NPASS Compound

Structure

NPC474573 OpenBabel07101718192D 57 62 0 0 1 0 0 0 0 0999 V2000 8.5000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2024 -4.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6398 -5.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5419 -6.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6887 -5.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5908 -6.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7377 -5.1316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5933 -6.6097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3614 -8.0660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5000 -4.8301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0000 -2.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0000 -5.6962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.7498 -7.3458 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.3364 -7.2788 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.3125 -8.3750 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -5.6962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5000 -1.3660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.8966 -6.4187 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.0556 -7.7059 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.0067 -8.0149 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -5.6962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -2.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -4.8301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -2.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.2024 -6.7788 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -1.3660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -3.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.9945 -5.8007 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.8477 -6.7277 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.1535 -7.0878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 15.7009 -7.6548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2319 -8.2734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5204 -9.3532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -6.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2146 -8.9930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -6.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4103 -7.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.0981 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -4.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.0981 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 51 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 27 1 0 0 0 0 11 38 1 0 0 0 0 12 37 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 14 39 1 0 0 0 0 15 20 1 0 0 0 0 15 52 1 0 0 0 0 16 25 1 0 0 0 0 16 54 1 0 0 0 0 17 26 1 0 0 0 0 17 53 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 21 37 1 0 0 0 0 22 29 1 0 0 0 0 22 40 1 0 0 0 0 23 34 1 0 0 0 0 23 41 1 0 0 0 0 24 28 1 0 0 0 0 24 42 1 0 0 0 0 25 30 1 0 0 0 0 25 43 1 0 0 0 0 26 31 1 0 0 0 0 26 44 1 0 0 0 0 27 38 1 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 38 1 0 0 0 0 29 45 1 0 0 0 0 30 32 1 0 0 0 0 30 46 1 0 0 0 0 31 33 1 0 0 0 0 31 56 1 0 0 0 0 32 36 1 0 0 0 0 32 51 1 0 0 0 0 33 35 1 0 0 0 0 33 55 1 0 0 0 0 34 37 1 0 0 0 0 34 39 1 0 0 0 0 35 52 1 0 0 0 0 35 53 1 0 0 0 0 36 54 1 0 0 0 0 36 55 1 0 0 0 0 39 47 1 0 0 0 0 48 57 1 0 0 0 0 49 57 2 0 0 0 0 50 57 2 0 0 0 0 56 57 1 0 0 0 0 M CHG 1 48 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	837.39
Volume:	795.749
LogP:	0.742
LogD:	0.872
LogS:	-2.538
# Rotatable Bonds:	13
TPSA:	274.42
# H-Bond Aceptor:	17
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.067
Synthetic Accessibility Score:	6.437
Fsp3:	0.949
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.872
MDCK Permeability:	4.0421080484520644e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.278
Human Intestinal Absorption (HIA):	0.506
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	79.35099792480469%
Volume Distribution (VD):	0.361
Pgp-substrate:	10.619684219360352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.911
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	0.934
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.69
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.716
Skin Sensitization:	0.246
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC474573

Natural Product ID:	NPC474573
*Common Name:**	Certonardoside A
IUPAC Name:	sodium;[(2R,3R,4S,5R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy-5-hydroxy-2-[(6R)-2-methyl-3-methylidene-6-[(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-3,4,6,8,15-pentahydroxy-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]heptoxy]oxan-4-yl] sulfate
Synonyms:
Standard InCHIKey:	DENOEXBJWKHRPT-DJJFBVFPSA-M
Standard InCHI:	InChI=1S/C39H66O17S.Na/c1-18(20(3)15-52-35-33(31(26(44)17-53-35)56-57(48,49)50)55-36-32(51-6)30(46)25(43)16-54-36)7-8-19(2)21-13-23(41)34-37(21,4)12-10-27-38(5)11-9-22(40)29(45)28(38)24(42)14-39(27,34)47;/h19-36,40-47H,1,7-17H2,2-6H3,(H,48,49,50);/q;+1/p-1/t19-,20?,21-,22+,23-,24+,25-,26-,27-,28+,29+,30+,31+,32-,33-,34-,35-,36+,37-,38-,39+;/m1./s1
SMILES:	CO[C@H]1[C@@H](OC[C@H]([C@@H]1O)O)O[C@H]1[C@H](OCC(C(=C)CC[C@H]([C@H]2C[C@H]([C@@H]3[C@]2(C)CC[C@H]2[C@@]3(O)C[C@@H]([C@@H]3[C@]2(C)CC[C@@H]([C@@H]3O)O)O)O)C)C)OC[C@H]([C@@H]1OS(=O)(=O)[O-])O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474261
PubChem CID:	23677777
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	7
Others	3

Activity Type	# Activity
Cell Line	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	100.0	ug.mL-1	PMID[516139]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	6.8	ug.mL-1	PMID[516139]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	100.0	ug.mL-1	PMID[516139]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	>	100.0	ug.mL-1	PMID[516139]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	EC50	>	100.0	ug.mL-1	PMID[516139]
NPT4337	Organism	Encephalomyocarditis virus	Encephalomyocarditis virus	EC50	>	100.0	ug.mL-1	PMID[516139]
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	EC50	>	100.0	ug.mL-1	PMID[516139]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	6.8	ug.mL-1	PMID[516139]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	>	6.8	ug.mL-1	PMID[516139]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	100.0	ug.mL-1	PMID[516139]

☑ 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 NPC474573 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	351
0.1-0.2	3065
0.2-0.3	8992
0.3-0.4	13771
0.4-0.5	7372
0.5-0.6	4802
0.6-0.7	2392
0.7-0.8	1323
0.8-0.85	471
0.85-0.9	145
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC475634
0.96	High Similarity	NPC475521
0.9333	High Similarity	NPC475312
0.9038	High Similarity	NPC473469
0.9	High Similarity	NPC76486
0.8922	High Similarity	NPC31346
0.8909	High Similarity	NPC476692
0.8909	High Similarity	NPC476691
0.89	High Similarity	NPC472989
0.8857	High Similarity	NPC181467
0.8846	High Similarity	NPC476361
0.8846	High Similarity	NPC476360
0.8846	High Similarity	NPC165033
0.8846	High Similarity	NPC273879
0.8824	High Similarity	NPC91497
0.8774	High Similarity	NPC180183
0.8774	High Similarity	NPC7213
0.8774	High Similarity	NPC246124
0.8762	High Similarity	NPC127801
0.8762	High Similarity	NPC473923
0.8762	High Similarity	NPC269627
0.8762	High Similarity	NPC208594
0.8762	High Similarity	NPC473476
0.8762	High Similarity	NPC242748
0.8762	High Similarity	NPC152584
0.8762	High Similarity	NPC160816
0.8762	High Similarity	NPC208477
0.8762	High Similarity	NPC69737
0.8762	High Similarity	NPC194842
0.875	High Similarity	NPC31907
0.875	High Similarity	NPC131479
0.875	High Similarity	NPC120123
0.875	High Similarity	NPC472252
0.875	High Similarity	NPC155010
0.875	High Similarity	NPC286969
0.875	High Similarity	NPC8039
0.875	High Similarity	NPC16520
0.875	High Similarity	NPC114874
0.875	High Similarity	NPC189852
0.875	High Similarity	NPC157659
0.875	High Similarity	NPC211879
0.875	High Similarity	NPC16573
0.875	High Similarity	NPC245280
0.875	High Similarity	NPC473020
0.8725	High Similarity	NPC473638
0.8716	High Similarity	NPC476693
0.8713	High Similarity	NPC473287
0.87	High Similarity	NPC473503
0.8692	High Similarity	NPC151134
0.8679	High Similarity	NPC63368
0.8679	High Similarity	NPC190395
0.8679	High Similarity	NPC54619
0.8679	High Similarity	NPC208650
0.8679	High Similarity	NPC14946
0.8667	High Similarity	NPC470885
0.8667	High Similarity	NPC187400
0.8667	High Similarity	NPC221562
0.8654	High Similarity	NPC312553
0.8654	High Similarity	NPC136816
0.8654	High Similarity	NPC159036
0.8654	High Similarity	NPC288694
0.8641	High Similarity	NPC471247
0.8627	High Similarity	NPC477223
0.8627	High Similarity	NPC477222
0.8624	High Similarity	NPC475354
0.8614	High Similarity	NPC469710
0.8614	High Similarity	NPC92196
0.8611	High Similarity	NPC470867
0.8611	High Similarity	NPC472717
0.86	High Similarity	NPC476669
0.8598	High Similarity	NPC6931
0.8598	High Similarity	NPC51172
0.8598	High Similarity	NPC125324
0.8598	High Similarity	NPC476513
0.8598	High Similarity	NPC476538
0.8598	High Similarity	NPC220427
0.8598	High Similarity	NPC49032
0.8598	High Similarity	NPC476541
0.8598	High Similarity	NPC159005
0.8598	High Similarity	NPC476539
0.8598	High Similarity	NPC476540
0.8585	High Similarity	NPC474569
0.8585	High Similarity	NPC309448
0.8558	High Similarity	NPC88000
0.8558	High Similarity	NPC309425
0.8558	High Similarity	NPC129372
0.8558	High Similarity	NPC160734
0.8558	High Similarity	NPC477225
0.8558	High Similarity	NPC4831
0.8558	High Similarity	NPC470168
0.8558	High Similarity	NPC472023
0.8558	High Similarity	NPC47566
0.8545	High Similarity	NPC476671
0.8544	High Similarity	NPC473616
0.8532	High Similarity	NPC475247
0.8532	High Similarity	NPC65167
0.8532	High Similarity	NPC197231
0.8532	High Similarity	NPC476547
0.8532	High Similarity	NPC114188
0.8532	High Similarity	NPC294129
0.8532	High Similarity	NPC472715
0.8519	High Similarity	NPC477027
0.8519	High Similarity	NPC43976
0.8519	High Similarity	NPC302057
0.8519	High Similarity	NPC296761
0.8519	High Similarity	NPC70204
0.8519	High Similarity	NPC306131
0.8519	High Similarity	NPC475670
0.8519	High Similarity	NPC51925
0.8519	High Similarity	NPC125361
0.8519	High Similarity	NPC477026
0.8519	High Similarity	NPC154085
0.8515	High Similarity	NPC475325
0.8515	High Similarity	NPC309866
0.8505	High Similarity	NPC226642
0.8505	High Similarity	NPC231340
0.8505	High Similarity	NPC94272
0.85	High Similarity	NPC473830
0.85	High Similarity	NPC476668
0.85	High Similarity	NPC204881
0.85	High Similarity	NPC473637
0.85	High Similarity	NPC293609
0.8491	Intermediate Similarity	NPC312774
0.8468	Intermediate Similarity	NPC477810
0.8468	Intermediate Similarity	NPC32707
0.8468	Intermediate Similarity	NPC167183
0.8462	Intermediate Similarity	NPC473200
0.8462	Intermediate Similarity	NPC7341
0.8455	Intermediate Similarity	NPC31896
0.8455	Intermediate Similarity	NPC263359
0.8455	Intermediate Similarity	NPC244431
0.8455	Intermediate Similarity	NPC472716
0.8455	Intermediate Similarity	NPC19888
0.8455	Intermediate Similarity	NPC32361
0.8455	Intermediate Similarity	NPC210569
0.8455	Intermediate Similarity	NPC477050
0.8426	Intermediate Similarity	NPC38217
0.8426	Intermediate Similarity	NPC472988
0.8426	Intermediate Similarity	NPC472896
0.8426	Intermediate Similarity	NPC128123
0.8426	Intermediate Similarity	NPC98696
0.8426	Intermediate Similarity	NPC472897
0.8421	Intermediate Similarity	NPC473566
0.8421	Intermediate Similarity	NPC475358
0.8416	Intermediate Similarity	NPC137004
0.8416	Intermediate Similarity	NPC277774
0.8416	Intermediate Similarity	NPC172838
0.8411	Intermediate Similarity	NPC472899
0.8411	Intermediate Similarity	NPC472898
0.8411	Intermediate Similarity	NPC472900
0.8411	Intermediate Similarity	NPC181845
0.84	Intermediate Similarity	NPC279329
0.84	Intermediate Similarity	NPC65550
0.8396	Intermediate Similarity	NPC213190
0.8396	Intermediate Similarity	NPC473198
0.8378	Intermediate Similarity	NPC79900
0.8378	Intermediate Similarity	NPC144068
0.8378	Intermediate Similarity	NPC476546
0.8378	Intermediate Similarity	NPC307642
0.8365	Intermediate Similarity	NPC280825
0.8365	Intermediate Similarity	NPC234287
0.8364	Intermediate Similarity	NPC477032
0.8364	Intermediate Similarity	NPC13190
0.8364	Intermediate Similarity	NPC472987
0.8364	Intermediate Similarity	NPC92710
0.8364	Intermediate Similarity	NPC477028
0.8364	Intermediate Similarity	NPC473021
0.8364	Intermediate Similarity	NPC124677
0.835	Intermediate Similarity	NPC304011
0.835	Intermediate Similarity	NPC121453
0.835	Intermediate Similarity	NPC139271
0.8349	Intermediate Similarity	NPC42482
0.8349	Intermediate Similarity	NPC477809
0.8349	Intermediate Similarity	NPC194207
0.8349	Intermediate Similarity	NPC22779
0.8349	Intermediate Similarity	NPC46190
0.8349	Intermediate Similarity	NPC73243
0.8349	Intermediate Similarity	NPC249265
0.8349	Intermediate Similarity	NPC224098
0.8349	Intermediate Similarity	NPC95051
0.8349	Intermediate Similarity	NPC232054
0.8349	Intermediate Similarity	NPC40440
0.8349	Intermediate Similarity	NPC150372
0.8349	Intermediate Similarity	NPC476835
0.8349	Intermediate Similarity	NPC208383
0.8349	Intermediate Similarity	NPC248746
0.8349	Intermediate Similarity	NPC475333
0.8349	Intermediate Similarity	NPC84956
0.8349	Intermediate Similarity	NPC475550
0.8349	Intermediate Similarity	NPC6806
0.8349	Intermediate Similarity	NPC244086
0.8349	Intermediate Similarity	NPC470433
0.8349	Intermediate Similarity	NPC300557
0.8349	Intermediate Similarity	NPC102016
0.8349	Intermediate Similarity	NPC218571
0.8349	Intermediate Similarity	NPC171073
0.8349	Intermediate Similarity	NPC309278
0.8333	Intermediate Similarity	NPC24960
0.8333	Intermediate Similarity	NPC470170
0.8333	Intermediate Similarity	NPC252253

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 NPC474573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	3208
0.2-0.3	3963
0.3-0.4	1032
0.4-0.5	362
0.5-0.6	250
0.6-0.7	39
0.7-0.8	10
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD8171	Discontinued
0.8053	Intermediate Similarity	NPD8133	Approved
0.8034	Intermediate Similarity	NPD8379	Approved
0.8034	Intermediate Similarity	NPD8296	Approved
0.8034	Intermediate Similarity	NPD8033	Approved
0.8034	Intermediate Similarity	NPD8335	Approved
0.8034	Intermediate Similarity	NPD8380	Approved
0.8034	Intermediate Similarity	NPD8378	Approved
0.7949	Intermediate Similarity	NPD8377	Approved
0.7949	Intermediate Similarity	NPD8294	Approved
0.7863	Intermediate Similarity	NPD7516	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7503	Approved
0.7217	Intermediate Similarity	NPD6412	Phase 2
0.72	Intermediate Similarity	NPD7507	Approved
0.7165	Intermediate Similarity	NPD7319	Approved
0.7094	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6928	Phase 2
0.6967	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8450	Suspended
0.6905	Remote Similarity	NPD8328	Phase 3
0.687	Remote Similarity	NPD8449	Approved
0.6822	Remote Similarity	NPD7736	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.6731	Remote Similarity	NPD7525	Registered
0.6693	Remote Similarity	NPD6370	Approved
0.6615	Remote Similarity	NPD8293	Discontinued
0.6596	Remote Similarity	NPD7625	Phase 1
0.6535	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD6054	Approved
0.6518	Remote Similarity	NPD8035	Phase 2
0.6518	Remote Similarity	NPD8034	Phase 2
0.6481	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6686	Approved
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6695	Phase 3
0.6385	Remote Similarity	NPD6067	Discontinued
0.6371	Remote Similarity	NPD8297	Approved
0.6371	Remote Similarity	NPD6882	Approved
0.6357	Remote Similarity	NPD6016	Approved
0.6357	Remote Similarity	NPD6015	Approved
0.6348	Remote Similarity	NPD7991	Discontinued
0.6336	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD7638	Approved
0.6321	Remote Similarity	NPD7645	Phase 2
0.6311	Remote Similarity	NPD1810	Approved
0.6311	Remote Similarity	NPD1811	Approved
0.6308	Remote Similarity	NPD5988	Approved
0.6306	Remote Similarity	NPD7750	Discontinued
0.6299	Remote Similarity	NPD6009	Approved
0.6288	Remote Similarity	NPD6616	Approved
0.6279	Remote Similarity	NPD6319	Approved
0.6273	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7639	Approved
0.6271	Remote Similarity	NPD7640	Approved
0.6241	Remote Similarity	NPD7078	Approved
0.6231	Remote Similarity	NPD8517	Approved
0.6231	Remote Similarity	NPD8516	Approved
0.6231	Remote Similarity	NPD8515	Approved
0.6231	Remote Similarity	NPD8513	Phase 3
0.6218	Remote Similarity	NPD4159	Approved
0.619	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5739	Approved
0.6148	Remote Similarity	NPD6402	Approved
0.6148	Remote Similarity	NPD6675	Approved
0.6148	Remote Similarity	NPD7128	Approved
0.6129	Remote Similarity	NPD6373	Approved
0.6129	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6931	Approved
0.6111	Remote Similarity	NPD6930	Phase 2
0.6095	Remote Similarity	NPD6942	Approved
0.6095	Remote Similarity	NPD7339	Approved
0.6074	Remote Similarity	NPD6033	Approved
0.6048	Remote Similarity	NPD7320	Approved
0.6048	Remote Similarity	NPD6881	Approved
0.6048	Remote Similarity	NPD6899	Approved
0.6038	Remote Similarity	NPD6933	Approved
0.6032	Remote Similarity	NPD8130	Phase 1
0.6032	Remote Similarity	NPD6650	Approved
0.6032	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2254	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD2686	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3168	Discontinued
0.5981	Remote Similarity	NPD6932	Approved
0.5969	Remote Similarity	NPD6940	Discontinued
0.5968	Remote Similarity	NPD5697	Approved
0.5968	Remote Similarity	NPD5701	Approved
0.5966	Remote Similarity	NPD4755	Approved
0.5963	Remote Similarity	NPD4748	Discontinued
0.5952	Remote Similarity	NPD7102	Approved
0.5952	Remote Similarity	NPD6883	Approved
0.5952	Remote Similarity	NPD7290	Approved
0.5952	Remote Similarity	NPD4634	Approved
0.5948	Remote Similarity	NPD7087	Discontinued
0.5946	Remote Similarity	NPD3669	Approved
0.5946	Remote Similarity	NPD4788	Approved
0.5946	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD7115	Discovery
0.592	Remote Similarity	NPD8174	Phase 2
0.5906	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6617	Approved
0.5906	Remote Similarity	NPD6847	Approved
0.5906	Remote Similarity	NPD6869	Approved
0.5902	Remote Similarity	NPD7632	Discontinued
0.59	Remote Similarity	NPD371	Approved
0.5897	Remote Similarity	NPD6399	Phase 3
0.5897	Remote Similarity	NPD4202	Approved
0.5896	Remote Similarity	NPD7604	Phase 2
0.5887	Remote Similarity	NPD6008	Approved
0.5873	Remote Similarity	NPD6012	Approved
0.5873	Remote Similarity	NPD6013	Approved
0.5873	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD6683	Phase 2
0.5868	Remote Similarity	NPD5285	Approved
0.5868	Remote Similarity	NPD4700	Approved
0.5868	Remote Similarity	NPD4696	Approved
0.5868	Remote Similarity	NPD5286	Approved
0.5865	Remote Similarity	NPD5983	Phase 2
0.5865	Remote Similarity	NPD4787	Phase 1
0.5849	Remote Similarity	NPD6924	Approved
0.5849	Remote Similarity	NPD4785	Approved
0.5849	Remote Similarity	NPD4784	Approved
0.5849	Remote Similarity	NPD6926	Approved
0.5847	Remote Similarity	NPD7748	Approved
0.5841	Remote Similarity	NPD6893	Approved
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD5776	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5833	Remote Similarity	NPD6925	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5827	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5344	Discontinued
0.5818	Remote Similarity	NPD7514	Phase 3
0.581	Remote Similarity	NPD4243	Approved
0.5809	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD6011	Approved
0.578	Remote Similarity	NPD6697	Approved
0.578	Remote Similarity	NPD6114	Approved
0.578	Remote Similarity	NPD7145	Approved
0.578	Remote Similarity	NPD6118	Approved
0.578	Remote Similarity	NPD6115	Approved
0.5772	Remote Similarity	NPD5225	Approved
0.5772	Remote Similarity	NPD5211	Phase 2
0.5772	Remote Similarity	NPD4633	Approved
0.5772	Remote Similarity	NPD5224	Approved
0.5772	Remote Similarity	NPD5226	Approved
0.576	Remote Similarity	NPD4767	Approved
0.576	Remote Similarity	NPD4768	Approved
0.5752	Remote Similarity	NPD4786	Approved
0.5746	Remote Similarity	NPD6921	Approved
0.5726	Remote Similarity	NPD4754	Approved
0.5726	Remote Similarity	NPD5174	Approved
0.5726	Remote Similarity	NPD5175	Approved
0.5691	Remote Similarity	NPD5223	Approved
0.5688	Remote Similarity	NPD6116	Phase 1
0.568	Remote Similarity	NPD5141	Approved
0.5678	Remote Similarity	NPD7515	Phase 2
0.5678	Remote Similarity	NPD7637	Suspended
0.5676	Remote Similarity	NPD7332	Phase 2
0.5676	Remote Similarity	NPD7509	Discontinued
0.5669	Remote Similarity	NPD4729	Approved
0.5669	Remote Similarity	NPD4730	Approved
0.5656	Remote Similarity	NPD4225	Approved
0.5643	Remote Similarity	NPD5956	Approved
0.5641	Remote Similarity	NPD6051	Approved
0.5641	Remote Similarity	NPD5328	Approved
0.5641	Remote Similarity	NPD4753	Phase 2
0.5635	Remote Similarity	NPD5357	Phase 1
0.5625	Remote Similarity	NPD6898	Phase 1
0.5625	Remote Similarity	NPD6902	Approved
0.5614	Remote Similarity	NPD3668	Phase 3
0.5606	Remote Similarity	NPD6274	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