NPASS Compound

Structure

CID188243 OpenBabel06191715572D 22 24 0 0 1 0 0 0 0 0999 V2000 5.1962 1.0000 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 1.7321 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 2.5981 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 -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 -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 -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 0.0000 -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 3 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 -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 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 21 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	302.415
LogP:	2.491
LogD:	2.793
LogS:	-4.114
# Rotatable Bonds:	3
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.943
Synthetic Accessibility Score:	2.679
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.625
MDCK Permeability:	2.6532085030339658e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	91.26763153076172%
Volume Distribution (VD):	0.699
Pgp-substrate:	6.965323448181152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.687
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	12.017
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.884
AMES Toxicity:	0.45
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.551
Skin Sensitization:	0.4
Carcinogencity:	0.591
Eye Corrosion:	0.004
Eye Irritation:	0.68
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC188243

Natural Product ID:	NPC188243
*Common Name:**	6,4'-Dimethyl-Naringenin
IUPAC Name:	7-hydroxy-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	6,4'-Dimethyl-Naringenin
Standard InCHIKey:	KFGFEKHSEPSVNO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-20-12-5-3-10(4-6-12)14-9-13(19)17-15(21-2)7-11(18)8-16(17)22-14/h3-8,14,18H,9H2,1-2H3
SMILES:	COc1ccc(cc1)C1CC(=O)c2c(cc(cc2O1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL233063
PubChem CID:	21721822
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15730265]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Johor, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Kelantan, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Pahang, Malaysia		PMID[26399961]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30081	Alpinia speciosa	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30081	Alpinia speciosa	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[Nippon Kogaku Zasshi, 91, (1970), 762]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30081	Alpinia speciosa	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	CC50	=	12000.0	nM	PMID[479871]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	92000.0	nM	PMID[479871]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	0.13	n.a.	PMID[479871]

☑ 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 NPC188243 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	343
0.1-0.2	1523
0.2-0.3	3905
0.3-0.4	10266
0.4-0.5	8020
0.5-0.6	3583
0.6-0.7	5564
0.7-0.8	5341
0.8-0.85	2236
0.85-0.9	1168
0.9-0.95	571
0.95-1	177

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6407
1.0	High Similarity	NPC110228
0.9925	High Similarity	NPC20709
0.9925	High Similarity	NPC265871
0.9925	High Similarity	NPC225153
0.9925	High Similarity	NPC140890
0.9925	High Similarity	NPC150648
0.9925	High Similarity	NPC310135
0.9925	High Similarity	NPC274784
0.9925	High Similarity	NPC222342
0.9925	High Similarity	NPC329203
0.9853	High Similarity	NPC10937
0.9853	High Similarity	NPC167624
0.9853	High Similarity	NPC107572
0.9853	High Similarity	NPC194432
0.9853	High Similarity	NPC182852
0.9853	High Similarity	NPC1089
0.9853	High Similarity	NPC125855
0.9853	High Similarity	NPC227579
0.9853	High Similarity	NPC166934
0.9853	High Similarity	NPC220998
0.9853	High Similarity	NPC76372
0.9853	High Similarity	NPC306829
0.9853	High Similarity	NPC223500
0.9853	High Similarity	NPC32739
0.9853	High Similarity	NPC161506
0.9853	High Similarity	NPC228504
0.9853	High Similarity	NPC265040
0.9853	High Similarity	NPC37496
0.9853	High Similarity	NPC324134
0.9853	High Similarity	NPC76338
0.9853	High Similarity	NPC64915
0.9853	High Similarity	NPC78
0.9853	High Similarity	NPC328164
0.9853	High Similarity	NPC166482
0.9853	High Similarity	NPC40833
0.9853	High Similarity	NPC148757
0.9853	High Similarity	NPC296917
0.9853	High Similarity	NPC324436
0.9853	High Similarity	NPC177354
0.9853	High Similarity	NPC66515
0.9852	High Similarity	NPC76445
0.9852	High Similarity	NPC129853
0.9852	High Similarity	NPC284550
0.9781	High Similarity	NPC75049
0.9781	High Similarity	NPC223812
0.9781	High Similarity	NPC175504
0.9781	High Similarity	NPC149026
0.9781	High Similarity	NPC316816
0.9781	High Similarity	NPC310130
0.9781	High Similarity	NPC278249
0.9781	High Similarity	NPC150408
0.9781	High Similarity	NPC85162
0.9781	High Similarity	NPC143896
0.9781	High Similarity	NPC68104
0.9781	High Similarity	NPC257097
0.9781	High Similarity	NPC91560
0.9781	High Similarity	NPC478086
0.9781	High Similarity	NPC185276
0.9781	High Similarity	NPC221432
0.9781	High Similarity	NPC81697
0.9781	High Similarity	NPC107177
0.9781	High Similarity	NPC39329
0.9781	High Similarity	NPC164980
0.9781	High Similarity	NPC214166
0.9781	High Similarity	NPC169591
0.9781	High Similarity	NPC77794
0.9781	High Similarity	NPC125894
0.9779	High Similarity	NPC324386
0.9779	High Similarity	NPC17170
0.9779	High Similarity	NPC110038
0.9779	High Similarity	NPC166689
0.9779	High Similarity	NPC4743
0.9779	High Similarity	NPC213322
0.9779	High Similarity	NPC156190
0.9779	High Similarity	NPC312391
0.9779	High Similarity	NPC96408
0.9779	High Similarity	NPC248372
0.9779	High Similarity	NPC258630
0.9779	High Similarity	NPC279650
0.9776	High Similarity	NPC287246
0.9776	High Similarity	NPC296490
0.9776	High Similarity	NPC12296
0.9776	High Similarity	NPC79943
0.9776	High Similarity	NPC13768
0.9776	High Similarity	NPC295261
0.9776	High Similarity	NPC32441
0.9776	High Similarity	NPC107586
0.9776	High Similarity	NPC243083
0.971	High Similarity	NPC209040
0.971	High Similarity	NPC131568
0.971	High Similarity	NPC473013
0.971	High Similarity	NPC236766
0.971	High Similarity	NPC473015
0.971	High Similarity	NPC235217
0.971	High Similarity	NPC131579
0.971	High Similarity	NPC197252
0.971	High Similarity	NPC473014
0.9704	High Similarity	NPC280284
0.9704	High Similarity	NPC124269
0.9704	High Similarity	NPC147686
0.9704	High Similarity	NPC329225
0.9704	High Similarity	NPC188947
0.9704	High Similarity	NPC472460
0.9704	High Similarity	NPC99333
0.9704	High Similarity	NPC118813
0.964	High Similarity	NPC312973
0.964	High Similarity	NPC470131
0.964	High Similarity	NPC111786
0.964	High Similarity	NPC470647
0.964	High Similarity	NPC285630
0.964	High Similarity	NPC142405
0.964	High Similarity	NPC83357
0.964	High Similarity	NPC473078
0.964	High Similarity	NPC67805
0.964	High Similarity	NPC470133
0.964	High Similarity	NPC246948
0.964	High Similarity	NPC20488
0.964	High Similarity	NPC214774
0.964	High Similarity	NPC54577
0.964	High Similarity	NPC470134
0.964	High Similarity	NPC195621
0.964	High Similarity	NPC176229
0.964	High Similarity	NPC267375
0.964	High Similarity	NPC88964
0.964	High Similarity	NPC475052
0.964	High Similarity	NPC301276
0.964	High Similarity	NPC109183
0.964	High Similarity	NPC472629
0.964	High Similarity	NPC127059
0.964	High Similarity	NPC470132
0.9635	High Similarity	NPC3188
0.9632	High Similarity	NPC261234
0.963	High Similarity	NPC84585
0.963	High Similarity	NPC188879
0.963	High Similarity	NPC476480
0.963	High Similarity	NPC290291
0.963	High Similarity	NPC275055
0.9627	High Similarity	NPC99854
0.9571	High Similarity	NPC300988
0.9571	High Similarity	NPC473077
0.9571	High Similarity	NPC10990
0.9571	High Similarity	NPC23728
0.9571	High Similarity	NPC283234
0.9571	High Similarity	NPC296998
0.9571	High Similarity	NPC472627
0.9571	High Similarity	NPC110303
0.9568	High Similarity	NPC470890
0.9568	High Similarity	NPC124780
0.9568	High Similarity	NPC319752
0.9568	High Similarity	NPC87486
0.9568	High Similarity	NPC271288
0.9568	High Similarity	NPC311144
0.9568	High Similarity	NPC470136
0.9568	High Similarity	NPC470135
0.9568	High Similarity	NPC39045
0.9565	High Similarity	NPC73028
0.9565	High Similarity	NPC147145
0.9565	High Similarity	NPC202981
0.9562	High Similarity	NPC69769
0.9562	High Similarity	NPC241100
0.9562	High Similarity	NPC159275
0.9556	High Similarity	NPC473887
0.9556	High Similarity	NPC13408
0.9556	High Similarity	NPC29353
0.9556	High Similarity	NPC194281
0.9556	High Similarity	NPC124784
0.9556	High Similarity	NPC127447
0.9556	High Similarity	NPC231772
0.9556	High Similarity	NPC240593
0.9556	High Similarity	NPC47815
0.9556	High Similarity	NPC234133
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC161191
0.9504	High Similarity	NPC160821
0.95	High Similarity	NPC299011
0.95	High Similarity	NPC228779
0.95	High Similarity	NPC474161
0.95	High Similarity	NPC187282
0.95	High Similarity	NPC24136
0.95	High Similarity	NPC476088
0.95	High Similarity	NPC215885
0.95	High Similarity	NPC476153
0.95	High Similarity	NPC290133
0.95	High Similarity	NPC2416
0.9496	High Similarity	NPC18585
0.9496	High Similarity	NPC471621
0.9496	High Similarity	NPC166138
0.9496	High Similarity	NPC106985
0.9496	High Similarity	NPC113770
0.9493	High Similarity	NPC110969
0.9493	High Similarity	NPC282300
0.9489	High Similarity	NPC303633
0.9489	High Similarity	NPC96565
0.9489	High Similarity	NPC216978
0.9489	High Similarity	NPC301217
0.9489	High Similarity	NPC53181
0.9489	High Similarity	NPC55018
0.9489	High Similarity	NPC316480
0.9489	High Similarity	NPC18260

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 NPC188243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	925
0.2-0.3	1524
0.3-0.4	2540
0.4-0.5	1910
0.5-0.6	1230
0.6-0.7	492
0.7-0.8	145
0.8-0.85	37
0.85-0.9	21
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9776	High Similarity	NPD1550	Clinical (unspecified phase)
0.9776	High Similarity	NPD1552	Clinical (unspecified phase)
0.9704	High Similarity	NPD1549	Phase 2
0.9291	High Similarity	NPD4378	Clinical (unspecified phase)
0.927	High Similarity	NPD2796	Approved
0.9197	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1240	Approved
0.9178	High Similarity	NPD2393	Clinical (unspecified phase)
0.9116	High Similarity	NPD8443	Clinical (unspecified phase)
0.911	High Similarity	NPD1934	Approved
0.9051	High Similarity	NPD1607	Approved
0.9041	High Similarity	NPD7411	Suspended
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.8993	High Similarity	NPD7075	Discontinued
0.8973	High Similarity	NPD4380	Phase 2
0.8919	High Similarity	NPD7096	Clinical (unspecified phase)
0.8867	High Similarity	NPD4381	Clinical (unspecified phase)
0.8819	High Similarity	NPD6799	Approved
0.8792	High Similarity	NPD7819	Suspended
0.8725	High Similarity	NPD6801	Discontinued
0.869	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD2801	Approved
0.8645	High Similarity	NPD6166	Phase 2
0.8645	High Similarity	NPD6168	Clinical (unspecified phase)
0.8645	High Similarity	NPD6167	Clinical (unspecified phase)
0.8623	High Similarity	NPD6859	Clinical (unspecified phase)
0.8591	High Similarity	NPD6599	Discontinued
0.8571	High Similarity	NPD1512	Approved
0.8571	High Similarity	NPD6959	Discontinued
0.8553	High Similarity	NPD3882	Suspended
0.8542	High Similarity	NPD7421	Clinical (unspecified phase)
0.8526	High Similarity	NPD7852	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD3750	Approved
0.8481	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1551	Phase 2
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8428	Intermediate Similarity	NPD7074	Phase 3
0.8389	Intermediate Similarity	NPD5403	Approved
0.8377	Intermediate Similarity	NPD3749	Approved
0.837	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD3817	Phase 2
0.8365	Intermediate Similarity	NPD7054	Approved
0.8345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7472	Approved
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3818	Discontinued
0.8288	Intermediate Similarity	NPD2800	Approved
0.8269	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD6797	Phase 2
0.8255	Intermediate Similarity	NPD5401	Approved
0.8252	Intermediate Similarity	NPD6651	Approved
0.8214	Intermediate Similarity	NPD4908	Phase 1
0.821	Intermediate Similarity	NPD7251	Discontinued
0.816	Intermediate Similarity	NPD7808	Phase 3
0.8151	Intermediate Similarity	NPD2344	Approved
0.8138	Intermediate Similarity	NPD7033	Discontinued
0.8138	Intermediate Similarity	NPD3748	Approved
0.8129	Intermediate Similarity	NPD1203	Approved
0.8108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD4628	Phase 3
0.8102	Intermediate Similarity	NPD1610	Phase 2
0.8099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6559	Discontinued
0.8085	Intermediate Similarity	NPD6832	Phase 2
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8082	Intermediate Similarity	NPD6100	Approved
0.8082	Intermediate Similarity	NPD6099	Approved
0.8074	Intermediate Similarity	NPD1548	Phase 1
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1243	Approved
0.8037	Intermediate Similarity	NPD5953	Discontinued
0.8026	Intermediate Similarity	NPD920	Approved
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8014	Intermediate Similarity	NPD2799	Discontinued
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD5402	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3268	Approved
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7933	Intermediate Similarity	NPD2309	Approved
0.7914	Intermediate Similarity	NPD5844	Phase 1
0.7914	Intermediate Similarity	NPD9717	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2797	Approved
0.7862	Intermediate Similarity	NPD943	Approved
0.7847	Intermediate Similarity	NPD2313	Discontinued
0.7842	Intermediate Similarity	NPD422	Phase 1
0.7821	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2798	Approved
0.7808	Intermediate Similarity	NPD5124	Phase 1
0.7808	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2654	Approved
0.7791	Intermediate Similarity	NPD4363	Phase 3
0.7791	Intermediate Similarity	NPD4360	Phase 2
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD3226	Approved
0.7687	Intermediate Similarity	NPD1933	Approved
0.7681	Intermediate Similarity	NPD9545	Approved
0.7676	Intermediate Similarity	NPD3225	Approved
0.7669	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.766	Intermediate Similarity	NPD3972	Approved
0.7651	Intermediate Similarity	NPD4308	Phase 3
0.764	Intermediate Similarity	NPD919	Approved
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD3267	Approved
0.761	Intermediate Similarity	NPD1465	Phase 2
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1241	Discontinued
0.7568	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6104	Discontinued
0.7546	Intermediate Similarity	NPD1247	Approved
0.7545	Intermediate Similarity	NPD1729	Discontinued
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7484	Intermediate Similarity	NPD7212	Phase 2
0.7484	Intermediate Similarity	NPD7213	Phase 3
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD4749	Approved
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4288	Approved
0.7451	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD230	Phase 1
0.745	Intermediate Similarity	NPD6355	Discontinued
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7438	Intermediate Similarity	NPD6844	Discontinued
0.7436	Intermediate Similarity	NPD4661	Approved
0.7436	Intermediate Similarity	NPD4662	Approved
0.7432	Intermediate Similarity	NPD6233	Phase 2
0.7425	Intermediate Similarity	NPD3751	Discontinued
0.7415	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7383	Intermediate Similarity	NPD4307	Phase 2
0.7383	Intermediate Similarity	NPD3140	Approved
0.7383	Intermediate Similarity	NPD3142	Approved
0.7375	Intermediate Similarity	NPD5890	Approved
0.7375	Intermediate Similarity	NPD5889	Approved
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD411	Approved
0.7365	Intermediate Similarity	NPD3764	Approved
0.7358	Intermediate Similarity	NPD7458	Discontinued
0.7356	Intermediate Similarity	NPD4287	Approved
0.7355	Intermediate Similarity	NPD3887	Approved
0.7346	Intermediate Similarity	NPD2296	Approved
0.7343	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD447	Suspended
0.7329	Intermediate Similarity	NPD7577	Discontinued
0.7325	Intermediate Similarity	NPD7447	Phase 1
0.7324	Intermediate Similarity	NPD17	Approved
0.7322	Intermediate Similarity	NPD7584	Approved
0.7305	Intermediate Similarity	NPD1894	Discontinued
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD8313	Approved
0.726	Intermediate Similarity	NPD1470	Approved
0.7246	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2354	Approved
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7222	Intermediate Similarity	NPD6280	Approved
0.7222	Intermediate Similarity	NPD6279	Approved
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6585	Discontinued
0.7202	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD4062	Phase 3
0.7197	Intermediate Similarity	NPD7440	Discontinued
0.7192	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6808	Phase 2
0.7179	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD8455	Phase 2

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