NPASS Compound

Structure

NPC473287 OpenBabel07101718182D 50 54 0 0 1 0 0 0 0 0999 V2000 11.4018 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2428 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1723 -3.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -3.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6045 -2.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0866 -6.6268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0134 -2.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7565 -1.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -3.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -3.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9155 -3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -3.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8666 -3.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.6788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7197 -4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4507 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2213 -3.4855 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.7076 -2.1473 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5000 -3.9468 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.5000 -5.6788 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.9276 -5.3396 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -3.9468 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4781 -4.1547 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -4.8128 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0000 -4.8128 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.1845 -6.0088 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.5827 -5.1492 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.6691 -5.5559 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.2334 -5.6998 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0000 -4.8128 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 12.0255 -4.7216 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.5000 -3.9468 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.5000 -3.9468 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0000 -4.8128 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -3.9468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.6788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3924 -6.9869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4487 -5.6492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4612 -6.5341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4903 -6.3689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -5.6788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -5.5448 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.0000 -6.5448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -7.5448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8787 -5.6487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0745 -4.4126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7687 -4.0525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -6.5448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -6.5448 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 46 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 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 33 1 0 0 0 0 13 34 1 0 0 0 0 14 47 1 0 0 0 0 15 21 1 0 0 0 0 15 35 1 0 0 0 0 16 22 1 0 0 0 0 16 48 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 20 26 1 0 0 0 0 20 36 1 0 0 0 0 21 25 1 0 0 0 0 21 49 1 0 0 0 0 22 27 1 0 0 0 0 22 46 1 0 0 0 0 23 33 1 0 0 0 0 23 35 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 0 0 0 0 26 37 1 0 0 0 0 27 30 1 0 0 0 0 27 38 1 0 0 0 0 28 29 1 0 0 0 0 28 39 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 32 1 0 0 0 0 30 41 1 0 0 0 0 31 34 1 0 0 0 0 31 35 1 0 0 0 0 32 47 1 0 0 0 0 32 48 1 0 0 0 0 35 42 1 0 0 0 0 43 50 1 0 0 0 0 44 50 2 0 0 0 0 45 50 2 0 0 0 0 49 50 1 0 0 0 0 M CHG 1 43 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	737.38
Volume:	711.388
LogP:	2.27
LogD:	1.943
LogS:	-2.407
# Rotatable Bonds:	12
TPSA:	235.73
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	6.077
Fsp3:	1.0
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:	-5.562
MDCK Permeability:	3.8317477446980774e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.503
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.38916778564453%
Volume Distribution (VD):	0.525
Pgp-substrate:	5.565474987030029%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.536
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	1.247
Half-life (T1/2):	0.36

ADMET: Toxicity

hERG Blockers:	0.569
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.594
Carcinogencity:	0.073
Eye Corrosion:	0.023
Eye Irritation:	0.014
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC473287

Natural Product ID:	NPC473287
*Common Name:**	Certonardoside J
IUPAC Name:	sodium;[(3S,4R,5R,6S,8S,9R,10S,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-[2-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methoxyoxan-2-yl]oxyethyl]-6-methylheptan-2-yl]-3,4,8,15,16-pentahydroxy-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-yl] sulfate
Synonyms:
Standard InCHIKey:	NLVHNQPHSCEZHU-LWFWFGOYSA-M
Standard InCHI:	InChI=1S/C35H62O14S.Na/c1-17(2)19(11-14-47-32-30(41)27(38)22(46-6)16-48-32)8-7-18(3)24-28(39)29(40)31-34(24,5)13-10-23-33(4)12-9-20(36)26(37)25(33)21(15-35(23,31)42)49-50(43,44)45;/h17-32,36-42H,7-16H2,1-6H3,(H,43,44,45);/q;+1/p-1/t18-,19-,20+,21+,22-,23-,24+,25+,26+,27+,28-,29-,30-,31-,32-,33-,34-,35+;/m1./s1
SMILES:	CO[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)OCC[C@H](C(C)C)CC[C@H]([C@H]1[C@@H](O)[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2O)O)OS(=O)(=O)[O-])O)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL395820
PubChem CID:	23675029
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
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	=	58.8	ug.mL-1	PMID[538017]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	67.4	ug.mL-1	PMID[538017]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	100.0	ug.mL-1	PMID[538017]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	=	81.1	ug.mL-1	PMID[538017]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	=	82.3	ug.mL-1	PMID[538017]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	EC50	>	58.8	ug.mL-1	PMID[538017]
NPT4337	Organism	Encephalomyocarditis virus	Encephalomyocarditis virus	EC50	>	58.8	ug.mL-1	PMID[538017]
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	EC50	>	58.8	ug.mL-1	PMID[538017]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	67.4	ug.mL-1	PMID[538017]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	>	67.4	ug.mL-1	PMID[538017]

☑ 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 NPC473287 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	578
0.1-0.2	5201
0.2-0.3	13277
0.3-0.4	11027
0.4-0.5	5489
0.5-0.6	3740
0.6-0.7	2235
0.7-0.8	889
0.8-0.85	190
0.85-0.9	38
0.9-0.95	25
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC473503
0.9775	High Similarity	NPC475325
0.9667	High Similarity	NPC469710
0.9663	High Similarity	NPC277774
0.9663	High Similarity	NPC476669
0.9565	High Similarity	NPC473638
0.9551	High Similarity	NPC293609
0.9551	High Similarity	NPC473637
0.9551	High Similarity	NPC476668
0.9551	High Similarity	NPC36372
0.9451	High Similarity	NPC92196
0.9438	High Similarity	NPC279329
0.9438	High Similarity	NPC223143
0.9362	High Similarity	NPC477225
0.9341	High Similarity	NPC477224
0.9341	High Similarity	NPC3538
0.9341	High Similarity	NPC309866
0.9341	High Similarity	NPC113500
0.9326	High Similarity	NPC102725
0.9326	High Similarity	NPC473472
0.9231	High Similarity	NPC167644
0.9231	High Similarity	NPC311246
0.9213	High Similarity	NPC281004
0.9149	High Similarity	NPC473616
0.9121	High Similarity	NPC204881
0.9121	High Similarity	NPC149966
0.9121	High Similarity	NPC5632
0.9121	High Similarity	NPC473830
0.9101	High Similarity	NPC140446
0.9101	High Similarity	NPC43912
0.9043	High Similarity	NPC477222
0.9043	High Similarity	NPC477223
0.9032	High Similarity	NPC473067
0.9032	High Similarity	NPC473064
0.9032	High Similarity	NPC473065
0.9011	High Similarity	NPC65550
0.9011	High Similarity	NPC473542
0.8925	High Similarity	NPC45959
0.8925	High Similarity	NPC252253
0.8925	High Similarity	NPC175
0.8925	High Similarity	NPC24960
0.8925	High Similarity	NPC473774
0.8901	High Similarity	NPC131466
0.8901	High Similarity	NPC20822
0.8901	High Similarity	NPC82955
0.8876	High Similarity	NPC290612
0.8842	High Similarity	NPC233649
0.8842	High Similarity	NPC470028
0.883	High Similarity	NPC477494
0.883	High Similarity	NPC474399
0.8817	High Similarity	NPC473726
0.8817	High Similarity	NPC149400
0.8817	High Similarity	NPC137004
0.8817	High Similarity	NPC172838
0.8817	High Similarity	NPC144790
0.8817	High Similarity	NPC88962
0.8737	High Similarity	NPC476510
0.8737	High Similarity	NPC296936
0.8737	High Similarity	NPC121453
0.8737	High Similarity	NPC304011
0.8737	High Similarity	NPC139271
0.8737	High Similarity	NPC142264
0.8723	High Similarity	NPC473851
0.8723	High Similarity	NPC222731
0.8723	High Similarity	NPC312678
0.8723	High Similarity	NPC179859
0.8723	High Similarity	NPC131693
0.8723	High Similarity	NPC253268
0.8723	High Similarity	NPC294686
0.8723	High Similarity	NPC174024
0.8723	High Similarity	NPC475436
0.8723	High Similarity	NPC291547
0.8713	High Similarity	NPC474573
0.871	High Similarity	NPC229801
0.871	High Similarity	NPC59006
0.871	High Similarity	NPC210759
0.871	High Similarity	NPC307167
0.8681	High Similarity	NPC472396
0.8646	High Similarity	NPC274200
0.8632	High Similarity	NPC57964
0.8632	High Similarity	NPC94582
0.8617	High Similarity	NPC297348
0.8617	High Similarity	NPC477451
0.8617	High Similarity	NPC177834
0.8617	High Similarity	NPC234352
0.8617	High Similarity	NPC250393
0.8617	High Similarity	NPC141769
0.8617	High Similarity	NPC48339
0.8617	High Similarity	NPC325828
0.8617	High Similarity	NPC249204
0.8617	High Similarity	NPC477547
0.8614	High Similarity	NPC475634
0.8571	High Similarity	NPC475574
0.8571	High Similarity	NPC476839
0.8571	High Similarity	NPC471240
0.8571	High Similarity	NPC476838
0.8557	High Similarity	NPC473518
0.8557	High Similarity	NPC291548
0.8542	High Similarity	NPC195297
0.8542	High Similarity	NPC473601
0.8526	High Similarity	NPC151214
0.8526	High Similarity	NPC305418
0.8526	High Similarity	NPC217205
0.8526	High Similarity	NPC471464
0.8526	High Similarity	NPC30687
0.8526	High Similarity	NPC264101
0.8526	High Similarity	NPC291203
0.8526	High Similarity	NPC191915
0.85	High Similarity	NPC475521
0.8495	Intermediate Similarity	NPC228059
0.8485	Intermediate Similarity	NPC134967
0.8485	Intermediate Similarity	NPC114700
0.8485	Intermediate Similarity	NPC470029
0.8485	Intermediate Similarity	NPC310138
0.8462	Intermediate Similarity	NPC475312
0.8462	Intermediate Similarity	NPC232044
0.8462	Intermediate Similarity	NPC273290
0.8454	Intermediate Similarity	NPC476112
0.8454	Intermediate Similarity	NPC470862
0.8454	Intermediate Similarity	NPC475207
0.8454	Intermediate Similarity	NPC115165
0.8454	Intermediate Similarity	NPC210157
0.8454	Intermediate Similarity	NPC232611
0.8454	Intermediate Similarity	NPC303069
0.8454	Intermediate Similarity	NPC51520
0.8454	Intermediate Similarity	NPC307534
0.8454	Intermediate Similarity	NPC470861
0.8454	Intermediate Similarity	NPC470591
0.8454	Intermediate Similarity	NPC83137
0.8444	Intermediate Similarity	NPC478054
0.8444	Intermediate Similarity	NPC241959
0.8438	Intermediate Similarity	NPC475351
0.8438	Intermediate Similarity	NPC6295
0.8438	Intermediate Similarity	NPC19400
0.8438	Intermediate Similarity	NPC107188
0.8438	Intermediate Similarity	NPC473610
0.8438	Intermediate Similarity	NPC473727
0.8438	Intermediate Similarity	NPC211354
0.8438	Intermediate Similarity	NPC107962
0.8438	Intermediate Similarity	NPC206003
0.8387	Intermediate Similarity	NPC128475
0.8384	Intermediate Similarity	NPC472081
0.8384	Intermediate Similarity	NPC478106
0.8384	Intermediate Similarity	NPC477172
0.8384	Intermediate Similarity	NPC476512
0.8384	Intermediate Similarity	NPC108227
0.8384	Intermediate Similarity	NPC31346
0.8352	Intermediate Similarity	NPC474156
0.8352	Intermediate Similarity	NPC227260
0.8351	Intermediate Similarity	NPC287483
0.8351	Intermediate Similarity	NPC238796
0.8351	Intermediate Similarity	NPC156377
0.8351	Intermediate Similarity	NPC475643
0.8351	Intermediate Similarity	NPC475625
0.8351	Intermediate Similarity	NPC203434
0.8351	Intermediate Similarity	NPC284104
0.8351	Intermediate Similarity	NPC116756
0.8351	Intermediate Similarity	NPC128572
0.8351	Intermediate Similarity	NPC30856
0.8351	Intermediate Similarity	NPC470864
0.8351	Intermediate Similarity	NPC252056
0.8351	Intermediate Similarity	NPC98018
0.8351	Intermediate Similarity	NPC84111
0.8351	Intermediate Similarity	NPC472989
0.8351	Intermediate Similarity	NPC103616
0.8351	Intermediate Similarity	NPC470865
0.8351	Intermediate Similarity	NPC132080
0.8351	Intermediate Similarity	NPC470863
0.8351	Intermediate Similarity	NPC232037
0.8351	Intermediate Similarity	NPC470866
0.8351	Intermediate Similarity	NPC160426
0.8351	Intermediate Similarity	NPC97700
0.8351	Intermediate Similarity	NPC184617
0.8351	Intermediate Similarity	NPC237071
0.8317	Intermediate Similarity	NPC312774
0.8286	Intermediate Similarity	NPC475354
0.8283	Intermediate Similarity	NPC41843
0.8283	Intermediate Similarity	NPC470030
0.828	Intermediate Similarity	NPC210658
0.828	Intermediate Similarity	NPC161928
0.8218	Intermediate Similarity	NPC139181
0.8218	Intermediate Similarity	NPC97260
0.8218	Intermediate Similarity	NPC476837
0.8182	Intermediate Similarity	NPC292775
0.8152	Intermediate Similarity	NPC320824
0.8132	Intermediate Similarity	NPC296734
0.8132	Intermediate Similarity	NPC470611
0.81	Intermediate Similarity	NPC20028
0.809	Intermediate Similarity	NPC67657
0.809	Intermediate Similarity	NPC177343
0.809	Intermediate Similarity	NPC18857
0.8081	Intermediate Similarity	NPC76486
0.8065	Intermediate Similarity	NPC266651
0.8061	Intermediate Similarity	NPC215570
0.8041	Intermediate Similarity	NPC182740
0.8041	Intermediate Similarity	NPC470623
0.8041	Intermediate Similarity	NPC18724
0.8041	Intermediate Similarity	NPC122083
0.8041	Intermediate Similarity	NPC323231
0.8041	Intermediate Similarity	NPC224003

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 NPC473287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	525
0.1-0.2	4670
0.2-0.3	2790
0.3-0.4	609
0.4-0.5	300
0.5-0.6	202
0.6-0.7	38
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8617	High Similarity	NPD8171	Discontinued
0.7912	Intermediate Similarity	NPD6928	Phase 2
0.7788	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7516	Approved
0.7281	Intermediate Similarity	NPD7328	Approved
0.7281	Intermediate Similarity	NPD7327	Approved
0.7241	Intermediate Similarity	NPD8296	Approved
0.7241	Intermediate Similarity	NPD8380	Approved
0.7241	Intermediate Similarity	NPD8335	Approved
0.7241	Intermediate Similarity	NPD8379	Approved
0.7241	Intermediate Similarity	NPD8378	Approved
0.7191	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8294	Approved
0.7155	Intermediate Similarity	NPD8377	Approved
0.7094	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD8133	Approved
0.7019	Intermediate Similarity	NPD7991	Discontinued
0.6882	Remote Similarity	NPD1810	Approved
0.6882	Remote Similarity	NPD1811	Approved
0.6739	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7507	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6629	Remote Similarity	NPD371	Approved
0.6559	Remote Similarity	NPD4787	Phase 1
0.6559	Remote Similarity	NPD2686	Approved
0.6559	Remote Similarity	NPD2687	Approved
0.6559	Remote Similarity	NPD2254	Approved
0.6525	Remote Similarity	NPD6940	Discontinued
0.6491	Remote Similarity	NPD8174	Phase 2
0.648	Remote Similarity	NPD7736	Approved
0.6436	Remote Similarity	NPD3669	Approved
0.6436	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6115	Approved
0.6429	Remote Similarity	NPD6697	Approved
0.6429	Remote Similarity	NPD6114	Approved
0.6429	Remote Similarity	NPD6118	Approved
0.6341	Remote Similarity	NPD6370	Approved
0.6333	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6116	Phase 1
0.627	Remote Similarity	NPD8293	Discontinued
0.6224	Remote Similarity	NPD6117	Approved
0.6179	Remote Similarity	NPD6059	Approved
0.6179	Remote Similarity	NPD6054	Approved
0.6139	Remote Similarity	NPD7525	Registered
0.6038	Remote Similarity	NPD7524	Approved
0.6032	Remote Similarity	NPD6067	Discontinued
0.6032	Remote Similarity	NPD8328	Phase 3
0.6031	Remote Similarity	NPD8449	Approved
0.602	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6700	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.5985	Remote Similarity	NPD8450	Suspended
0.5984	Remote Similarity	NPD7492	Approved
0.5979	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD1700	Approved
0.5963	Remote Similarity	NPD6702	Approved
0.5963	Remote Similarity	NPD8034	Phase 2
0.5963	Remote Similarity	NPD6703	Approved
0.5963	Remote Similarity	NPD8035	Phase 2
0.596	Remote Similarity	NPD3703	Phase 2
0.596	Remote Similarity	NPD3702	Approved
0.5952	Remote Similarity	NPD5988	Approved
0.5938	Remote Similarity	NPD6616	Approved
0.5932	Remote Similarity	NPD6686	Approved
0.5932	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7625	Phase 1
0.592	Remote Similarity	NPD6319	Approved
0.5891	Remote Similarity	NPD7078	Approved
0.5876	Remote Similarity	NPD4245	Approved
0.5876	Remote Similarity	NPD4244	Approved
0.5868	Remote Similarity	NPD8297	Approved
0.5868	Remote Similarity	NPD6882	Approved
0.5826	Remote Similarity	NPD4159	Approved
0.5812	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6009	Approved
0.5789	Remote Similarity	NPD7638	Approved
0.5784	Remote Similarity	NPD5364	Discontinued
0.5773	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3698	Phase 2
0.5773	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD1779	Approved
0.5769	Remote Similarity	NPD1780	Approved
0.5755	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.575	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7639	Approved
0.5739	Remote Similarity	NPD7640	Approved
0.5725	Remote Similarity	NPD6033	Approved
0.5701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD4632	Approved
0.567	Remote Similarity	NPD5360	Phase 3
0.567	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6695	Phase 3
0.5657	Remote Similarity	NPD5777	Approved
0.5648	Remote Similarity	NPD8308	Discontinued
0.5641	Remote Similarity	NPD7632	Discontinued
0.563	Remote Similarity	NPD7128	Approved
0.563	Remote Similarity	NPD6402	Approved
0.563	Remote Similarity	NPD5739	Approved
0.563	Remote Similarity	NPD6675	Approved
0.562	Remote Similarity	NPD6372	Approved
0.562	Remote Similarity	NPD6373	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