NPASS Compound

Structure

NPC469910 OpenBabel07101719402D 27 28 0 0 1 0 0 0 0 0999 V2000 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1646 -4.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7488 -6.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -5.6862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.9209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5408 -7.3335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 -5.9953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 15 23 1 6 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 13 1 1 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	383.076
LogP:	-0.193
LogD:	0.797
LogS:	-2.179
# Rotatable Bonds:	6
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	5.056
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.196
MDCK Permeability:	7.659519178560004e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.856
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	65.92073822021484%
Volume Distribution (VD):	0.365
Pgp-substrate:	44.861576080322266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	2.892
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.555
Carcinogencity:	0.283
Eye Corrosion:	0.013
Eye Irritation:	0.039
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC469910

Natural Product ID:	NPC469910
*Common Name:**	Cnicin
IUPAC Name:	n.a.
Synonyms:	Cnicin
Standard InCHIKey:	ZTDFZLVUIVPZDU-ZWSPDTATSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5-,14-8-/t15-,16+,17-,18-/m1/s1
SMILES:	C/C/1=C/CC/C(=C/[C@@H]2[C@H](C(=C)C(=O)O2)[C@H](C1)OC(=O)C(=C)[C@@H](CO)O)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1257707
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO40799	Bovine platelets	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1431933]
NPO21525	Centaurea spinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180824]
NPO32860	cnicus benedictus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO3204	Centaurea malacitana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358646]
NPO21525	Centaurea spinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3204	Centaurea malacitana	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
GI50	2
IC50	22
MIC	7
Others	7

Activity Type	# Activity
Cell Line	11
CELL-LINE	1
Individual Protein	7
NON-MOLECULAR	5
Organism	6
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2716	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Escherichia coli K-12	IC50	=	16700.0	nM	PMID[506684]
NPT2717	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	10300.0	nM	PMID[506684]
NPT2717	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Inhibition	=	64.0	%	PMID[506684]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	37800.0	nM	PMID[506687]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	37400.0	nM	PMID[506687]
NPT168	Cell Line	P388	Mus musculus	IC50	=	6600.0	nM	PMID[506688]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13200.0	nM	PMID[506688]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	13200.0	nM	PMID[506688]
NPT2309	Cell Line	CAPAN-1	Homo sapiens	IC50	=	93000.0	nM	PMID[506690]
NPT2306	Cell Line	Ca-Ski	Homo sapiens	IC50	>=	100000.0	nM	PMID[506690]
NPT1938	Cell Line	Calu-6	Homo sapiens	IC50	=	44000.0	nM	PMID[506690]
NPT2489	Cell Line	MeWo	Homo sapiens	IC50	>=	100000.0	nM	PMID[506690]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	27000.0	nM	PMID[506690]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	80000.0	nM	PMID[506690]
NPT5373	Individual Protein	Methionine aminopeptidase 2	Homo sapiens	Inhibition	=	9.0	%	PMID[506690]
NPT2716	Individual Protein	UDP-N-acetylglucosamine 1-carboxyvinyltransferase	Escherichia coli K-12	IC50	=	16700.0	nM	PMID[506690]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	3520.0	nM	PMID[506685]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3520.0	nM	PMID[506686]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1.25	ug.mL-1	PMID[506687]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	5.0	ug.mL-1	PMID[506687]
NPT35	Others	n.a.		T1/2	<	7.0	hr	PMID[506689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	25000.0	nM	PMID[506689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	92.0	%	PMID[506689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	19.0	%	PMID[506689]
NPT2	Others	Unspecified		IC50	=	16700.0	nM	PMID[506689]
NPT2	Others	Unspecified		Inhibition	=	97.0	%	PMID[506689]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MBC	=	200.0	uM	PMID[506689]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[506690]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[506690]
NPT27	Others	Unspecified		IC50	>=	100000.0	nM	PMID[506690]
NPT27	Others	Unspecified		IC50	=	82000.0	nM	PMID[506690]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32.0	ug.mL-1	PMID[506690]
NPT2	Others	Unspecified		IC50	=	20400.0	nM	PMID[506690]
NPT2	Others	Unspecified		IC50	=	10300.0	nM	PMID[506690]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	17906.06	nM	PMID[506691]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[506691]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	17920.0	nM	PMID[506691]

☑ 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 NPC469910 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	174
0.1-0.2	1212
0.2-0.3	4955
0.3-0.4	11521
0.4-0.5	13188
0.5-0.6	7311
0.6-0.7	3208
0.7-0.8	915
0.8-0.85	107
0.85-0.9	52
0.9-0.95	35
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC476803
0.975	High Similarity	NPC158756
0.963	High Similarity	NPC470755
0.9524	High Similarity	NPC474232
0.9383	High Similarity	NPC169575
0.9383	High Similarity	NPC40746
0.9383	High Similarity	NPC131669
0.9383	High Similarity	NPC473390
0.9375	High Similarity	NPC24417
0.9286	High Similarity	NPC476805
0.9286	High Similarity	NPC475819
0.9268	High Similarity	NPC476804
0.9259	High Similarity	NPC229825
0.9157	High Similarity	NPC255307
0.9125	High Similarity	NPC98557
0.9125	High Similarity	NPC167881
0.9059	High Similarity	NPC473715
0.9048	High Similarity	NPC475461
0.9048	High Similarity	NPC305475
0.9036	High Similarity	NPC191476
0.9036	High Similarity	NPC114979
0.9036	High Similarity	NPC96259
0.9036	High Similarity	NPC141193
0.9	High Similarity	NPC196653
0.9	High Similarity	NPC471465
0.8989	High Similarity	NPC477921
0.8966	High Similarity	NPC473321
0.8916	High Similarity	NPC59097
0.8902	High Similarity	NPC52861
0.8876	High Similarity	NPC477922
0.8876	High Similarity	NPC471142
0.8875	High Similarity	NPC171204
0.8875	High Similarity	NPC141789
0.8875	High Similarity	NPC116177
0.8875	High Similarity	NPC320630
0.8875	High Similarity	NPC476028
0.8875	High Similarity	NPC7563
0.8864	High Similarity	NPC288240
0.8864	High Similarity	NPC295204
0.8864	High Similarity	NPC162205
0.8864	High Similarity	NPC273579
0.8851	High Similarity	NPC473619
0.8765	High Similarity	NPC108816
0.8765	High Similarity	NPC93763
0.875	High Similarity	NPC68819
0.8706	High Similarity	NPC21469
0.869	High Similarity	NPC116543
0.8659	High Similarity	NPC270126
0.8652	High Similarity	NPC469645
0.8652	High Similarity	NPC475302
0.8652	High Similarity	NPC469692
0.8636	High Similarity	NPC469368
0.8636	High Similarity	NPC475855
0.8605	High Similarity	NPC150755
0.8587	High Similarity	NPC471144
0.8571	High Similarity	NPC230800
0.8571	High Similarity	NPC473859
0.8556	High Similarity	NPC121825
0.8554	High Similarity	NPC281132
0.8537	High Similarity	NPC267231
0.8523	High Similarity	NPC474032
0.8506	High Similarity	NPC266957
0.8495	Intermediate Similarity	NPC475949
0.8495	Intermediate Similarity	NPC288876
0.8488	Intermediate Similarity	NPC165162
0.8462	Intermediate Similarity	NPC475659
0.8444	Intermediate Similarity	NPC475912
0.8444	Intermediate Similarity	NPC125674
0.8444	Intermediate Similarity	NPC228451
0.8444	Intermediate Similarity	NPC475838
0.8427	Intermediate Similarity	NPC144133
0.8427	Intermediate Similarity	NPC179394
0.8415	Intermediate Similarity	NPC97516
0.8415	Intermediate Similarity	NPC474760
0.8409	Intermediate Similarity	NPC287089
0.8391	Intermediate Similarity	NPC469483
0.8375	Intermediate Similarity	NPC58956
0.8375	Intermediate Similarity	NPC295633
0.8375	Intermediate Similarity	NPC269206
0.837	Intermediate Similarity	NPC279621
0.837	Intermediate Similarity	NPC306041
0.8352	Intermediate Similarity	NPC303942
0.8352	Intermediate Similarity	NPC57405
0.8352	Intermediate Similarity	NPC474247
0.8316	Intermediate Similarity	NPC471148
0.8276	Intermediate Similarity	NPC261380
0.8272	Intermediate Similarity	NPC476355
0.8272	Intermediate Similarity	NPC48641
0.8272	Intermediate Similarity	NPC140287
0.8261	Intermediate Similarity	NPC36954
0.8261	Intermediate Similarity	NPC471141
0.8261	Intermediate Similarity	NPC270013
0.8261	Intermediate Similarity	NPC14961
0.825	Intermediate Similarity	NPC163003
0.8214	Intermediate Similarity	NPC89128
0.8214	Intermediate Similarity	NPC19841
0.8211	Intermediate Similarity	NPC185141
0.8211	Intermediate Similarity	NPC133907
0.8211	Intermediate Similarity	NPC474339
0.8211	Intermediate Similarity	NPC164598
0.8211	Intermediate Similarity	NPC46998
0.8211	Intermediate Similarity	NPC128733
0.8211	Intermediate Similarity	NPC110443
0.8202	Intermediate Similarity	NPC202672
0.8152	Intermediate Similarity	NPC81386
0.8152	Intermediate Similarity	NPC474035
0.814	Intermediate Similarity	NPC89555
0.814	Intermediate Similarity	NPC474959
0.814	Intermediate Similarity	NPC475046
0.814	Intermediate Similarity	NPC11383
0.814	Intermediate Similarity	NPC310450
0.814	Intermediate Similarity	NPC85772
0.814	Intermediate Similarity	NPC474252
0.8132	Intermediate Similarity	NPC184463
0.8132	Intermediate Similarity	NPC30515
0.8125	Intermediate Similarity	NPC149371
0.8111	Intermediate Similarity	NPC206001
0.8111	Intermediate Similarity	NPC218927
0.8072	Intermediate Similarity	NPC123360
0.8072	Intermediate Similarity	NPC235906
0.8049	Intermediate Similarity	NPC476590
0.8049	Intermediate Similarity	NPC114727
0.8046	Intermediate Similarity	NPC475947
0.8046	Intermediate Similarity	NPC250315
0.8046	Intermediate Similarity	NPC284472
0.8046	Intermediate Similarity	NPC229799
0.8046	Intermediate Similarity	NPC286770
0.8043	Intermediate Similarity	NPC212486
0.8043	Intermediate Similarity	NPC476300
0.8043	Intermediate Similarity	NPC165383
0.8043	Intermediate Similarity	NPC179746
0.8043	Intermediate Similarity	NPC81419
0.8023	Intermediate Similarity	NPC25684
0.8023	Intermediate Similarity	NPC301477
0.8023	Intermediate Similarity	NPC141810
0.8023	Intermediate Similarity	NPC281949
0.8022	Intermediate Similarity	NPC473448
0.8022	Intermediate Similarity	NPC129419
0.8022	Intermediate Similarity	NPC476004
0.8022	Intermediate Similarity	NPC474761
0.8022	Intermediate Similarity	NPC51004
0.8021	Intermediate Similarity	NPC47880
0.8	Intermediate Similarity	NPC187268
0.8	Intermediate Similarity	NPC141191
0.8	Intermediate Similarity	NPC477302
0.8	Intermediate Similarity	NPC470239
0.8	Intermediate Similarity	NPC99651
0.8	Intermediate Similarity	NPC136879
0.8	Intermediate Similarity	NPC470244
0.8	Intermediate Similarity	NPC475210
0.8	Intermediate Similarity	NPC473326
0.798	Intermediate Similarity	NPC477513
0.7979	Intermediate Similarity	NPC476315
0.7978	Intermediate Similarity	NPC50637
0.7978	Intermediate Similarity	NPC261721
0.7959	Intermediate Similarity	NPC100487
0.7959	Intermediate Similarity	NPC220964
0.7959	Intermediate Similarity	NPC475676
0.7957	Intermediate Similarity	NPC471147
0.7955	Intermediate Similarity	NPC70424
0.7955	Intermediate Similarity	NPC243618
0.7952	Intermediate Similarity	NPC155587
0.7935	Intermediate Similarity	NPC261607
0.7935	Intermediate Similarity	NPC12172
0.7935	Intermediate Similarity	NPC300312
0.7935	Intermediate Similarity	NPC111114
0.7935	Intermediate Similarity	NPC208886
0.7912	Intermediate Similarity	NPC268298
0.7912	Intermediate Similarity	NPC130359
0.7912	Intermediate Similarity	NPC14901
0.7912	Intermediate Similarity	NPC307411
0.7912	Intermediate Similarity	NPC295312
0.7895	Intermediate Similarity	NPC471462
0.7895	Intermediate Similarity	NPC169205
0.7889	Intermediate Similarity	NPC160138
0.7889	Intermediate Similarity	NPC72513
0.7889	Intermediate Similarity	NPC178215
0.7882	Intermediate Similarity	NPC11796
0.7882	Intermediate Similarity	NPC218817
0.7872	Intermediate Similarity	NPC304886
0.7865	Intermediate Similarity	NPC283085
0.7865	Intermediate Similarity	NPC223871
0.7865	Intermediate Similarity	NPC473669
0.7865	Intermediate Similarity	NPC66346
0.7865	Intermediate Similarity	NPC286338
0.7865	Intermediate Similarity	NPC110710
0.7865	Intermediate Similarity	NPC473651
0.7865	Intermediate Similarity	NPC132496
0.7865	Intermediate Similarity	NPC1083
0.7865	Intermediate Similarity	NPC231009
0.7865	Intermediate Similarity	NPC82795
0.7865	Intermediate Similarity	NPC473478
0.7865	Intermediate Similarity	NPC107986
0.7865	Intermediate Similarity	NPC103284
0.7857	Intermediate Similarity	NPC475871
0.7857	Intermediate Similarity	NPC4620
0.7857	Intermediate Similarity	NPC475945
0.7857	Intermediate Similarity	NPC474165
0.7857	Intermediate Similarity	NPC69171
0.7857	Intermediate Similarity	NPC301207

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 NPC469910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1799
0.2-0.3	3745
0.3-0.4	2304
0.4-0.5	755
0.5-0.6	313
0.6-0.7	43
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7684	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6698	Approved
0.7634	Intermediate Similarity	NPD5785	Approved
0.7634	Intermediate Similarity	NPD46	Approved
0.7629	Intermediate Similarity	NPD4225	Approved
0.7553	Intermediate Similarity	NPD7983	Approved
0.7473	Intermediate Similarity	NPD5363	Approved
0.7473	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.7404	Intermediate Similarity	NPD6371	Approved
0.7333	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD4270	Approved
0.7303	Intermediate Similarity	NPD4252	Approved
0.7303	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.7079	Intermediate Similarity	NPD4271	Approved
0.7079	Intermediate Similarity	NPD4268	Approved
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7033	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD4249	Approved
0.6947	Remote Similarity	NPD4251	Approved
0.6947	Remote Similarity	NPD4250	Approved
0.6939	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7115	Discovery
0.6804	Remote Similarity	NPD5370	Suspended
0.6804	Remote Similarity	NPD1695	Approved
0.6774	Remote Similarity	NPD5209	Approved
0.6774	Remote Similarity	NPD6435	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7839	Suspended
0.6729	Remote Similarity	NPD6686	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6101	Approved
0.6609	Remote Similarity	NPD8515	Approved
0.6609	Remote Similarity	NPD8517	Approved
0.6609	Remote Similarity	NPD8516	Approved
0.6609	Remote Similarity	NPD8513	Phase 3
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD5282	Discontinued
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5331	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD4790	Discontinued
0.6476	Remote Similarity	NPD5344	Discontinued
0.6458	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4756	Discovery
0.6353	Remote Similarity	NPD3197	Phase 1
0.6333	Remote Similarity	NPD8074	Phase 3
0.6279	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD2204	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.6195	Remote Similarity	NPD6053	Discontinued
0.619	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6110	Phase 1
0.6136	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7638	Approved
0.6095	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6083	Remote Similarity	NPD7830	Approved
0.6075	Remote Similarity	NPD6648	Approved
0.6071	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6421	Discontinued
0.6	Remote Similarity	NPD6422	Discontinued
0.5984	Remote Similarity	NPD8273	Phase 1
0.5965	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4228	Discovery
0.5918	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8444	Approved
0.5909	Remote Similarity	NPD6647	Phase 2
0.5893	Remote Similarity	NPD5697	Approved
0.5891	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6084	Phase 2
0.5888	Remote Similarity	NPD6083	Phase 2
0.5888	Remote Similarity	NPD7902	Approved
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8451	Approved
0.5849	Remote Similarity	NPD5695	Phase 3
0.5847	Remote Similarity	NPD7500	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6881	Approved
0.584	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD3732	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5833	Remote Similarity	NPD6319	Approved
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD6649	Approved
0.5806	Remote Similarity	NPD8448	Approved
0.5804	Remote Similarity	NPD6675	Approved
0.5804	Remote Similarity	NPD7128	Approved
0.5804	Remote Similarity	NPD5739	Approved
0.5804	Remote Similarity	NPD6402	Approved
0.5798	Remote Similarity	NPD7641	Discontinued
0.5789	Remote Similarity	NPD6372	Approved
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6373	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5776	Remote Similarity	NPD8297	Approved
0.5772	Remote Similarity	NPD8340	Approved
0.5772	Remote Similarity	NPD8342	Approved
0.5772	Remote Similarity	NPD8341	Approved
0.5772	Remote Similarity	NPD8299	Approved
0.5758	Remote Similarity	NPD3667	Approved
0.5755	Remote Similarity	NPD7748	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.5752	Remote Similarity	NPD6412	Phase 2
0.5747	Remote Similarity	NPD368	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD2067	Discontinued
0.5739	Remote Similarity	NPD7102	Approved
0.5732	Remote Similarity	NPD3172	Approved
0.5726	Remote Similarity	NPD7507	Approved
0.5714	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6011	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.5686	Remote Similarity	NPD5330	Approved
0.5686	Remote Similarity	NPD6684	Approved
0.5686	Remote Similarity	NPD7146	Approved
0.5686	Remote Similarity	NPD7521	Approved
0.5686	Remote Similarity	NPD6409	Approved
0.5686	Remote Similarity	NPD3618	Phase 1
0.5686	Remote Similarity	NPD7334	Approved
0.5682	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD6927	Phase 3
0.5676	Remote Similarity	NPD5211	Phase 2
0.5676	Remote Similarity	NPD7632	Discontinued
0.5669	Remote Similarity	NPD8391	Approved
0.5669	Remote Similarity	NPD8392	Approved
0.5669	Remote Similarity	NPD8390	Approved
0.5667	Remote Similarity	NPD3704	Approved
0.5667	Remote Similarity	NPD7331	Phase 2
0.5663	Remote Similarity	NPD3195	Phase 2
0.5663	Remote Similarity	NPD3196	Approved
0.5663	Remote Similarity	NPD4266	Approved
0.5663	Remote Similarity	NPD3728	Approved
0.5663	Remote Similarity	NPD3194	Approved
0.5663	Remote Similarity	NPD3730	Approved
0.5652	Remote Similarity	NPD6413	Approved
0.5645	Remote Similarity	NPD7492	Approved
0.5644	Remote Similarity	NPD3666	Approved
0.5644	Remote Similarity	NPD3133	Approved
0.5644	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4786	Approved
0.5644	Remote Similarity	NPD3665	Phase 1
0.5641	Remote Similarity	NPD6882	Approved
0.5631	Remote Similarity	NPD7524	Approved
0.5625	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7900	Approved
0.5607	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD4634	Approved
0.56	Remote Similarity	NPD6616	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