NPASS Compound

Structure

CID23728 OpenBabel06191715352D 24 27 0 0 1 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 -2.5981 0.5000 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 -6.0622 3.5000 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 -0.0000 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 2.0000 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 -4.3301 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 -0.8660 1.5000 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 -5.1962 3.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 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 -3.4641 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 6 2 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 17 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 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 13 17 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 12 1 6 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.12
Volume:	334.32
LogP:	4.284
LogD:	3.865
LogS:	-4.641
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.851
Synthetic Accessibility Score:	3.244
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	1.8327047655475326e-05
Pgp-inhibitor:	0.898
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	98.07152557373047%
Volume Distribution (VD):	0.548
Pgp-substrate:	1.230022668838501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.941
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	12.394
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.28
Rat Oral Acute Toxicity:	0.438
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.107
Carcinogencity:	0.87
Eye Corrosion:	0.003
Eye Irritation:	0.173
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC23728

Natural Product ID:	NPC23728
*Common Name:**	Abyssinone I
IUPAC Name:	(2S)-2-(2,2-dimethylchromen-6-yl)-7-hydroxy-2,3-dihydrochromen-4-one
Synonyms:	Abyssinone I
Standard InCHIKey:	MITHUEHYZARDCT-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-20(2)8-7-13-9-12(3-6-17(13)24-20)18-11-16(22)15-5-4-14(21)10-19(15)23-18/h3-10,18,21H,11H2,1-2H3/t18-/m0/s1
SMILES:	CC1(C)C=Cc2cc(ccc2O1)[C@@H]1CC(=O)c2ccc(cc2O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455626
PubChem CID:	442152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	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]
NPO8526	Erythrina abyssinica	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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	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
MIC	8
Others	9

Activity Type	# Activity
Cell Line	5
Individual Protein	3
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	10.1	%	PMID[451397]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.5	n.a.	PMID[451397]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.0	%	PMID[451397]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	33.9	%	PMID[451397]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	0.0	%	PMID[451397]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	13.8	%	PMID[451397]
NPT660	Cell Line	SW480	Homo sapiens	Inhibition	=	17.4	%	PMID[451397]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[451395]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	2.9	%	PMID[451397]
NPT2	Others	Unspecified		Inhibition	=	23.1	%	PMID[451397]

☑ 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 NPC23728 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	368
0.1-0.2	1534
0.2-0.3	3788
0.3-0.4	10110
0.4-0.5	8375
0.5-0.6	3604
0.6-0.7	5849
0.7-0.8	5242
0.8-0.85	2072
0.85-0.9	1123
0.9-0.95	448
0.95-1	184

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC110303
0.9929	High Similarity	NPC54577
0.9929	High Similarity	NPC83357
0.9929	High Similarity	NPC246948
0.9929	High Similarity	NPC475052
0.9929	High Similarity	NPC470647
0.9929	High Similarity	NPC301276
0.9929	High Similarity	NPC195621
0.9929	High Similarity	NPC176229
0.9929	High Similarity	NPC267375
0.9929	High Similarity	NPC88964
0.9929	High Similarity	NPC20488
0.9929	High Similarity	NPC160821
0.9929	High Similarity	NPC67805
0.9929	High Similarity	NPC214774
0.9929	High Similarity	NPC142405
0.9929	High Similarity	NPC132592
0.9929	High Similarity	NPC312973
0.9929	High Similarity	NPC111786
0.9858	High Similarity	NPC473077
0.9858	High Similarity	NPC296998
0.9858	High Similarity	NPC283234
0.9857	High Similarity	NPC209040
0.9789	High Similarity	NPC161191
0.9786	High Similarity	NPC149026
0.9786	High Similarity	NPC316816
0.9786	High Similarity	NPC39329
0.9786	High Similarity	NPC175504
0.9786	High Similarity	NPC310130
0.9786	High Similarity	NPC68104
0.9786	High Similarity	NPC143896
0.9786	High Similarity	NPC91560
0.9786	High Similarity	NPC150408
0.9786	High Similarity	NPC164980
0.9786	High Similarity	NPC478086
0.9786	High Similarity	NPC38219
0.9786	High Similarity	NPC221432
0.9786	High Similarity	NPC75049
0.9786	High Similarity	NPC214166
0.9786	High Similarity	NPC169591
0.9786	High Similarity	NPC257097
0.9718	High Similarity	NPC97716
0.9718	High Similarity	NPC237635
0.9718	High Similarity	NPC201731
0.9718	High Similarity	NPC104406
0.9718	High Similarity	NPC24673
0.9718	High Similarity	NPC79469
0.9716	High Similarity	NPC319752
0.9716	High Similarity	NPC473015
0.9716	High Similarity	NPC131579
0.9716	High Similarity	NPC131568
0.9716	High Similarity	NPC197252
0.9716	High Similarity	NPC236766
0.9716	High Similarity	NPC473013
0.9714	High Similarity	NPC40833
0.9714	High Similarity	NPC1089
0.9714	High Similarity	NPC10937
0.9714	High Similarity	NPC220998
0.9714	High Similarity	NPC182852
0.9714	High Similarity	NPC194432
0.9714	High Similarity	NPC296917
0.9714	High Similarity	NPC32739
0.9714	High Similarity	NPC37496
0.9714	High Similarity	NPC166934
0.9714	High Similarity	NPC177354
0.9714	High Similarity	NPC148757
0.9714	High Similarity	NPC76338
0.9714	High Similarity	NPC228504
0.9714	High Similarity	NPC66515
0.9714	High Similarity	NPC107572
0.9714	High Similarity	NPC226636
0.9714	High Similarity	NPC306829
0.9714	High Similarity	NPC11561
0.9714	High Similarity	NPC64915
0.9714	High Similarity	NPC265040
0.9714	High Similarity	NPC324134
0.9714	High Similarity	NPC324436
0.9714	High Similarity	NPC125855
0.9714	High Similarity	NPC167624
0.9714	High Similarity	NPC161506
0.9714	High Similarity	NPC76372
0.9714	High Similarity	NPC147145
0.9714	High Similarity	NPC78
0.9714	High Similarity	NPC227579
0.9714	High Similarity	NPC166482
0.9714	High Similarity	NPC223500
0.9714	High Similarity	NPC328164
0.9653	High Similarity	NPC472633
0.965	High Similarity	NPC6511
0.965	High Similarity	NPC321623
0.965	High Similarity	NPC266572
0.965	High Similarity	NPC189087
0.9648	High Similarity	NPC470134
0.9648	High Similarity	NPC285630
0.9648	High Similarity	NPC109183
0.9648	High Similarity	NPC476088
0.9648	High Similarity	NPC470131
0.9648	High Similarity	NPC474161
0.9648	High Similarity	NPC473078
0.9648	High Similarity	NPC470132
0.9648	High Similarity	NPC127059
0.9648	High Similarity	NPC470133
0.9645	High Similarity	NPC107177
0.9645	High Similarity	NPC223812
0.9645	High Similarity	NPC18585
0.9645	High Similarity	NPC85162
0.9645	High Similarity	NPC125894
0.9645	High Similarity	NPC106985
0.9645	High Similarity	NPC166138
0.9645	High Similarity	NPC185276
0.9645	High Similarity	NPC219915
0.9645	High Similarity	NPC77794
0.9645	High Similarity	NPC81697
0.9645	High Similarity	NPC278249
0.9643	High Similarity	NPC110038
0.9643	High Similarity	NPC258630
0.9643	High Similarity	NPC248372
0.9643	High Similarity	NPC324386
0.9643	High Similarity	NPC156590
0.9643	High Similarity	NPC110969
0.9643	High Similarity	NPC312391
0.9643	High Similarity	NPC205006
0.9643	High Similarity	NPC96408
0.9643	High Similarity	NPC147688
0.9643	High Similarity	NPC279650
0.9643	High Similarity	NPC17170
0.9643	High Similarity	NPC3188
0.9643	High Similarity	NPC64908
0.9643	High Similarity	NPC156190
0.9643	High Similarity	NPC166689
0.9643	High Similarity	NPC4743
0.9643	High Similarity	NPC213322
0.9643	High Similarity	NPC103362
0.9643	High Similarity	NPC118840
0.9589	High Similarity	NPC223701
0.9589	High Similarity	NPC7989
0.9589	High Similarity	NPC472583
0.9583	High Similarity	NPC104236
0.9583	High Similarity	NPC473016
0.9583	High Similarity	NPC5173
0.9583	High Similarity	NPC164205
0.958	High Similarity	NPC472627
0.9577	High Similarity	NPC235217
0.9577	High Similarity	NPC470136
0.9577	High Similarity	NPC470135
0.9577	High Similarity	NPC39045
0.9577	High Similarity	NPC473014
0.9577	High Similarity	NPC234629
0.9577	High Similarity	NPC311741
0.9574	High Similarity	NPC144499
0.9574	High Similarity	NPC78803
0.9574	High Similarity	NPC214236
0.9574	High Similarity	NPC299080
0.9574	High Similarity	NPC217083
0.9574	High Similarity	NPC59739
0.9574	High Similarity	NPC62840
0.9574	High Similarity	NPC293852
0.9571	High Similarity	NPC159275
0.9571	High Similarity	NPC172986
0.9571	High Similarity	NPC110228
0.9571	High Similarity	NPC305355
0.9571	High Similarity	NPC261227
0.9571	High Similarity	NPC6407
0.9571	High Similarity	NPC472409
0.9571	High Similarity	NPC150522
0.9571	High Similarity	NPC69769
0.9571	High Similarity	NPC235239
0.9571	High Similarity	NPC188243
0.9571	High Similarity	NPC241100
0.9571	High Similarity	NPC475680
0.9571	High Similarity	NPC270883
0.9517	High Similarity	NPC471115
0.9517	High Similarity	NPC29777
0.9517	High Similarity	NPC61258
0.9517	High Similarity	NPC188403
0.9514	High Similarity	NPC168085
0.9514	High Similarity	NPC296869
0.951	High Similarity	NPC477955
0.951	High Similarity	NPC472629
0.951	High Similarity	NPC228779
0.9507	High Similarity	NPC59522
0.9504	High Similarity	NPC282300
0.95	High Similarity	NPC274784
0.95	High Similarity	NPC265871
0.95	High Similarity	NPC222342
0.95	High Similarity	NPC301217
0.95	High Similarity	NPC220062
0.95	High Similarity	NPC303633
0.95	High Similarity	NPC96565
0.95	High Similarity	NPC217186
0.95	High Similarity	NPC329203
0.95	High Similarity	NPC23257
0.95	High Similarity	NPC11566
0.95	High Similarity	NPC20709
0.95	High Similarity	NPC310135
0.95	High Similarity	NPC150648
0.95	High Similarity	NPC18260
0.95	High Similarity	NPC55018
0.95	High Similarity	NPC140890
0.95	High Similarity	NPC53181

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 NPC23728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	941
0.2-0.3	1511
0.3-0.4	2544
0.4-0.5	1979
0.5-0.6	1195
0.6-0.7	431
0.7-0.8	171
0.8-0.85	31
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9441	High Similarity	NPD7410	Clinical (unspecified phase)
0.9429	High Similarity	NPD1549	Phase 2
0.9357	High Similarity	NPD1552	Clinical (unspecified phase)
0.9357	High Similarity	NPD1550	Clinical (unspecified phase)
0.9306	High Similarity	NPD4378	Clinical (unspecified phase)
0.9252	High Similarity	NPD4380	Phase 2
0.9189	High Similarity	NPD7411	Suspended
0.9149	High Similarity	NPD2796	Approved
0.9133	High Similarity	NPD8443	Clinical (unspecified phase)
0.9078	High Similarity	NPD1510	Phase 2
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.9013	High Similarity	NPD7075	Discontinued
0.894	High Similarity	NPD7096	Clinical (unspecified phase)
0.8929	High Similarity	NPD1240	Approved
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8874	High Similarity	NPD6801	Discontinued
0.8816	High Similarity	NPD7819	Suspended
0.8803	High Similarity	NPD1607	Approved
0.875	High Similarity	NPD1934	Approved
0.8671	High Similarity	NPD7852	Clinical (unspecified phase)
0.8625	High Similarity	NPD7804	Clinical (unspecified phase)
0.8599	High Similarity	NPD6959	Discontinued
0.8591	High Similarity	NPD6799	Approved
0.8581	High Similarity	NPD7768	Phase 2
0.8571	High Similarity	NPD7421	Clinical (unspecified phase)
0.8514	High Similarity	NPD3750	Approved
0.8467	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD2801	Approved
0.8438	Intermediate Similarity	NPD6166	Phase 2
0.8438	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD5403	Approved
0.8418	Intermediate Similarity	NPD5494	Approved
0.8408	Intermediate Similarity	NPD3749	Approved
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8355	Intermediate Similarity	NPD1512	Approved
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8289	Intermediate Similarity	NPD5401	Approved
0.8282	Intermediate Similarity	NPD7054	Approved
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8232	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.82	Intermediate Similarity	NPD1243	Approved
0.82	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD920	Approved
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD3748	Approved
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8163	Intermediate Similarity	NPD6651	Approved
0.8158	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2935	Discontinued
0.8095	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5124	Phase 1
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8084	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5953	Discontinued
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8061	Intermediate Similarity	NPD7286	Phase 2
0.8054	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD7033	Discontinued
0.8052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5402	Approved
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2344	Approved
0.7935	Intermediate Similarity	NPD2534	Approved
0.7935	Intermediate Similarity	NPD2532	Approved
0.7935	Intermediate Similarity	NPD2533	Approved
0.7931	Intermediate Similarity	NPD4360	Phase 2
0.7931	Intermediate Similarity	NPD4363	Phase 3
0.7917	Intermediate Similarity	NPD1203	Approved
0.7908	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7877	Intermediate Similarity	NPD6832	Phase 2
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD1548	Phase 1
0.7841	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD919	Approved
0.777	Intermediate Similarity	NPD3268	Approved
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2309	Approved
0.774	Intermediate Similarity	NPD2798	Approved
0.7736	Intermediate Similarity	NPD3226	Approved
0.7712	Intermediate Similarity	NPD2346	Discontinued
0.7708	Intermediate Similarity	NPD9717	Approved
0.7697	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD4308	Phase 3
0.7671	Intermediate Similarity	NPD2797	Approved
0.7667	Intermediate Similarity	NPD943	Approved
0.765	Intermediate Similarity	NPD7584	Approved
0.7643	Intermediate Similarity	NPD7390	Discontinued
0.764	Intermediate Similarity	NPD5889	Approved
0.764	Intermediate Similarity	NPD5890	Approved
0.7639	Intermediate Similarity	NPD422	Phase 1
0.7625	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3225	Approved
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD1729	Discontinued
0.7584	Intermediate Similarity	NPD4625	Phase 3
0.7584	Intermediate Similarity	NPD4361	Phase 2
0.7584	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6585	Discontinued
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.7485	Intermediate Similarity	NPD6844	Discontinued
0.7483	Intermediate Similarity	NPD9545	Approved
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7466	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5711	Approved
0.744	Intermediate Similarity	NPD5710	Approved
0.7434	Intermediate Similarity	NPD1613	Approved
0.7434	Intermediate Similarity	NPD4307	Phase 2
0.7434	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3266	Approved
0.7432	Intermediate Similarity	NPD3267	Approved
0.7421	Intermediate Similarity	NPD7212	Phase 2
0.7421	Intermediate Similarity	NPD7213	Phase 3
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7414	Intermediate Similarity	NPD8312	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7401	Intermediate Similarity	NPD4287	Approved
0.7399	Intermediate Similarity	NPD6104	Discontinued
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7577	Discontinued
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7368	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD9493	Approved
0.7342	Intermediate Similarity	NPD7003	Approved
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7325	Intermediate Similarity	NPD2424	Discontinued
0.7322	Intermediate Similarity	NPD6782	Approved
0.7322	Intermediate Similarity	NPD6779	Approved
0.7322	Intermediate Similarity	NPD6780	Approved
0.7322	Intermediate Similarity	NPD6781	Approved
0.7322	Intermediate Similarity	NPD6777	Approved
0.7322	Intermediate Similarity	NPD6778	Approved
0.7322	Intermediate Similarity	NPD6776	Approved
0.7308	Intermediate Similarity	NPD5408	Approved
0.7308	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD5406	Approved
0.7308	Intermediate Similarity	NPD5404	Approved
0.7303	Intermediate Similarity	NPD1296	Phase 2
0.7303	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3764	Approved
0.7297	Intermediate Similarity	NPD4749	Approved
0.7296	Intermediate Similarity	NPD3887	Approved
0.7296	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3823	Discontinued
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7234	Intermediate Similarity	NPD7585	Approved
0.723	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7222	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD5049	Phase 3
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3140	Approved
0.7208	Intermediate Similarity	NPD3142	Approved
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7435	Discontinued
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD1164	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