NPASS Compound

Structure

NPC245452 OpenBabel07101719252D 42 46 0 0 1 0 0 0 0 0999 V2000 -4.3187 3.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8233 -0.0178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0646 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5097 2.9658 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6143 1.9713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8917 1.7902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8052 1.3835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7872 2.7847 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 -5.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5278 1.5645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9098 0.3890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 3.1915 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 -2.5962 3.3725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 37 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 16 2 0 0 0 0 8 27 1 0 0 0 0 8 38 1 0 0 0 0 9 27 1 0 0 0 0 9 39 1 0 0 0 0 10 1 1 6 0 0 0 10 18 1 0 0 0 0 10 40 1 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 13 14 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 17 2 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 16 41 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 1 0 0 0 19 23 1 0 0 0 0 19 33 2 0 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 20 34 1 6 0 0 0 21 23 2 0 0 0 0 21 41 1 0 0 0 0 22 37 1 6 0 0 0 23 42 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 1 0 0 0 24 35 1 0 0 0 0 25 38 1 1 0 0 0 25 40 1 0 0 0 0 26 39 1 0 0 0 0 26 42 1 6 0 0 0 27 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.16
Volume:	543.527
LogP:	1.15
LogD:	0.268
LogS:	-4.963
# Rotatable Bonds:	7
TPSA:	238.2
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.921
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.383
MDCK Permeability:	8.95194989425363e-06
Pgp-inhibitor:	0.041
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.902
20% Bioavailability (F20%):	0.162
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	88.90935516357422%
Volume Distribution (VD):	0.664
Pgp-substrate:	15.438212394714355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.026

ADMET: Excretion

Clearance (CL):	2.75
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.834
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.923
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.406
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC245452

Natural Product ID:	NPC245452
*Common Name:**	Quercetin 3-O-(3-O-Methyl-Alpha-L-Rhamnopyranosyl-(1->5)-O-Beta-D-Apiofuranoside)
IUPAC Name:	3-[(2S,3R,4R)-4-[[(2R,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	LMDMJKAWOYEAEK-RNXNSVIDSA-N
Standard InCHI:	InChI=1S/C27H30O15/c1-10-18(32)22(37-2)20(34)25(40-10)38-8-27(36)9-39-26(24(27)35)42-23-19(33)17-15(31)6-12(28)7-16(17)41-21(23)11-3-4-13(29)14(30)5-11/h3-7,10,18,20,22,24-26,28-32,34-36H,8-9H2,1-2H3/t10-,18-,20+,22+,24-,25+,26-,27+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@]2(CO[C@H]([C@@H]2O)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)O)O1)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1642199
PubChem CID:	53317404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	20000.0	nM	PMID[534489]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	22000.0	nM	PMID[534489]
NPT2	Others	Unspecified		IC50	=	19100.0	nM	PMID[534489]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[534489]

☑ 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 NPC245452 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	446
0.1-0.2	1735
0.2-0.3	3762
0.3-0.4	9138
0.4-0.5	9349
0.5-0.6	4621
0.6-0.7	5575
0.7-0.8	5423
0.8-0.85	1677
0.85-0.9	534
0.9-0.95	429
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC127546
0.9812	High Similarity	NPC52550
0.9812	High Similarity	NPC317489
0.9812	High Similarity	NPC223424
0.9812	High Similarity	NPC84362
0.9812	High Similarity	NPC173637
0.9752	High Similarity	NPC225434
0.9752	High Similarity	NPC223747
0.9752	High Similarity	NPC476771
0.9752	High Similarity	NPC203050
0.9752	High Similarity	NPC120099
0.9752	High Similarity	NPC219904
0.975	High Similarity	NPC274618
0.975	High Similarity	NPC276222
0.975	High Similarity	NPC56077
0.975	High Similarity	NPC328940
0.975	High Similarity	NPC67037
0.975	High Similarity	NPC135599
0.975	High Similarity	NPC118284
0.975	High Similarity	NPC145038
0.975	High Similarity	NPC73855
0.975	High Similarity	NPC179950
0.975	High Similarity	NPC281131
0.975	High Similarity	NPC277174
0.975	High Similarity	NPC253662
0.975	High Similarity	NPC88789
0.975	High Similarity	NPC255615
0.975	High Similarity	NPC308404
0.975	High Similarity	NPC113968
0.9691	High Similarity	NPC95866
0.9691	High Similarity	NPC206123
0.9691	High Similarity	NPC244776
0.9691	High Similarity	NPC116864
0.9689	High Similarity	NPC265530
0.9689	High Similarity	NPC48640
0.9689	High Similarity	NPC149244
0.9689	High Similarity	NPC226304
0.9689	High Similarity	NPC325555
0.9688	High Similarity	NPC240431
0.9688	High Similarity	NPC277205
0.9688	High Similarity	NPC55786
0.9688	High Similarity	NPC34531
0.9688	High Similarity	NPC19388
0.9632	High Similarity	NPC33054
0.9632	High Similarity	NPC476772
0.9632	High Similarity	NPC203259
0.9632	High Similarity	NPC153755
0.9632	High Similarity	NPC175107
0.9632	High Similarity	NPC471725
0.9632	High Similarity	NPC134532
0.9632	High Similarity	NPC235575
0.9632	High Similarity	NPC176740
0.9632	High Similarity	NPC471748
0.9632	High Similarity	NPC155877
0.9632	High Similarity	NPC190003
0.963	High Similarity	NPC52382
0.963	High Similarity	NPC270578
0.9627	High Similarity	NPC197285
0.9627	High Similarity	NPC21100
0.9627	High Similarity	NPC254306
0.9625	High Similarity	NPC19709
0.9573	High Similarity	NPC42773
0.9573	High Similarity	NPC101026
0.9573	High Similarity	NPC21666
0.9573	High Similarity	NPC4390
0.9573	High Similarity	NPC24043
0.9573	High Similarity	NPC45522
0.9573	High Similarity	NPC169977
0.9571	High Similarity	NPC29958
0.9571	High Similarity	NPC20505
0.9571	High Similarity	NPC259896
0.9571	High Similarity	NPC72249
0.9571	High Similarity	NPC136042
0.9571	High Similarity	NPC235260
0.9571	High Similarity	NPC255157
0.9571	High Similarity	NPC67105
0.9571	High Similarity	NPC155763
0.9571	High Similarity	NPC67326
0.9571	High Similarity	NPC254855
0.9571	High Similarity	NPC156869
0.9568	High Similarity	NPC92565
0.9568	High Similarity	NPC160156
0.9565	High Similarity	NPC311830
0.9565	High Similarity	NPC22832
0.9563	High Similarity	NPC189142
0.9563	High Similarity	NPC473043
0.9563	High Similarity	NPC150164
0.9563	High Similarity	NPC77660
0.9521	High Similarity	NPC473071
0.9521	High Similarity	NPC473073
0.9515	High Similarity	NPC19108
0.9515	High Similarity	NPC220173
0.9515	High Similarity	NPC294629
0.9515	High Similarity	NPC473327
0.9515	High Similarity	NPC16194
0.9515	High Similarity	NPC476472
0.9515	High Similarity	NPC294815
0.9512	High Similarity	NPC60735
0.9512	High Similarity	NPC261254
0.9512	High Similarity	NPC117260
0.9512	High Similarity	NPC476405
0.9512	High Similarity	NPC26230
0.9509	High Similarity	NPC138927
0.9509	High Similarity	NPC227508
0.9506	High Similarity	NPC115674
0.9506	High Similarity	NPC210073
0.9503	High Similarity	NPC88023
0.9503	High Similarity	NPC222936
0.9503	High Similarity	NPC270335
0.9503	High Similarity	NPC243930
0.9503	High Similarity	NPC284960
0.9503	High Similarity	NPC168822
0.9503	High Similarity	NPC309025
0.9503	High Similarity	NPC191306
0.9464	High Similarity	NPC473072
0.9458	High Similarity	NPC122467
0.9458	High Similarity	NPC471669
0.9458	High Similarity	NPC154741
0.9458	High Similarity	NPC202908
0.9458	High Similarity	NPC89127
0.9458	High Similarity	NPC65563
0.9458	High Similarity	NPC292019
0.9458	High Similarity	NPC296018
0.9458	High Similarity	NPC472385
0.9458	High Similarity	NPC198324
0.9458	High Similarity	NPC470949
0.9458	High Similarity	NPC14187
0.9451	High Similarity	NPC84265
0.9451	High Similarity	NPC245014
0.9451	High Similarity	NPC282987
0.9451	High Similarity	NPC285197
0.9451	High Similarity	NPC212748
0.9448	High Similarity	NPC229729
0.9448	High Similarity	NPC275454
0.9444	High Similarity	NPC72016
0.9441	High Similarity	NPC127782
0.9441	High Similarity	NPC300537
0.9401	High Similarity	NPC476773
0.9401	High Similarity	NPC168584
0.9401	High Similarity	NPC251417
0.9401	High Similarity	NPC89052
0.9401	High Similarity	NPC173837
0.9401	High Similarity	NPC139571
0.9401	High Similarity	NPC217520
0.9401	High Similarity	NPC35167
0.9398	High Similarity	NPC223426
0.9398	High Similarity	NPC81042
0.9398	High Similarity	NPC34267
0.9398	High Similarity	NPC210094
0.9398	High Similarity	NPC43211
0.9398	High Similarity	NPC264735
0.9398	High Similarity	NPC115760
0.9398	High Similarity	NPC214621
0.9398	High Similarity	NPC237435
0.9398	High Similarity	NPC135277
0.9398	High Similarity	NPC253685
0.9398	High Similarity	NPC477848
0.9398	High Similarity	NPC49344
0.9398	High Similarity	NPC101191
0.939	High Similarity	NPC105025
0.939	High Similarity	NPC45638
0.939	High Similarity	NPC469931
0.939	High Similarity	NPC58053
0.939	High Similarity	NPC201292
0.939	High Similarity	NPC475942
0.939	High Similarity	NPC93337
0.939	High Similarity	NPC226294
0.939	High Similarity	NPC195257
0.939	High Similarity	NPC209296
0.939	High Similarity	NPC186807
0.9387	High Similarity	NPC5778
0.9387	High Similarity	NPC236934
0.9387	High Similarity	NPC8856
0.9383	High Similarity	NPC29830
0.9379	High Similarity	NPC182045
0.9375	High Similarity	NPC320283
0.9375	High Similarity	NPC111929
0.9375	High Similarity	NPC472459
0.9375	High Similarity	NPC41121
0.9345	High Similarity	NPC473682
0.9345	High Similarity	NPC110941
0.9345	High Similarity	NPC470443
0.9345	High Similarity	NPC192539
0.9345	High Similarity	NPC241423
0.9345	High Similarity	NPC470444
0.9345	High Similarity	NPC473571
0.9345	High Similarity	NPC126784
0.9341	High Similarity	NPC219043
0.9341	High Similarity	NPC48984
0.9341	High Similarity	NPC473862
0.9341	High Similarity	NPC169733
0.9341	High Similarity	NPC61904
0.9341	High Similarity	NPC233994
0.9341	High Similarity	NPC8573
0.9341	High Similarity	NPC144097
0.9341	High Similarity	NPC211532
0.9333	High Similarity	NPC51326
0.9333	High Similarity	NPC231194
0.9333	High Similarity	NPC150767
0.9333	High Similarity	NPC78734

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 NPC245452 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	901
0.2-0.3	1916
0.3-0.4	2746
0.4-0.5	1900
0.5-0.6	899
0.6-0.7	279
0.7-0.8	106
0.8-0.85	16
0.85-0.9	6
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD6797	Phase 2
0.9573	High Similarity	NPD7251	Discontinued
0.9398	High Similarity	NPD4338	Clinical (unspecified phase)
0.9398	High Similarity	NPD7808	Phase 3
0.939	High Similarity	NPD7054	Approved
0.9333	High Similarity	NPD7472	Approved
0.9329	High Similarity	NPD3818	Discontinued
0.9217	High Similarity	NPD7074	Phase 3
0.9074	High Similarity	NPD4381	Clinical (unspecified phase)
0.9042	High Similarity	NPD7804	Clinical (unspecified phase)
0.8976	High Similarity	NPD6167	Clinical (unspecified phase)
0.8976	High Similarity	NPD6166	Phase 2
0.8976	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD3882	Suspended
0.8834	High Similarity	NPD3817	Phase 2
0.8827	High Similarity	NPD1934	Approved
0.8773	High Similarity	NPD2393	Clinical (unspecified phase)
0.8688	High Similarity	NPD1512	Approved
0.8659	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD1511	Approved
0.8555	High Similarity	NPD6559	Discontinued
0.8503	High Similarity	NPD7075	Discontinued
0.8476	Intermediate Similarity	NPD4380	Phase 2
0.8443	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5402	Approved
0.8373	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5403	Approved
0.8286	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD5494	Approved
0.8171	Intermediate Similarity	NPD5401	Approved
0.8132	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD3751	Discontinued
0.8092	Intermediate Similarity	NPD3787	Discontinued
0.8075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7685	Pre-registration
0.8025	Intermediate Similarity	NPD1549	Phase 2
0.8024	Intermediate Similarity	NPD1653	Approved
0.7964	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7929	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD919	Approved
0.791	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD2796	Approved
0.7895	Intermediate Similarity	NPD7819	Suspended
0.7882	Intermediate Similarity	NPD7411	Suspended
0.7865	Intermediate Similarity	NPD5844	Phase 1
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7829	Intermediate Similarity	NPD1247	Approved
0.7829	Intermediate Similarity	NPD6959	Discontinued
0.7816	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD6190	Approved
0.7753	Intermediate Similarity	NPD7473	Discontinued
0.774	Intermediate Similarity	NPD3926	Phase 2
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7733	Intermediate Similarity	NPD37	Approved
0.7708	Intermediate Similarity	NPD7435	Discontinued
0.7702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1613	Approved
0.7701	Intermediate Similarity	NPD4966	Approved
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4965	Approved
0.768	Intermediate Similarity	NPD7584	Approved
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD3749	Approved
0.765	Intermediate Similarity	NPD8313	Approved
0.765	Intermediate Similarity	NPD8312	Approved
0.7636	Intermediate Similarity	NPD7266	Discontinued
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1240	Approved
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7485	Intermediate Similarity	NPD943	Approved
0.7475	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7874	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.7474	Intermediate Similarity	NPD6535	Approved
0.7462	Intermediate Similarity	NPD7701	Phase 2
0.7453	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7240	Approved
0.7439	Intermediate Similarity	NPD230	Phase 1
0.7439	Intermediate Similarity	NPD1933	Approved
0.7433	Intermediate Similarity	NPD8434	Phase 2
0.7427	Intermediate Similarity	NPD2532	Approved
0.7427	Intermediate Similarity	NPD2534	Approved
0.7427	Intermediate Similarity	NPD2533	Approved
0.7424	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7401	Intermediate Similarity	NPD7768	Phase 2
0.7396	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8455	Phase 2
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7700	Phase 2
0.7358	Intermediate Similarity	NPD7699	Phase 2
0.735	Intermediate Similarity	NPD7783	Phase 2
0.735	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7801	Approved
0.7341	Intermediate Similarity	NPD920	Approved
0.7337	Intermediate Similarity	NPD2800	Approved
0.7312	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8320	Phase 1
0.731	Intermediate Similarity	NPD8319	Approved
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD6823	Phase 2
0.7286	Intermediate Similarity	NPD7585	Approved
0.7262	Intermediate Similarity	NPD2935	Discontinued
0.7249	Intermediate Similarity	NPD8150	Discontinued
0.7236	Intermediate Similarity	NPD7583	Approved
0.7235	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1243	Approved
0.7229	Intermediate Similarity	NPD447	Suspended
0.7225	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3748	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD1091	Approved
0.712	Intermediate Similarity	NPD2403	Approved
0.7118	Intermediate Similarity	NPD2344	Approved
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4360	Phase 2
0.7113	Intermediate Similarity	NPD4363	Phase 3
0.7112	Intermediate Similarity	NPD5953	Discontinued
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7107	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7680	Approved
0.7073	Intermediate Similarity	NPD7930	Approved
0.7062	Intermediate Similarity	NPD3226	Approved
0.7062	Intermediate Similarity	NPD7458	Discontinued
0.7043	Intermediate Similarity	NPD2163	Approved
0.7039	Intermediate Similarity	NPD6844	Discontinued
0.7035	Intermediate Similarity	NPD6674	Discontinued
0.7035	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD6832	Phase 2
0.703	Intermediate Similarity	NPD4908	Phase 1
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD5710	Approved
0.7011	Intermediate Similarity	NPD5711	Approved
0.7005	Intermediate Similarity	NPD7286	Phase 2
0.6994	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2494	Approved
0.6985	Remote Similarity	NPD2493	Approved
0.6982	Remote Similarity	NPD6651	Approved
0.6974	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6213	Phase 3
0.6974	Remote Similarity	NPD6212	Phase 3
0.6971	Remote Similarity	NPD7390	Discontinued
0.697	Remote Similarity	NPD9494	Approved
0.6954	Remote Similarity	NPD2309	Approved
0.6952	Remote Similarity	NPD7907	Approved
0.6951	Remote Similarity	NPD1203	Approved
0.695	Remote Similarity	NPD5006	Approved
0.695	Remote Similarity	NPD5005	Approved
0.6946	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2313	Discontinued
0.6933	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2346	Discontinued
0.6914	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4361	Phase 2
0.6901	Remote Similarity	NPD2799	Discontinued
0.69	Remote Similarity	NPD3450	Approved
0.69	Remote Similarity	NPD3452	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