NPASS Compound

Structure

NPC476055 OpenBabel07101718272D 26 28 0 0 0 0 0 0 0 0999 V2000 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 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 -3.4641 -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 2.5981 -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 -0.8660 -0.5000 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 -2.5981 -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 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 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -4.3301 1.5000 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 17 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 26 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	357.82
LogP:	4.247
LogD:	2.885
LogS:	-3.884
# Rotatable Bonds:	3
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	3.06
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.926
MDCK Permeability:	1.2851729479734786e-05
Pgp-inhibitor:	0.1
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	98.23916625976562%
Volume Distribution (VD):	0.546
Pgp-substrate:	2.0255961418151855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.441
CYP2C19-inhibitor:	0.514
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	2.418
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.238
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.926
Carcinogencity:	0.09
Eye Corrosion:	0.022
Eye Irritation:	0.941
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC476055

Natural Product ID:	NPC476055
*Common Name:**	Fremontin
IUPAC Name:	3-[2,4-dihydroxy-5-(2-methylbut-3-en-2-yl)phenyl]-5,7-dihydroxychromen-4-one
Synonyms:	Fremontin
Standard InCHIKey:	XWUWFNSZQDCXCD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-4-20(2,3)13-7-11(14(22)8-15(13)23)12-9-26-17-6-10(21)5-16(24)18(17)19(12)25/h4-9,21-24H,1H2,2-3H3
SMILES:	C=CC(C)(C)c1cc(c2coc3cc(cc(c3c2=O)O)O)c(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523643
PubChem CID:	5487268
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO2575	Psorothamnus fremontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26469557]
NPO2575	Psorothamnus fremontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2681536]
NPO2575	Psorothamnus fremontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11841	Psorothamnus arborescens	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	4
Others	14

Activity Type	# Activity
Cell Line	2
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	134000.0	nM	PMID[545361]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	78500.0	nM	PMID[545361]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	93.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	24.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	0.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	65.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	87.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	81.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	90.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	58.0	%	PMID[545360]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	92.0	%	PMID[545360]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	123000.0	nM	PMID[545361]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	75300.0	nM	PMID[545361]

☑ 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 NPC476055 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	403
0.1-0.2	1688
0.2-0.3	3818
0.3-0.4	9677
0.4-0.5	8936
0.5-0.6	3842
0.6-0.7	5667
0.7-0.8	4681
0.8-0.85	2016
0.85-0.9	1589
0.9-0.95	302
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC55832
0.9783	High Similarity	NPC26051
0.9783	High Similarity	NPC268204
0.9783	High Similarity	NPC52789
0.971	High Similarity	NPC204985
0.971	High Similarity	NPC259166
0.971	High Similarity	NPC48624
0.971	High Similarity	NPC11056
0.971	High Similarity	NPC213659
0.971	High Similarity	NPC215311
0.971	High Similarity	NPC144118
0.971	High Similarity	NPC219917
0.971	High Similarity	NPC253822
0.971	High Similarity	NPC101366
0.971	High Similarity	NPC172250
0.971	High Similarity	NPC80962
0.971	High Similarity	NPC326109
0.964	High Similarity	NPC469404
0.9638	High Similarity	NPC283429
0.9638	High Similarity	NPC295384
0.9565	High Similarity	NPC279668
0.9565	High Similarity	NPC55162
0.9565	High Similarity	NPC309154
0.9565	High Similarity	NPC278323
0.9565	High Similarity	NPC12175
0.9565	High Similarity	NPC90665
0.9504	High Similarity	NPC475705
0.9504	High Similarity	NPC117836
0.9504	High Similarity	NPC51887
0.9504	High Similarity	NPC11700
0.9504	High Similarity	NPC476178
0.9496	High Similarity	NPC477956
0.9493	High Similarity	NPC162680
0.9493	High Similarity	NPC209560
0.9493	High Similarity	NPC294409
0.9493	High Similarity	NPC116632
0.9493	High Similarity	NPC472419
0.9493	High Similarity	NPC181124
0.9493	High Similarity	NPC7013
0.9493	High Similarity	NPC303644
0.9493	High Similarity	NPC23870
0.9444	High Similarity	NPC471114
0.9441	High Similarity	NPC10990
0.9441	High Similarity	NPC300988
0.9437	High Similarity	NPC234629
0.9437	High Similarity	NPC311741
0.9424	High Similarity	NPC21350
0.942	High Similarity	NPC87545
0.942	High Similarity	NPC66349
0.942	High Similarity	NPC25287
0.942	High Similarity	NPC249606
0.942	High Similarity	NPC186838
0.942	High Similarity	NPC12165
0.942	High Similarity	NPC1486
0.942	High Similarity	NPC235428
0.942	High Similarity	NPC168105
0.942	High Similarity	NPC150399
0.942	High Similarity	NPC98115
0.942	High Similarity	NPC477244
0.942	High Similarity	NPC477242
0.942	High Similarity	NPC477243
0.942	High Similarity	NPC41461
0.942	High Similarity	NPC274109
0.9379	High Similarity	NPC476185
0.9379	High Similarity	NPC321896
0.9379	High Similarity	NPC188403
0.9375	High Similarity	NPC266572
0.9375	High Similarity	NPC39195
0.9362	High Similarity	NPC321980
0.9362	High Similarity	NPC470089
0.9362	High Similarity	NPC110969
0.9362	High Similarity	NPC470087
0.9357	High Similarity	NPC472366
0.9357	High Similarity	NPC470211
0.9353	High Similarity	NPC317119
0.9353	High Similarity	NPC153979
0.9348	High Similarity	NPC234560
0.9348	High Similarity	NPC131039
0.9348	High Similarity	NPC13575
0.9348	High Similarity	NPC156092
0.9348	High Similarity	NPC39426
0.931	High Similarity	NPC317492
0.9306	High Similarity	NPC24673
0.9306	High Similarity	NPC104406
0.9306	High Similarity	NPC97716
0.9306	High Similarity	NPC222298
0.9306	High Similarity	NPC201731
0.9306	High Similarity	NPC51070
0.9306	High Similarity	NPC237635
0.9306	High Similarity	NPC308200
0.9306	High Similarity	NPC79469
0.9301	High Similarity	NPC271288
0.9296	High Similarity	NPC226636
0.9296	High Similarity	NPC297600
0.9296	High Similarity	NPC11561
0.9291	High Similarity	NPC265178
0.9291	High Similarity	NPC270883
0.9291	High Similarity	NPC159275
0.9291	High Similarity	NPC241100
0.9291	High Similarity	NPC172986
0.9291	High Similarity	NPC261227
0.9286	High Similarity	NPC243528
0.9286	High Similarity	NPC251681
0.9286	High Similarity	NPC471620
0.9281	High Similarity	NPC24394
0.9281	High Similarity	NPC213603
0.9275	High Similarity	NPC286336
0.9275	High Similarity	NPC103842
0.9247	High Similarity	NPC29777
0.9247	High Similarity	NPC471115
0.9241	High Similarity	NPC145467
0.9241	High Similarity	NPC6511
0.9241	High Similarity	NPC168085
0.9236	High Similarity	NPC299011
0.9236	High Similarity	NPC477955
0.9236	High Similarity	NPC25844
0.9231	High Similarity	NPC301751
0.9231	High Similarity	NPC245482
0.9231	High Similarity	NPC68104
0.9231	High Similarity	NPC106985
0.9231	High Similarity	NPC91560
0.9231	High Similarity	NPC75049
0.9231	High Similarity	NPC221432
0.9231	High Similarity	NPC166138
0.9231	High Similarity	NPC169591
0.9231	High Similarity	NPC175504
0.9231	High Similarity	NPC18585
0.9231	High Similarity	NPC164980
0.9231	High Similarity	NPC143896
0.9231	High Similarity	NPC149026
0.9231	High Similarity	NPC257097
0.9231	High Similarity	NPC39329
0.9231	High Similarity	NPC310130
0.9231	High Similarity	NPC150408
0.9225	High Similarity	NPC118840
0.9225	High Similarity	NPC3188
0.9225	High Similarity	NPC64908
0.9225	High Similarity	NPC232021
0.9225	High Similarity	NPC282300
0.9225	High Similarity	NPC147688
0.9225	High Similarity	NPC40118
0.9225	High Similarity	NPC103362
0.9225	High Similarity	NPC205006
0.9225	High Similarity	NPC49108
0.9225	High Similarity	NPC156590
0.9225	High Similarity	NPC126534
0.922	High Similarity	NPC217186
0.922	High Similarity	NPC18260
0.922	High Similarity	NPC216978
0.922	High Similarity	NPC78913
0.922	High Similarity	NPC96565
0.922	High Similarity	NPC53181
0.922	High Similarity	NPC301217
0.922	High Similarity	NPC220062
0.922	High Similarity	NPC303633
0.922	High Similarity	NPC55018
0.9214	High Similarity	NPC212767
0.9203	High Similarity	NPC188646
0.9203	High Similarity	NPC312318
0.9203	High Similarity	NPC204960
0.9203	High Similarity	NPC472365
0.9203	High Similarity	NPC28753
0.9203	High Similarity	NPC242294
0.9203	High Similarity	NPC18877
0.9203	High Similarity	NPC20560
0.9203	High Similarity	NPC223354
0.9203	High Similarity	NPC337373
0.9203	High Similarity	NPC144051
0.9203	High Similarity	NPC82225
0.9203	High Similarity	NPC175098
0.9203	High Similarity	NPC56031
0.9203	High Similarity	NPC27643
0.9203	High Similarity	NPC159623
0.9203	High Similarity	NPC192304
0.9203	High Similarity	NPC263670
0.9203	High Similarity	NPC139813
0.9203	High Similarity	NPC294593
0.9178	High Similarity	NPC38545
0.9178	High Similarity	NPC10027
0.9178	High Similarity	NPC171916
0.9178	High Similarity	NPC65775
0.9172	High Similarity	NPC296998
0.9172	High Similarity	NPC23728
0.9172	High Similarity	NPC110303
0.9172	High Similarity	NPC473077
0.9167	High Similarity	NPC197252
0.9167	High Similarity	NPC236766
0.9167	High Similarity	NPC473015
0.9167	High Similarity	NPC311144
0.9167	High Similarity	NPC209040
0.9167	High Similarity	NPC273538
0.9167	High Similarity	NPC224714
0.9167	High Similarity	NPC184649
0.9167	High Similarity	NPC303185
0.9167	High Similarity	NPC473013
0.9167	High Similarity	NPC216538
0.9167	High Similarity	NPC319752
0.9161	High Similarity	NPC220998
0.9161	High Similarity	NPC32739
0.9161	High Similarity	NPC10937

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 NPC476055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	974
0.2-0.3	1552
0.3-0.4	2611
0.4-0.5	1986
0.5-0.6	1110
0.6-0.7	369
0.7-0.8	113
0.8-0.85	46
0.85-0.9	17
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD1510	Phase 2
0.9167	High Similarity	NPD4378	Clinical (unspecified phase)
0.9058	High Similarity	NPD1240	Approved
0.8986	High Similarity	NPD4380	Phase 2
0.8929	High Similarity	NPD1607	Approved
0.8904	High Similarity	NPD7410	Clinical (unspecified phase)
0.8881	High Similarity	NPD1549	Phase 2
0.8873	High Similarity	NPD2796	Approved
0.8811	High Similarity	NPD1552	Clinical (unspecified phase)
0.8811	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD8443	Clinical (unspecified phase)
0.8684	High Similarity	NPD2393	Clinical (unspecified phase)
0.8684	High Similarity	NPD7819	Suspended
0.8675	High Similarity	NPD7411	Suspended
0.8636	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD2800	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8531	High Similarity	NPD6651	Approved
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8442	Intermediate Similarity	NPD2801	Approved
0.8428	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD3750	Approved
0.8377	Intermediate Similarity	NPD1934	Approved
0.8367	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD1511	Approved
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6232	Discontinued
0.8288	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD2534	Approved
0.8278	Intermediate Similarity	NPD2533	Approved
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD6959	Discontinued
0.8224	Intermediate Similarity	NPD1512	Approved
0.8176	Intermediate Similarity	NPD5494	Approved
0.817	Intermediate Similarity	NPD920	Approved
0.8165	Intermediate Similarity	NPD3749	Approved
0.8163	Intermediate Similarity	NPD2799	Discontinued
0.816	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1551	Phase 2
0.8099	Intermediate Similarity	NPD2798	Approved
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1243	Approved
0.8061	Intermediate Similarity	NPD5953	Discontinued
0.8054	Intermediate Similarity	NPD2344	Approved
0.8041	Intermediate Similarity	NPD3748	Approved
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD3817	Phase 2
0.8026	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7949	Intermediate Similarity	NPD7458	Discontinued
0.7943	Intermediate Similarity	NPD3972	Approved
0.7939	Intermediate Similarity	NPD7286	Phase 2
0.7935	Intermediate Similarity	NPD5403	Approved
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6100	Approved
0.7867	Intermediate Similarity	NPD6099	Approved
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7843	Intermediate Similarity	NPD2309	Approved
0.7834	Intermediate Similarity	NPD3226	Approved
0.7831	Intermediate Similarity	NPD7054	Approved
0.7812	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD5401	Approved
0.7798	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7003	Approved
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7683	Intermediate Similarity	NPD1247	Approved
0.7669	Intermediate Similarity	NPD919	Approved
0.7655	Intermediate Similarity	NPD1203	Approved
0.7655	Intermediate Similarity	NPD1470	Approved
0.7647	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7614	Intermediate Similarity	NPD4360	Phase 2
0.7614	Intermediate Similarity	NPD4363	Phase 3
0.7597	Intermediate Similarity	NPD2654	Approved
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7571	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4361	Phase 2
0.7566	Intermediate Similarity	NPD7033	Discontinued
0.7535	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1164	Approved
0.7534	Intermediate Similarity	NPD2797	Approved
0.7517	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7448	Intermediate Similarity	NPD9717	Approved
0.7447	Intermediate Similarity	NPD9493	Approved
0.743	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7407	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7378	Intermediate Similarity	NPD4288	Approved
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1876	Approved
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD5761	Phase 2
0.7317	Intermediate Similarity	NPD5760	Phase 2
0.7297	Intermediate Similarity	NPD3266	Approved
0.7297	Intermediate Similarity	NPD3267	Approved
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6104	Discontinued
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD2296	Approved
0.7256	Intermediate Similarity	NPD37	Approved
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.723	Intermediate Similarity	NPD3225	Approved
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6776	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6782	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7211	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD9494	Approved
0.7195	Intermediate Similarity	NPD5890	Approved
0.7195	Intermediate Similarity	NPD5889	Approved
0.7191	Intermediate Similarity	NPD4287	Approved
0.719	Intermediate Similarity	NPD4307	Phase 2
0.7188	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1651	Approved
0.717	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD6844	Discontinued
0.7152	Intermediate Similarity	NPD6280	Approved
0.7152	Intermediate Similarity	NPD6279	Approved
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4966	Approved
0.7114	Intermediate Similarity	NPD1283	Approved
0.7113	Intermediate Similarity	NPD1241	Discontinued
0.7097	Intermediate Similarity	NPD7698	Approved
0.7097	Intermediate Similarity	NPD7435	Discontinued
0.7097	Intermediate Similarity	NPD7697	Approved
0.7097	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD8151	Discontinued
0.7083	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)

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