NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.08
Volume:	232.713
LogP:	2.375
LogD:	2.062
LogS:	-3.061
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.794
Synthetic Accessibility Score:	1.975
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	2.6470283046364784e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.509
Plasma Protein Binding (PPB):	90.97306060791016%
Volume Distribution (VD):	0.548
Pgp-substrate:	3.839526414871216%

ADMET: Metabolism

CYP1A2-inhibitor:	0.474
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.498
CYP2C19-substrate:	0.21
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	1.24
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.73
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.24
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.664
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC249067

Natural Product ID:	NPC249067
*Common Name:**	Benzoin
IUPAC Name:	2-hydroxy-1,2-diphenylethanone
Synonyms:	Benzoin; Benzoin Tincture
Standard InCHIKey:	ISAOCJYIOMOJEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
SMILES:	c1ccc(cc1)C(C(=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190677
PubChem CID:	8400
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0001331] Benzoins

*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
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542343]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	roots	n.a.	n.a.	PMID[14664512]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25172742]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677276]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26371	Sorghum bicolor	Species	Poaceae	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
AC50	2
IC50	4
Ki	15
Others	8
Potency	21

Activity Type	# Activity
Individual Protein	23
Organism	8
Others	18
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	2220.0	nM	PMID[526107]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	7250.0	nM	PMID[526107]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	>	100000.0	nM	PMID[526107]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[526107]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	2220.0	nM	PMID[526108]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	7250.0	nM	PMID[526108]
NPT2610	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Oryctolagus cuniculus	Ki	>	100000.0	nM	PMID[526108]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[526108]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[526108]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	7210.0	nM	PMID[526109]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	2670.0	nM	PMID[526109]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[526109]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[526109]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	12589.3	nM	PMID[526110]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[526110]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	79.4	nM	PMID[526112]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4.6	nM	PMID[526111]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29849.3	nM	PMID[526112]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[526111]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[526111]
NPT1444	Individual Protein	PI3-kinase p110-alpha subunit	Homo sapiens	IC50	=	2120000.0	nM	PMID[526116]
NPT2	Others	Unspecified		Ki	>	100000.0	nM	PMID[526109]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9528.3	nM	PMID[526110]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5221.3	nM	PMID[526111]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11995.5	nM	PMID[526110]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[526111]
NPT35	Others	n.a.		LogD7.4	n.a.	2.13	n.a.	PMID[526114]
NPT35	Others	n.a.		Solubility	n.a.	64600.0	nM	PMID[526114]
NPT2	Others	Unspecified		AC50	n.a.	707.9	nM	PMID[526115]
NPT2	Others	Unspecified		Ac50	n.a.	0.7079	uM	PMID[526115]
NPT2	Others	Unspecified		Ac50	n.a.	10.0	uM	PMID[526115]
NPT2	Others	Unspecified		AC50	n.a.	10000.0	nM	PMID[526115]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	25.25	%	PMID[526117]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.837	%	PMID[526118]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.04	%	PMID[526119]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[526120]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[526120]
NPT2	Others	Unspecified		Potency	n.a.	68591.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2433.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14958.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38900	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	67962.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	8485.2	nM	PubChem BioAssay data set

☑ 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 NPC249067 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	251
0.1-0.2	1205
0.2-0.3	3281
0.3-0.4	9920
0.4-0.5	11372
0.5-0.6	11079
0.6-0.7	4891
0.7-0.8	655
0.8-0.85	38
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.898	High Similarity	NPC289201
0.8932	High Similarity	NPC211439
0.8611	High Similarity	NPC196673
0.8598	High Similarity	NPC158282
0.8544	High Similarity	NPC255676
0.8515	High Similarity	NPC160548
0.8515	High Similarity	NPC175852
0.8515	High Similarity	NPC210529
0.8447	Intermediate Similarity	NPC25458
0.8426	Intermediate Similarity	NPC212718
0.84	Intermediate Similarity	NPC206764
0.8396	Intermediate Similarity	NPC141523
0.8393	Intermediate Similarity	NPC249435
0.8381	Intermediate Similarity	NPC105899
0.8333	Intermediate Similarity	NPC317280
0.8333	Intermediate Similarity	NPC329387
0.8283	Intermediate Similarity	NPC110704
0.8252	Intermediate Similarity	NPC217621
0.8208	Intermediate Similarity	NPC134120
0.8198	Intermediate Similarity	NPC285350
0.819	Intermediate Similarity	NPC160382
0.8182	Intermediate Similarity	NPC62765
0.8173	Intermediate Similarity	NPC42211
0.8158	Intermediate Similarity	NPC472708
0.8155	Intermediate Similarity	NPC229242
0.8148	Intermediate Similarity	NPC17525
0.8148	Intermediate Similarity	NPC318327
0.8119	Intermediate Similarity	NPC34243
0.8119	Intermediate Similarity	NPC261181
0.8108	Intermediate Similarity	NPC11824
0.81	Intermediate Similarity	NPC141607
0.81	Intermediate Similarity	NPC187725
0.8095	Intermediate Similarity	NPC304873
0.8091	Intermediate Similarity	NPC114682
0.8077	Intermediate Similarity	NPC118343
0.8058	Intermediate Similarity	NPC156021
0.8058	Intermediate Similarity	NPC253423
0.8019	Intermediate Similarity	NPC274443
0.8019	Intermediate Similarity	NPC329556
0.8018	Intermediate Similarity	NPC272524
0.8017	Intermediate Similarity	NPC472981
0.8	Intermediate Similarity	NPC476003
0.8	Intermediate Similarity	NPC116842
0.8	Intermediate Similarity	NPC21162
0.8	Intermediate Similarity	NPC252544
0.8	Intermediate Similarity	NPC474057
0.8	Intermediate Similarity	NPC321252
0.7966	Intermediate Similarity	NPC285394
0.7965	Intermediate Similarity	NPC23402
0.7965	Intermediate Similarity	NPC322197
0.7963	Intermediate Similarity	NPC69332
0.7963	Intermediate Similarity	NPC29989
0.7963	Intermediate Similarity	NPC95178
0.7961	Intermediate Similarity	NPC61944
0.7928	Intermediate Similarity	NPC268388
0.7928	Intermediate Similarity	NPC66208
0.7928	Intermediate Similarity	NPC177576
0.7925	Intermediate Similarity	NPC244427
0.7925	Intermediate Similarity	NPC284477
0.7925	Intermediate Similarity	NPC222390
0.7921	Intermediate Similarity	NPC317645
0.7913	Intermediate Similarity	NPC184527
0.7909	Intermediate Similarity	NPC95172
0.7909	Intermediate Similarity	NPC88141
0.7905	Intermediate Similarity	NPC228435
0.7895	Intermediate Similarity	NPC158157
0.789	Intermediate Similarity	NPC34715
0.789	Intermediate Similarity	NPC226699
0.7876	Intermediate Similarity	NPC306740
0.787	Intermediate Similarity	NPC172483
0.7869	Intermediate Similarity	NPC102829
0.7869	Intermediate Similarity	NPC120488
0.7845	Intermediate Similarity	NPC473767
0.7835	Intermediate Similarity	NPC273758
0.783	Intermediate Similarity	NPC282895
0.7818	Intermediate Similarity	NPC224584
0.7812	Intermediate Similarity	NPC117180
0.7812	Intermediate Similarity	NPC12936
0.7812	Intermediate Similarity	NPC273033
0.7798	Intermediate Similarity	NPC6984
0.7798	Intermediate Similarity	NPC70843
0.7788	Intermediate Similarity	NPC12695
0.7788	Intermediate Similarity	NPC474363
0.7778	Intermediate Similarity	NPC261573
0.7778	Intermediate Similarity	NPC7151
0.7778	Intermediate Similarity	NPC216297
0.7778	Intermediate Similarity	NPC473662
0.7778	Intermediate Similarity	NPC120693
0.7778	Intermediate Similarity	NPC318107
0.7778	Intermediate Similarity	NPC8931
0.7768	Intermediate Similarity	NPC474314
0.7768	Intermediate Similarity	NPC471188
0.7768	Intermediate Similarity	NPC186128
0.7759	Intermediate Similarity	NPC41567
0.7759	Intermediate Similarity	NPC318173
0.7755	Intermediate Similarity	NPC304538
0.775	Intermediate Similarity	NPC295664
0.7732	Intermediate Similarity	NPC329319
0.7732	Intermediate Similarity	NPC103326
0.7732	Intermediate Similarity	NPC87299
0.7732	Intermediate Similarity	NPC99394
0.7731	Intermediate Similarity	NPC65627
0.7731	Intermediate Similarity	NPC223351
0.7727	Intermediate Similarity	NPC470391
0.7727	Intermediate Similarity	NPC203732
0.7727	Intermediate Similarity	NPC249811
0.7719	Intermediate Similarity	NPC474685
0.7719	Intermediate Similarity	NPC186933
0.7719	Intermediate Similarity	NPC93181
0.7714	Intermediate Similarity	NPC249912
0.7714	Intermediate Similarity	NPC92754
0.7714	Intermediate Similarity	NPC276775
0.7712	Intermediate Similarity	NPC216216
0.7708	Intermediate Similarity	NPC71664
0.7706	Intermediate Similarity	NPC269457
0.77	Intermediate Similarity	NPC194326
0.7699	Intermediate Similarity	NPC128368
0.7692	Intermediate Similarity	NPC130398
0.7685	Intermediate Similarity	NPC474365
0.7685	Intermediate Similarity	NPC301943
0.7679	Intermediate Similarity	NPC260818
0.7679	Intermediate Similarity	NPC210089
0.7677	Intermediate Similarity	NPC95965
0.7677	Intermediate Similarity	NPC99482
0.7677	Intermediate Similarity	NPC123476
0.7664	Intermediate Similarity	NPC112552
0.7658	Intermediate Similarity	NPC265407
0.7658	Intermediate Similarity	NPC317305
0.7658	Intermediate Similarity	NPC83628
0.7658	Intermediate Similarity	NPC469636
0.7658	Intermediate Similarity	NPC85493
0.7647	Intermediate Similarity	NPC295034
0.7642	Intermediate Similarity	NPC225060
0.7642	Intermediate Similarity	NPC35448
0.7642	Intermediate Similarity	NPC78701
0.7636	Intermediate Similarity	NPC188677
0.7632	Intermediate Similarity	NPC242136
0.7632	Intermediate Similarity	NPC477411
0.7627	Intermediate Similarity	NPC473136
0.7627	Intermediate Similarity	NPC473243
0.7627	Intermediate Similarity	NPC159525
0.7615	Intermediate Similarity	NPC242913
0.7615	Intermediate Similarity	NPC171831
0.7615	Intermediate Similarity	NPC280616
0.7611	Intermediate Similarity	NPC321852
0.7611	Intermediate Similarity	NPC79496
0.7603	Intermediate Similarity	NPC74507
0.7603	Intermediate Similarity	NPC164014
0.7603	Intermediate Similarity	NPC234890
0.7593	Intermediate Similarity	NPC320891
0.7589	Intermediate Similarity	NPC326187
0.7586	Intermediate Similarity	NPC325646
0.7586	Intermediate Similarity	NPC28951
0.7583	Intermediate Similarity	NPC86900
0.7583	Intermediate Similarity	NPC217756
0.7573	Intermediate Similarity	NPC476484
0.757	Intermediate Similarity	NPC146351
0.757	Intermediate Similarity	NPC280869
0.7568	Intermediate Similarity	NPC303264
0.7563	Intermediate Similarity	NPC248363
0.7551	Intermediate Similarity	NPC475199
0.7551	Intermediate Similarity	NPC283012
0.7549	Intermediate Similarity	NPC231591
0.7549	Intermediate Similarity	NPC199567
0.7547	Intermediate Similarity	NPC103048
0.7547	Intermediate Similarity	NPC270654
0.7545	Intermediate Similarity	NPC13495
0.7545	Intermediate Similarity	NPC163734
0.7545	Intermediate Similarity	NPC219913
0.7544	Intermediate Similarity	NPC161611
0.7542	Intermediate Similarity	NPC158222
0.7542	Intermediate Similarity	NPC204784
0.7542	Intermediate Similarity	NPC188814
0.7542	Intermediate Similarity	NPC476645
0.7542	Intermediate Similarity	NPC195262
0.7541	Intermediate Similarity	NPC275576
0.7541	Intermediate Similarity	NPC236405
0.7525	Intermediate Similarity	NPC69057
0.7523	Intermediate Similarity	NPC135784
0.7523	Intermediate Similarity	NPC60679
0.7522	Intermediate Similarity	NPC265513
0.7522	Intermediate Similarity	NPC474157
0.7521	Intermediate Similarity	NPC80605
0.7521	Intermediate Similarity	NPC471466
0.7521	Intermediate Similarity	NPC228739
0.7521	Intermediate Similarity	NPC323440
0.7521	Intermediate Similarity	NPC222968
0.75	Intermediate Similarity	NPC120545
0.75	Intermediate Similarity	NPC301857
0.75	Intermediate Similarity	NPC130899
0.75	Intermediate Similarity	NPC61153
0.75	Intermediate Similarity	NPC283590
0.75	Intermediate Similarity	NPC70624
0.75	Intermediate Similarity	NPC31936
0.75	Intermediate Similarity	NPC156139
0.75	Intermediate Similarity	NPC226093
0.75	Intermediate Similarity	NPC475282
0.75	Intermediate Similarity	NPC70859
0.75	Intermediate Similarity	NPC161304
0.748	Intermediate Similarity	NPC169913

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 NPC249067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	901
0.2-0.3	1203
0.3-0.4	2685
0.4-0.5	2513
0.5-0.6	1210
0.6-0.7	328
0.7-0.8	68
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1237	Approved
0.8515	High Similarity	NPD9495	Approved
0.8182	Intermediate Similarity	NPD9256	Approved
0.8182	Intermediate Similarity	NPD9258	Approved
0.8119	Intermediate Similarity	NPD1202	Approved
0.8077	Intermediate Similarity	NPD1238	Approved
0.8019	Intermediate Similarity	NPD1929	Approved
0.8019	Intermediate Similarity	NPD1930	Approved
0.8019	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD5157	Phase 1
0.7966	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD5159	Phase 2
0.7876	Intermediate Similarity	NPD2629	Approved
0.7818	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD942	Approved
0.7778	Intermediate Similarity	NPD9257	Approved
0.7778	Intermediate Similarity	NPD9259	Approved
0.7757	Intermediate Similarity	NPD1932	Approved
0.7736	Intermediate Similarity	NPD2066	Phase 3
0.7719	Intermediate Similarity	NPD5951	Approved
0.7573	Intermediate Similarity	NPD1239	Approved
0.7522	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD9491	Approved
0.7438	Intermediate Similarity	NPD4878	Approved
0.7414	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD9294	Approved
0.7364	Intermediate Similarity	NPD6647	Phase 2
0.7358	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1201	Approved
0.7355	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2329	Discontinued
0.7333	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7008	Discontinued
0.7297	Intermediate Similarity	NPD164	Approved
0.7288	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4106	Approved
0.7273	Intermediate Similarity	NPD4136	Approved
0.7273	Intermediate Similarity	NPD4135	Approved
0.7264	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD9263	Approved
0.7257	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9264	Approved
0.7257	Intermediate Similarity	NPD9267	Approved
0.7232	Intermediate Similarity	NPD5048	Discontinued
0.7222	Intermediate Similarity	NPD1565	Approved
0.7222	Intermediate Similarity	NPD1566	Phase 3
0.7222	Intermediate Similarity	NPD1564	Approved
0.7212	Intermediate Similarity	NPD800	Approved
0.72	Intermediate Similarity	NPD4980	Approved
0.7196	Intermediate Similarity	NPD1693	Approved
0.7196	Intermediate Similarity	NPD9260	Approved
0.7193	Intermediate Similarity	NPD2182	Approved
0.7193	Intermediate Similarity	NPD74	Approved
0.7193	Intermediate Similarity	NPD9266	Approved
0.719	Intermediate Similarity	NPD5306	Approved
0.719	Intermediate Similarity	NPD5305	Approved
0.717	Intermediate Similarity	NPD1508	Approved
0.7167	Intermediate Similarity	NPD9545	Approved
0.7165	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD9508	Approved
0.7154	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1090	Approved
0.7143	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD1086	Approved
0.7143	Intermediate Similarity	NPD5909	Discontinued
0.7143	Intermediate Similarity	NPD9493	Approved
0.7131	Intermediate Similarity	NPD4879	Approved
0.713	Intermediate Similarity	NPD1989	Approved
0.712	Intermediate Similarity	NPD1164	Approved
0.7107	Intermediate Similarity	NPD4102	Approved
0.7107	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4105	Approved
0.71	Intermediate Similarity	NPD226	Approved
0.7094	Intermediate Similarity	NPD5277	Phase 2
0.7073	Intermediate Similarity	NPD4807	Approved
0.7073	Intermediate Similarity	NPD4806	Approved
0.7073	Intermediate Similarity	NPD6287	Discontinued
0.7071	Intermediate Similarity	NPD9490	Approved
0.7054	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1241	Discontinued
0.7019	Intermediate Similarity	NPD650	Approved
0.7016	Intermediate Similarity	NPD3972	Approved
0.7009	Intermediate Similarity	NPD1088	Approved
0.7008	Intermediate Similarity	NPD5204	Approved
0.7	Intermediate Similarity	NPD1240	Approved
0.6983	Remote Similarity	NPD2067	Discontinued
0.6975	Remote Similarity	NPD1246	Approved
0.6972	Remote Similarity	NPD2859	Approved
0.6972	Remote Similarity	NPD1843	Approved
0.6972	Remote Similarity	NPD2860	Approved
0.6953	Remote Similarity	NPD5201	Approved
0.6953	Remote Similarity	NPD5203	Approved
0.6953	Remote Similarity	NPD4617	Approved
0.6953	Remote Similarity	NPD4620	Approved
0.6944	Remote Similarity	NPD1563	Approved
0.6929	Remote Similarity	NPD2798	Approved
0.6917	Remote Similarity	NPD1510	Phase 2
0.6916	Remote Similarity	NPD7609	Phase 3
0.6911	Remote Similarity	NPD2345	Approved
0.6911	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1876	Approved
0.6903	Remote Similarity	NPD9261	Approved
0.6903	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6039	Approved
0.6894	Remote Similarity	NPD1607	Approved
0.6889	Remote Similarity	NPD1549	Phase 2
0.6881	Remote Similarity	NPD2933	Approved
0.6881	Remote Similarity	NPD2934	Approved
0.687	Remote Similarity	NPD4453	Approved
0.687	Remote Similarity	NPD4452	Approved
0.687	Remote Similarity	NPD943	Approved
0.687	Remote Similarity	NPD4445	Approved
0.6857	Remote Similarity	NPD1087	Approved
0.6857	Remote Similarity	NPD4793	Discontinued
0.6852	Remote Similarity	NPD7631	Approved
0.685	Remote Similarity	NPD2628	Approved
0.685	Remote Similarity	NPD2625	Approved
0.685	Remote Similarity	NPD2159	Approved
0.685	Remote Similarity	NPD1203	Approved
0.685	Remote Similarity	NPD2626	Approved
0.685	Remote Similarity	NPD2160	Approved
0.685	Remote Similarity	NPD2627	Approved
0.6846	Remote Similarity	NPD2313	Discontinued
0.6846	Remote Similarity	NPD3764	Approved
0.6838	Remote Similarity	NPD1317	Discontinued
0.6833	Remote Similarity	NPD9281	Approved
0.6822	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7236	Approved
0.681	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.68	Remote Similarity	NPD227	Approved
0.68	Remote Similarity	NPD225	Approved
0.6794	Remote Similarity	NPD7713	Phase 3
0.6788	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD3020	Approved
0.6772	Remote Similarity	NPD1888	Phase 1
0.6769	Remote Similarity	NPD6966	Discovery
0.6757	Remote Similarity	NPD3495	Discontinued
0.6748	Remote Similarity	NPD1894	Discontinued
0.6742	Remote Similarity	NPD5119	Approved
0.6742	Remote Similarity	NPD6309	Approved
0.6742	Remote Similarity	NPD6310	Approved
0.6742	Remote Similarity	NPD6311	Approved
0.6742	Remote Similarity	NPD5121	Approved
0.6742	Remote Similarity	NPD5120	Approved
0.6729	Remote Similarity	NPD5347	Phase 2
0.6729	Remote Similarity	NPD5346	Phase 2
0.6718	Remote Similarity	NPD4621	Approved
0.6718	Remote Similarity	NPD4619	Approved
0.6715	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD9609	Approved
0.6696	Remote Similarity	NPD9611	Approved
0.6696	Remote Similarity	NPD9612	Approved
0.6694	Remote Similarity	NPD1245	Approved
0.6693	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7715	Approved
0.6667	Remote Similarity	NPD9716	Approved
0.6641	Remote Similarity	NPD2199	Approved
0.6641	Remote Similarity	NPD1574	Approved
0.6641	Remote Similarity	NPD2198	Approved
0.6641	Remote Similarity	NPD5667	Approved
0.664	Remote Similarity	NPD1104	Approved
0.664	Remote Similarity	NPD2932	Approved
0.664	Remote Similarity	NPD3019	Approved
0.664	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4198	Discontinued
0.6639	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7798	Approved
0.662	Remote Similarity	NPD5403	Approved
0.6618	Remote Similarity	NPD2935	Discontinued
0.6615	Remote Similarity	NPD3663	Approved
0.6615	Remote Similarity	NPD3662	Phase 3
0.6615	Remote Similarity	NPD3661	Approved
0.6615	Remote Similarity	NPD3664	Approved
0.6614	Remote Similarity	NPD9717	Approved
0.6613	Remote Similarity	NPD7009	Phase 2
0.6612	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5401	Approved
0.6591	Remote Similarity	NPD6798	Discontinued
0.6589	Remote Similarity	NPD2797	Approved
0.6589	Remote Similarity	NPD1593	Approved
0.6587	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD969	Suspended
0.6579	Remote Similarity	NPD1616	Discontinued
0.6579	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7239	Suspended
0.6569	Remote Similarity	NPD2344	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