NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	257.684
LogP:	5.237
LogD:	4.203
LogS:	-4.218
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	2.773
Fsp3:	0.467
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:	-4.591
MDCK Permeability:	1.554612936160993e-05
Pgp-inhibitor:	0.646
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	98.89472198486328%
Volume Distribution (VD):	6.396
Pgp-substrate:	3.4024198055267334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.616
CYP2C9-inhibitor:	0.775
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	13.225
Half-life (T1/2):	0.246

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.592
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.755
Skin Sensitization:	0.661
Carcinogencity:	0.088
Eye Corrosion:	0.452
Eye Irritation:	0.987
Respiratory Toxicity:	0.346

Download Data

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

Natural Product: NPC79241

Natural Product ID:	NPC79241
*Common Name:**	Xanthorrizol
IUPAC Name:	2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol
Synonyms:	Xanthorrizol
Standard InCHIKey:	FKWGCEDRLNNZOZ-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3/t12-/m1/s1
SMILES:	CC(=CCC[C@H](c1ccc(c(c1)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460033
PubChem CID:	93135
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473422]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	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	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	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]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12175	Iostephane heterophylla	Species	Asteraceae	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
ED50	1
IC50	5
MIC	27
Others	37

Activity Type	# Activity
CELL-LINE	1
Individual Protein	5
Organism	46
Others	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1573	Individual Protein	Enoyl-[acyl-carrier-protein] reductase	Escherichia coli K-12	-TdeltaS	=	-32.25	kcal/mol	PMID[489592]
NPT1573	Individual Protein	Enoyl-[acyl-carrier-protein] reductase	Escherichia coli K-12	deltaG	=	-14.98	kcal/mol	PMID[489592]
NPT1573	Individual Protein	Enoyl-[acyl-carrier-protein] reductase	Escherichia coli K-12	Km	=	2300.0	nM	PMID[489592]
NPT1573	Individual Protein	Enoyl-[acyl-carrier-protein] reductase	Escherichia coli K-12	Km	=	1900.0	nM	PMID[489592]
NPT1573	Individual Protein	Enoyl-[acyl-carrier-protein] reductase	Escherichia coli K-12	IC50	=	17130.0	nM	PMID[489592]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[489590]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[489590]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	16.0	ug.mL-1	PMID[489590]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[489590]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	32.0	ug.mL-1	PMID[489590]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[489590]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[489590]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	ED50	>	32.0	mg.kg-1	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	1.52	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	7.03	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	35.75	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	99.98	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	95.33	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	1.91	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	8.72	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	48.56	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	91.13	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	96.87	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	17.12	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	23.39	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	33.57	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	96.92	%	PMID[489590]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	102.1	%	PMID[489590]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	20.0	%	PMID[489591]
NPT19	Organism	Escherichia coli	Escherichia coli	Ratio	=	2.0	n.a.	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.125	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.05	ug.mL-1	PMID[489592]
NPT27	Others	Unspecified		Drug uptake	=	0.23	pM	PMID[489592]
NPT27	Others	Unspecified		Drug uptake	=	76.65	pM	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.0	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	256.0	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2.0	ug.mL-1	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	8.0	ug.mL-1	PMID[489592]
NPT2	Others	Unspecified		-TdeltaS	=	-38.69	kcal/mol	PMID[489592]
NPT2	Others	Unspecified		-TdeltaS	=	-33.17	kcal/mol	PMID[489592]
NPT2	Others	Unspecified		deltaG	=	-15.1	kcal/mol	PMID[489592]
NPT2	Others	Unspecified		deltaG	=	-10.61	kcal/mol	PMID[489592]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	0.354	n.a.	PMID[489592]
NPT2	Others	Unspecified		Km	=	53600.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	44360.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	18200.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	3700.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	42700.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	36640.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	15280.0	nM	PMID[489592]
NPT2	Others	Unspecified		Km	=	4100.0	nM	PMID[489592]
NPT2	Others	Unspecified		IC50	=	75660.0	nM	PMID[489592]
NPT2	Others	Unspecified		IC50	=	57330.0	nM	PMID[489592]
NPT2	Others	Unspecified		IC50	=	37660.0	nM	PMID[489592]
NPT2	Others	Unspecified		IC50	=	19740.0	nM	PMID[489592]

☑ 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 NPC79241 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	298
0.1-0.2	1825
0.2-0.3	4570
0.3-0.4	13649
0.4-0.5	6745
0.5-0.6	9947
0.6-0.7	4283
0.7-0.8	1014
0.8-0.85	215
0.85-0.9	109
0.9-0.95	34
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6597
0.989	High Similarity	NPC312132
0.989	High Similarity	NPC259512
0.9785	High Similarity	NPC72729
0.9677	High Similarity	NPC33675
0.9677	High Similarity	NPC299762
0.9479	High Similarity	NPC475225
0.9474	High Similarity	NPC252105
0.9451	High Similarity	NPC231150
0.9375	High Similarity	NPC471228
0.9375	High Similarity	NPC235762
0.9247	High Similarity	NPC245187
0.9247	High Similarity	NPC152415
0.9192	High Similarity	NPC66834
0.9184	High Similarity	NPC117115
0.9184	High Similarity	NPC47284
0.9167	High Similarity	NPC174911
0.9158	High Similarity	NPC77492
0.914	High Similarity	NPC3358
0.914	High Similarity	NPC162314
0.914	High Similarity	NPC306884
0.914	High Similarity	NPC147284
0.914	High Similarity	NPC94139
0.914	High Similarity	NPC210497
0.914	High Similarity	NPC55903
0.913	High Similarity	NPC192
0.9121	High Similarity	NPC27974
0.91	High Similarity	NPC64586
0.9091	High Similarity	NPC21594
0.9091	High Similarity	NPC53740
0.9091	High Similarity	NPC310456
0.9072	High Similarity	NPC477685
0.9032	High Similarity	NPC306074
0.9032	High Similarity	NPC304541
0.9011	High Similarity	NPC407
0.9011	High Similarity	NPC307235
0.901	High Similarity	NPC58865
0.9	High Similarity	NPC151477
0.8969	High Similarity	NPC48730
0.8969	High Similarity	NPC248396
0.8969	High Similarity	NPC129373
0.8958	High Similarity	NPC152097
0.8947	High Similarity	NPC8392
0.8947	High Similarity	NPC222146
0.8911	High Similarity	NPC306295
0.8901	High Similarity	NPC155393
0.8889	High Similarity	NPC238696
0.8889	High Similarity	NPC218879
0.8889	High Similarity	NPC475580
0.8889	High Similarity	NPC244513
0.8889	High Similarity	NPC227458
0.8889	High Similarity	NPC272029
0.8878	High Similarity	NPC80800
0.8878	High Similarity	NPC12221
0.8866	High Similarity	NPC122005
0.8866	High Similarity	NPC260775
0.8866	High Similarity	NPC252821
0.8842	High Similarity	NPC316301
0.8842	High Similarity	NPC27323
0.8842	High Similarity	NPC289769
0.8842	High Similarity	NPC76938
0.8835	High Similarity	NPC224527
0.8824	High Similarity	NPC299568
0.8824	High Similarity	NPC186385
0.8817	High Similarity	NPC318325
0.8817	High Similarity	NPC242240
0.8817	High Similarity	NPC123273
0.8817	High Similarity	NPC258219
0.8812	High Similarity	NPC232523
0.8812	High Similarity	NPC320439
0.8812	High Similarity	NPC204901
0.8812	High Similarity	NPC158253
0.88	High Similarity	NPC37802
0.8791	High Similarity	NPC150837
0.8791	High Similarity	NPC286904
0.8788	High Similarity	NPC269212
0.8788	High Similarity	NPC108497
0.8776	High Similarity	NPC70677
0.8776	High Similarity	NPC130756
0.8776	High Similarity	NPC12931
0.8776	High Similarity	NPC225506
0.8763	High Similarity	NPC156313
0.8763	High Similarity	NPC474073
0.8763	High Similarity	NPC475078
0.875	High Similarity	NPC250323
0.875	High Similarity	NPC228452
0.875	High Similarity	NPC32714
0.8738	High Similarity	NPC132720
0.8737	High Similarity	NPC29373
0.8737	High Similarity	NPC271440
0.8725	High Similarity	NPC174981
0.8713	High Similarity	NPC12640
0.8713	High Similarity	NPC99836
0.8713	High Similarity	NPC201662
0.871	High Similarity	NPC19680
0.871	High Similarity	NPC25493
0.871	High Similarity	NPC113460
0.8667	High Similarity	NPC715
0.8654	High Similarity	NPC260323
0.8654	High Similarity	NPC266937
0.8654	High Similarity	NPC470770
0.8654	High Similarity	NPC176279
0.8654	High Similarity	NPC77772
0.8654	High Similarity	NPC469912
0.8654	High Similarity	NPC151537
0.8654	High Similarity	NPC54373
0.8641	High Similarity	NPC19808
0.8641	High Similarity	NPC33728
0.8632	High Similarity	NPC204210
0.8632	High Similarity	NPC155908
0.8617	High Similarity	NPC177420
0.8617	High Similarity	NPC280347
0.8602	High Similarity	NPC23167
0.86	High Similarity	NPC24327
0.86	High Similarity	NPC12870
0.8586	High Similarity	NPC211885
0.8585	High Similarity	NPC195922
0.8571	High Similarity	NPC46940
0.8571	High Similarity	NPC177962
0.8571	High Similarity	NPC225464
0.8571	High Similarity	NPC302371
0.8571	High Similarity	NPC26615
0.8571	High Similarity	NPC62867
0.8558	High Similarity	NPC13482
0.8558	High Similarity	NPC141782
0.8557	High Similarity	NPC144682
0.8557	High Similarity	NPC274678
0.8544	High Similarity	NPC11554
0.8529	High Similarity	NPC469913
0.8529	High Similarity	NPC155072
0.8529	High Similarity	NPC271274
0.8526	High Similarity	NPC55561
0.8515	High Similarity	NPC323810
0.8505	High Similarity	NPC84999
0.8505	High Similarity	NPC246760
0.85	High Similarity	NPC51015
0.8495	Intermediate Similarity	NPC197783
0.8491	Intermediate Similarity	NPC319803
0.8491	Intermediate Similarity	NPC190212
0.8491	Intermediate Similarity	NPC23804
0.8485	Intermediate Similarity	NPC92730
0.8485	Intermediate Similarity	NPC128723
0.8478	Intermediate Similarity	NPC474354
0.8476	Intermediate Similarity	NPC95716
0.8469	Intermediate Similarity	NPC132271
0.8469	Intermediate Similarity	NPC292730
0.8469	Intermediate Similarity	NPC216520
0.8469	Intermediate Similarity	NPC473388
0.8469	Intermediate Similarity	NPC202986
0.8469	Intermediate Similarity	NPC82664
0.8462	Intermediate Similarity	NPC314187
0.8454	Intermediate Similarity	NPC128062
0.8447	Intermediate Similarity	NPC474352
0.8431	Intermediate Similarity	NPC471350
0.8431	Intermediate Similarity	NPC138942
0.8421	Intermediate Similarity	NPC70436
0.8416	Intermediate Similarity	NPC24404
0.8416	Intermediate Similarity	NPC168829
0.8416	Intermediate Similarity	NPC313030
0.8416	Intermediate Similarity	NPC106396
0.8416	Intermediate Similarity	NPC168393
0.8416	Intermediate Similarity	NPC71002
0.8416	Intermediate Similarity	NPC242342
0.8416	Intermediate Similarity	NPC302219
0.8416	Intermediate Similarity	NPC222522
0.8416	Intermediate Similarity	NPC249828
0.8416	Intermediate Similarity	NPC146798
0.8416	Intermediate Similarity	NPC85479
0.8416	Intermediate Similarity	NPC53051
0.8416	Intermediate Similarity	NPC94351
0.8416	Intermediate Similarity	NPC168303
0.8416	Intermediate Similarity	NPC233827
0.8404	Intermediate Similarity	NPC184169
0.84	Intermediate Similarity	NPC10588
0.84	Intermediate Similarity	NPC130103
0.84	Intermediate Similarity	NPC294741
0.84	Intermediate Similarity	NPC166761
0.8396	Intermediate Similarity	NPC471179
0.8396	Intermediate Similarity	NPC166995
0.8387	Intermediate Similarity	NPC248817
0.8387	Intermediate Similarity	NPC175313
0.8387	Intermediate Similarity	NPC474211
0.8384	Intermediate Similarity	NPC32674
0.8381	Intermediate Similarity	NPC224870
0.8381	Intermediate Similarity	NPC296683
0.837	Intermediate Similarity	NPC168855
0.8367	Intermediate Similarity	NPC26244
0.835	Intermediate Similarity	NPC477814
0.835	Intermediate Similarity	NPC54765
0.8349	Intermediate Similarity	NPC477136
0.8333	Intermediate Similarity	NPC469719
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC288411
0.8333	Intermediate Similarity	NPC120719
0.8333	Intermediate Similarity	NPC102216
0.8333	Intermediate Similarity	NPC35797
0.8333	Intermediate Similarity	NPC312304
0.8318	Intermediate Similarity	NPC117846
0.8318	Intermediate Similarity	NPC263753
0.8317	Intermediate Similarity	NPC192032

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 NPC79241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1037
0.2-0.3	1322
0.3-0.4	2930
0.4-0.5	1905
0.5-0.6	1126
0.6-0.7	425
0.7-0.8	73
0.8-0.85	12
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.989	High Similarity	NPD288	Approved
0.978	High Similarity	NPD844	Approved
0.914	High Similarity	NPD845	Approved
0.8969	High Similarity	NPD289	Clinical (unspecified phase)
0.8842	High Similarity	NPD1432	Clinical (unspecified phase)
0.8824	High Similarity	NPD4750	Phase 3
0.8673	High Similarity	NPD3020	Approved
0.8571	High Similarity	NPD7635	Approved
0.8557	High Similarity	NPD1809	Phase 2
0.8529	High Similarity	NPD1444	Approved
0.8529	High Similarity	NPD1445	Approved
0.8447	Intermediate Similarity	NPD2342	Discontinued
0.8367	Intermediate Similarity	NPD2859	Approved
0.8367	Intermediate Similarity	NPD2860	Approved
0.8317	Intermediate Similarity	NPD940	Approved
0.8317	Intermediate Similarity	NPD846	Approved
0.8286	Intermediate Similarity	NPD3021	Approved
0.8286	Intermediate Similarity	NPD1792	Phase 2
0.8286	Intermediate Similarity	NPD3022	Approved
0.828	Intermediate Similarity	NPD111	Approved
0.8265	Intermediate Similarity	NPD2933	Approved
0.8265	Intermediate Similarity	NPD2934	Approved
0.7838	Intermediate Similarity	NPD6671	Approved
0.7788	Intermediate Similarity	NPD3091	Approved
0.7748	Intermediate Similarity	NPD1791	Approved
0.7748	Intermediate Similarity	NPD1793	Approved
0.7714	Intermediate Similarity	NPD9500	Approved
0.7692	Intermediate Similarity	NPD4749	Approved
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7658	Intermediate Similarity	NPD2228	Approved
0.7658	Intermediate Similarity	NPD2229	Approved
0.7658	Intermediate Similarity	NPD2234	Approved
0.7652	Intermediate Similarity	NPD3019	Approved
0.7652	Intermediate Similarity	NPD2932	Approved
0.7652	Intermediate Similarity	NPD4626	Approved
0.7652	Intermediate Similarity	NPD1751	Approved
0.7652	Intermediate Similarity	NPD4059	Approved
0.7632	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD497	Approved
0.7565	Intermediate Similarity	NPD4093	Discontinued
0.7542	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD9273	Approved
0.75	Intermediate Similarity	NPD495	Approved
0.75	Intermediate Similarity	NPD498	Approved
0.75	Intermediate Similarity	NPD496	Approved
0.7478	Intermediate Similarity	NPD5304	Approved
0.7478	Intermediate Similarity	NPD5303	Approved
0.7477	Intermediate Similarity	NPD228	Approved
0.7477	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9610	Approved
0.7477	Intermediate Similarity	NPD9608	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7434	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1201	Approved
0.7373	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2286	Discontinued
0.735	Intermediate Similarity	NPD3095	Discontinued
0.735	Intermediate Similarity	NPD4589	Approved
0.7345	Intermediate Similarity	NPD1398	Phase 1
0.7345	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6696	Suspended
0.7317	Intermediate Similarity	NPD4625	Phase 3
0.7311	Intermediate Similarity	NPD2233	Approved
0.7311	Intermediate Similarity	NPD2230	Approved
0.7311	Intermediate Similarity	NPD2232	Approved
0.7304	Intermediate Similarity	NPD7340	Approved
0.7304	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1983	Approved
0.7288	Intermediate Similarity	NPD1980	Approved
0.7288	Intermediate Similarity	NPD1981	Approved
0.7281	Intermediate Similarity	NPD9618	Approved
0.7281	Intermediate Similarity	NPD9614	Approved
0.7273	Intermediate Similarity	NPD3094	Phase 2
0.7265	Intermediate Similarity	NPD5691	Approved
0.7258	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9379	Approved
0.7257	Intermediate Similarity	NPD9377	Approved
0.7234	Intermediate Similarity	NPD9294	Approved
0.7217	Intermediate Similarity	NPD709	Approved
0.7213	Intermediate Similarity	NPD2194	Approved
0.7213	Intermediate Similarity	NPD2195	Approved
0.7203	Intermediate Similarity	NPD1778	Approved
0.7196	Intermediate Similarity	NPD1616	Discontinued
0.7196	Intermediate Similarity	NPD3028	Approved
0.7193	Intermediate Similarity	NPD5283	Phase 1
0.7158	Intermediate Similarity	NPD9088	Approved
0.7154	Intermediate Similarity	NPD5736	Approved
0.7154	Intermediate Similarity	NPD3636	Approved
0.7154	Intermediate Similarity	NPD3637	Approved
0.7154	Intermediate Similarity	NPD3635	Approved
0.7154	Intermediate Similarity	NPD2861	Phase 2
0.7131	Intermediate Similarity	NPD1470	Approved
0.713	Intermediate Similarity	NPD475	Phase 2
0.7129	Intermediate Similarity	NPD1101	Approved
0.7117	Intermediate Similarity	NPD290	Approved
0.7107	Intermediate Similarity	NPD1755	Approved
0.7105	Intermediate Similarity	NPD1138	Approved
0.7097	Intermediate Similarity	NPD2605	Approved
0.7097	Intermediate Similarity	NPD2606	Approved
0.7094	Intermediate Similarity	NPD9615	Approved
0.7094	Intermediate Similarity	NPD9613	Approved
0.7094	Intermediate Similarity	NPD9616	Approved
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7054	Intermediate Similarity	NPD2684	Approved
0.7049	Intermediate Similarity	NPD1283	Approved
0.704	Intermediate Similarity	NPD5156	Approved
0.704	Intermediate Similarity	NPD5155	Approved
0.7034	Intermediate Similarity	NPD7330	Discontinued
0.7034	Intermediate Similarity	NPD316	Approved
0.7031	Intermediate Similarity	NPD4097	Suspended
0.7027	Intermediate Similarity	NPD968	Approved
0.7018	Intermediate Similarity	NPD1137	Approved
0.7018	Intermediate Similarity	NPD1139	Approved
0.7016	Intermediate Similarity	NPD1712	Approved
0.7008	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD3023	Approved
0.7	Intermediate Similarity	NPD3026	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6992	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1089	Approved
0.699	Remote Similarity	NPD1090	Approved
0.699	Remote Similarity	NPD1086	Approved
0.6975	Remote Similarity	NPD3025	Approved
0.6975	Remote Similarity	NPD1651	Approved
0.6975	Remote Similarity	NPD3024	Approved
0.6975	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4818	Approved
0.6972	Remote Similarity	NPD4817	Approved
0.696	Remote Similarity	NPD3595	Approved
0.696	Remote Similarity	NPD3594	Approved
0.696	Remote Similarity	NPD4908	Phase 1
0.6942	Remote Similarity	NPD1611	Approved
0.6935	Remote Similarity	NPD4624	Approved
0.693	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD256	Approved
0.6923	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD2667	Approved
0.6917	Remote Similarity	NPD2668	Approved
0.6917	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9266	Approved
0.6903	Remote Similarity	NPD74	Approved
0.6893	Remote Similarity	NPD800	Approved
0.6891	Remote Similarity	NPD1759	Phase 1
0.6887	Remote Similarity	NPD1693	Approved
0.6885	Remote Similarity	NPD1608	Approved
0.687	Remote Similarity	NPD6099	Approved
0.687	Remote Similarity	NPD6100	Approved
0.6869	Remote Similarity	NPD9089	Approved
0.6864	Remote Similarity	NPD7636	Approved
0.6864	Remote Similarity	NPD9493	Approved
0.686	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3143	Discontinued
0.6857	Remote Similarity	NPD1088	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.685	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9244	Approved
0.6846	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD9263	Approved
0.6814	Remote Similarity	NPD9264	Approved
0.6814	Remote Similarity	NPD9267	Approved
0.681	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD7843	Approved
0.6807	Remote Similarity	NPD16	Approved
0.6807	Remote Similarity	NPD856	Approved
0.6807	Remote Similarity	NPD1758	Phase 1
0.6803	Remote Similarity	NPD1281	Approved
0.68	Remote Similarity	NPD6584	Phase 3
0.6794	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1409	Phase 3
0.678	Remote Similarity	NPD6387	Discontinued
0.6777	Remote Similarity	NPD9381	Approved
0.6777	Remote Similarity	NPD9384	Approved
0.6768	Remote Similarity	NPD9093	Approved
0.6767	Remote Similarity	NPD4257	Approved
0.6767	Remote Similarity	NPD4256	Phase 2
0.6757	Remote Similarity	NPD4229	Approved
0.6757	Remote Similarity	NPD3680	Approved
0.6757	Remote Similarity	NPD4231	Approved
0.6757	Remote Similarity	NPD3683	Approved
0.6757	Remote Similarity	NPD3682	Approved
0.6757	Remote Similarity	NPD3681	Approved
0.6752	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1548	Phase 1
0.6748	Remote Similarity	NPD3070	Discontinued
0.6748	Remote Similarity	NPD2231	Phase 2
0.6748	Remote Similarity	NPD2235	Phase 2
0.6746	Remote Similarity	NPD2237	Approved
0.6744	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6346	Approved
0.6744	Remote Similarity	NPD3620	Phase 2
0.6744	Remote Similarity	NPD2238	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data