NPASS Compound

Structure

NPC254855 OpenBabel07101718202D 44 48 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 10 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 23 1 0 0 0 0 9 30 1 0 0 0 0 10 11 2 0 0 0 0 10 31 1 0 0 0 0 11 32 1 0 0 0 0 12 16 2 0 0 0 0 12 33 1 0 0 0 0 13 16 1 0 0 0 0 13 40 1 0 0 0 0 14 6 1 6 0 0 0 14 17 1 0 0 0 0 14 41 1 0 0 0 0 15 7 1 6 0 0 0 15 18 1 0 0 0 0 15 42 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 34 1 1 0 0 0 18 21 1 0 0 0 0 18 35 1 6 0 0 0 19 24 1 0 0 0 0 19 36 2 0 0 0 0 20 22 1 0 0 0 0 20 37 1 6 0 0 0 21 25 1 0 0 0 0 21 38 1 6 0 0 0 22 26 1 0 0 0 0 22 39 1 1 0 0 0 23 24 2 0 0 0 0 23 40 1 0 0 0 0 24 43 1 0 0 0 0 25 27 1 0 0 0 0 25 44 1 1 0 0 0 26 41 1 0 0 0 0 26 44 1 6 0 0 0 27 42 1 0 0 0 0 27 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.15
Volume:	561.108
LogP:	-0.66
LogD:	-0.415
LogS:	-2.999
# Rotatable Bonds:	7
TPSA:	289.66
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	4.785
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.532
MDCK Permeability:	1.9244580471422523e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	84.37129211425781%
Volume Distribution (VD):	0.687
Pgp-substrate:	18.52317237854004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.345
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.422
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.812
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.861
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.144
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC254855

Natural Product ID:	NPC254855
*Common Name:**	Quercetin 3-O-(2-O-Beta-D-Glucopyranosyl)-Beta-D-Galactopyranoside
IUPAC Name:	3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	RDUAJIJVNHKTQC-PABQPRPFSA-N
Standard InCHI:	InChI=1S/C27H30O17/c28-6-14-17(34)20(37)22(39)26(41-14)44-25-21(38)18(35)15(7-29)42-27(25)43-24-19(36)16-12(33)4-9(30)5-13(16)40-23(24)8-1-2-10(31)11(32)3-8/h1-5,14-15,17-18,20-22,25-35,37-39H,6-7H2/t14-,15-,17-,18+,20+,21+,22-,25-,26+,27+/m1/s1
SMILES:	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452919
PubChem CID:	14185728
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170670]
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20004577]

☑ 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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	48.2	%	PMID[550068]
NPT2	Others	Unspecified	Activity	=	66.0	%	PMID[550068]
NPT2	Others	Unspecified	Activity	=	54.0	%	PMID[550068]

☑ 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 NPC254855 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	494
0.1-0.2	1929
0.2-0.3	4557
0.3-0.4	10027
0.4-0.5	7955
0.5-0.6	4622
0.6-0.7	5729
0.7-0.8	4953
0.8-0.85	1437
0.85-0.9	435
0.9-0.95	419
0.95-1	140

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259896
1.0	High Similarity	NPC136042
1.0	High Similarity	NPC29958
1.0	High Similarity	NPC67326
1.0	High Similarity	NPC156869
1.0	High Similarity	NPC255157
0.9938	High Similarity	NPC176740
0.9938	High Similarity	NPC471725
0.9938	High Similarity	NPC33054
0.9938	High Similarity	NPC155877
0.9938	High Similarity	NPC134532
0.9938	High Similarity	NPC26230
0.9938	High Similarity	NPC471748
0.9938	High Similarity	NPC60735
0.9938	High Similarity	NPC203259
0.9875	High Similarity	NPC67105
0.9875	High Similarity	NPC285197
0.9875	High Similarity	NPC95866
0.9874	High Similarity	NPC275454
0.9815	High Similarity	NPC473327
0.9815	High Similarity	NPC16194
0.9815	High Similarity	NPC476472
0.9815	High Similarity	NPC253685
0.9815	High Similarity	NPC220173
0.9815	High Similarity	NPC294815
0.9815	High Similarity	NPC19108
0.9812	High Similarity	NPC227508
0.9811	High Similarity	NPC88789
0.9811	High Similarity	NPC145038
0.9811	High Similarity	NPC56077
0.9811	High Similarity	NPC179950
0.9811	High Similarity	NPC253662
0.9811	High Similarity	NPC8856
0.9811	High Similarity	NPC276222
0.9811	High Similarity	NPC118284
0.9811	High Similarity	NPC274618
0.9811	High Similarity	NPC308404
0.9811	High Similarity	NPC281131
0.9755	High Similarity	NPC122467
0.9755	High Similarity	NPC219043
0.9755	High Similarity	NPC470949
0.9755	High Similarity	NPC14187
0.9755	High Similarity	NPC202908
0.9755	High Similarity	NPC292019
0.9755	High Similarity	NPC471669
0.9755	High Similarity	NPC89127
0.9755	High Similarity	NPC8573
0.9755	High Similarity	NPC65563
0.975	High Similarity	NPC92565
0.975	High Similarity	NPC173637
0.975	High Similarity	NPC160156
0.975	High Similarity	NPC52550
0.975	High Similarity	NPC317489
0.975	High Similarity	NPC84362
0.975	High Similarity	NPC127546
0.975	High Similarity	NPC223424
0.9748	High Similarity	NPC277205
0.9748	High Similarity	NPC240431
0.9748	High Similarity	NPC19388
0.9748	High Similarity	NPC55786
0.9695	High Similarity	NPC89052
0.9695	High Similarity	NPC173837
0.9695	High Similarity	NPC251417
0.9693	High Similarity	NPC294629
0.9689	High Similarity	NPC86008
0.9689	High Similarity	NPC52382
0.9689	High Similarity	NPC225434
0.9689	High Similarity	NPC120099
0.9689	High Similarity	NPC270578
0.9689	High Similarity	NPC203050
0.9689	High Similarity	NPC219904
0.9689	High Similarity	NPC223747
0.9688	High Similarity	NPC21100
0.9688	High Similarity	NPC197285
0.9688	High Similarity	NPC210073
0.9688	High Similarity	NPC113968
0.9688	High Similarity	NPC115674
0.9688	High Similarity	NPC135599
0.9688	High Similarity	NPC277174
0.9688	High Similarity	NPC73855
0.9688	High Similarity	NPC328940
0.9636	High Similarity	NPC241423
0.9636	High Similarity	NPC192539
0.9636	High Similarity	NPC473682
0.9636	High Similarity	NPC470444
0.9636	High Similarity	NPC473571
0.9636	High Similarity	NPC110941
0.9636	High Similarity	NPC470443
0.9636	High Similarity	NPC126784
0.9634	High Similarity	NPC473862
0.9634	High Similarity	NPC169733
0.9634	High Similarity	NPC48984
0.963	High Similarity	NPC244776
0.963	High Similarity	NPC218488
0.963	High Similarity	NPC206123
0.963	High Similarity	NPC235260
0.963	High Similarity	NPC20505
0.963	High Similarity	NPC155763
0.963	High Similarity	NPC116864
0.9627	High Similarity	NPC265530
0.9627	High Similarity	NPC226304
0.9627	High Similarity	NPC325555
0.9623	High Similarity	NPC77660
0.9623	High Similarity	NPC189142
0.9578	High Similarity	NPC473073
0.9578	High Similarity	NPC473071
0.9576	High Similarity	NPC37668
0.9576	High Similarity	NPC113836
0.9576	High Similarity	NPC253521
0.9573	High Similarity	NPC81042
0.9573	High Similarity	NPC223426
0.9573	High Similarity	NPC214621
0.9573	High Similarity	NPC34267
0.9571	High Similarity	NPC180918
0.9571	High Similarity	NPC3583
0.9571	High Similarity	NPC190003
0.9571	High Similarity	NPC175107
0.9571	High Similarity	NPC245452
0.9571	High Similarity	NPC259152
0.9571	High Similarity	NPC153755
0.9568	High Similarity	NPC209296
0.9568	High Similarity	NPC138927
0.9568	High Similarity	NPC105283
0.9568	High Similarity	NPC195257
0.9565	High Similarity	NPC255615
0.9565	High Similarity	NPC67037
0.9563	High Similarity	NPC270335
0.9563	High Similarity	NPC168822
0.9563	High Similarity	NPC29830
0.9563	High Similarity	NPC19709
0.9563	High Similarity	NPC191306
0.956	High Similarity	NPC64305
0.956	High Similarity	NPC135846
0.956	High Similarity	NPC297987
0.956	High Similarity	NPC170052
0.9521	High Similarity	NPC470718
0.9521	High Similarity	NPC470446
0.9521	High Similarity	NPC162394
0.9521	High Similarity	NPC470447
0.9521	High Similarity	NPC156785
0.9521	High Similarity	NPC241781
0.9521	High Similarity	NPC473072
0.9521	High Similarity	NPC470445
0.9521	High Similarity	NPC470449
0.9515	High Similarity	NPC144097
0.9515	High Similarity	NPC61904
0.9512	High Similarity	NPC42773
0.9512	High Similarity	NPC101026
0.9512	High Similarity	NPC4390
0.9512	High Similarity	NPC21666
0.9512	High Similarity	NPC45522
0.9512	High Similarity	NPC24043
0.9512	High Similarity	NPC169977
0.9509	High Similarity	NPC245014
0.9509	High Similarity	NPC84265
0.9509	High Similarity	NPC150767
0.9509	High Similarity	NPC231194
0.9509	High Similarity	NPC78734
0.9509	High Similarity	NPC282987
0.9509	High Similarity	NPC51326
0.9506	High Similarity	NPC149244
0.9506	High Similarity	NPC48640
0.9503	High Similarity	NPC22832
0.9503	High Similarity	NPC311830
0.9503	High Similarity	NPC34531
0.95	High Similarity	NPC473043
0.9497	High Similarity	NPC136761
0.9497	High Similarity	NPC470405
0.9497	High Similarity	NPC304741
0.9497	High Similarity	NPC471079
0.9464	High Similarity	NPC249560
0.9464	High Similarity	NPC470717
0.9464	High Similarity	NPC148710
0.9464	High Similarity	NPC25946
0.9464	High Similarity	NPC460984
0.9464	High Similarity	NPC470720
0.9464	High Similarity	NPC470451
0.9464	High Similarity	NPC275977
0.9464	High Similarity	NPC223860
0.9464	High Similarity	NPC21359
0.9464	High Similarity	NPC470455
0.9464	High Similarity	NPC470713
0.9458	High Similarity	NPC258044
0.9458	High Similarity	NPC139571
0.9458	High Similarity	NPC217520
0.9458	High Similarity	NPC35167
0.9458	High Similarity	NPC267680
0.9458	High Similarity	NPC293626
0.9458	High Similarity	NPC217387
0.9458	High Similarity	NPC196127
0.9455	High Similarity	NPC135277
0.9455	High Similarity	NPC49344
0.9455	High Similarity	NPC101191
0.9455	High Similarity	NPC210094
0.9455	High Similarity	NPC115760
0.9455	High Similarity	NPC43211
0.9455	High Similarity	NPC198199
0.9455	High Similarity	NPC237435
0.9451	High Similarity	NPC476405
0.9451	High Similarity	NPC117260

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 NPC254855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	981
0.2-0.3	2068
0.3-0.4	2736
0.4-0.5	1769
0.5-0.6	800
0.6-0.7	246
0.7-0.8	97
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9938	High Similarity	NPD6797	Phase 2
0.9876	High Similarity	NPD7251	Discontinued
0.9693	High Similarity	NPD7808	Phase 3
0.963	High Similarity	NPD7472	Approved
0.9568	High Similarity	NPD7054	Approved
0.9455	High Similarity	NPD4338	Clinical (unspecified phase)
0.939	High Similarity	NPD7074	Phase 3
0.9212	High Similarity	NPD7804	Clinical (unspecified phase)
0.9152	High Similarity	NPD3818	Discontinued
0.9146	High Similarity	NPD6168	Clinical (unspecified phase)
0.9146	High Similarity	NPD6166	Phase 2
0.9146	High Similarity	NPD6167	Clinical (unspecified phase)
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.8773	High Similarity	NPD3817	Phase 2
0.8765	High Similarity	NPD1934	Approved
0.8742	High Similarity	NPD1512	Approved
0.8712	High Similarity	NPD2393	Clinical (unspecified phase)
0.8655	High Similarity	NPD7993	Clinical (unspecified phase)
0.8616	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD3882	Suspended
0.8598	High Similarity	NPD2801	Approved
0.8528	High Similarity	NPD4380	Phase 2
0.8494	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD5402	Approved
0.8344	Intermediate Similarity	NPD5403	Approved
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8286	Intermediate Similarity	NPD6559	Discontinued
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5401	Approved
0.8161	Intermediate Similarity	NPD3751	Discontinued
0.816	Intermediate Similarity	NPD6799	Approved
0.814	Intermediate Similarity	NPD3787	Discontinued
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1549	Phase 2
0.8072	Intermediate Similarity	NPD1653	Approved
0.8023	Intermediate Similarity	NPD5494	Approved
0.7989	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD8312	Approved
0.7977	Intermediate Similarity	NPD6959	Discontinued
0.7941	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7853	Intermediate Similarity	NPD7228	Approved
0.784	Intermediate Similarity	NPD2796	Approved
0.7836	Intermediate Similarity	NPD7819	Suspended
0.7824	Intermediate Similarity	NPD7411	Suspended
0.7809	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.775	Intermediate Similarity	NPD1613	Approved
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8455	Phase 2
0.7727	Intermediate Similarity	NPD6232	Discontinued
0.7711	Intermediate Similarity	NPD6190	Approved
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6776	Approved
0.7684	Intermediate Similarity	NPD6782	Approved
0.7684	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD6778	Approved
0.7684	Intermediate Similarity	NPD6777	Approved
0.7684	Intermediate Similarity	NPD6779	Approved
0.7684	Intermediate Similarity	NPD6780	Approved
0.7683	Intermediate Similarity	NPD7266	Discontinued
0.767	Intermediate Similarity	NPD7199	Phase 2
0.7657	Intermediate Similarity	NPD919	Approved
0.7656	Intermediate Similarity	NPD7435	Discontinued
0.7641	Intermediate Similarity	NPD8151	Discontinued
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1247	Approved
0.7565	Intermediate Similarity	NPD7698	Approved
0.7565	Intermediate Similarity	NPD7697	Approved
0.7565	Intermediate Similarity	NPD7696	Phase 3
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7545	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3750	Approved
0.7538	Intermediate Similarity	NPD7584	Approved
0.7531	Intermediate Similarity	NPD1240	Approved
0.7531	Intermediate Similarity	NPD943	Approved
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD7240	Approved
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7471	Intermediate Similarity	NPD37	Approved
0.7443	Intermediate Similarity	NPD4966	Approved
0.7443	Intermediate Similarity	NPD4965	Approved
0.7443	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD1607	Approved
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7870	Phase 2
0.7436	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6535	Approved
0.7421	Intermediate Similarity	NPD6534	Approved
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7401	Intermediate Similarity	NPD3749	Approved
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.7387	Intermediate Similarity	NPD7783	Phase 2
0.7387	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1933	Approved
0.7378	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7346	Intermediate Similarity	NPD3027	Phase 3
0.7345	Intermediate Similarity	NPD7768	Phase 2
0.7337	Intermediate Similarity	NPD4628	Phase 3
0.7301	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD3748	Approved
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7202	Intermediate Similarity	NPD2935	Discontinued
0.7196	Intermediate Similarity	NPD8434	Phase 2
0.7196	Intermediate Similarity	NPD8150	Discontinued
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD447	Suspended
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2533	Approved
0.7158	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7585	Approved
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.71	Intermediate Similarity	NPD7583	Approved
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD920	Approved
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2800	Approved
0.7074	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD5953	Discontinued
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD7680	Approved
0.7011	Intermediate Similarity	NPD7390	Discontinued
0.701	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6213	Phase 3
0.701	Intermediate Similarity	NPD6212	Phase 3
0.7006	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD2313	Discontinued
0.6983	Remote Similarity	NPD6844	Discontinued
0.6977	Remote Similarity	NPD1243	Approved
0.6977	Remote Similarity	NPD6674	Discontinued
0.6977	Remote Similarity	NPD1652	Phase 2
0.697	Remote Similarity	NPD4908	Phase 1
0.697	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7286	Phase 2
0.6951	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD6651	Approved
0.6918	Remote Similarity	NPD1548	Phase 1
0.691	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9494	Approved
0.6886	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5124	Phase 1
0.686	Remote Similarity	NPD2346	Discontinued
0.686	Remote Similarity	NPD2344	Approved
0.6852	Remote Similarity	NPD1610	Phase 2
0.6842	Remote Similarity	NPD2799	Discontinued
0.6839	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3225	Approved
0.6813	Remote Similarity	NPD5353	Approved
0.681	Remote Similarity	NPD9269	Phase 2
0.6809	Remote Similarity	NPD2163	Approved
0.6805	Remote Similarity	NPD4060	Phase 1
0.6791	Remote Similarity	NPD2403	Approved
0.6786	Remote Similarity	NPD3268	Approved
0.678	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7930	Approved
0.6774	Remote Similarity	NPD5710	Approved
0.6774	Remote Similarity	NPD5711	Approved
0.6765	Remote Similarity	NPD4340	Discontinued

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