NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.12
Volume:	199.927
LogP:	3.277
LogD:	3.267
LogS:	-2.945
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	1.817
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.6
MDCK Permeability:	1.8931143131339923e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	94.86991119384766%
Volume Distribution (VD):	3.913
Pgp-substrate:	9.227931022644043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.795
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.447
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	10.073
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.292
Skin Sensitization:	0.861
Carcinogencity:	0.086
Eye Corrosion:	0.974
Eye Irritation:	0.988
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC275627

Natural Product ID:	NPC275627
*Common Name:**	Butylated Hydroxyanisole
IUPAC Name:	2-tert-butyl-4-methoxyphenol
Synonyms:	Butylated Hydroxyanisole; E320
Standard InCHIKey:	MRBKEAMVRSLQPH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3
SMILES:	CC(C)(C)c1cc(ccc1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL192451
PubChem CID:	8456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[22703163]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[24328283]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[24704554]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32935986]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23548	Leonurus heterophyllus	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	13
Others	32
Potency	33

Activity Type	# Activity
Individual Protein	14
NON-MOLECULAR	1
Organism	9
Others	53
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	14125.4	nM	PMID[453827]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	22387.2	nM	PMID[453828]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	19952.6	nM	PMID[453827]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[453827]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	34376.2	nM	PMID[453830]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[453827]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	15386.5	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61810.8	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	55088.9	nM	PubChem BioAssay data set
NPT1	Others	Radical scavenging activity		Activity	=	92.6	%	PMID[453826]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[453827]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[453827]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	16511.3	nM	PMID[453827]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[453827]
NPT702	Individual Protein	UDP-glucuronosyltransferase 1-6	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[453829]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Activity	=	500.0	pm/min/mg	PMID[453829]
NPT1	Others	Radical scavenging activity		Activity	=	92.6	%	PMID[453831]
NPT610	Others	Molecular identity unknown		Potency	n.a.	50118.7	nM	PMID[453830]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[453828]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	10.0	%	PMID[453832]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.7	g/day	PMID[453832]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	7.4	g	PMID[453832]
NPT32	Organism	Mus musculus	Mus musculus	TGI	=	50.0	%	PMID[453832]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FC	=	0.4	n.a.	PMID[453832]
NPT35	Others	n.a.		IC50	=	19000.0	nM	PMID[453833]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.99	%	PMID[453834]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.26	%	PMID[453835]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.01	%	PMID[453836]
NPT1	Others	Radical scavenging activity		IC50	=	4.5	ug/ml	PMID[11170672]
NPT1	Others	Radical scavenging activity		IC50	=	21	ug/ml	PMID[11141121]
NPT1	Others	Radical scavenging activity		IC50	=	43000	nM	PMID[19464173]
NPT1	Others	Radical scavenging activity		IC50	=	79160	nM	PMID[18986201]
NPT1	Others	Radical scavenging activity		IC50	=	16.67	ug/ml	PMID[19683932]
NPT2	Others	Unspecified		IC50	=	4.65	ug/ml	PMID[19683932]
NPT2	Others	Unspecified		IC50	=	32.92	ug/ml	PMID[19683932]
NPT2	Others	Unspecified		IC50	=	68.82	ug/ml	PMID[19683932]
NPT2	Others	Unspecified		IC50	=	2.65	ug/ml	PMID[19683932]
NPT1	Others	Radical scavenging activity		IC50	=	29	ug/ml	PMID[20034709]
NPT1	Others	Radical scavenging activity		Activity	=	72.34	%	PMID[20403702]
NPT1	Others	Radical scavenging activity		Activity	=	62	%	PMID[20542693]
NPT2	Others	Unspecified		Activity	=	86	%	PMID[20542693]
NPT35	Others	n.a.		Activity	=	79.1	%	PMID[20947350]
NPT1	Others	Radical scavenging activity		Activity	=	170	ug	PMID[20947350]
NPT2	Others	Unspecified		Activity	=	16.1	ug	PMID[20947350]
NPT2	Others	Unspecified		Activity	=	748.7	nmol	PMID[20947350]
NPT2	Others	Unspecified		Activity	=	8052.7	nmol	PMID[20947350]
NPT2	Others	Unspecified		Activity	=	76.5	%	PMID[20947350]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	0	pm/min/mg	PMID[10836148]
NPT1	Others	Radical scavenging activity		IC50	=	14.35	ug/ml	DOI[10.1007/s00044-011-9915-7]
NPT1	Others	Radical scavenging activity		IC50	=	28200	nM	PMID[24185379]
NPT2	Others	Unspecified		Potency	n.a.	6872.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49098	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30700.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55088.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61254.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27361.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	61810.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68729.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61810.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Inhibition	=	12.02	%	PMID[26631319]
NPT2	Others	Unspecified		Inhibition	=	17.95	%	PMID[26631319]
NPT2	Others	Unspecified		Inhibition	=	25.58	%	PMID[26631319]
NPT2	Others	Unspecified		Inhibition	=	32.03	%	PMID[26631319]
NPT2	Others	Unspecified		Activity	=	13.87	%	PMID[27318538]
NPT2	Others	Unspecified		Activity	=	17.95	%	PMID[27318538]
NPT2	Others	Unspecified		Activity	=	25.58	%	PMID[27318538]
NPT2	Others	Unspecified		Activity	=	32.03	%	PMID[27318538]
NPT2	Others	Unspecified		Activity	=	36.87	%	PMID[27318538]

☑ 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 NPC275627 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	286
0.1-0.2	1883
0.2-0.3	4557
0.3-0.4	13201
0.4-0.5	5196
0.5-0.6	7744
0.6-0.7	7444
0.7-0.8	2123
0.8-0.85	217
0.85-0.9	40
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC98372
0.9612	High Similarity	NPC233320
0.9107	High Similarity	NPC471449
0.8972	High Similarity	NPC241549
0.8962	High Similarity	NPC30416
0.8868	High Similarity	NPC47284
0.8857	High Similarity	NPC269212
0.8818	High Similarity	NPC474920
0.8796	High Similarity	NPC75440
0.8785	High Similarity	NPC53740
0.8783	High Similarity	NPC129176
0.8774	High Similarity	NPC130817
0.8772	High Similarity	NPC51341
0.875	High Similarity	NPC473718
0.8704	High Similarity	NPC320439
0.8684	High Similarity	NPC283616
0.8679	High Similarity	NPC12870
0.8679	High Similarity	NPC24327
0.8673	High Similarity	NPC69539
0.8667	High Similarity	NPC248396
0.8667	High Similarity	NPC48730
0.8667	High Similarity	NPC129373
0.8661	High Similarity	NPC470837
0.8654	High Similarity	NPC152097
0.8644	High Similarity	NPC248557
0.8621	High Similarity	NPC100108
0.8621	High Similarity	NPC277798
0.8611	High Similarity	NPC155072
0.8609	High Similarity	NPC32152
0.8596	High Similarity	NPC187993
0.8596	High Similarity	NPC238176
0.8584	High Similarity	NPC808
0.8571	High Similarity	NPC33675
0.8571	High Similarity	NPC260775
0.8571	High Similarity	NPC35344
0.8571	High Similarity	NPC299762
0.8571	High Similarity	NPC141003
0.8559	High Similarity	NPC195873
0.8544	High Similarity	NPC152415
0.8534	High Similarity	NPC474131
0.8534	High Similarity	NPC232295
0.8509	High Similarity	NPC290470
0.8509	High Similarity	NPC154256
0.8509	High Similarity	NPC150624
0.8505	High Similarity	NPC108497
0.8491	Intermediate Similarity	NPC130756
0.8491	Intermediate Similarity	NPC12931
0.8491	Intermediate Similarity	NPC70677
0.8482	Intermediate Similarity	NPC228452
0.8476	Intermediate Similarity	NPC475078
0.8476	Intermediate Similarity	NPC470161
0.8468	Intermediate Similarity	NPC168657
0.8462	Intermediate Similarity	NPC475529
0.8462	Intermediate Similarity	NPC45663
0.8462	Intermediate Similarity	NPC96423
0.8462	Intermediate Similarity	NPC473875
0.8455	Intermediate Similarity	NPC201959
0.8447	Intermediate Similarity	NPC55903
0.8447	Intermediate Similarity	NPC29373
0.844	Intermediate Similarity	NPC113457
0.8435	Intermediate Similarity	NPC244816
0.8435	Intermediate Similarity	NPC50521
0.8435	Intermediate Similarity	NPC221549
0.8435	Intermediate Similarity	NPC69261
0.8435	Intermediate Similarity	NPC33270
0.8426	Intermediate Similarity	NPC474603
0.8426	Intermediate Similarity	NPC12987
0.8426	Intermediate Similarity	NPC475225
0.8426	Intermediate Similarity	NPC475580
0.8421	Intermediate Similarity	NPC232165
0.8421	Intermediate Similarity	NPC301321
0.8421	Intermediate Similarity	NPC283169
0.8417	Intermediate Similarity	NPC252962
0.8411	Intermediate Similarity	NPC252105
0.8411	Intermediate Similarity	NPC477685
0.8411	Intermediate Similarity	NPC12221
0.8393	Intermediate Similarity	NPC54373
0.8393	Intermediate Similarity	NPC266937
0.8393	Intermediate Similarity	NPC77772
0.8393	Intermediate Similarity	NPC470770
0.839	Intermediate Similarity	NPC48623
0.839	Intermediate Similarity	NPC168707
0.8362	Intermediate Similarity	NPC63010
0.8362	Intermediate Similarity	NPC190514
0.8361	Intermediate Similarity	NPC176590
0.8361	Intermediate Similarity	NPC47288
0.835	Intermediate Similarity	NPC306074
0.8333	Intermediate Similarity	NPC471228
0.8333	Intermediate Similarity	NPC235762
0.8333	Intermediate Similarity	NPC61685
0.8333	Intermediate Similarity	NPC276737
0.8333	Intermediate Similarity	NPC22610
0.8319	Intermediate Similarity	NPC46586
0.8319	Intermediate Similarity	NPC204535
0.8319	Intermediate Similarity	NPC49441
0.8319	Intermediate Similarity	NPC62867
0.8319	Intermediate Similarity	NPC135414
0.8319	Intermediate Similarity	NPC474864
0.8319	Intermediate Similarity	NPC177962
0.8318	Intermediate Similarity	NPC174911
0.8318	Intermediate Similarity	NPC130103
0.8318	Intermediate Similarity	NPC72729
0.8306	Intermediate Similarity	NPC153019
0.8302	Intermediate Similarity	NPC79241
0.8302	Intermediate Similarity	NPC474073
0.8302	Intermediate Similarity	NPC6597
0.8293	Intermediate Similarity	NPC206028
0.8291	Intermediate Similarity	NPC184302
0.8288	Intermediate Similarity	NPC169450
0.8286	Intermediate Similarity	NPC222146
0.8273	Intermediate Similarity	NPC310456
0.8261	Intermediate Similarity	NPC167934
0.8261	Intermediate Similarity	NPC53906
0.8257	Intermediate Similarity	NPC272029
0.825	Intermediate Similarity	NPC474130
0.825	Intermediate Similarity	NPC261992
0.8241	Intermediate Similarity	NPC80800
0.8235	Intermediate Similarity	NPC475839
0.8235	Intermediate Similarity	NPC476165
0.8235	Intermediate Similarity	NPC285289
0.823	Intermediate Similarity	NPC156840
0.823	Intermediate Similarity	NPC8547
0.823	Intermediate Similarity	NPC173746
0.823	Intermediate Similarity	NPC257124
0.8224	Intermediate Similarity	NPC252821
0.8224	Intermediate Similarity	NPC122005
0.8224	Intermediate Similarity	NPC100870
0.8214	Intermediate Similarity	NPC473524
0.8208	Intermediate Similarity	NPC259512
0.8208	Intermediate Similarity	NPC312132
0.8205	Intermediate Similarity	NPC329980
0.8205	Intermediate Similarity	NPC139047
0.8198	Intermediate Similarity	NPC66834
0.8197	Intermediate Similarity	NPC112596
0.8197	Intermediate Similarity	NPC245060
0.819	Intermediate Similarity	NPC27323
0.819	Intermediate Similarity	NPC316301
0.819	Intermediate Similarity	NPC289769
0.819	Intermediate Similarity	NPC245187
0.819	Intermediate Similarity	NPC141090
0.8182	Intermediate Similarity	NPC190086
0.8182	Intermediate Similarity	NPC276962
0.8182	Intermediate Similarity	NPC147896
0.8175	Intermediate Similarity	NPC211352
0.8167	Intermediate Similarity	NPC188997
0.8167	Intermediate Similarity	NPC152946
0.8167	Intermediate Similarity	NPC246967
0.8167	Intermediate Similarity	NPC77789
0.8167	Intermediate Similarity	NPC18128
0.8167	Intermediate Similarity	NPC302211
0.8165	Intermediate Similarity	NPC233827
0.816	Intermediate Similarity	NPC258073
0.8158	Intermediate Similarity	NPC26615
0.8158	Intermediate Similarity	NPC302371
0.8151	Intermediate Similarity	NPC102639
0.8148	Intermediate Similarity	NPC225506
0.8145	Intermediate Similarity	NPC266868
0.8145	Intermediate Similarity	NPC190144
0.8142	Intermediate Similarity	NPC137685
0.8136	Intermediate Similarity	NPC121866
0.8136	Intermediate Similarity	NPC281298
0.8136	Intermediate Similarity	NPC310338
0.8131	Intermediate Similarity	NPC88420
0.8125	Intermediate Similarity	NPC306295
0.812	Intermediate Similarity	NPC164386
0.812	Intermediate Similarity	NPC219070
0.812	Intermediate Similarity	NPC470759
0.812	Intermediate Similarity	NPC195466
0.812	Intermediate Similarity	NPC127894
0.812	Intermediate Similarity	NPC474933
0.812	Intermediate Similarity	NPC15860
0.812	Intermediate Similarity	NPC320864
0.812	Intermediate Similarity	NPC293619
0.8115	Intermediate Similarity	NPC76119
0.8115	Intermediate Similarity	NPC133407
0.8115	Intermediate Similarity	NPC28476
0.8115	Intermediate Similarity	NPC477213
0.8115	Intermediate Similarity	NPC4286
0.8108	Intermediate Similarity	NPC164576
0.8108	Intermediate Similarity	NPC469913
0.8108	Intermediate Similarity	NPC54765
0.8099	Intermediate Similarity	NPC248786
0.8095	Intermediate Similarity	NPC94139
0.8095	Intermediate Similarity	NPC147284
0.8095	Intermediate Similarity	NPC162314
0.8095	Intermediate Similarity	NPC3358
0.8095	Intermediate Similarity	NPC27578
0.8095	Intermediate Similarity	NPC210497
0.8095	Intermediate Similarity	NPC85595
0.8095	Intermediate Similarity	NPC251549
0.8095	Intermediate Similarity	NPC289624
0.8095	Intermediate Similarity	NPC306884
0.8095	Intermediate Similarity	NPC51262
0.8091	Intermediate Similarity	NPC38079
0.8091	Intermediate Similarity	NPC108875
0.8087	Intermediate Similarity	NPC190212
0.8083	Intermediate Similarity	NPC476633
0.808	Intermediate Similarity	NPC192687
0.808	Intermediate Similarity	NPC224157
0.808	Intermediate Similarity	NPC325003

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 NPC275627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	1084
0.2-0.3	1513
0.3-0.4	2678
0.4-0.5	1809
0.5-0.6	1089
0.6-0.7	560
0.7-0.8	109
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9029	High Similarity	NPD289	Clinical (unspecified phase)
0.8919	High Similarity	NPD6671	Approved
0.8333	Intermediate Similarity	NPD6696	Suspended
0.8305	Intermediate Similarity	NPD3496	Discontinued
0.8286	Intermediate Similarity	NPD844	Approved
0.8273	Intermediate Similarity	NPD968	Approved
0.823	Intermediate Similarity	NPD228	Approved
0.8208	Intermediate Similarity	NPD288	Approved
0.819	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD2861	Phase 2
0.8099	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD1398	Phase 1
0.8067	Intermediate Similarity	NPD4626	Approved
0.8058	Intermediate Similarity	NPD9295	Approved
0.8017	Intermediate Similarity	NPD2233	Approved
0.8017	Intermediate Similarity	NPD2230	Approved
0.8017	Intermediate Similarity	NPD2232	Approved
0.7949	Intermediate Similarity	NPD7157	Approved
0.7944	Intermediate Similarity	NPD1809	Phase 2
0.7925	Intermediate Similarity	NPD845	Approved
0.7917	Intermediate Similarity	NPD1778	Approved
0.7903	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7340	Approved
0.7876	Intermediate Similarity	NPD290	Approved
0.7845	Intermediate Similarity	NPD7635	Approved
0.7807	Intermediate Similarity	NPD2684	Approved
0.7805	Intermediate Similarity	NPD4749	Approved
0.7797	Intermediate Similarity	NPD709	Approved
0.7795	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD600	Approved
0.7778	Intermediate Similarity	NPD596	Approved
0.7727	Intermediate Similarity	NPD3020	Approved
0.7692	Intermediate Similarity	NPD1138	Approved
0.7686	Intermediate Similarity	NPD5691	Approved
0.7686	Intermediate Similarity	NPD1357	Approved
0.7642	Intermediate Similarity	NPD1611	Approved
0.7642	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD4624	Approved
0.7615	Intermediate Similarity	NPD2860	Approved
0.7615	Intermediate Similarity	NPD2859	Approved
0.7607	Intermediate Similarity	NPD1137	Approved
0.7607	Intermediate Similarity	NPD1139	Approved
0.7597	Intermediate Similarity	NPD839	Approved
0.7597	Intermediate Similarity	NPD840	Approved
0.7589	Intermediate Similarity	NPD846	Approved
0.7589	Intermediate Similarity	NPD940	Approved
0.7586	Intermediate Similarity	NPD4750	Phase 3
0.7578	Intermediate Similarity	NPD4625	Phase 3
0.7559	Intermediate Similarity	NPD1712	Approved
0.7557	Intermediate Similarity	NPD4097	Suspended
0.7542	Intermediate Similarity	NPD821	Approved
0.7542	Intermediate Similarity	NPD7843	Approved
0.7541	Intermediate Similarity	NPD5585	Approved
0.7538	Intermediate Similarity	NPD4060	Phase 1
0.7523	Intermediate Similarity	NPD2934	Approved
0.7523	Intermediate Similarity	NPD2933	Approved
0.7519	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD4908	Phase 1
0.748	Intermediate Similarity	NPD2668	Approved
0.748	Intermediate Similarity	NPD6584	Phase 3
0.748	Intermediate Similarity	NPD2667	Approved
0.7478	Intermediate Similarity	NPD1444	Approved
0.7478	Intermediate Similarity	NPD1445	Approved
0.7459	Intermediate Similarity	NPD1548	Phase 1
0.7442	Intermediate Similarity	NPD3027	Phase 3
0.744	Intermediate Similarity	NPD2231	Phase 2
0.744	Intermediate Similarity	NPD2235	Phase 2
0.7436	Intermediate Similarity	NPD3021	Approved
0.7436	Intermediate Similarity	NPD3022	Approved
0.7436	Intermediate Similarity	NPD5451	Approved
0.7422	Intermediate Similarity	NPD2237	Approved
0.7405	Intermediate Similarity	NPD2238	Phase 2
0.7405	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3620	Phase 2
0.7398	Intermediate Similarity	NPD1651	Approved
0.7385	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1669	Approved
0.7381	Intermediate Similarity	NPD5327	Phase 3
0.7364	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD111	Approved
0.7323	Intermediate Similarity	NPD8651	Approved
0.7323	Intermediate Similarity	NPD1283	Approved
0.7317	Intermediate Similarity	NPD3091	Approved
0.7311	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7095	Approved
0.7302	Intermediate Similarity	NPD1608	Approved
0.7288	Intermediate Similarity	NPD1792	Phase 2
0.7287	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1793	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1791	Approved
0.7273	Intermediate Similarity	NPD4140	Approved
0.7273	Intermediate Similarity	NPD1613	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7265	Intermediate Similarity	NPD2342	Discontinued
0.7259	Intermediate Similarity	NPD6099	Approved
0.7259	Intermediate Similarity	NPD6100	Approved
0.7258	Intermediate Similarity	NPD3443	Approved
0.7258	Intermediate Similarity	NPD3444	Approved
0.7258	Intermediate Similarity	NPD3445	Approved
0.7244	Intermediate Similarity	NPD6582	Phase 2
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6583	Phase 3
0.7244	Intermediate Similarity	NPD4359	Approved
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7222	Intermediate Similarity	NPD1091	Approved
0.7218	Intermediate Similarity	NPD5735	Approved
0.7213	Intermediate Similarity	NPD6387	Discontinued
0.7213	Intermediate Similarity	NPD2557	Approved
0.7209	Intermediate Similarity	NPD3691	Phase 2
0.7209	Intermediate Similarity	NPD3690	Phase 2
0.7209	Intermediate Similarity	NPD7905	Discontinued
0.7207	Intermediate Similarity	NPD9296	Approved
0.719	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3134	Approved
0.7176	Intermediate Similarity	NPD1024	Discontinued
0.7165	Intermediate Similarity	NPD1481	Phase 2
0.7164	Intermediate Similarity	NPD6353	Approved
0.7164	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7131	Intermediate Similarity	NPD595	Approved
0.7131	Intermediate Similarity	NPD497	Approved
0.7131	Intermediate Similarity	NPD593	Approved
0.7119	Intermediate Similarity	NPD1358	Approved
0.7109	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5535	Approved
0.7097	Intermediate Similarity	NPD7644	Approved
0.7094	Intermediate Similarity	NPD9697	Approved
0.7087	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3705	Approved
0.7087	Intermediate Similarity	NPD3092	Approved
0.7087	Intermediate Similarity	NPD1281	Approved
0.7077	Intermediate Similarity	NPD2798	Approved
0.7077	Intermediate Similarity	NPD558	Phase 2
0.7068	Intermediate Similarity	NPD2674	Phase 3
0.7063	Intermediate Similarity	NPD3019	Approved
0.7063	Intermediate Similarity	NPD2932	Approved
0.7063	Intermediate Similarity	NPD4059	Approved
0.7063	Intermediate Similarity	NPD17	Approved
0.705	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD498	Approved
0.7049	Intermediate Similarity	NPD496	Approved
0.7049	Intermediate Similarity	NPD592	Approved
0.7049	Intermediate Similarity	NPD495	Approved
0.7049	Intermediate Similarity	NPD594	Approved
0.7043	Intermediate Similarity	NPD1242	Phase 1
0.7042	Intermediate Similarity	NPD6090	Discontinued
0.704	Intermediate Similarity	NPD1182	Approved
0.7037	Intermediate Similarity	NPD6653	Approved
0.7031	Intermediate Similarity	NPD1840	Phase 2
0.7031	Intermediate Similarity	NPD3972	Approved
0.7016	Intermediate Similarity	NPD9493	Approved
0.7007	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD4098	Discontinued
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6992	Remote Similarity	NPD3268	Approved
0.6992	Remote Similarity	NPD9614	Approved
0.6992	Remote Similarity	NPD9618	Approved
0.6992	Remote Similarity	NPD1039	Discontinued
0.699	Remote Similarity	NPD9088	Approved
0.6984	Remote Similarity	NPD3049	Approved
0.6978	Remote Similarity	NPD5177	Phase 3
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3685	Discontinued
0.6963	Remote Similarity	NPD6355	Discontinued
0.696	Remote Similarity	NPD5536	Phase 2
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6944	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7477	Discontinued
0.694	Remote Similarity	NPD4870	Approved
0.6937	Remote Similarity	NPD9365	Approved
0.6929	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD1751	Approved
0.6929	Remote Similarity	NPD5846	Approved
0.6929	Remote Similarity	NPD6516	Phase 2
0.6929	Remote Similarity	NPD3095	Discontinued
0.6929	Remote Similarity	NPD4589	Approved
0.6923	Remote Similarity	NPD2922	Phase 1
0.6923	Remote Similarity	NPD9500	Approved
0.6911	Remote Similarity	NPD1241	Discontinued
0.6911	Remote Similarity	NPD2234	Approved
0.6911	Remote Similarity	NPD2228	Approved
0.6911	Remote Similarity	NPD2229	Approved
0.6906	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7041	Phase 2
0.6899	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD5736	Approved
0.6894	Remote Similarity	NPD9494	Approved
0.6894	Remote Similarity	NPD3018	Phase 2
0.6889	Remote Similarity	NPD1240	Approved
0.688	Remote Similarity	NPD3596	Phase 2
0.6879	Remote Similarity	NPD3692	Discontinued
0.687	Remote Similarity	NPD987	Approved
0.687	Remote Similarity	NPD9273	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