NPASS Compound

Structure

CID24673 OpenBabel06191715352D 25 28 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 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 -0.8660 -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 2.5981 -3.5000 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 6.0622 -4.5000 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 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 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 3.4641 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	340.473
LogP:	4.172
LogD:	3.279
LogS:	-3.44
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	2.871
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:	-4.703
MDCK Permeability:	1.9429182430030778e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	99.65052032470703%
Volume Distribution (VD):	0.422
Pgp-substrate:	1.0972217321395874%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	3.697
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.516
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.308
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.642
Skin Sensitization:	0.533
Carcinogencity:	0.913
Eye Corrosion:	0.004
Eye Irritation:	0.358
Respiratory Toxicity:	0.621

Download Data

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

Natural Product: NPC24673

Natural Product ID:	NPC24673
*Common Name:**	Derrone
IUPAC Name:	5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethylpyrano[2,3-h]chromen-4-one
Synonyms:	derrone
Standard InCHIKey:	ZSYPWSSGRVZENH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O5/c1-20(2)8-7-13-16(25-20)9-15(22)17-18(23)14(10-24-19(13)17)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3
SMILES:	CC1(C)C=Cc2c(cc(c3c(=O)c(coc23)c2ccc(cc2)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL393223
PubChem CID:	14704457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4761	Derris robusta	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]
NPO4761	Derris robusta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4761	Derris robusta	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
MIC	4
Others	9

Activity Type	# Activity
Cell Line	8
Individual Protein	3
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	26000.0	nM	PMID[531569]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	20000.0	nM	PMID[531569]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	13000.0	nM	PMID[531569]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	21.0	%	PMID[531570]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.4	n.a.	PMID[531570]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.0	%	PMID[531570]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	23.7	%	PMID[531570]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	0.0	%	PMID[531570]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	13.6	%	PMID[531570]
NPT660	Cell Line	SW480	Homo sapiens	Inhibition	=	0.0	%	PMID[531570]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	11.0	%	PMID[531570]
NPT2	Others	Unspecified		Inhibition	=	30.8	%	PMID[531570]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.81	ug.mL-1	PMID[531571]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	7.81	ug.mL-1	PMID[531571]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	7.81	ug.mL-1	PMID[531571]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	7.81	ug.mL-1	PMID[531571]

☑ 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 NPC24673 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	392
0.1-0.2	1741
0.2-0.3	3980
0.3-0.4	10573
0.4-0.5	7814
0.5-0.6	3937
0.6-0.7	5737
0.7-0.8	4546
0.8-0.85	2004
0.85-0.9	1369
0.9-0.95	506
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97716
1.0	High Similarity	NPC237635
1.0	High Similarity	NPC104406
1.0	High Similarity	NPC79469
1.0	High Similarity	NPC201731
0.9929	High Similarity	NPC6511
0.9929	High Similarity	NPC266572
0.979	High Similarity	NPC188403
0.972	High Similarity	NPC5173
0.9718	High Similarity	NPC23728
0.9718	High Similarity	NPC110303
0.9718	High Similarity	NPC296998
0.9718	High Similarity	NPC473077
0.9716	High Similarity	NPC319752
0.9716	High Similarity	NPC311741
0.9716	High Similarity	NPC234629
0.9714	High Similarity	NPC62840
0.9714	High Similarity	NPC299080
0.9714	High Similarity	NPC59739
0.9714	High Similarity	NPC217083
0.9714	High Similarity	NPC78803
0.9714	High Similarity	NPC226636
0.9714	High Similarity	NPC11561
0.9714	High Similarity	NPC214236
0.9714	High Similarity	NPC293852
0.965	High Similarity	NPC160821
0.965	High Similarity	NPC132592
0.965	High Similarity	NPC244407
0.965	High Similarity	NPC161191
0.965	High Similarity	NPC321623
0.965	High Similarity	NPC189087
0.9648	High Similarity	NPC176229
0.9648	High Similarity	NPC475052
0.9648	High Similarity	NPC111786
0.9648	High Similarity	NPC312973
0.9648	High Similarity	NPC470647
0.9648	High Similarity	NPC301276
0.9648	High Similarity	NPC54577
0.9648	High Similarity	NPC474161
0.9648	High Similarity	NPC246948
0.9648	High Similarity	NPC88964
0.9648	High Similarity	NPC476088
0.9648	High Similarity	NPC142405
0.9648	High Similarity	NPC195621
0.9648	High Similarity	NPC267375
0.9648	High Similarity	NPC20488
0.9648	High Similarity	NPC67805
0.9648	High Similarity	NPC83357
0.9648	High Similarity	NPC214774
0.9645	High Similarity	NPC18585
0.9645	High Similarity	NPC106985
0.9645	High Similarity	NPC166138
0.9645	High Similarity	NPC219915
0.9645	High Similarity	NPC38219
0.9643	High Similarity	NPC156590
0.9643	High Similarity	NPC110969
0.9643	High Similarity	NPC205006
0.9643	High Similarity	NPC118840
0.9643	High Similarity	NPC147688
0.9643	High Similarity	NPC64908
0.9643	High Similarity	NPC103362
0.9583	High Similarity	NPC474052
0.958	High Similarity	NPC14001
0.958	High Similarity	NPC283234
0.958	High Similarity	NPC166757
0.9577	High Similarity	NPC209040
0.9574	High Similarity	NPC144499
0.9571	High Similarity	NPC159275
0.9571	High Similarity	NPC204985
0.9571	High Similarity	NPC172986
0.9571	High Similarity	NPC215311
0.9571	High Similarity	NPC172250
0.9571	High Similarity	NPC150522
0.9571	High Similarity	NPC259166
0.9571	High Similarity	NPC219917
0.9571	High Similarity	NPC48624
0.9571	High Similarity	NPC213659
0.9571	High Similarity	NPC305355
0.9571	High Similarity	NPC235239
0.9571	High Similarity	NPC144118
0.9571	High Similarity	NPC261227
0.9571	High Similarity	NPC80962
0.9571	High Similarity	NPC241100
0.9571	High Similarity	NPC326109
0.9571	High Similarity	NPC475680
0.9571	High Similarity	NPC270883
0.9524	High Similarity	NPC470681
0.9517	High Similarity	NPC471115
0.9517	High Similarity	NPC472633
0.9517	High Similarity	NPC29777
0.9517	High Similarity	NPC61258
0.9514	High Similarity	NPC168085
0.9514	High Similarity	NPC296869
0.951	High Similarity	NPC477955
0.951	High Similarity	NPC220418
0.951	High Similarity	NPC124729
0.9507	High Similarity	NPC164980
0.9507	High Similarity	NPC221432
0.9507	High Similarity	NPC91560
0.9507	High Similarity	NPC478086
0.9507	High Similarity	NPC75049
0.9507	High Similarity	NPC310130
0.9507	High Similarity	NPC149026
0.9507	High Similarity	NPC169591
0.9507	High Similarity	NPC68104
0.9507	High Similarity	NPC214166
0.9507	High Similarity	NPC175504
0.9507	High Similarity	NPC316816
0.9507	High Similarity	NPC257097
0.9507	High Similarity	NPC150408
0.9507	High Similarity	NPC39329
0.9507	High Similarity	NPC143896
0.9504	High Similarity	NPC3188
0.9504	High Similarity	NPC282300
0.9504	High Similarity	NPC52789
0.9504	High Similarity	NPC469404
0.9504	High Similarity	NPC268204
0.9504	High Similarity	NPC55832
0.9504	High Similarity	NPC26051
0.95	High Similarity	NPC96565
0.95	High Similarity	NPC301217
0.95	High Similarity	NPC220062
0.95	High Similarity	NPC303633
0.95	High Similarity	NPC283429
0.95	High Similarity	NPC217186
0.95	High Similarity	NPC295384
0.95	High Similarity	NPC18260
0.95	High Similarity	NPC473076
0.95	High Similarity	NPC55018
0.95	High Similarity	NPC53181
0.95	High Similarity	NPC216978
0.95	High Similarity	NPC23257
0.95	High Similarity	NPC78913
0.9459	High Similarity	NPC282307
0.9459	High Similarity	NPC170026
0.9456	High Similarity	NPC223701
0.9456	High Similarity	NPC7989
0.9456	High Similarity	NPC472583
0.9448	High Similarity	NPC317492
0.9448	High Similarity	NPC473016
0.9444	High Similarity	NPC180477
0.9441	High Similarity	NPC273538
0.9441	High Similarity	NPC216538
0.9441	High Similarity	NPC197252
0.9441	High Similarity	NPC257236
0.9441	High Similarity	NPC236766
0.9441	High Similarity	NPC131568
0.9441	High Similarity	NPC179970
0.9441	High Similarity	NPC278175
0.9441	High Similarity	NPC473013
0.9441	High Similarity	NPC469953
0.9441	High Similarity	NPC224714
0.9441	High Similarity	NPC131579
0.9441	High Similarity	NPC473015
0.9441	High Similarity	NPC271288
0.9437	High Similarity	NPC76338
0.9437	High Similarity	NPC306829
0.9437	High Similarity	NPC220998
0.9437	High Similarity	NPC228504
0.9437	High Similarity	NPC227579
0.9437	High Similarity	NPC78
0.9437	High Similarity	NPC166482
0.9437	High Similarity	NPC223500
0.9437	High Similarity	NPC328164
0.9437	High Similarity	NPC107572
0.9437	High Similarity	NPC177354
0.9437	High Similarity	NPC64915
0.9437	High Similarity	NPC265040
0.9437	High Similarity	NPC182852
0.9437	High Similarity	NPC10937
0.9437	High Similarity	NPC40833
0.9437	High Similarity	NPC125855
0.9437	High Similarity	NPC296917
0.9437	High Similarity	NPC1089
0.9437	High Similarity	NPC324436
0.9437	High Similarity	NPC76372
0.9437	High Similarity	NPC148757
0.9437	High Similarity	NPC66515
0.9437	High Similarity	NPC32739
0.9437	High Similarity	NPC324134
0.9437	High Similarity	NPC161506
0.9437	High Similarity	NPC194432
0.9437	High Similarity	NPC147145
0.9437	High Similarity	NPC37496
0.9437	High Similarity	NPC166934
0.9437	High Similarity	NPC167624
0.9433	High Similarity	NPC253822
0.9433	High Similarity	NPC471587
0.9433	High Similarity	NPC101366
0.9433	High Similarity	NPC69769
0.9429	High Similarity	NPC201395
0.9429	High Similarity	NPC124269
0.9429	High Similarity	NPC131130
0.9429	High Similarity	NPC17848
0.9429	High Similarity	NPC21350
0.9388	High Similarity	NPC31627
0.9388	High Similarity	NPC476238
0.9388	High Similarity	NPC285623
0.9388	High Similarity	NPC327269
0.9379	High Similarity	NPC208303

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 NPC24673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	992
0.2-0.3	1495
0.3-0.4	2628
0.4-0.5	1959
0.5-0.6	1151
0.6-0.7	361
0.7-0.8	130
0.8-0.85	43
0.85-0.9	20
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9441	High Similarity	NPD7410	Clinical (unspecified phase)
0.9441	High Similarity	NPD4378	Clinical (unspecified phase)
0.9214	High Similarity	NPD1510	Phase 2
0.9155	High Similarity	NPD1549	Phase 2
0.9149	High Similarity	NPD2796	Approved
0.9122	High Similarity	NPD4380	Phase 2
0.9085	High Similarity	NPD1552	Clinical (unspecified phase)
0.9085	High Similarity	NPD1550	Clinical (unspecified phase)
0.906	High Similarity	NPD7411	Suspended
0.9007	High Similarity	NPD8443	Clinical (unspecified phase)
0.894	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD1240	Approved
0.8889	High Similarity	NPD7075	Discontinued
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8816	High Similarity	NPD7819	Suspended
0.8803	High Similarity	NPD1607	Approved
0.8766	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD6801	Discontinued
0.8701	High Similarity	NPD7768	Phase 2
0.8671	High Similarity	NPD7852	Clinical (unspecified phase)
0.8639	High Similarity	NPD3750	Approved
0.8627	High Similarity	NPD1934	Approved
0.8591	High Similarity	NPD6799	Approved
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD7421	Clinical (unspecified phase)
0.8509	High Similarity	NPD7804	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6959	Discontinued
0.8477	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD5403	Approved
0.8408	Intermediate Similarity	NPD3749	Approved
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8367	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1243	Approved
0.8322	Intermediate Similarity	NPD2800	Approved
0.8302	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD920	Approved
0.8299	Intermediate Similarity	NPD3748	Approved
0.8289	Intermediate Similarity	NPD5401	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5953	Discontinued
0.8176	Intermediate Similarity	NPD2799	Discontinued
0.8171	Intermediate Similarity	NPD7054	Approved
0.817	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2313	Discontinued
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD7472	Approved
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD2344	Approved
0.8061	Intermediate Similarity	NPD7286	Phase 2
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD2533	Approved
0.8024	Intermediate Similarity	NPD6559	Discontinued
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7973	Intermediate Similarity	NPD5124	Phase 1
0.7973	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD7033	Discontinued
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1203	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7901	Intermediate Similarity	NPD919	Approved
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7877	Intermediate Similarity	NPD6832	Phase 2
0.787	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2798	Approved
0.7857	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD2309	Approved
0.7848	Intermediate Similarity	NPD3226	Approved
0.7829	Intermediate Similarity	NPD4360	Phase 2
0.7829	Intermediate Similarity	NPD4363	Phase 3
0.7815	Intermediate Similarity	NPD4308	Phase 3
0.7805	Intermediate Similarity	NPD1247	Approved
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD3268	Approved
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.774	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3225	Approved
0.7712	Intermediate Similarity	NPD2346	Discontinued
0.7708	Intermediate Similarity	NPD9717	Approved
0.7684	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4361	Phase 2
0.7671	Intermediate Similarity	NPD2797	Approved
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD422	Phase 1
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7607	Intermediate Similarity	NPD4288	Approved
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7588	Intermediate Similarity	NPD1729	Discontinued
0.7584	Intermediate Similarity	NPD4625	Phase 3
0.7554	Intermediate Similarity	NPD7584	Approved
0.755	Intermediate Similarity	NPD4307	Phase 2
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7531	Intermediate Similarity	NPD5889	Approved
0.7531	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2654	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9545	Approved
0.7469	Intermediate Similarity	NPD6585	Discontinued
0.7466	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7003	Approved
0.744	Intermediate Similarity	NPD5710	Approved
0.744	Intermediate Similarity	NPD5711	Approved
0.7432	Intermediate Similarity	NPD3267	Approved
0.7432	Intermediate Similarity	NPD3266	Approved
0.7419	Intermediate Similarity	NPD5406	Approved
0.7419	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD5408	Approved
0.7419	Intermediate Similarity	NPD5404	Approved
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3764	Approved
0.7401	Intermediate Similarity	NPD4287	Approved
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD6844	Discontinued
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1164	Approved
0.7315	Intermediate Similarity	NPD1470	Approved
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7303	Intermediate Similarity	NPD1296	Phase 2
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6104	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7289	Intermediate Similarity	NPD2296	Approved
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD7577	Discontinued
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7177	Discontinued
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7222	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7213	Phase 3
0.7205	Intermediate Similarity	NPD7212	Phase 2
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4477	Approved
0.7197	Intermediate Similarity	NPD4476	Approved
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2354	Approved
0.7188	Intermediate Similarity	NPD3887	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7169	Intermediate Similarity	NPD6280	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