NPASS Compound

Structure

CID226331 OpenBabel06191716022D 22 23 0 0 0 0 0 0 0 0999 V2000 3.0981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 O 0 3 0 0 0 0 0 0 0 0 0 0 0.1988 -2.0090 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 12 1 0 0 0 0 4 8 1 0 0 0 0 4 11 2 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 21 1 0 0 0 0 M CHG 2 20 -1 21 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.841
LogD:	2.802
LogS:	-3.446
# Rotatable Bonds:	1
TPSA:	115.28
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	3.381
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	9.670827239460777e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	96.45606231689453%
Volume Distribution (VD):	0.621
Pgp-substrate:	4.486110687255859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.876
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	13.522
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.667
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.926
Carcinogencity:	0.177
Eye Corrosion:	0.007
Eye Irritation:	0.945
Respiratory Toxicity:	0.244

Download Data

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

Natural Product: NPC226331

Natural Product ID:	NPC226331
*Common Name:**	Cyanidin Chloride
IUPAC Name:	2-(3,4-dihydroxyphenyl)chromenylium-3,5,7-triol;chloride
Synonyms:	Cyanidin Chloride
Standard InCHIKey:	COAWNPJQKJEHPG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6.ClH/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7;/h1-6H,(H4-,16,17,18,19,20);1H
SMILES:	c1cc(c(cc1c1c(cc2c(cc(cc2[o+]1)O)O)[O-])O)O.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511367
PubChem CID:	68247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002993] 7-hydroxyflavonoids

*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
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	Wrocław, Poland	2004–2005	DOI[10.1016/J.FOODCHEM.2006.08.014]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775096]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[1622242]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16659156]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16668466]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20963508]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	Tekirdag, Turkey		PMID[24499198]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25053043]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070365]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25369450]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[25369450]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Hypocotyl	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10189	Abutilon theophrasti	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7635	Glycine max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10189	Abutilon theophrasti	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	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
IC50	3
Others	1

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1566	Individual Protein	Glyoxalase I	Homo sapiens	IC50	=	11700.0	nM	PMID[481391]
NPT1592	Individual Protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	=	1410.0	nM	PMID[481393]
NPT2	Others	Unspecified		Inhibition	=	12.0	%	PMID[481392]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	IC50	=	10300.0	nM	PMID[481394]

☑ 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 NPC226331 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	572
0.1-0.2	2287
0.2-0.3	5830
0.3-0.4	11551
0.4-0.5	4811
0.5-0.6	4255
0.6-0.7	5149
0.7-0.8	4765
0.8-0.85	1910
0.85-0.9	1001
0.9-0.95	459
0.95-1	107

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46274
0.9917	High Similarity	NPC250432
0.9917	High Similarity	NPC5447
0.968	High Similarity	NPC86655
0.968	High Similarity	NPC261619
0.968	High Similarity	NPC15658
0.968	High Similarity	NPC78770
0.968	High Similarity	NPC185604
0.968	High Similarity	NPC126029
0.968	High Similarity	NPC61477
0.968	High Similarity	NPC202762
0.968	High Similarity	NPC219876
0.96	High Similarity	NPC268342
0.96	High Similarity	NPC220825
0.96	High Similarity	NPC268266
0.96	High Similarity	NPC42760
0.9524	High Similarity	NPC127624
0.9453	High Similarity	NPC121812
0.9453	High Similarity	NPC112939
0.9453	High Similarity	NPC151224
0.9453	High Similarity	NPC94750
0.9453	High Similarity	NPC112246
0.9453	High Similarity	NPC164787
0.9453	High Similarity	NPC470356
0.9453	High Similarity	NPC474206
0.9449	High Similarity	NPC11060
0.9421	High Similarity	NPC97432
0.9421	High Similarity	NPC190454
0.938	High Similarity	NPC474639
0.938	High Similarity	NPC248727
0.938	High Similarity	NPC162659
0.938	High Similarity	NPC16435
0.938	High Similarity	NPC270456
0.938	High Similarity	NPC230734
0.938	High Similarity	NPC302701
0.938	High Similarity	NPC306441
0.938	High Similarity	NPC269091
0.938	High Similarity	NPC227503
0.938	High Similarity	NPC265433
0.9375	High Similarity	NPC317380
0.9365	High Similarity	NPC91291
0.9308	High Similarity	NPC176051
0.9308	High Similarity	NPC326797
0.9308	High Similarity	NPC276490
0.9308	High Similarity	NPC107551
0.9308	High Similarity	NPC211549
0.9308	High Similarity	NPC103976
0.9308	High Similarity	NPC474282
0.9308	High Similarity	NPC102904
0.9302	High Similarity	NPC61946
0.9302	High Similarity	NPC47398
0.9302	High Similarity	NPC260898
0.9302	High Similarity	NPC473413
0.9302	High Similarity	NPC234333
0.9297	High Similarity	NPC229442
0.9297	High Similarity	NPC168059
0.928	High Similarity	NPC470699
0.9237	High Similarity	NPC236306
0.9237	High Similarity	NPC260741
0.9237	High Similarity	NPC127218
0.9237	High Similarity	NPC245207
0.9237	High Similarity	NPC25966
0.9237	High Similarity	NPC70682
0.9237	High Similarity	NPC473739
0.9237	High Similarity	NPC232164
0.9237	High Similarity	NPC319647
0.9231	High Similarity	NPC234952
0.9231	High Similarity	NPC470802
0.9225	High Similarity	NPC256307
0.9225	High Similarity	NPC66840
0.9225	High Similarity	NPC106215
0.92	High Similarity	NPC181361
0.9194	High Similarity	NPC122792
0.9194	High Similarity	NPC228972
0.9167	High Similarity	NPC184797
0.9167	High Similarity	NPC309124
0.9154	High Similarity	NPC195022
0.9147	High Similarity	NPC263064
0.9147	High Similarity	NPC475840
0.9134	High Similarity	NPC45824
0.9127	High Similarity	NPC293054
0.9127	High Similarity	NPC82679
0.9127	High Similarity	NPC246620
0.9127	High Similarity	NPC159968
0.9127	High Similarity	NPC169474
0.9127	High Similarity	NPC282000
0.9127	High Similarity	NPC324112
0.9127	High Similarity	NPC74817
0.9127	High Similarity	NPC124452
0.9127	High Similarity	NPC50368
0.9127	High Similarity	NPC236791
0.9127	High Similarity	NPC266555
0.9127	High Similarity	NPC210355
0.912	High Similarity	NPC167571
0.912	High Similarity	NPC278552
0.912	High Similarity	NPC207179
0.9106	High Similarity	NPC145780
0.9098	High Similarity	NPC35216
0.9098	High Similarity	NPC178054
0.9098	High Similarity	NPC471389
0.9091	High Similarity	NPC32630
0.9084	High Similarity	NPC472336
0.9084	High Similarity	NPC173660
0.9084	High Similarity	NPC472334
0.9077	High Similarity	NPC170694
0.907	High Similarity	NPC474134
0.907	High Similarity	NPC201587
0.907	High Similarity	NPC470752
0.907	High Similarity	NPC131128
0.907	High Similarity	NPC253105
0.9062	High Similarity	NPC234488
0.9062	High Similarity	NPC474481
0.9062	High Similarity	NPC311680
0.9062	High Similarity	NPC299221
0.9062	High Similarity	NPC51840
0.9062	High Similarity	NPC214860
0.9055	High Similarity	NPC154866
0.9048	High Similarity	NPC214406
0.9048	High Similarity	NPC103823
0.9048	High Similarity	NPC44748
0.9048	High Similarity	NPC28730
0.9048	High Similarity	NPC78974
0.9048	High Similarity	NPC18924
0.9048	High Similarity	NPC223136
0.903	High Similarity	NPC59841
0.903	High Similarity	NPC2613
0.903	High Similarity	NPC107161
0.903	High Similarity	NPC204347
0.903	High Similarity	NPC475891
0.9023	High Similarity	NPC259519
0.9023	High Similarity	NPC22317
0.9015	High Similarity	NPC38874
0.9015	High Similarity	NPC94994
0.9008	High Similarity	NPC472337
0.9	High Similarity	NPC36661
0.8992	High Similarity	NPC472597
0.8992	High Similarity	NPC309787
0.8984	High Similarity	NPC10225
0.8984	High Similarity	NPC58164
0.8976	High Similarity	NPC216836
0.8968	High Similarity	NPC105925
0.8968	High Similarity	NPC60885
0.8968	High Similarity	NPC57490
0.8968	High Similarity	NPC298757
0.8968	High Similarity	NPC233410
0.8968	High Similarity	NPC299584
0.8968	High Similarity	NPC117214
0.8968	High Similarity	NPC203133
0.8968	High Similarity	NPC251855
0.8968	High Similarity	NPC472093
0.8968	High Similarity	NPC221077
0.8968	High Similarity	NPC17943
0.8968	High Similarity	NPC193544
0.8968	High Similarity	NPC265483
0.8968	High Similarity	NPC208950
0.8968	High Similarity	NPC116907
0.8968	High Similarity	NPC475169
0.8968	High Similarity	NPC234400
0.8968	High Similarity	NPC82483
0.8963	High Similarity	NPC274721
0.8963	High Similarity	NPC155392
0.8963	High Similarity	NPC81638
0.8963	High Similarity	NPC135767
0.896	High Similarity	NPC228922
0.896	High Similarity	NPC84086
0.896	High Similarity	NPC197757
0.896	High Similarity	NPC136319
0.896	High Similarity	NPC121115
0.8955	High Similarity	NPC265075
0.8955	High Similarity	NPC247291
0.8947	High Similarity	NPC471388
0.8947	High Similarity	NPC292487
0.8931	High Similarity	NPC478085
0.8931	High Similarity	NPC160697
0.8923	High Similarity	NPC184447
0.8923	High Similarity	NPC35932
0.8923	High Similarity	NPC160991
0.8923	High Similarity	NPC16208
0.8923	High Similarity	NPC7903
0.8923	High Similarity	NPC6451
0.8915	High Similarity	NPC126836
0.8915	High Similarity	NPC472338
0.8906	High Similarity	NPC31707
0.8906	High Similarity	NPC63179
0.8906	High Similarity	NPC266691
0.8906	High Similarity	NPC28765
0.8906	High Similarity	NPC222572
0.8906	High Similarity	NPC72529
0.8906	High Similarity	NPC87224
0.8898	High Similarity	NPC223953
0.8897	High Similarity	NPC317237
0.8897	High Similarity	NPC93323
0.8897	High Similarity	NPC28440
0.8897	High Similarity	NPC280092
0.8897	High Similarity	NPC12641
0.8897	High Similarity	NPC469313
0.8897	High Similarity	NPC473108
0.8897	High Similarity	NPC138227
0.8897	High Similarity	NPC45257
0.8897	High Similarity	NPC44530

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 NPC226331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	497
0.1-0.2	1042
0.2-0.3	1914
0.3-0.4	2684
0.4-0.5	1625
0.5-0.6	937
0.6-0.7	309
0.7-0.8	90
0.8-0.85	34
0.85-0.9	11
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1529	Clinical (unspecified phase)
0.9917	High Similarity	NPD1530	Clinical (unspecified phase)
0.968	High Similarity	NPD1612	Clinical (unspecified phase)
0.968	High Similarity	NPD1613	Approved
0.8837	High Similarity	NPD3027	Phase 3
0.88	High Similarity	NPD1610	Phase 2
0.8629	High Similarity	NPD1548	Phase 1
0.8473	Intermediate Similarity	NPD4908	Phase 1
0.8429	Intermediate Similarity	NPD1511	Approved
0.8346	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1934	Approved
0.831	Intermediate Similarity	NPD1512	Approved
0.8271	Intermediate Similarity	NPD4625	Phase 3
0.8231	Intermediate Similarity	NPD4749	Approved
0.8163	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD2861	Phase 2
0.8069	Intermediate Similarity	NPD1653	Approved
0.8065	Intermediate Similarity	NPD228	Approved
0.8054	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2801	Approved
0.7985	Intermediate Similarity	NPD3018	Phase 2
0.7956	Intermediate Similarity	NPD1558	Phase 1
0.7939	Intermediate Similarity	NPD422	Phase 1
0.7919	Intermediate Similarity	NPD1465	Phase 2
0.782	Intermediate Similarity	NPD2983	Phase 2
0.782	Intermediate Similarity	NPD2982	Phase 2
0.7812	Intermediate Similarity	NPD6671	Approved
0.781	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6166	Phase 2
0.7806	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1091	Approved
0.7746	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2981	Phase 2
0.7697	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.7686	Intermediate Similarity	NPD1242	Phase 1
0.7656	Intermediate Similarity	NPD5283	Phase 1
0.7639	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3021	Approved
0.7619	Intermediate Similarity	NPD3022	Approved
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.7586	Intermediate Similarity	NPD3750	Approved
0.7571	Intermediate Similarity	NPD4060	Phase 1
0.7556	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6100	Approved
0.7552	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD7054	Approved
0.752	Intermediate Similarity	NPD968	Approved
0.7517	Intermediate Similarity	NPD1652	Phase 2
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7447	Phase 1
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.748	Intermediate Similarity	NPD940	Approved
0.748	Intermediate Similarity	NPD846	Approved
0.746	Intermediate Similarity	NPD290	Approved
0.7453	Intermediate Similarity	NPD6797	Phase 2
0.7453	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD943	Approved
0.7432	Intermediate Similarity	NPD7212	Phase 2
0.7432	Intermediate Similarity	NPD7213	Phase 3
0.7419	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4538	Approved
0.7413	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4536	Approved
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7402	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD6674	Discontinued
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7379	Intermediate Similarity	NPD3540	Phase 1
0.7379	Intermediate Similarity	NPD7266	Discontinued
0.7372	Intermediate Similarity	NPD8651	Approved
0.7368	Intermediate Similarity	NPD4678	Approved
0.7368	Intermediate Similarity	NPD4675	Approved
0.7362	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5960	Phase 3
0.7361	Intermediate Similarity	NPD5588	Approved
0.7357	Intermediate Similarity	NPD7095	Approved
0.7347	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD1240	Approved
0.731	Intermediate Similarity	NPD3539	Phase 1
0.7308	Intermediate Similarity	NPD7075	Discontinued
0.7308	Intermediate Similarity	NPD7843	Approved
0.7299	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD8053	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD8054	Approved
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7228	Approved
0.7266	Intermediate Similarity	NPD6584	Phase 3
0.7266	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6516	Phase 2
0.7259	Intermediate Similarity	NPD5846	Approved
0.7256	Intermediate Similarity	NPD7808	Phase 3
0.7246	Intermediate Similarity	NPD3225	Approved
0.7244	Intermediate Similarity	NPD4967	Phase 2
0.7244	Intermediate Similarity	NPD4966	Approved
0.7244	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD3748	Approved
0.7233	Intermediate Similarity	NPD6232	Discontinued
0.723	Intermediate Similarity	NPD3892	Phase 2
0.7226	Intermediate Similarity	NPD1608	Approved
0.7226	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1607	Approved
0.7215	Intermediate Similarity	NPD5494	Approved
0.7209	Intermediate Similarity	NPD4750	Phase 3
0.7203	Intermediate Similarity	NPD3620	Phase 2
0.7203	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7183	Intermediate Similarity	NPD6798	Discontinued
0.7176	Intermediate Similarity	NPD5535	Approved
0.7162	Intermediate Similarity	NPD5177	Phase 3
0.7153	Intermediate Similarity	NPD447	Suspended
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7153	Intermediate Similarity	NPD3705	Approved
0.7152	Intermediate Similarity	NPD7549	Discontinued
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5058	Phase 3
0.7123	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6696	Suspended
0.7115	Intermediate Similarity	NPD7819	Suspended
0.7101	Intermediate Similarity	NPD1481	Phase 2
0.7099	Intermediate Similarity	NPD7473	Discontinued
0.7097	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6559	Discontinued
0.7089	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6799	Approved
0.7086	Intermediate Similarity	NPD4357	Discontinued
0.7086	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4005	Discontinued
0.7078	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2796	Approved
0.7071	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5402	Approved
0.707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2677	Approved
0.7067	Intermediate Similarity	NPD6190	Approved
0.7063	Intermediate Similarity	NPD1296	Phase 2
0.705	Intermediate Similarity	NPD6582	Phase 2
0.705	Intermediate Similarity	NPD6583	Phase 3
0.7042	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4123	Phase 3
0.7037	Intermediate Similarity	NPD5536	Phase 2
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD4340	Discontinued
0.7029	Intermediate Similarity	NPD1611	Approved
0.7027	Intermediate Similarity	NPD1375	Discontinued
0.7023	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7124	Phase 2
0.7019	Intermediate Similarity	NPD3787	Discontinued
0.7014	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7466	Approved
0.6992	Remote Similarity	NPD1398	Phase 1
0.6987	Remote Similarity	NPD7411	Suspended
0.6985	Remote Similarity	NPD1182	Approved
0.6981	Remote Similarity	NPD3749	Approved
0.698	Remote Similarity	NPD2424	Discontinued
0.6974	Remote Similarity	NPD1774	Approved
0.6959	Remote Similarity	NPD2935	Discontinued
0.6957	Remote Similarity	NPD3496	Discontinued
0.6957	Remote Similarity	NPD6959	Discontinued
0.6954	Remote Similarity	NPD2219	Phase 1
0.6951	Remote Similarity	NPD3751	Discontinued
0.695	Remote Similarity	NPD1203	Approved
0.6948	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5403	Approved
0.6944	Remote Similarity	NPD3268	Approved
0.6943	Remote Similarity	NPD6801	Discontinued
0.6935	Remote Similarity	NPD2859	Approved
0.6935	Remote Similarity	NPD2860	Approved
0.6934	Remote Similarity	NPD1357	Approved
0.6933	Remote Similarity	NPD3060	Approved
0.6929	Remote Similarity	NPD291	Approved
0.6928	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6599	Discontinued
0.6918	Remote Similarity	NPD7768	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