NPASS Compound

Structure

CID165106 OpenBabel06191715532D 26 27 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -6.0622 0.5000 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 -5.1962 -3.0000 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 -6.0622 -2.5000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -6.0622 -1.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 2 1 1 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	391.297
LogP:	4.737
LogD:	4.257
LogS:	-5.057
# Rotatable Bonds:	9
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	2.626
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.94
MDCK Permeability:	2.261436566186603e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	90.75487518310547%
Volume Distribution (VD):	1.435
Pgp-substrate:	2.233783006668091%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	10.916
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.364
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.885
Carcinogencity:	0.221
Eye Corrosion:	0.015
Eye Irritation:	0.134
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC165106

Natural Product ID:	NPC165106
*Common Name:**	Terameprocol
IUPAC Name:	4-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
Synonyms:	EM-1421; Terameprocol
Standard InCHIKey:	ORQFDHFZSMXRLM-IYBDPMFKSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3/t15-,16+
SMILES:	COc1cc(ccc1OC)C[C@H]([C@H](Cc1ccc(c(c1)OC)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL90983
PubChem CID:	476861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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
EC50	1
ED50	1
GI50	6
IC50	28
MIC	8
Others	79

Activity Type	# Activity
Cell Line	60
CELL-LINE	1
NON-MOLECULAR	5
Organism	35
Others	20
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	11700.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4400.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	8240.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	5970.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6480.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6980.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	9910.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	8820.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4470.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4180.0	nM	PMID[476943]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	11080.0	nM	PMID[476943]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	18.5	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	25.3	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	45.0	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	61.0	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	70.0	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	78.7	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	Inhibition	=	90.3	%	PMID[476944]
NPT3886	Cell Line	COS-1	Chlorocebus aethiops	IC50	=	11090.0	nM	PMID[476944]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	28800.0	nM	PMID[476945]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	16600.0	nM	PMID[476946]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	23.0	%	PMID[476946]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	31.0	%	PMID[476946]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	42400.0	nM	PMID[476946]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	44500.0	nM	PMID[476946]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	61500.0	nM	PMID[476946]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	70.0	%	PMID[476946]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	2500.0	nM	PMID[476946]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	<=	10000.0	nM	PMID[476947]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	<=	10000.0	nM	PMID[476947]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<=	10000.0	nM	PMID[476947]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	<=	10000.0	nM	PMID[476947]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	170.7	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	168.0	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	331.5	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	615.3	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	477.8	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	597.2	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	5.87	ug.mL-1	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	79.64	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	52.93	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	33.16	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	5.06	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	-5.88	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Inhibition	=	-12.79	%	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	8.527	10'-5/min	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	1.971	10'-4/min	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	2.799	10'-4/min	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	3.976	10'-4/min	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	4.434	10'-4/min	PMID[476948]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	4.724	10'-4/min	PMID[476948]
NPT1125	Cell Line	T98G	Homo sapiens	GI50	>	50000.0	nM	PMID[476949]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	50000.0	nM	PMID[476949]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	5360.0	nM	PMID[476949]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	4540.0	nM	PMID[476949]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	17100.0	nM	PMID[476949]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	20000.0	nM	PMID[476956]
NPT2	Others	Unspecified		Selectivity index	=	13.7	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	36.4	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	19.4	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	26.8	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	24.7	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	22.9	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	16.1	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	18.1	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	33.5	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	38.3	n.a.	PMID[476943]
NPT2	Others	Unspecified		Selectivity index	=	14.4	n.a.	PMID[476943]
NPT27	Others	Unspecified		Mortality	=	0.0	n.a.	PMID[476943]
NPT27	Others	Unspecified		Mortality	=	1.0	n.a.	PMID[476943]
NPT32	Organism	Mus musculus	Mus musculus	Change	=	-2.66	%	PMID[476943]
NPT32	Organism	Mus musculus	Mus musculus	Change	=	-2.8	%	PMID[476943]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.0	n.a.	PMID[476945]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	14800.0	nM	PMID[476945]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5000.0	nM	PMID[476946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.0	%	PMID[476946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	94.0	%	PMID[476946]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	1000.0	mg.kg-1	PMID[476946]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<=	10000.0	nM	PMID[476947]
NPT35	Others	n.a.		Stability	=	503.0	mg/ml	PMID[476947]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	IC50	=	330.0	ug.mL-1	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	67.72	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	44.7	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	27.31	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	11.51	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	4.06	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	8.13	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Inhibition	=	9.48	%	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00143	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00245	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00322	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00392	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00425	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00407	/min	PMID[476948]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	Activity	=	0.00401	/min	PMID[476948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	50000.0	nM	PMID[476949]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	-logMIC	=	4.35	n.a.	PMID[476950]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	-logMIC	=	4.95	n.a.	PMID[476950]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-5.2	%	PMID[476951]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.57	%	PMID[476952]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	14.64	%	PMID[476953]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.64	%	PMID[476954]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.0	%	PMID[476955]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	20000.0	nM	PMID[476956]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	20000.0	nM	PMID[476956]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20000.0	nM	PMID[476956]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	20000.0	nM	PMID[476956]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	20000.0	nM	PMID[476956]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	20000.0	nM	PMID[476956]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	20000.0	nM	PMID[476956]
NPT20950	CELL-LINE	Erythrocyte	n.a.	HC10	>	20.0	uM	PMID[476956]

☑ 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 NPC165106 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	437
0.1-0.2	1752
0.2-0.3	4626
0.3-0.4	13951
0.4-0.5	4114
0.5-0.6	7149
0.6-0.7	7515
0.7-0.8	2493
0.8-0.85	531
0.85-0.9	87
0.9-0.95	35
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9813	High Similarity	NPC473264
0.9813	High Similarity	NPC475815
0.9813	High Similarity	NPC47194
0.9722	High Similarity	NPC9341
0.9722	High Similarity	NPC81067
0.9545	High Similarity	NPC474040
0.9375	High Similarity	NPC95614
0.9375	High Similarity	NPC227217
0.9375	High Similarity	NPC344161
0.9375	High Similarity	NPC232316
0.9375	High Similarity	NPC165133
0.9375	High Similarity	NPC56214
0.9375	High Similarity	NPC117780
0.9375	High Similarity	NPC242885
0.9286	High Similarity	NPC310338
0.9286	High Similarity	NPC281298
0.9211	High Similarity	NPC216929
0.9211	High Similarity	NPC312713
0.9211	High Similarity	NPC38996
0.9211	High Similarity	NPC160380
0.9211	High Similarity	NPC301641
0.9211	High Similarity	NPC57268
0.9211	High Similarity	NPC65933
0.9211	High Similarity	NPC477886
0.9211	High Similarity	NPC126935
0.9211	High Similarity	NPC172676
0.9211	High Similarity	NPC80241
0.9196	High Similarity	NPC470626
0.9196	High Similarity	NPC474214
0.9143	High Similarity	NPC292792
0.913	High Similarity	NPC85488
0.9115	High Similarity	NPC474320
0.9115	High Similarity	NPC475961
0.9115	High Similarity	NPC254625
0.9107	High Similarity	NPC293619
0.9052	High Similarity	NPC280704
0.9052	High Similarity	NPC31344
0.9052	High Similarity	NPC470887
0.9052	High Similarity	NPC317769
0.8974	High Similarity	NPC34902
0.8974	High Similarity	NPC121783
0.8974	High Similarity	NPC18449
0.8966	High Similarity	NPC30462
0.8957	High Similarity	NPC207613
0.8952	High Similarity	NPC12714
0.8952	High Similarity	NPC310905
0.8947	High Similarity	NPC15805
0.8898	High Similarity	NPC228771
0.8898	High Similarity	NPC266705
0.8898	High Similarity	NPC17348
0.8898	High Similarity	NPC29008
0.8898	High Similarity	NPC9067
0.8898	High Similarity	NPC148627
0.8889	High Similarity	NPC249788
0.8879	High Similarity	NPC470212
0.8879	High Similarity	NPC343720
0.8879	High Similarity	NPC312675
0.8879	High Similarity	NPC473853
0.8879	High Similarity	NPC262156
0.8879	High Similarity	NPC184651
0.8879	High Similarity	NPC113865
0.8879	High Similarity	NPC324571
0.8879	High Similarity	NPC54872
0.885	High Similarity	NPC123948
0.8824	High Similarity	NPC274356
0.8824	High Similarity	NPC50683
0.8824	High Similarity	NPC285725
0.8824	High Similarity	NPC206882
0.8824	High Similarity	NPC112571
0.8818	High Similarity	NPC137685
0.8793	High Similarity	NPC472596
0.8774	High Similarity	NPC300166
0.8772	High Similarity	NPC280001
0.8772	High Similarity	NPC185738
0.875	High Similarity	NPC158737
0.875	High Similarity	NPC98745
0.875	High Similarity	NPC5428
0.875	High Similarity	NPC223807
0.875	High Similarity	NPC118533
0.875	High Similarity	NPC127587
0.875	High Similarity	NPC177167
0.875	High Similarity	NPC165045
0.8729	High Similarity	NPC471693
0.8729	High Similarity	NPC282496
0.8729	High Similarity	NPC233526
0.8716	High Similarity	NPC258171
0.8696	High Similarity	NPC277460
0.8678	High Similarity	NPC21867
0.8678	High Similarity	NPC158471
0.8678	High Similarity	NPC222127
0.8678	High Similarity	NPC129570
0.8678	High Similarity	NPC57119
0.8678	High Similarity	NPC226862
0.8678	High Similarity	NPC128208
0.8678	High Similarity	NPC277458
0.8678	High Similarity	NPC307050
0.8678	High Similarity	NPC82862
0.8678	High Similarity	NPC184733
0.8678	High Similarity	NPC165128
0.8678	High Similarity	NPC470084
0.8678	High Similarity	NPC282703
0.8678	High Similarity	NPC45774
0.8678	High Similarity	NPC11258
0.8667	High Similarity	NPC186845
0.8667	High Similarity	NPC76451
0.8667	High Similarity	NPC213711
0.8667	High Similarity	NPC40352
0.8667	High Similarity	NPC9891
0.8667	High Similarity	NPC88297
0.8649	High Similarity	NPC475852
0.8644	High Similarity	NPC261661
0.8644	High Similarity	NPC71090
0.8636	High Similarity	NPC75440
0.8636	High Similarity	NPC201959
0.8621	High Similarity	NPC24474
0.8621	High Similarity	NPC311595
0.8611	High Similarity	NPC241224
0.8609	High Similarity	NPC86947
0.8609	High Similarity	NPC164386
0.8607	High Similarity	NPC475875
0.8607	High Similarity	NPC476748
0.8595	High Similarity	NPC473092
0.8595	High Similarity	NPC202904
0.8595	High Similarity	NPC8050
0.8595	High Similarity	NPC189248
0.8595	High Similarity	NPC473093
0.8595	High Similarity	NPC21563
0.8595	High Similarity	NPC106511
0.8584	High Similarity	NPC204120
0.8583	High Similarity	NPC193544
0.8583	High Similarity	NPC472093
0.8583	High Similarity	NPC53305
0.8583	High Similarity	NPC475169
0.8583	High Similarity	NPC17943
0.8583	High Similarity	NPC57490
0.8583	High Similarity	NPC105925
0.8583	High Similarity	NPC257589
0.8583	High Similarity	NPC203133
0.8583	High Similarity	NPC208950
0.8583	High Similarity	NPC298757
0.8583	High Similarity	NPC221077
0.8583	High Similarity	NPC116907
0.8583	High Similarity	NPC233410
0.8583	High Similarity	NPC251855
0.8583	High Similarity	NPC117214
0.8571	High Similarity	NPC197757
0.8571	High Similarity	NPC173746
0.8571	High Similarity	NPC228922
0.8571	High Similarity	NPC156840
0.8571	High Similarity	NPC279379
0.8571	High Similarity	NPC8547
0.8571	High Similarity	NPC257124
0.8559	High Similarity	NPC290451
0.8559	High Similarity	NPC127389
0.8547	High Similarity	NPC474565
0.8545	High Similarity	NPC227894
0.8537	High Similarity	NPC181079
0.8537	High Similarity	NPC42300
0.8537	High Similarity	NPC145305
0.8537	High Similarity	NPC174495
0.8537	High Similarity	NPC241522
0.8537	High Similarity	NPC173308
0.8537	High Similarity	NPC224157
0.8537	High Similarity	NPC233224
0.8537	High Similarity	NPC92164
0.8537	High Similarity	NPC242807
0.8537	High Similarity	NPC64201
0.8537	High Similarity	NPC275950
0.8537	High Similarity	NPC187998
0.8537	High Similarity	NPC153739
0.8537	High Similarity	NPC257582
0.8537	High Similarity	NPC192687
0.8537	High Similarity	NPC271208
0.8537	High Similarity	NPC77040
0.8525	High Similarity	NPC149008
0.8525	High Similarity	NPC54321
0.8525	High Similarity	NPC328682
0.8525	High Similarity	NPC207702
0.8525	High Similarity	NPC283114
0.8525	High Similarity	NPC281864
0.8522	High Similarity	NPC268317
0.8512	High Similarity	NPC223953
0.8512	High Similarity	NPC92207
0.8512	High Similarity	NPC17837
0.8512	High Similarity	NPC304630
0.8512	High Similarity	NPC127937
0.85	High Similarity	NPC94276
0.85	High Similarity	NPC114901
0.85	High Similarity	NPC109822
0.85	High Similarity	NPC293701
0.85	High Similarity	NPC48990
0.8496	Intermediate Similarity	NPC165646
0.8491	Intermediate Similarity	NPC470161
0.8487	Intermediate Similarity	NPC41562
0.8482	Intermediate Similarity	NPC31279
0.8475	Intermediate Similarity	NPC224814
0.8475	Intermediate Similarity	NPC14007
0.8475	Intermediate Similarity	NPC189844
0.8475	Intermediate Similarity	NPC60962
0.8475	Intermediate Similarity	NPC166759

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 NPC165106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1035
0.2-0.3	1332
0.3-0.4	2731
0.4-0.5	1842
0.5-0.6	1023
0.6-0.7	638
0.7-0.8	166
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5283	Phase 1
0.8772	High Similarity	NPD5536	Phase 2
0.8571	High Similarity	NPD228	Approved
0.8537	High Similarity	NPD5111	Phase 2
0.8537	High Similarity	NPD5110	Phase 2
0.8537	High Similarity	NPD5109	Approved
0.8393	Intermediate Similarity	NPD3022	Approved
0.8393	Intermediate Similarity	NPD3021	Approved
0.8333	Intermediate Similarity	NPD2981	Phase 2
0.8306	Intermediate Similarity	NPD3027	Phase 3
0.8264	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2983	Phase 2
0.8264	Intermediate Similarity	NPD2982	Phase 2
0.825	Intermediate Similarity	NPD3705	Approved
0.823	Intermediate Similarity	NPD5451	Approved
0.8203	Intermediate Similarity	NPD6895	Approved
0.8203	Intermediate Similarity	NPD6896	Approved
0.8145	Intermediate Similarity	NPD3018	Phase 2
0.8142	Intermediate Similarity	NPD2684	Approved
0.812	Intermediate Similarity	NPD7157	Approved
0.8115	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD2922	Phase 1
0.8047	Intermediate Similarity	NPD3657	Discovery
0.8017	Intermediate Similarity	NPD5535	Approved
0.8017	Intermediate Similarity	NPD7843	Approved
0.8	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1651	Approved
0.8	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD3620	Phase 2
0.7953	Intermediate Similarity	NPD5718	Phase 2
0.7909	Intermediate Similarity	NPD3020	Approved
0.7851	Intermediate Similarity	NPD1357	Approved
0.7829	Intermediate Similarity	NPD4060	Phase 1
0.7823	Intermediate Similarity	NPD5327	Phase 3
0.782	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1281	Approved
0.7787	Intermediate Similarity	NPD2667	Approved
0.7787	Intermediate Similarity	NPD2668	Approved
0.7739	Intermediate Similarity	NPD1358	Approved
0.7734	Intermediate Similarity	NPD7095	Approved
0.7721	Intermediate Similarity	NPD7124	Phase 2
0.7705	Intermediate Similarity	NPD5585	Approved
0.7705	Intermediate Similarity	NPD5691	Approved
0.7704	Intermediate Similarity	NPD6331	Phase 2
0.7704	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD4110	Phase 3
0.7704	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2808	Discontinued
0.768	Intermediate Similarity	NPD1669	Approved
0.7667	Intermediate Similarity	NPD6387	Discontinued
0.7656	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3134	Approved
0.7647	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6516	Phase 2
0.7642	Intermediate Similarity	NPD5846	Approved
0.7642	Intermediate Similarity	NPD4626	Approved
0.7638	Intermediate Similarity	NPD4624	Approved
0.7636	Intermediate Similarity	NPD2859	Approved
0.7636	Intermediate Similarity	NPD2860	Approved
0.7619	Intermediate Similarity	NPD1283	Approved
0.7603	Intermediate Similarity	NPD3596	Phase 2
0.76	Intermediate Similarity	NPD2232	Approved
0.76	Intermediate Similarity	NPD2230	Approved
0.76	Intermediate Similarity	NPD2233	Approved
0.7597	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD3847	Discontinued
0.7578	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2861	Phase 2
0.7557	Intermediate Similarity	NPD2979	Phase 3
0.7557	Intermediate Similarity	NPD1613	Approved
0.7557	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2933	Approved
0.7545	Intermediate Similarity	NPD2934	Approved
0.7537	Intermediate Similarity	NPD2438	Suspended
0.7537	Intermediate Similarity	NPD2161	Phase 2
0.7537	Intermediate Similarity	NPD3539	Phase 1
0.7521	Intermediate Similarity	NPD6671	Approved
0.7521	Intermediate Similarity	NPD709	Approved
0.7519	Intermediate Similarity	NPD4908	Phase 1
0.7519	Intermediate Similarity	NPD6111	Discontinued
0.7518	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4162	Approved
0.75	Intermediate Similarity	NPD17	Approved
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD6584	Phase 3
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7482	Intermediate Similarity	NPD4584	Approved
0.7481	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2674	Phase 3
0.7481	Intermediate Similarity	NPD3540	Phase 1
0.748	Intermediate Similarity	NPD6581	Approved
0.748	Intermediate Similarity	NPD6580	Approved
0.748	Intermediate Similarity	NPD1876	Approved
0.7479	Intermediate Similarity	NPD1139	Approved
0.7479	Intermediate Similarity	NPD1137	Approved
0.746	Intermediate Similarity	NPD3972	Approved
0.7444	Intermediate Similarity	NPD2653	Approved
0.7424	Intermediate Similarity	NPD1558	Phase 1
0.7419	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3443	Approved
0.7419	Intermediate Similarity	NPD3445	Approved
0.7419	Intermediate Similarity	NPD3444	Approved
0.7417	Intermediate Similarity	NPD1138	Approved
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3145	Approved
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3144	Approved
0.7405	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4359	Approved
0.7391	Intermediate Similarity	NPD5241	Discontinued
0.7381	Intermediate Similarity	NPD1610	Phase 2
0.7381	Intermediate Similarity	NPD1611	Approved
0.7377	Intermediate Similarity	NPD2557	Approved
0.7372	Intermediate Similarity	NPD4236	Phase 3
0.7372	Intermediate Similarity	NPD4237	Approved
0.7372	Intermediate Similarity	NPD5177	Phase 3
0.7368	Intermediate Similarity	NPD5735	Approved
0.7368	Intermediate Similarity	NPD3028	Approved
0.7364	Intermediate Similarity	NPD7905	Discontinued
0.736	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1375	Discontinued
0.735	Intermediate Similarity	NPD968	Approved
0.7344	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8651	Approved
0.7339	Intermediate Similarity	NPD1182	Approved
0.7333	Intermediate Similarity	NPD4108	Discontinued
0.7323	Intermediate Similarity	NPD1608	Approved
0.7323	Intermediate Similarity	NPD1840	Phase 2
0.7313	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4140	Approved
0.7293	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6873	Phase 2
0.7288	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD2531	Phase 2
0.7273	Intermediate Similarity	NPD821	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7266	Intermediate Similarity	NPD6582	Phase 2
0.7266	Intermediate Similarity	NPD6583	Phase 3
0.7254	Intermediate Similarity	NPD6031	Approved
0.7254	Intermediate Similarity	NPD6030	Approved
0.7254	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6674	Discontinued
0.7232	Intermediate Similarity	NPD9296	Approved
0.7232	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6876	Approved
0.7222	Intermediate Similarity	NPD6875	Approved
0.7222	Intermediate Similarity	NPD7028	Phase 2
0.7218	Intermediate Similarity	NPD3530	Approved
0.7218	Intermediate Similarity	NPD7265	Discontinued
0.7218	Intermediate Similarity	NPD3532	Approved
0.7218	Intermediate Similarity	NPD8032	Phase 2
0.7218	Intermediate Similarity	NPD3531	Approved
0.7218	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1241	Discontinued
0.7203	Intermediate Similarity	NPD2883	Discontinued
0.7188	Intermediate Similarity	NPD2231	Phase 2
0.7188	Intermediate Similarity	NPD2235	Phase 2
0.7185	Intermediate Similarity	NPD6353	Approved
0.7185	Intermediate Similarity	NPD4097	Suspended
0.7183	Intermediate Similarity	NPD52	Approved
0.7183	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7526	Approved
0.7176	Intermediate Similarity	NPD9494	Approved
0.7172	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7110	Phase 1
0.7165	Intermediate Similarity	NPD3496	Discontinued
0.7164	Intermediate Similarity	NPD2238	Phase 2
0.7164	Intermediate Similarity	NPD3109	Approved
0.7164	Intermediate Similarity	NPD3110	Approved
0.7155	Intermediate Similarity	NPD291	Approved
0.7154	Intermediate Similarity	NPD4098	Discontinued
0.7153	Intermediate Similarity	NPD4017	Approved
0.7153	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD3049	Approved
0.7132	Intermediate Similarity	NPD6543	Approved
0.7132	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4536	Approved
0.7132	Intermediate Similarity	NPD4538	Approved
0.7132	Intermediate Similarity	NPD6539	Approved
0.7132	Intermediate Similarity	NPD4749	Approved
0.7132	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3685	Discontinued
0.7132	Intermediate Similarity	NPD6540	Phase 3
0.7132	Intermediate Similarity	NPD6542	Approved
0.7123	Intermediate Similarity	NPD37	Approved
0.7123	Intermediate Similarity	NPD7298	Approved
0.7122	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4123	Phase 3
0.7105	Intermediate Similarity	NPD288	Approved
0.7101	Intermediate Similarity	NPD5762	Approved
0.7101	Intermediate Similarity	NPD5763	Approved
0.7099	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2798	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