NPASS Compound

Structure

NPC148710 OpenBabel07101719152D 46 50 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 2 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 -9.5263 4.5000 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 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 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 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 41 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 42 1 0 0 0 0 12 7 1 6 0 0 0 12 17 1 0 0 0 0 12 43 1 0 0 0 0 13 8 1 1 0 0 0 13 18 1 0 0 0 0 13 44 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 14 25 2 0 0 0 0 15 32 1 0 0 0 0 16 27 2 0 0 0 0 16 33 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 26 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 23 1 0 0 0 0 21 38 1 1 0 0 0 22 28 1 0 0 0 0 22 39 1 1 0 0 0 23 29 1 0 0 0 0 23 40 1 6 0 0 0 24 26 2 0 0 0 0 24 45 1 0 0 0 0 25 27 1 0 0 0 0 25 45 1 0 0 0 0 26 41 1 0 0 0 0 27 46 1 0 0 0 0 28 42 1 6 0 0 0 28 43 1 0 0 0 0 29 44 1 0 0 0 0 29 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.18
Volume:	595.7
LogP:	-0.436
LogD:	-0.431
LogS:	-2.428
# Rotatable Bonds:	8
TPSA:	278.66
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.121
Synthetic Accessibility Score:	4.84
Fsp3:	0.483
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.477
MDCK Permeability:	3.828274202533066e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	71.58744049072266%
Volume Distribution (VD):	0.777
Pgp-substrate:	19.24544334411621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.167
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.215
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC148710

Natural Product ID:	NPC148710
*Common Name:**	5,7-Dihydroxy-3-Methoxy-6-C-Methylflavone 8,4'-Di-O-Beta-D-Glucopyranoside
IUPAC Name:	5,7-dihydroxy-3-methoxy-6-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:
Standard InCHIKey:	IMPLZIZVOPEGNS-ZPOJWXRKSA-N
Standard InCHI:	InChI=1S/C29H34O17/c1-9-15(32)14-19(36)26(41-2)24(10-3-5-11(6-4-10)42-28-22(39)20(37)17(34)12(7-30)43-28)45-25(14)27(16(9)33)46-29-23(40)21(38)18(35)13(8-31)44-29/h3-6,12-13,17-18,20-23,28-35,37-40H,7-8H2,1-2H3/t12-,13-,17-,18-,20+,21+,22-,23-,28-,29+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)c2oc3c(O[C@@H]4O[C@H](CO)[C@H]([C@@H]([C@H]4O)O)O)c(O)c(c(c3c(=O)c2OC)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2253068
PubChem CID:	71489594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003540] Flavonoid-8-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
NPO15650	Picea neoveitchii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22901896]
NPO15650	Picea neoveitchii	Species	Pinaceae	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
Others	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1493	Organism	Ceratocystis paradoxa	Ceratocystis paradoxa	GI	=	0.0	%	PMID[495868]
NPT1494	Organism	Alternaria mali	Alternaria mali	GI	=	43.4	%	PMID[495868]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	GI	=	41.4	%	PMID[495868]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	GI	=	30.6	%	PMID[495868]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	64.4	%	PMID[495868]
NPT1493	Organism	Ceratocystis paradoxa	Ceratocystis paradoxa	IZ	=	0.0	mm	PMID[495868]
NPT1494	Organism	Alternaria mali	Alternaria mali	IZ	=	4.3	mm	PMID[495868]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	IZ	=	4.8	mm	PMID[495868]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	IZ	=	5.7	mm	PMID[495868]

☑ 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 NPC148710 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	476
0.1-0.2	1952
0.2-0.3	4435
0.3-0.4	10055
0.4-0.5	8057
0.5-0.6	4657
0.6-0.7	5710
0.7-0.8	4793
0.8-0.85	1505
0.85-0.9	617
0.9-0.95	341
0.95-1	99

Similarity Score	Similarity Level	Natural Product ID
0.9821	High Similarity	NPC473571
0.9821	High Similarity	NPC470443
0.9821	High Similarity	NPC470444
0.9821	High Similarity	NPC126784
0.9821	High Similarity	NPC473682
0.9821	High Similarity	NPC241423
0.9821	High Similarity	NPC110941
0.9762	High Similarity	NPC168584
0.9706	High Similarity	NPC470445
0.9706	High Similarity	NPC470447
0.9706	High Similarity	NPC470446
0.9706	High Similarity	NPC473072
0.9706	High Similarity	NPC470449
0.9702	High Similarity	NPC169733
0.9702	High Similarity	NPC8573
0.9702	High Similarity	NPC65563
0.9702	High Similarity	NPC470949
0.9649	High Similarity	NPC470451
0.9649	High Similarity	NPC470455
0.9647	High Similarity	NPC473071
0.9647	High Similarity	NPC473073
0.9643	High Similarity	NPC16194
0.9643	High Similarity	NPC294629
0.9643	High Similarity	NPC19108
0.9643	High Similarity	NPC476472
0.9643	High Similarity	NPC473327
0.9643	High Similarity	NPC220173
0.9643	High Similarity	NPC294815
0.9583	High Similarity	NPC208668
0.9583	High Similarity	NPC169977
0.9583	High Similarity	NPC204693
0.9583	High Similarity	NPC42773
0.9583	High Similarity	NPC21666
0.9583	High Similarity	NPC101026
0.9583	High Similarity	NPC24043
0.9583	High Similarity	NPC45522
0.9529	High Similarity	NPC89052
0.9529	High Similarity	NPC173837
0.9529	High Similarity	NPC251417
0.9527	High Similarity	NPC102028
0.9527	High Similarity	NPC142996
0.9524	High Similarity	NPC203259
0.9524	High Similarity	NPC33054
0.9524	High Similarity	NPC259152
0.9524	High Similarity	NPC117260
0.9524	High Similarity	NPC256760
0.9524	High Similarity	NPC26230
0.9524	High Similarity	NPC476405
0.9524	High Similarity	NPC60735
0.9524	High Similarity	NPC176740
0.9524	High Similarity	NPC155877
0.9524	High Similarity	NPC3583
0.9524	High Similarity	NPC471725
0.9524	High Similarity	NPC471748
0.9524	High Similarity	NPC134532
0.9474	High Similarity	NPC192539
0.9471	High Similarity	NPC471669
0.9471	High Similarity	NPC202908
0.9471	High Similarity	NPC122467
0.9471	High Similarity	NPC89127
0.9471	High Similarity	NPC255799
0.9471	High Similarity	NPC472384
0.9471	High Similarity	NPC268533
0.9471	High Similarity	NPC219043
0.9471	High Similarity	NPC48984
0.9471	High Similarity	NPC472382
0.9471	High Similarity	NPC472385
0.9471	High Similarity	NPC472380
0.9471	High Similarity	NPC198324
0.9471	High Similarity	NPC292019
0.9471	High Similarity	NPC14187
0.9467	High Similarity	NPC236191
0.9467	High Similarity	NPC25724
0.9467	High Similarity	NPC239549
0.9467	High Similarity	NPC51774
0.9464	High Similarity	NPC245014
0.9464	High Similarity	NPC67326
0.9464	High Similarity	NPC22195
0.9464	High Similarity	NPC67105
0.9464	High Similarity	NPC282987
0.9464	High Similarity	NPC156869
0.9464	High Similarity	NPC254855
0.9464	High Similarity	NPC84265
0.9464	High Similarity	NPC150767
0.9464	High Similarity	NPC29958
0.9464	High Similarity	NPC183357
0.9464	High Similarity	NPC136042
0.9464	High Similarity	NPC78734
0.9464	High Similarity	NPC21190
0.9464	High Similarity	NPC259896
0.9464	High Similarity	NPC255157
0.9464	High Similarity	NPC95866
0.9464	High Similarity	NPC218488
0.9464	High Similarity	NPC285197
0.9425	High Similarity	NPC64755
0.9412	High Similarity	NPC253685
0.9412	High Similarity	NPC264735
0.9412	High Similarity	NPC49344
0.9412	High Similarity	NPC101191
0.9412	High Similarity	NPC43211
0.9412	High Similarity	NPC210094
0.9412	High Similarity	NPC477848
0.9412	High Similarity	NPC115760
0.9412	High Similarity	NPC108202
0.9412	High Similarity	NPC237435
0.9412	High Similarity	NPC472607
0.9412	High Similarity	NPC135277
0.9408	High Similarity	NPC48773
0.9408	High Similarity	NPC156977
0.9408	High Similarity	NPC301683
0.9408	High Similarity	NPC475155
0.9408	High Similarity	NPC205076
0.9408	High Similarity	NPC267254
0.9408	High Similarity	NPC307518
0.9405	High Similarity	NPC170675
0.9405	High Similarity	NPC225434
0.9405	High Similarity	NPC209296
0.9405	High Similarity	NPC203050
0.9405	High Similarity	NPC226294
0.9405	High Similarity	NPC52382
0.9405	High Similarity	NPC186807
0.9405	High Similarity	NPC471457
0.9405	High Similarity	NPC105025
0.9405	High Similarity	NPC472381
0.9405	High Similarity	NPC475942
0.9405	High Similarity	NPC223747
0.9405	High Similarity	NPC210042
0.9405	High Similarity	NPC270578
0.9405	High Similarity	NPC227508
0.9405	High Similarity	NPC469931
0.9405	High Similarity	NPC58053
0.9405	High Similarity	NPC86008
0.9405	High Similarity	NPC45638
0.9405	High Similarity	NPC219904
0.9405	High Similarity	NPC95855
0.9405	High Similarity	NPC120099
0.9405	High Similarity	NPC201292
0.9405	High Similarity	NPC93337
0.9405	High Similarity	NPC472383
0.9405	High Similarity	NPC195257
0.9405	High Similarity	NPC112755
0.9364	High Similarity	NPC36138
0.9357	High Similarity	NPC211532
0.9357	High Similarity	NPC473862
0.9357	High Similarity	NPC233994
0.9353	High Similarity	NPC4390
0.9349	High Similarity	NPC51326
0.9349	High Similarity	NPC293004
0.9349	High Similarity	NPC471416
0.9349	High Similarity	NPC177731
0.9349	High Similarity	NPC105095
0.9349	High Similarity	NPC44558
0.9349	High Similarity	NPC105511
0.9349	High Similarity	NPC206123
0.9349	High Similarity	NPC194483
0.9349	High Similarity	NPC231194
0.9349	High Similarity	NPC224462
0.9349	High Similarity	NPC44328
0.9349	High Similarity	NPC34287
0.9349	High Similarity	NPC52353
0.9349	High Similarity	NPC474434
0.9349	High Similarity	NPC79056
0.9345	High Similarity	NPC92565
0.9345	High Similarity	NPC226304
0.9345	High Similarity	NPC325555
0.9345	High Similarity	NPC223424
0.9345	High Similarity	NPC93099
0.9345	High Similarity	NPC84362
0.9345	High Similarity	NPC45618
0.9345	High Similarity	NPC265530
0.9345	High Similarity	NPC58716
0.9345	High Similarity	NPC173637
0.9345	High Similarity	NPC127546
0.9345	High Similarity	NPC275454
0.9345	High Similarity	NPC477502
0.9345	High Similarity	NPC317489
0.9345	High Similarity	NPC52550
0.9345	High Similarity	NPC160156
0.9345	High Similarity	NPC146792
0.931	High Similarity	NPC470713
0.931	High Similarity	NPC460984
0.931	High Similarity	NPC470416
0.931	High Similarity	NPC470717
0.931	High Similarity	NPC470720
0.931	High Similarity	NPC21359
0.931	High Similarity	NPC25946
0.931	High Similarity	NPC49690
0.9302	High Similarity	NPC475261
0.9298	High Similarity	NPC198199
0.9294	High Similarity	NPC180918
0.9294	High Similarity	NPC175107
0.9294	High Similarity	NPC153755
0.9294	High Similarity	NPC172807
0.9294	High Similarity	NPC254540
0.9294	High Similarity	NPC190003
0.9294	High Similarity	NPC211594
0.9294	High Similarity	NPC472386
0.929	High Similarity	NPC5319
0.929	High Similarity	NPC471287
0.929	High Similarity	NPC43587

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 NPC148710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	992
0.2-0.3	2088
0.3-0.4	2738
0.4-0.5	1754
0.5-0.6	803
0.6-0.7	229
0.7-0.8	94
0.8-0.85	23
0.85-0.9	3
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD7251	Discontinued
0.9527	High Similarity	NPD7808	Phase 3
0.9524	High Similarity	NPD6797	Phase 2
0.9464	High Similarity	NPD7472	Approved
0.9412	High Similarity	NPD4338	Clinical (unspecified phase)
0.9405	High Similarity	NPD7054	Approved
0.9349	High Similarity	NPD7074	Phase 3
0.929	High Similarity	NPD7804	Clinical (unspecified phase)
0.9006	High Similarity	NPD3818	Discontinued
0.9	High Similarity	NPD6168	Clinical (unspecified phase)
0.9	High Similarity	NPD6166	Phase 2
0.9	High Similarity	NPD6167	Clinical (unspecified phase)
0.8757	High Similarity	NPD4381	Clinical (unspecified phase)
0.869	High Similarity	NPD2801	Approved
0.869	High Similarity	NPD2393	Clinical (unspecified phase)
0.8631	High Similarity	NPD1934	Approved
0.8538	High Similarity	NPD7075	Discontinued
0.8529	High Similarity	NPD3817	Phase 2
0.848	Intermediate Similarity	NPD3882	Suspended
0.847	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD5494	Approved
0.8427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD4380	Phase 2
0.8363	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD5402	Approved
0.8304	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD6559	Discontinued
0.8274	Intermediate Similarity	NPD1512	Approved
0.8266	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1511	Approved
0.8111	Intermediate Similarity	NPD5844	Phase 1
0.8087	Intermediate Similarity	NPD8313	Approved
0.8087	Intermediate Similarity	NPD8312	Approved
0.8065	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD7228	Approved
0.8031	Intermediate Similarity	NPD7435	Discontinued
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6959	Discontinued
0.7978	Intermediate Similarity	NPD1247	Approved
0.7969	Intermediate Similarity	NPD6777	Approved
0.7969	Intermediate Similarity	NPD6782	Approved
0.7969	Intermediate Similarity	NPD6779	Approved
0.7969	Intermediate Similarity	NPD6776	Approved
0.7969	Intermediate Similarity	NPD6780	Approved
0.7969	Intermediate Similarity	NPD6778	Approved
0.7969	Intermediate Similarity	NPD6781	Approved
0.7965	Intermediate Similarity	NPD1653	Approved
0.7956	Intermediate Similarity	NPD3751	Discontinued
0.7943	Intermediate Similarity	NPD7819	Suspended
0.7938	Intermediate Similarity	NPD7697	Approved
0.7938	Intermediate Similarity	NPD7696	Phase 3
0.7938	Intermediate Similarity	NPD7698	Approved
0.7933	Intermediate Similarity	NPD3787	Discontinued
0.7933	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD5403	Approved
0.7903	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD7701	Phase 2
0.7841	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD6799	Approved
0.7829	Intermediate Similarity	NPD7411	Suspended
0.7828	Intermediate Similarity	NPD8151	Discontinued
0.7806	Intermediate Similarity	NPD7871	Phase 2
0.7806	Intermediate Similarity	NPD7870	Phase 2
0.7798	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5401	Approved
0.7789	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7874	Approved
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7772	Intermediate Similarity	NPD7699	Phase 2
0.7772	Intermediate Similarity	NPD7700	Phase 2
0.7765	Intermediate Similarity	NPD919	Approved
0.7751	Intermediate Similarity	NPD1549	Phase 2
0.775	Intermediate Similarity	NPD7783	Phase 2
0.775	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8455	Phase 2
0.7708	Intermediate Similarity	NPD6534	Approved
0.7708	Intermediate Similarity	NPD6535	Approved
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7240	Approved
0.767	Intermediate Similarity	NPD6599	Discontinued
0.7667	Intermediate Similarity	NPD6234	Discontinued
0.7662	Intermediate Similarity	NPD7801	Approved
0.765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7584	Approved
0.7633	Intermediate Similarity	NPD2796	Approved
0.7614	Intermediate Similarity	NPD6823	Phase 2
0.76	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD37	Approved
0.7582	Intermediate Similarity	NPD7199	Phase 2
0.7574	Intermediate Similarity	NPD1510	Phase 2
0.7556	Intermediate Similarity	NPD4967	Phase 2
0.7556	Intermediate Similarity	NPD4966	Approved
0.7556	Intermediate Similarity	NPD4965	Approved
0.7538	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD8320	Phase 1
0.7538	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7487	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD7266	Discontinued
0.7459	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1613	Approved
0.7427	Intermediate Similarity	NPD2935	Discontinued
0.7416	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8434	Phase 2
0.7356	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1240	Approved
0.7337	Intermediate Similarity	NPD943	Approved
0.7337	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6212	Phase 3
0.7296	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6213	Phase 3
0.7288	Intermediate Similarity	NPD2534	Approved
0.7288	Intermediate Similarity	NPD2532	Approved
0.7288	Intermediate Similarity	NPD2533	Approved
0.7286	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3027	Phase 3
0.7257	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD7585	Approved
0.7251	Intermediate Similarity	NPD1607	Approved
0.7241	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3749	Approved
0.7228	Intermediate Similarity	NPD7680	Approved
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD920	Approved
0.7206	Intermediate Similarity	NPD7583	Approved
0.7202	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2800	Approved
0.72	Intermediate Similarity	NPD6674	Discontinued
0.7193	Intermediate Similarity	NPD1933	Approved
0.7193	Intermediate Similarity	NPD230	Phase 1
0.7183	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5953	Discontinued
0.7159	Intermediate Similarity	NPD4628	Phase 3
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.7157	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3226	Approved
0.7118	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6844	Discontinued
0.7098	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD447	Suspended
0.7085	Intermediate Similarity	NPD4360	Phase 2
0.7085	Intermediate Similarity	NPD4363	Phase 3
0.7069	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6651	Approved
0.7039	Intermediate Similarity	NPD7390	Discontinued
0.7029	Intermediate Similarity	NPD1551	Phase 2
0.7018	Intermediate Similarity	NPD2313	Discontinued
0.7006	Intermediate Similarity	NPD1243	Approved
0.7005	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8059	Phase 3
0.7	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2346	Discontinued
0.6983	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6233	Phase 2
0.6971	Remote Similarity	NPD3748	Approved
0.6971	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6099	Approved
0.6932	Remote Similarity	NPD6100	Approved
0.693	Remote Similarity	NPD7907	Approved
0.6919	Remote Similarity	NPD6798	Discontinued
0.6919	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6355	Discontinued
0.6897	Remote Similarity	NPD5124	Phase 1
0.6895	Remote Similarity	NPD5711	Approved
0.6895	Remote Similarity	NPD5710	Approved
0.6887	Remote Similarity	NPD7930	Approved
0.6875	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7033	Discontinued
0.6872	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5353	Approved
0.6842	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD9494	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6837	Remote Similarity	NPD7549	Discontinued
0.6833	Remote Similarity	NPD8067	Phase 3
0.6818	Remote Similarity	NPD7097	Phase 1
0.6806	Remote Similarity	NPD7229	Phase 3
0.6802	Remote Similarity	NPD6832	Phase 2
0.6802	Remote Similarity	NPD4908	Phase 1
0.6798	Remote Similarity	NPD2344	Approved
0.6796	Remote Similarity	NPD2493	Approved
0.6796	Remote Similarity	NPD2494	Approved
0.6786	Remote Similarity	NPD1091	Approved
0.6784	Remote Similarity	NPD2798	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