NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.16
Volume:	213.756
LogP:	4.304
LogD:	2.405
LogS:	-3.284
# Rotatable Bonds:	9
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	1.558
Fsp3:	0.909
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.871
MDCK Permeability:	3.16571349685546e-05
Pgp-inhibitor:	0.065
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.865
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.66
Plasma Protein Binding (PPB):	95.5693588256836%
Volume Distribution (VD):	0.287
Pgp-substrate:	2.8169476985931396%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.314
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.515
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	2.361
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.549
Carcinogencity:	0.109
Eye Corrosion:	0.98
Eye Irritation:	0.987
Respiratory Toxicity:	0.649

Download Data

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

Natural Product: NPC14227

Natural Product ID:	NPC14227
*Common Name:**	Undecanoate
IUPAC Name:	undecanoic acid
Synonyms:	Undecanoate
Standard InCHIKey:	ZDPHROOEEOARMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
SMILES:	CCCCCCCCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL108030
PubChem CID:	8180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0003086] Medium-chain fatty acids

*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
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23213	Bistorta officinalis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31286	Dolichos lablab	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26378	Bistorta manshuriensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23213	Bistorta officinalis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26378	Bistorta manshuriensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3808	Elaeagnus angustifolia	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24644	Hansenia forbesii	Species	Apiaceae	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
NPO25443	NPC14227	Raw	Fruit	0.1	0.1	0.1	mg/100g	Database [DUKE]
NPO42044	NPC14227	n.a.	n.a.	9	n.a.	n.a.	mg/g of DW	PMID[35056798]

☑ 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	4
IC50	2
Ki	1
Others	10
Potency	7

Activity Type	# Activity
NON-MOLECULAR	1
Organism	6
Others	10
SINGLE PROTEIN	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	22137.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	175.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	35085.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17584.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49559.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	8813.1	nM	PubChem BioAssay data set
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	4466835.92	nM	PMID[491164]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	4470000.0	nM	PMID[491165]
NPT35	Others	n.a.		LogP	=	4.42	n.a.	PMID[491165]
NPT35	Others	n.a.		pKa	=	4.9	n.a.	PMID[491165]
NPT35	Others	n.a.		LogD	=	2.12	n.a.	PMID[491165]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Log 1/I50	=	2.35	1/M	PMID[491165]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	deltaA	=	0.19	n.a.	PMID[491166]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	mortality	=	51.3	%	PMID[491167]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	mortality	=	96.0	%	PMID[491167]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	mortality	=	98.5	%	PMID[491167]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Ki	=	108.0	nM	PMID[491168]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	1600.0	nM	PMID[491168]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Emax	=	93.0	%	PMID[491168]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	4360.0	nM	PMID[491168]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	Emax	=	82.0	%	PMID[491168]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	7700.0	nM	PMID[491169]
NPT23071	SINGLE PROTEIN	G-protein coupled receptor 84	Homo sapiens	EC50	=	8600.0	nM	PMID[491169]

☑ 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 NPC14227 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	862
0.1-0.2	13881
0.2-0.3	16623
0.3-0.4	8598
0.4-0.5	2132
0.5-0.6	333
0.6-0.7	139
0.7-0.8	64
0.8-0.85	28
0.85-0.9	13
0.9-0.95	9
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC113928
1.0	High Similarity	NPC154186
1.0	High Similarity	NPC301585
1.0	High Similarity	NPC301696
1.0	High Similarity	NPC201844
1.0	High Similarity	NPC261080
1.0	High Similarity	NPC279026
0.9474	High Similarity	NPC171736
0.9474	High Similarity	NPC216630
0.9474	High Similarity	NPC307783
0.9474	High Similarity	NPC209970
0.9474	High Similarity	NPC149184
0.9474	High Similarity	NPC196924
0.9459	High Similarity	NPC183424
0.9459	High Similarity	NPC294085
0.9459	High Similarity	NPC118968
0.9459	High Similarity	NPC214610
0.9231	High Similarity	NPC67462
0.9189	High Similarity	NPC268826
0.9167	High Similarity	NPC155263
0.9	High Similarity	NPC19305
0.9	High Similarity	NPC74845
0.9	High Similarity	NPC255837
0.8889	High Similarity	NPC156630
0.878	High Similarity	NPC8219
0.878	High Similarity	NPC55023
0.8684	High Similarity	NPC22903
0.8684	High Similarity	NPC305660
0.8684	High Similarity	NPC54980
0.8684	High Similarity	NPC201622
0.8649	High Similarity	NPC134782
0.8571	High Similarity	NPC314679
0.8571	High Similarity	NPC30195
0.8571	High Similarity	NPC12438
0.85	High Similarity	NPC163746
0.85	High Similarity	NPC103286
0.8462	Intermediate Similarity	NPC31551
0.8462	Intermediate Similarity	NPC219536
0.8372	Intermediate Similarity	NPC324004
0.8372	Intermediate Similarity	NPC328497
0.8372	Intermediate Similarity	NPC21844
0.8333	Intermediate Similarity	NPC175342
0.8293	Intermediate Similarity	NPC301528
0.8293	Intermediate Similarity	NPC129972
0.8293	Intermediate Similarity	NPC71317
0.825	Intermediate Similarity	NPC12156
0.825	Intermediate Similarity	NPC250028
0.825	Intermediate Similarity	NPC161097
0.825	Intermediate Similarity	NPC28598
0.825	Intermediate Similarity	NPC149299
0.825	Intermediate Similarity	NPC256163
0.825	Intermediate Similarity	NPC40597
0.8205	Intermediate Similarity	NPC73245
0.8182	Intermediate Similarity	NPC131770
0.8182	Intermediate Similarity	NPC324793
0.8182	Intermediate Similarity	NPC200618
0.8182	Intermediate Similarity	NPC477878
0.8182	Intermediate Similarity	NPC106872
0.8049	Intermediate Similarity	NPC248763
0.8049	Intermediate Similarity	NPC325452
0.8049	Intermediate Similarity	NPC53541
0.8	Intermediate Similarity	NPC223249
0.8	Intermediate Similarity	NPC304162
0.8	Intermediate Similarity	NPC80234
0.7857	Intermediate Similarity	NPC203531
0.7857	Intermediate Similarity	NPC236579
0.7857	Intermediate Similarity	NPC289686
0.7838	Intermediate Similarity	NPC328710
0.7838	Intermediate Similarity	NPC18224
0.7826	Intermediate Similarity	NPC90904
0.7805	Intermediate Similarity	NPC165533
0.7778	Intermediate Similarity	NPC180534
0.7727	Intermediate Similarity	NPC166287
0.7674	Intermediate Similarity	NPC76051
0.7674	Intermediate Similarity	NPC317128
0.766	Intermediate Similarity	NPC470412
0.766	Intermediate Similarity	NPC470410
0.7609	Intermediate Similarity	NPC26253
0.7561	Intermediate Similarity	NPC3531
0.75	Intermediate Similarity	NPC109026
0.75	Intermediate Similarity	NPC252843
0.75	Intermediate Similarity	NPC287231
0.75	Intermediate Similarity	NPC47363
0.75	Intermediate Similarity	NPC174368
0.75	Intermediate Similarity	NPC158179
0.75	Intermediate Similarity	NPC469781
0.75	Intermediate Similarity	NPC281245
0.7447	Intermediate Similarity	NPC50457
0.7436	Intermediate Similarity	NPC317203
0.7347	Intermediate Similarity	NPC36061
0.7347	Intermediate Similarity	NPC72722
0.7347	Intermediate Similarity	NPC1813
0.7347	Intermediate Similarity	NPC294548
0.7347	Intermediate Similarity	NPC139029
0.7333	Intermediate Similarity	NPC63182
0.7333	Intermediate Similarity	NPC52700
0.7333	Intermediate Similarity	NPC105329
0.7333	Intermediate Similarity	NPC145045
0.7317	Intermediate Similarity	NPC326532
0.7292	Intermediate Similarity	NPC100096
0.725	Intermediate Similarity	NPC80641
0.725	Intermediate Similarity	NPC154642
0.725	Intermediate Similarity	NPC80396
0.72	Intermediate Similarity	NPC281972
0.72	Intermediate Similarity	NPC290563
0.72	Intermediate Similarity	NPC85813
0.72	Intermediate Similarity	NPC424
0.72	Intermediate Similarity	NPC25417
0.72	Intermediate Similarity	NPC6095
0.72	Intermediate Similarity	NPC23155
0.72	Intermediate Similarity	NPC320588
0.72	Intermediate Similarity	NPC32467
0.72	Intermediate Similarity	NPC154245
0.72	Intermediate Similarity	NPC88966
0.72	Intermediate Similarity	NPC87564
0.72	Intermediate Similarity	NPC469937
0.72	Intermediate Similarity	NPC53463
0.72	Intermediate Similarity	NPC87394
0.72	Intermediate Similarity	NPC261831
0.7179	Intermediate Similarity	NPC57499
0.7174	Intermediate Similarity	NPC326957
0.7143	Intermediate Similarity	NPC18357
0.7111	Intermediate Similarity	NPC273545
0.7021	Intermediate Similarity	NPC216130
0.7	Intermediate Similarity	NPC301398
0.7	Intermediate Similarity	NPC70387
0.7	Intermediate Similarity	NPC196442
0.7	Intermediate Similarity	NPC223374
0.7	Intermediate Similarity	NPC321062
0.7	Intermediate Similarity	NPC86545
0.6923	Remote Similarity	NPC187777
0.6923	Remote Similarity	NPC18951
0.6923	Remote Similarity	NPC179764
0.6923	Remote Similarity	NPC477201
0.6875	Remote Similarity	NPC476469
0.6842	Remote Similarity	NPC168982
0.68	Remote Similarity	NPC92114
0.6792	Remote Similarity	NPC225929
0.675	Remote Similarity	NPC127142
0.675	Remote Similarity	NPC286498
0.675	Remote Similarity	NPC7814
0.675	Remote Similarity	NPC154396
0.6744	Remote Similarity	NPC81263
0.6735	Remote Similarity	NPC55678
0.6735	Remote Similarity	NPC305182
0.6735	Remote Similarity	NPC224227
0.6731	Remote Similarity	NPC274290
0.6731	Remote Similarity	NPC473863
0.6731	Remote Similarity	NPC54766
0.6667	Remote Similarity	NPC176500
0.6667	Remote Similarity	NPC149209
0.6667	Remote Similarity	NPC128996
0.66	Remote Similarity	NPC262968
0.66	Remote Similarity	NPC314084
0.66	Remote Similarity	NPC287811
0.6579	Remote Similarity	NPC153439
0.6579	Remote Similarity	NPC221192
0.6579	Remote Similarity	NPC196434
0.6579	Remote Similarity	NPC79887
0.6579	Remote Similarity	NPC29561
0.6579	Remote Similarity	NPC4962
0.6579	Remote Similarity	NPC222997
0.6579	Remote Similarity	NPC42403
0.6545	Remote Similarity	NPC475821
0.6545	Remote Similarity	NPC470363
0.6545	Remote Similarity	NPC274927
0.6545	Remote Similarity	NPC17935
0.6545	Remote Similarity	NPC469924
0.6545	Remote Similarity	NPC106851
0.6531	Remote Similarity	NPC149821
0.6531	Remote Similarity	NPC250919
0.6531	Remote Similarity	NPC5413
0.65	Remote Similarity	NPC125575
0.65	Remote Similarity	NPC322892
0.65	Remote Similarity	NPC286695
0.6471	Remote Similarity	NPC161366
0.6471	Remote Similarity	NPC310746
0.6458	Remote Similarity	NPC249754
0.6429	Remote Similarity	NPC243532
0.6429	Remote Similarity	NPC251042
0.6429	Remote Similarity	NPC235242
0.6429	Remote Similarity	NPC469921
0.6429	Remote Similarity	NPC174447
0.6429	Remote Similarity	NPC122521
0.641	Remote Similarity	NPC236797
0.641	Remote Similarity	NPC147096
0.641	Remote Similarity	NPC24506
0.641	Remote Similarity	NPC185041
0.641	Remote Similarity	NPC225783
0.641	Remote Similarity	NPC112242
0.641	Remote Similarity	NPC163556
0.64	Remote Similarity	NPC59051
0.6364	Remote Similarity	NPC34416
0.6346	Remote Similarity	NPC309606
0.6346	Remote Similarity	NPC139545
0.6346	Remote Similarity	NPC39633
0.6327	Remote Similarity	NPC207292
0.6316	Remote Similarity	NPC40082
0.6316	Remote Similarity	NPC201939
0.6316	Remote Similarity	NPC198118

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 NPC14227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1332
0.1-0.2	5129
0.2-0.3	1777
0.3-0.4	597
0.4-0.5	224
0.5-0.6	51
0.6-0.7	18
0.7-0.8	15
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD633	Phase 3
1.0	High Similarity	NPD9448	Phase 2
0.9474	High Similarity	NPD2270	Approved
0.9459	High Similarity	NPD9655	Approved
0.878	High Similarity	NPD3199	Clinical (unspecified phase)
0.8684	High Similarity	NPD3206	Approved
0.8571	High Similarity	NPD634	Phase 3
0.7857	Intermediate Similarity	NPD387	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD622	Approved
0.7727	Intermediate Similarity	NPD9431	Approved
0.7727	Intermediate Similarity	NPD9430	Approved
0.7561	Intermediate Similarity	NPD77	Approved
0.7561	Intermediate Similarity	NPD9450	Approved
0.75	Intermediate Similarity	NPD3186	Phase 1
0.75	Intermediate Similarity	NPD2699	Approved
0.7347	Intermediate Similarity	NPD3172	Approved
0.7317	Intermediate Similarity	NPD9513	Phase 1
0.72	Intermediate Similarity	NPD3728	Approved
0.72	Intermediate Similarity	NPD3196	Approved
0.72	Intermediate Similarity	NPD4266	Approved
0.72	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3195	Phase 2
0.72	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3194	Approved
0.72	Intermediate Similarity	NPD3730	Approved
0.7073	Intermediate Similarity	NPD9449	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9638	Phase 2
0.675	Remote Similarity	NPD8857	Approved
0.6667	Remote Similarity	NPD2266	Phase 2
0.6667	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.66	Remote Similarity	NPD29	Approved
0.66	Remote Similarity	NPD28	Approved
0.6591	Remote Similarity	NPD9635	Discontinued
0.6585	Remote Similarity	NPD9447	Approved
0.6545	Remote Similarity	NPD3198	Approved
0.6531	Remote Similarity	NPD3173	Approved
0.6316	Remote Similarity	NPD9676	Phase 3
0.617	Remote Similarity	NPD9019	Approved
0.614	Remote Similarity	NPD9656	Approved
0.6102	Remote Similarity	NPD3197	Phase 1
0.6102	Remote Similarity	NPD7909	Approved
0.6098	Remote Similarity	NPD5383	Approved
0.6098	Remote Similarity	NPD2272	Approved
0.5918	Remote Similarity	NPD4222	Approved
0.5918	Remote Similarity	NPD3174	Discontinued
0.5902	Remote Similarity	NPD4224	Phase 2
0.5893	Remote Similarity	NPD9438	Approved
0.5893	Remote Similarity	NPD9439	Approved
0.5882	Remote Similarity	NPD9016	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD9454	Approved
0.575	Remote Similarity	NPD62	Approved
0.5714	Remote Similarity	NPD73	Approved
0.5645	Remote Similarity	NPD375	Phase 2
0.561	Remote Similarity	NPD8618	Approved
0.561	Remote Similarity	NPD8590	Approved
0.56	Remote Similarity	NPD39	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