3	1561
0.3-0.4	2658
0.4-0.5	1858
0.5-0.6	1063
0.6-0.7	502
0.7-0.8	163
0.8-0.85	25
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9122	High Similarity	NPD2393	Clinical (unspecified phase)
0.8874	High Similarity	NPD3882	Suspended
0.8867	High Similarity	NPD2801	Approved
0.88	High Similarity	NPD1934	Approved
0.8767	High Similarity	NPD1511	Approved
0.8714	High Similarity	NPD943	Approved
0.8714	High Similarity	NPD1240	Approved
0.8649	High Similarity	NPD1512	Approved
0.8627	High Similarity	NPD4868	Clinical (unspecified phase)
0.8601	High Similarity	NPD1510	Phase 2
0.8592	High Similarity	NPD1607	Approved
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.8543	High Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD6232	Discontinued
0.8428	Intermediate Similarity	NPD7473	Discontinued
0.8392	Intermediate Similarity	NPD230	Phase 1
0.8375	Intermediate Similarity	NPD3818	Discontinued
0.8365	Intermediate Similarity	NPD6166	Phase 2
0.8365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1549	Phase 2
0.8288	Intermediate Similarity	NPD2935	Discontinued
0.8258	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7819	Suspended
0.8231	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD5494	Approved
0.8224	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8163	Intermediate Similarity	NPD2796	Approved
0.816	Intermediate Similarity	NPD7074	Phase 3
0.8146	Intermediate Similarity	NPD6799	Approved
0.8141	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD7411	Suspended
0.8121	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD3027	Phase 3
0.811	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD9494	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8098	Intermediate Similarity	NPD5844	Phase 1
0.8089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6801	Discontinued
0.8071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3750	Approved
0.8054	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7973	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6651	Approved
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7949	Intermediate Similarity	NPD6599	Discontinued
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2800	Approved
0.7872	Intermediate Similarity	NPD9269	Phase 2
0.7853	Intermediate Similarity	NPD3926	Phase 2
0.7847	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6959	Discontinued
0.784	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD919	Approved
0.7823	Intermediate Similarity	NPD1613	Approved
0.7823	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7768	Phase 2
0.7805	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7792	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.7716	Intermediate Similarity	NPD6234	Discontinued
0.7682	Intermediate Similarity	NPD1551	Phase 2
0.7682	Intermediate Similarity	NPD6100	Approved
0.7682	Intermediate Similarity	NPD6099	Approved
0.7679	Intermediate Similarity	NPD5953	Discontinued
0.7662	Intermediate Similarity	NPD6190	Approved
0.7654	Intermediate Similarity	NPD3749	Approved
0.7647	Intermediate Similarity	NPD1243	Approved
0.7643	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD5402	Approved
0.7632	Intermediate Similarity	NPD2344	Approved
0.7625	Intermediate Similarity	NPD37	Approved
0.7622	Intermediate Similarity	NPD3972	Approved
0.7597	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9268	Approved
0.7571	Intermediate Similarity	NPD5536	Phase 2
0.7568	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4357	Discontinued
0.7564	Intermediate Similarity	NPD7390	Discontinued
0.756	Intermediate Similarity	NPD7286	Phase 2
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD3226	Approved
0.7533	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD5403	Approved
0.753	Intermediate Similarity	NPD5242	Approved
0.7529	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.745	Intermediate Similarity	NPD2313	Discontinued
0.7444	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD4908	Phase 1
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2798	Approved
0.7405	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5401	Approved
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7396	Intermediate Similarity	NPD7228	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7384	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD1608	Approved
0.7372	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5710	Approved
0.7347	Intermediate Similarity	NPD1470	Approved
0.7347	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD6385	Approved
0.7346	Intermediate Similarity	NPD6386	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1651	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD2983	Phase 2
0.7329	Intermediate Similarity	NPD2982	Phase 2
0.7326	Intermediate Similarity	NPD7685	Pre-registration
0.7317	Intermediate Similarity	NPD5353	Approved
0.731	Intermediate Similarity	NPD422	Phase 1
0.731	Intermediate Similarity	NPD1610	Phase 2
0.7308	Intermediate Similarity	NPD2654	Approved
0.7279	Intermediate Similarity	NPD1876	Approved
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD1653	Approved
0.7266	Intermediate Similarity	NPD228	Approved
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7261	Intermediate Similarity	NPD8166	Discontinued
0.726	Intermediate Similarity	NPD2981	Phase 2
0.7239	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.723	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD5405	Approved
0.7226	Intermediate Similarity	NPD5404	Approved
0.7226	Intermediate Similarity	NPD5406	Approved
0.7226	Intermediate Similarity	NPD5408	Approved
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6832	Phase 2
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.7192	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD1933	Approved
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.7163	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD9493	Approved
0.7122	Intermediate Similarity	NPD3021	Approved
0.7122	Intermediate Similarity	NPD3022	Approved
0.7117	Intermediate Similarity	NPD3455	Phase 2
0.7117	Intermediate Similarity	NPD824	Approved
0.7114	Intermediate Similarity	NPD1164	Approved
0.7108	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD2354	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7095	Intermediate Similarity	NPD4749	Approved
0.7088	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7075	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1281	Approved
0.707	Intermediate Similarity	NPD7266	Discontinued
0.7067	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6782	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