NPASS Compound

Structure

NPC473071 OpenBabel07101719252D 45 50 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 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 1.7321 -5.0000 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 -2.5981 -3.5000 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 -5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 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 2.5981 -4.5000 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 -1.7321 -3.0000 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 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 1 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 -2.5981 -1.5000 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 5.1962 -0.0000 0.0000 C 0 0 2 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 -3.4641 -2.0000 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 -0.8660 2.5000 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 3.4641 -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 0.8660 2.5000 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 -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 -4.4152 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 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 -0.8660 -3.5000 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 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 29 1 0 0 0 0 7 39 1 0 0 0 0 7 40 1 0 0 0 0 8 1 1 1 0 0 0 8 16 1 0 0 0 0 8 41 1 0 0 0 0 9 23 1 0 0 0 0 10 11 2 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 12 15 1 0 0 0 0 12 42 1 0 0 0 0 13 24 2 0 0 0 0 13 39 1 0 0 0 0 14 6 1 6 0 0 0 14 17 1 0 0 0 0 14 43 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 32 1 6 0 0 0 17 21 1 0 0 0 0 17 33 1 1 0 0 0 18 24 1 0 0 0 0 18 34 1 0 0 0 0 19 25 1 0 0 0 0 19 35 2 0 0 0 0 20 22 1 0 0 0 0 20 36 1 1 0 0 0 21 26 1 0 0 0 0 21 37 1 6 0 0 0 22 27 1 0 0 0 0 22 38 1 1 0 0 0 23 25 2 0 0 0 0 23 42 1 0 0 0 0 24 40 1 0 0 0 0 25 44 1 0 0 0 0 26 28 1 0 0 0 0 26 45 1 1 0 0 0 27 41 1 0 0 0 0 27 45 1 6 0 0 0 28 43 1 0 0 0 0 28 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.15
Volume:	569.847
LogP:	0.038
LogD:	-0.196
LogS:	-3.897
# Rotatable Bonds:	6
TPSA:	267.66
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	4.939
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.424
MDCK Permeability:	3.165007728966884e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.338
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	85.27991485595703%
Volume Distribution (VD):	0.639
Pgp-substrate:	16.510770797729492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.164
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	1.335
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.85
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.817
Carcinogencity:	0.143
Eye Corrosion:	0.003
Eye Irritation:	0.253
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC473071

Natural Product ID:	NPC473071
*Common Name:**	ARIBHQKYRYPXOK-NQEPOGRXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ARIBHQKYRYPXOK-NQEPOGRXSA-N
Standard InCHI:	InChI=1S/C28H30O17/c1-8-16(32)20(36)22(38)27(41-8)45-26-21(37)17(33)14(6-29)43-28(26)44-25-19(35)15-12(5-13-24(18(15)34)40-7-39-13)42-23(25)9-2-3-10(30)11(31)4-9/h2-5,8,14,16-17,20-22,26-34,36-38H,6-7H2,1H3/t8-,14+,16-,17+,20+,21-,22+,26+,27-,28-/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC5=C(C(=C4C3=O)O)OCO5)C6=CC(=C(C=C6)O)O)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609096
PubChem CID:	n.a.
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
NPO33494	atriplex littoralis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26290401]

☑ 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	15

Activity Type	# Activity
Cell Line	15

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT885	Cell Line	PBL	Activity	=	178.8	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	181.0	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	15.3	%	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	14.1	%	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	15.1	%	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	1.7	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	1.2	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	1.3	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	187.0	n.a.	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	98.9	%	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	97.7	%	PMID[517633]
NPT885	Cell Line	PBL	Activity	=	102.2	%	PMID[517633]

☑ 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 NPC473071 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	466
0.1-0.2	1818
0.2-0.3	4107
0.3-0.4	9691
0.4-0.5	8439
0.5-0.6	4729
0.6-0.7	5617
0.7-0.8	5049
0.8-0.85	1568
0.85-0.9	694
0.9-0.95	389
0.95-1	130

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473073
0.994	High Similarity	NPC473072
0.982	High Similarity	NPC473571
0.982	High Similarity	NPC126784
0.982	High Similarity	NPC241423
0.982	High Similarity	NPC473682
0.982	High Similarity	NPC470443
0.982	High Similarity	NPC470444
0.982	High Similarity	NPC110941
0.9819	High Similarity	NPC65563
0.9819	High Similarity	NPC8573
0.9819	High Similarity	NPC470949
0.9819	High Similarity	NPC169733
0.9704	High Similarity	NPC470449
0.9704	High Similarity	NPC470445
0.9704	High Similarity	NPC470447
0.9704	High Similarity	NPC470446
0.9699	High Similarity	NPC169977
0.9699	High Similarity	NPC21666
0.9699	High Similarity	NPC101026
0.9699	High Similarity	NPC24043
0.9699	High Similarity	NPC45522
0.9699	High Similarity	NPC42773
0.9647	High Similarity	NPC470451
0.9647	High Similarity	NPC470455
0.9647	High Similarity	NPC148710
0.9641	High Similarity	NPC16194
0.9641	High Similarity	NPC476472
0.9641	High Similarity	NPC473327
0.9641	High Similarity	NPC220173
0.9641	High Similarity	NPC19108
0.9641	High Similarity	NPC294815
0.9639	High Similarity	NPC60735
0.9639	High Similarity	NPC3583
0.9639	High Similarity	NPC33054
0.9639	High Similarity	NPC203259
0.9639	High Similarity	NPC117260
0.9639	High Similarity	NPC471748
0.9639	High Similarity	NPC26230
0.9639	High Similarity	NPC471725
0.9639	High Similarity	NPC134532
0.9639	High Similarity	NPC476405
0.9639	High Similarity	NPC176740
0.9639	High Similarity	NPC259152
0.9639	High Similarity	NPC155877
0.9583	High Similarity	NPC472385
0.9583	High Similarity	NPC198324
0.9581	High Similarity	NPC204693
0.9578	High Similarity	NPC282987
0.9578	High Similarity	NPC29958
0.9578	High Similarity	NPC156869
0.9578	High Similarity	NPC259896
0.9578	High Similarity	NPC136042
0.9578	High Similarity	NPC255157
0.9578	High Similarity	NPC67105
0.9578	High Similarity	NPC245014
0.9578	High Similarity	NPC285197
0.9578	High Similarity	NPC67326
0.9578	High Similarity	NPC254855
0.9578	High Similarity	NPC95866
0.9578	High Similarity	NPC84265
0.9527	High Similarity	NPC168584
0.9527	High Similarity	NPC89052
0.9527	High Similarity	NPC173837
0.9527	High Similarity	NPC251417
0.9524	High Similarity	NPC210094
0.9524	High Similarity	NPC101191
0.9524	High Similarity	NPC43211
0.9524	High Similarity	NPC49344
0.9524	High Similarity	NPC264735
0.9524	High Similarity	NPC135277
0.9524	High Similarity	NPC477848
0.9524	High Similarity	NPC253685
0.9524	High Similarity	NPC115760
0.9524	High Similarity	NPC237435
0.9521	High Similarity	NPC245452
0.9518	High Similarity	NPC186807
0.9518	High Similarity	NPC120099
0.9518	High Similarity	NPC93337
0.9518	High Similarity	NPC226294
0.9518	High Similarity	NPC227508
0.9518	High Similarity	NPC45638
0.9518	High Similarity	NPC219904
0.9518	High Similarity	NPC201292
0.9518	High Similarity	NPC225434
0.9518	High Similarity	NPC58053
0.9518	High Similarity	NPC105025
0.9518	High Similarity	NPC203050
0.9518	High Similarity	NPC475942
0.9518	High Similarity	NPC469931
0.9518	High Similarity	NPC223747
0.9474	High Similarity	NPC36138
0.9471	High Similarity	NPC192539
0.9467	High Similarity	NPC472384
0.9467	High Similarity	NPC48984
0.9467	High Similarity	NPC268533
0.9467	High Similarity	NPC219043
0.9467	High Similarity	NPC472382
0.9467	High Similarity	NPC14187
0.9467	High Similarity	NPC122467
0.9467	High Similarity	NPC471669
0.9467	High Similarity	NPC292019
0.9467	High Similarity	NPC202908
0.9467	High Similarity	NPC233994
0.9467	High Similarity	NPC472380
0.9467	High Similarity	NPC89127
0.9467	High Similarity	NPC211532
0.9464	High Similarity	NPC236191
0.9464	High Similarity	NPC51774
0.9464	High Similarity	NPC239549
0.9464	High Similarity	NPC4390
0.9461	High Similarity	NPC206123
0.9461	High Similarity	NPC22195
0.9461	High Similarity	NPC183357
0.9461	High Similarity	NPC72249
0.9461	High Similarity	NPC21190
0.9458	High Similarity	NPC173637
0.9458	High Similarity	NPC45618
0.9458	High Similarity	NPC317489
0.9458	High Similarity	NPC275454
0.9458	High Similarity	NPC146792
0.9458	High Similarity	NPC265530
0.9458	High Similarity	NPC76482
0.9458	High Similarity	NPC84362
0.9458	High Similarity	NPC127546
0.9458	High Similarity	NPC325555
0.9458	High Similarity	NPC223424
0.9458	High Similarity	NPC52550
0.9458	High Similarity	NPC226304
0.9458	High Similarity	NPC58716
0.9419	High Similarity	NPC470416
0.9408	High Similarity	NPC472607
0.9408	High Similarity	NPC102028
0.9408	High Similarity	NPC294629
0.9408	High Similarity	NPC142996
0.9405	High Similarity	NPC301683
0.9405	High Similarity	NPC254540
0.9405	High Similarity	NPC48773
0.9405	High Similarity	NPC156977
0.9405	High Similarity	NPC175107
0.9405	High Similarity	NPC205076
0.9405	High Similarity	NPC211594
0.9405	High Similarity	NPC267254
0.9405	High Similarity	NPC172807
0.9405	High Similarity	NPC307518
0.9405	High Similarity	NPC153755
0.9405	High Similarity	NPC190003
0.9401	High Similarity	NPC170675
0.9401	High Similarity	NPC209296
0.9401	High Similarity	NPC52382
0.9401	High Similarity	NPC476771
0.9401	High Similarity	NPC210042
0.9401	High Similarity	NPC471457
0.9401	High Similarity	NPC472381
0.9401	High Similarity	NPC195257
0.9401	High Similarity	NPC270578
0.9401	High Similarity	NPC86008
0.9401	High Similarity	NPC95855
0.9401	High Similarity	NPC112755
0.9401	High Similarity	NPC472383
0.9398	High Similarity	NPC281131
0.9398	High Similarity	NPC145038
0.9398	High Similarity	NPC210073
0.9398	High Similarity	NPC197285
0.9398	High Similarity	NPC21100
0.9398	High Similarity	NPC179950
0.9398	High Similarity	NPC73855
0.9398	High Similarity	NPC255615
0.9398	High Similarity	NPC8856
0.9398	High Similarity	NPC254306
0.9398	High Similarity	NPC67037
0.9398	High Similarity	NPC253662
0.9398	High Similarity	NPC276222
0.9398	High Similarity	NPC113968
0.9398	High Similarity	NPC115674
0.9398	High Similarity	NPC274618
0.9398	High Similarity	NPC135599
0.9398	High Similarity	NPC118284
0.9398	High Similarity	NPC277174
0.9398	High Similarity	NPC99957
0.9398	High Similarity	NPC181616
0.9398	High Similarity	NPC328940
0.9398	High Similarity	NPC308404
0.9398	High Similarity	NPC56077
0.9398	High Similarity	NPC88789
0.936	High Similarity	NPC107987
0.9353	High Similarity	NPC257714
0.9353	High Similarity	NPC473862
0.9345	High Similarity	NPC474434
0.9345	High Similarity	NPC44558
0.9345	High Similarity	NPC20505
0.9345	High Similarity	NPC51326
0.9345	High Similarity	NPC231194
0.9345	High Similarity	NPC471416
0.9345	High Similarity	NPC244776
0.9345	High Similarity	NPC105511
0.9345	High Similarity	NPC155763
0.9345	High Similarity	NPC116864
0.9345	High Similarity	NPC224462
0.9345	High Similarity	NPC235260

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 NPC473071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	951
0.2-0.3	2015
0.3-0.4	2747
0.4-0.5	1802
0.5-0.6	829
0.6-0.7	266
0.7-0.8	104
0.8-0.85	19
0.85-0.9	7
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9639	High Similarity	NPD6797	Phase 2
0.9581	High Similarity	NPD7251	Discontinued
0.9524	High Similarity	NPD7808	Phase 3
0.9524	High Similarity	NPD4338	Clinical (unspecified phase)
0.9461	High Similarity	NPD7472	Approved
0.9401	High Similarity	NPD7054	Approved
0.9231	High Similarity	NPD7074	Phase 3
0.9226	High Similarity	NPD3818	Discontinued
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8947	High Similarity	NPD7804	Clinical (unspecified phase)
0.8802	High Similarity	NPD3882	Suspended
0.8795	High Similarity	NPD2801	Approved
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.8631	High Similarity	NPD3817	Phase 2
0.8623	High Similarity	NPD1934	Approved
0.8462	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD5494	Approved
0.8418	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5402	Approved
0.8373	Intermediate Similarity	NPD1512	Approved
0.8268	Intermediate Similarity	NPD6559	Discontinued
0.8256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD1511	Approved
0.8208	Intermediate Similarity	NPD7075	Discontinued
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.8162	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD1653	Approved
0.8045	Intermediate Similarity	NPD3751	Discontinued
0.8045	Intermediate Similarity	NPD7228	Approved
0.8035	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD5403	Approved
0.7988	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD1247	Approved
0.7929	Intermediate Similarity	NPD6799	Approved
0.7901	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5401	Approved
0.7877	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6959	Discontinued
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.7753	Intermediate Similarity	NPD919	Approved
0.7753	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD7435	Discontinued
0.7738	Intermediate Similarity	NPD1549	Phase 2
0.7722	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7684	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3926	Phase 2
0.7676	Intermediate Similarity	NPD7240	Approved
0.767	Intermediate Similarity	NPD37	Approved
0.7657	Intermediate Similarity	NPD6599	Discontinued
0.7653	Intermediate Similarity	NPD7698	Approved
0.7653	Intermediate Similarity	NPD7697	Approved
0.7653	Intermediate Similarity	NPD7696	Phase 3
0.764	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD4965	Approved
0.7627	Intermediate Similarity	NPD7819	Suspended
0.7619	Intermediate Similarity	NPD2796	Approved
0.7614	Intermediate Similarity	NPD7411	Suspended
0.7602	Intermediate Similarity	NPD6190	Approved
0.7588	Intermediate Similarity	NPD7701	Phase 2
0.7572	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1510	Phase 2
0.755	Intermediate Similarity	NPD8151	Discontinued
0.7525	Intermediate Similarity	NPD7870	Phase 2
0.7525	Intermediate Similarity	NPD7871	Phase 2
0.7514	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.7512	Intermediate Similarity	NPD7874	Approved
0.7512	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7475	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7783	Phase 2
0.7471	Intermediate Similarity	NPD7266	Discontinued
0.7446	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8455	Phase 2
0.7425	Intermediate Similarity	NPD1613	Approved
0.7425	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3749	Approved
0.7389	Intermediate Similarity	NPD7801	Approved
0.7382	Intermediate Similarity	NPD8434	Phase 2
0.7363	Intermediate Similarity	NPD7584	Approved
0.7337	Intermediate Similarity	NPD6823	Phase 2
0.7326	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD943	Approved
0.7321	Intermediate Similarity	NPD1240	Approved
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7264	Intermediate Similarity	NPD8319	Approved
0.7264	Intermediate Similarity	NPD8320	Phase 1
0.7259	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD3750	Approved
0.7235	Intermediate Similarity	NPD1607	Approved
0.7214	Intermediate Similarity	NPD7680	Approved
0.7209	Intermediate Similarity	NPD2935	Discontinued
0.7202	Intermediate Similarity	NPD8150	Discontinued
0.7191	Intermediate Similarity	NPD920	Approved
0.7186	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD447	Suspended
0.7158	Intermediate Similarity	NPD7768	Phase 2
0.7156	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7126	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1551	Phase 2
0.7107	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6212	Phase 3
0.7107	Intermediate Similarity	NPD6213	Phase 3
0.7101	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.699	Remote Similarity	NPD7585	Approved
0.6989	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1243	Approved
0.6984	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5953	Discontinued
0.6976	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2344	Approved
0.6966	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD7033	Discontinued
0.6942	Remote Similarity	NPD7583	Approved
0.6923	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD9494	Approved
0.6923	Remote Similarity	NPD3226	Approved
0.6916	Remote Similarity	NPD7907	Approved
0.6912	Remote Similarity	NPD5006	Approved
0.6912	Remote Similarity	NPD5005	Approved
0.6911	Remote Similarity	NPD2163	Approved
0.6901	Remote Similarity	NPD6798	Discontinued
0.69	Remote Similarity	NPD4360	Phase 2
0.69	Remote Similarity	NPD4363	Phase 3
0.6895	Remote Similarity	NPD2403	Approved
0.6893	Remote Similarity	NPD6674	Discontinued
0.6879	Remote Similarity	NPD6355	Discontinued
0.6878	Remote Similarity	NPD5711	Approved
0.6878	Remote Similarity	NPD5710	Approved
0.6875	Remote Similarity	NPD7286	Phase 2
0.6867	Remote Similarity	NPD1091	Approved
0.6863	Remote Similarity	NPD2494	Approved
0.6863	Remote Similarity	NPD2493	Approved
0.6837	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8059	Phase 3
0.6835	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7390	Discontinued
0.6828	Remote Similarity	NPD5353	Approved
0.6822	Remote Similarity	NPD4111	Phase 1
0.6822	Remote Similarity	NPD4665	Approved
0.6821	Remote Similarity	NPD7549	Discontinued
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.6816	Remote Similarity	NPD2309	Approved
0.6802	Remote Similarity	NPD2313	Discontinued
0.6798	Remote Similarity	NPD4420	Approved
0.6798	Remote Similarity	NPD1652	Phase 2
0.6792	Remote Similarity	NPD7930	Approved
0.6786	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4908	Phase 1
0.6784	Remote Similarity	NPD6832	Phase 2
0.678	Remote Similarity	NPD3450	Approved
0.678	Remote Similarity	NPD2346	Discontinued
0.678	Remote Similarity	NPD3452	Approved
0.6765	Remote Similarity	NPD2798	Approved
0.6763	Remote Similarity	NPD4583	Approved
0.6763	Remote Similarity	NPD4582	Approved
0.6761	Remote Similarity	NPD2799	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