NPASS Compound

Structure

NPC211120 OpenBabel07101718192D 24 25 0 0 0 0 0 0 0 0999 V2000 -6.0622 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -3.4641 1.0000 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 -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 -1.7321 0.0000 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 0.8660 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.0000 1.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	342.927
LogP:	3.149
LogD:	3.271
LogS:	-5.169
# Rotatable Bonds:	7
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	1.994
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.778
MDCK Permeability:	3.2783693313831463e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.857
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.233

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	84.19749450683594%
Volume Distribution (VD):	0.574
Pgp-substrate:	8.980493545532227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.61

ADMET: Excretion

Clearance (CL):	10.395
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.354
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.415
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.865
Carcinogencity:	0.443
Eye Corrosion:	0.009
Eye Irritation:	0.971
Respiratory Toxicity:	0.831

Download Data

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

Natural Product: NPC211120

Natural Product ID:	NPC211120
*Common Name:**	4,2',4',6'-Tetramethoxychalcone
IUPAC Name:	(E)-3-(4-methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	JQNMAEHFTQBROH-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-21-14-8-5-13(6-9-14)7-10-16(20)19-17(23-3)11-15(22-2)12-18(19)24-4/h5-12H,1-4H3/b10-7+
SMILES:	COc1ccc(cc1)/C=C/C(=O)c1c(cc(cc1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL32339
PubChem CID:	5378566
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids

*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
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820110]
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1
IC50	5
Others	11

Activity Type	# Activity
Cell Line	12
NON-MOLECULAR	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15200.0	nM	PMID[517991]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	100.0	%	PMID[517991]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	19600.0	nM	PMID[517994]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	46600.0	nM	PMID[517994]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	13500.0	nM	PMID[517994]
NPT1229	Cell Line	Huh-7	Homo sapiens	Survival	=	39.0	%	PMID[517996]
NPT492	Cell Line	Caco-2	Homo sapiens	Survival	=	32.0	%	PMID[517996]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Survival	=	26.0	%	PMID[517996]
NPT393	Cell Line	HCT-116	Homo sapiens	Survival	=	19.0	%	PMID[517996]
NPT306	Cell Line	PC-3	Homo sapiens	Survival	=	33.0	%	PMID[517996]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Survival	=	14.0	%	PMID[517996]
NPT941	Cell Line	HaCaT	Homo sapiens	Survival	=	21.0	%	PMID[517996]
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	4600.0	nM	PMID[517990]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	6.28	n.a.	PMID[517993]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	5.2	10'-7mol/cm2	PMID[517993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Cmin	=	10.0	umol/L	PMID[517995]
NPT2	Others	Unspecified		Survival	=	62.0	%	PMID[517996]

☑ 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 NPC211120 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	412
0.1-0.2	1839
0.2-0.3	5185
0.3-0.4	11952
0.4-0.5	5300
0.5-0.6	4574
0.6-0.7	6392
0.7-0.8	5014
0.8-0.85	1310
0.85-0.9	589
0.9-0.95	104
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC65041
0.9606	High Similarity	NPC188646
0.9606	High Similarity	NPC242294
0.9606	High Similarity	NPC139813
0.9606	High Similarity	NPC56031
0.9606	High Similarity	NPC192304
0.9606	High Similarity	NPC312318
0.9606	High Similarity	NPC263670
0.9606	High Similarity	NPC472365
0.9606	High Similarity	NPC337373
0.9606	High Similarity	NPC175098
0.9606	High Similarity	NPC223354
0.9597	High Similarity	NPC475017
0.9531	High Similarity	NPC286336
0.9531	High Similarity	NPC125269
0.9528	High Similarity	NPC87231
0.9528	High Similarity	NPC101294
0.9528	High Similarity	NPC473655
0.9528	High Similarity	NPC205468
0.9528	High Similarity	NPC129132
0.9528	High Similarity	NPC182428
0.9528	High Similarity	NPC212631
0.9528	High Similarity	NPC257756
0.9453	High Similarity	NPC204960
0.9453	High Similarity	NPC294593
0.9453	High Similarity	NPC159623
0.9453	High Similarity	NPC144051
0.9453	High Similarity	NPC28753
0.9453	High Similarity	NPC82225
0.9453	High Similarity	NPC18877
0.9453	High Similarity	NPC20560
0.9449	High Similarity	NPC284424
0.9449	High Similarity	NPC262359
0.9449	High Similarity	NPC278556
0.9449	High Similarity	NPC308037
0.9449	High Similarity	NPC64359
0.9385	High Similarity	NPC249606
0.9385	High Similarity	NPC98115
0.9385	High Similarity	NPC186838
0.9385	High Similarity	NPC476333
0.9385	High Similarity	NPC150399
0.9385	High Similarity	NPC12165
0.9385	High Similarity	NPC477242
0.9385	High Similarity	NPC41461
0.9385	High Similarity	NPC25287
0.9385	High Similarity	NPC477243
0.9385	High Similarity	NPC477244
0.9385	High Similarity	NPC473391
0.9385	High Similarity	NPC168105
0.9385	High Similarity	NPC1486
0.9385	High Similarity	NPC66349
0.9385	High Similarity	NPC254741
0.9385	High Similarity	NPC472367
0.9385	High Similarity	NPC472364
0.9385	High Similarity	NPC274109
0.9313	High Similarity	NPC317119
0.9313	High Similarity	NPC472419
0.9313	High Similarity	NPC153979
0.9313	High Similarity	NPC44573
0.9313	High Similarity	NPC188879
0.9308	High Similarity	NPC156092
0.9308	High Similarity	NPC99854
0.9308	High Similarity	NPC131039
0.9308	High Similarity	NPC13575
0.9302	High Similarity	NPC292998
0.9297	High Similarity	NPC186097
0.9297	High Similarity	NPC475009
0.9297	High Similarity	NPC66384
0.9297	High Similarity	NPC128348
0.9297	High Similarity	NPC112192
0.9297	High Similarity	NPC189106
0.9297	High Similarity	NPC313618
0.9297	High Similarity	NPC164236
0.9297	High Similarity	NPC309717
0.9297	High Similarity	NPC475008
0.9291	High Similarity	NPC247779
0.9286	High Similarity	NPC473907
0.9242	High Similarity	NPC21350
0.9242	High Similarity	NPC472368
0.9242	High Similarity	NPC124269
0.9237	High Similarity	NPC240593
0.9237	High Similarity	NPC213603
0.9237	High Similarity	NPC61546
0.9237	High Similarity	NPC72452
0.9237	High Similarity	NPC161196
0.9231	High Similarity	NPC103842
0.9213	High Similarity	NPC473894
0.9206	High Similarity	NPC475496
0.9206	High Similarity	NPC49852
0.9173	High Similarity	NPC472366
0.9173	High Similarity	NPC477956
0.9173	High Similarity	NPC470211
0.9173	High Similarity	NPC11566
0.9167	High Similarity	NPC209560
0.9167	High Similarity	NPC162680
0.9167	High Similarity	NPC294409
0.9167	High Similarity	NPC181124
0.9167	High Similarity	NPC250266
0.9167	High Similarity	NPC7013
0.9167	High Similarity	NPC116632
0.9167	High Similarity	NPC259685
0.9167	High Similarity	NPC266597
0.9167	High Similarity	NPC303644
0.9154	High Similarity	NPC27643
0.9134	High Similarity	NPC80694
0.9134	High Similarity	NPC186098
0.912	High Similarity	NPC255073
0.9104	High Similarity	NPC172250
0.9104	High Similarity	NPC215311
0.9104	High Similarity	NPC171094
0.9104	High Similarity	NPC144118
0.9104	High Similarity	NPC80962
0.9104	High Similarity	NPC326109
0.9104	High Similarity	NPC219917
0.9104	High Similarity	NPC48624
0.9104	High Similarity	NPC11056
0.9104	High Similarity	NPC204985
0.9104	High Similarity	NPC213659
0.9104	High Similarity	NPC259166
0.9098	High Similarity	NPC17848
0.9098	High Similarity	NPC12175
0.9098	High Similarity	NPC99333
0.9098	High Similarity	NPC243528
0.9098	High Similarity	NPC188947
0.9098	High Similarity	NPC309154
0.9098	High Similarity	NPC276905
0.9098	High Similarity	NPC55162
0.9098	High Similarity	NPC280284
0.9098	High Similarity	NPC90665
0.9098	High Similarity	NPC471620
0.9098	High Similarity	NPC279668
0.9098	High Similarity	NPC278323
0.9098	High Similarity	NPC251681
0.9091	High Similarity	NPC29353
0.9091	High Similarity	NPC127447
0.9091	High Similarity	NPC124784
0.9091	High Similarity	NPC234133
0.9091	High Similarity	NPC13408
0.9091	High Similarity	NPC194281
0.9091	High Similarity	NPC47815
0.9091	High Similarity	NPC231772
0.9091	High Similarity	NPC473887
0.9077	High Similarity	NPC229646
0.9055	High Similarity	NPC264428
0.9055	High Similarity	NPC305518
0.9055	High Similarity	NPC128428
0.9055	High Similarity	NPC41721
0.9037	High Similarity	NPC185607
0.9037	High Similarity	NPC268204
0.9037	High Similarity	NPC470089
0.9037	High Similarity	NPC52789
0.9037	High Similarity	NPC26051
0.9037	High Similarity	NPC321980
0.9037	High Similarity	NPC103362
0.9037	High Similarity	NPC110969
0.9037	High Similarity	NPC470087
0.9037	High Similarity	NPC469404
0.9037	High Similarity	NPC55832
0.9037	High Similarity	NPC49108
0.903	High Similarity	NPC295384
0.903	High Similarity	NPC283429
0.903	High Similarity	NPC136095
0.903	High Similarity	NPC109232
0.9023	High Similarity	NPC157855
0.9023	High Similarity	NPC253616
0.9023	High Similarity	NPC103001
0.9023	High Similarity	NPC275055
0.9023	High Similarity	NPC290291
0.9015	High Similarity	NPC39426
0.9015	High Similarity	NPC46869
0.9015	High Similarity	NPC234560
0.8992	High Similarity	NPC185497
0.8971	High Similarity	NPC11561
0.8971	High Similarity	NPC119663
0.8971	High Similarity	NPC226636
0.8971	High Similarity	NPC147145
0.8971	High Similarity	NPC471417
0.8963	High Similarity	NPC110228
0.8963	High Similarity	NPC284550
0.8963	High Similarity	NPC270883
0.8963	High Similarity	NPC281207
0.8963	High Similarity	NPC150522
0.8963	High Similarity	NPC269652
0.8963	High Similarity	NPC188243
0.8963	High Similarity	NPC241100
0.8963	High Similarity	NPC261227
0.8963	High Similarity	NPC253822
0.8963	High Similarity	NPC6407
0.8963	High Similarity	NPC129853
0.8963	High Similarity	NPC159275
0.8963	High Similarity	NPC172986
0.8963	High Similarity	NPC265178
0.8963	High Similarity	NPC76445
0.8963	High Similarity	NPC472409
0.8963	High Similarity	NPC101366
0.8963	High Similarity	NPC69769
0.8963	High Similarity	NPC58229
0.8947	High Similarity	NPC87545
0.8947	High Similarity	NPC268081
0.8947	High Similarity	NPC235428

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 NPC211120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	1000
0.2-0.3	1515
0.3-0.4	2707
0.4-0.5	1864
0.5-0.6	1143
0.6-0.7	375
0.7-0.8	135
0.8-0.85	27
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9297	High Similarity	NPD1240	Approved
0.9237	High Similarity	NPD2796	Approved
0.9154	High Similarity	NPD1607	Approved
0.9015	High Similarity	NPD1510	Phase 2
0.8905	High Similarity	NPD6799	Approved
0.8815	High Similarity	NPD1549	Phase 2
0.8741	High Similarity	NPD1550	Clinical (unspecified phase)
0.8741	High Similarity	NPD1552	Clinical (unspecified phase)
0.8705	High Similarity	NPD4378	Clinical (unspecified phase)
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8531	High Similarity	NPD6599	Discontinued
0.8478	Intermediate Similarity	NPD2654	Approved
0.8472	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6832	Phase 2
0.8403	Intermediate Similarity	NPD4380	Phase 2
0.8372	Intermediate Similarity	NPD3972	Approved
0.8356	Intermediate Similarity	NPD7819	Suspended
0.8356	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1243	Approved
0.8321	Intermediate Similarity	NPD3748	Approved
0.8288	Intermediate Similarity	NPD6801	Discontinued
0.8273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD1511	Approved
0.8231	Intermediate Similarity	NPD2801	Approved
0.8231	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD920	Approved
0.8188	Intermediate Similarity	NPD7075	Discontinued
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD6651	Approved
0.8169	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1934	Approved
0.8156	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2935	Discontinued
0.8129	Intermediate Similarity	NPD1551	Phase 2
0.8125	Intermediate Similarity	NPD1512	Approved
0.812	Intermediate Similarity	NPD2798	Approved
0.8085	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5494	Approved
0.8069	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD5403	Approved
0.8067	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5401	Approved
0.8056	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD2799	Discontinued
0.7922	Intermediate Similarity	NPD3926	Phase 2
0.791	Intermediate Similarity	NPD1203	Approved
0.7899	Intermediate Similarity	NPD943	Approved
0.7881	Intermediate Similarity	NPD7768	Phase 2
0.7874	Intermediate Similarity	NPD1241	Discontinued
0.7871	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1933	Approved
0.7842	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1876	Approved
0.7832	Intermediate Similarity	NPD2800	Approved
0.7829	Intermediate Similarity	NPD3749	Approved
0.782	Intermediate Similarity	NPD9717	Approved
0.7817	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6166	Phase 2
0.7756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6232	Discontinued
0.7721	Intermediate Similarity	NPD1019	Discontinued
0.7707	Intermediate Similarity	NPD7473	Discontinued
0.7697	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD9493	Approved
0.7687	Intermediate Similarity	NPD2534	Approved
0.7687	Intermediate Similarity	NPD2532	Approved
0.7687	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD1247	Approved
0.7677	Intermediate Similarity	NPD6959	Discontinued
0.7676	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3818	Discontinued
0.7655	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD3266	Approved
0.7647	Intermediate Similarity	NPD3267	Approved
0.7626	Intermediate Similarity	NPD1296	Phase 2
0.7626	Intermediate Similarity	NPD2313	Discontinued
0.7625	Intermediate Similarity	NPD5953	Discontinued
0.761	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7054	Approved
0.761	Intermediate Similarity	NPD7286	Phase 2
0.7603	Intermediate Similarity	NPD2309	Approved
0.7576	Intermediate Similarity	NPD9545	Approved
0.7562	Intermediate Similarity	NPD7472	Approved
0.7562	Intermediate Similarity	NPD7074	Phase 3
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4307	Phase 2
0.7518	Intermediate Similarity	NPD3142	Approved
0.7518	Intermediate Similarity	NPD3140	Approved
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD5536	Phase 2
0.7481	Intermediate Similarity	NPD422	Phase 1
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7463	Intermediate Similarity	NPD17	Approved
0.7448	Intermediate Similarity	NPD1471	Phase 3
0.7444	Intermediate Similarity	NPD1548	Phase 1
0.7431	Intermediate Similarity	NPD7033	Discontinued
0.7423	Intermediate Similarity	NPD7808	Phase 3
0.7423	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2797	Approved
0.7388	Intermediate Similarity	NPD1651	Approved
0.7383	Intermediate Similarity	NPD7390	Discontinued
0.7379	Intermediate Similarity	NPD6100	Approved
0.7379	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD3226	Approved
0.7365	Intermediate Similarity	NPD3887	Approved
0.7362	Intermediate Similarity	NPD6559	Discontinued
0.736	Intermediate Similarity	NPD9261	Approved
0.7357	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4908	Phase 1
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7338	Intermediate Similarity	NPD6280	Approved
0.7338	Intermediate Similarity	NPD6279	Approved
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2353	Approved
0.7319	Intermediate Similarity	NPD3225	Approved
0.7317	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2403	Approved
0.731	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4308	Phase 3
0.7299	Intermediate Similarity	NPD1608	Approved
0.7286	Intermediate Similarity	NPD3018	Phase 2
0.7284	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD5890	Approved
0.7273	Intermediate Similarity	NPD5889	Approved
0.7256	Intermediate Similarity	NPD6104	Discontinued
0.7255	Intermediate Similarity	NPD7458	Discontinued
0.7254	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD411	Approved
0.725	Intermediate Similarity	NPD5242	Approved
0.7244	Intermediate Similarity	NPD4288	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD447	Suspended
0.7219	Intermediate Similarity	NPD4662	Approved
0.7219	Intermediate Similarity	NPD4661	Approved
0.7208	Intermediate Similarity	NPD6585	Discontinued
0.7188	Intermediate Similarity	NPD3134	Approved
0.7188	Intermediate Similarity	NPD6808	Phase 2
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7003	Approved
0.7174	Intermediate Similarity	NPD2981	Phase 2
0.7161	Intermediate Similarity	NPD6385	Approved
0.7161	Intermediate Similarity	NPD6386	Approved
0.7153	Intermediate Similarity	NPD3847	Discontinued
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7134	Intermediate Similarity	NPD1729	Discontinued
0.7134	Intermediate Similarity	NPD5353	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2354	Approved
0.7133	Intermediate Similarity	NPD3764	Approved
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7132	Intermediate Similarity	NPD1358	Approved
0.7132	Intermediate Similarity	NPD9263	Approved
0.7122	Intermediate Similarity	NPD2983	Phase 2
0.7122	Intermediate Similarity	NPD2982	Phase 2
0.7122	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5535	Approved
0.7101	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD1281	Approved
0.7091	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5710	Approved
0.7081	Intermediate Similarity	NPD5711	Approved
0.7077	Intermediate Similarity	NPD74	Approved
0.7077	Intermediate Similarity	NPD9266	Approved
0.707	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD1894	Discontinued
0.7051	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6971	Discontinued
0.7042	Intermediate Similarity	NPD9494	Approved
0.7027	Intermediate Similarity	NPD5406	Approved
0.7027	Intermediate Similarity	NPD5405	Approved
0.7027	Intermediate Similarity	NPD5408	Approved
0.7027	Intermediate Similarity	NPD5404	Approved
0.7025	Intermediate Similarity	NPD2296	Approved
0.7023	Intermediate Similarity	NPD5451	Approved
0.7013	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4363	Phase 3
0.6994	Remote Similarity	NPD4360	Phase 2
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6355	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