NPASS Compound

Structure

NPC472133 OpenBabel07101718292D 56 61 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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 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 6.0622 -1.5000 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 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 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 -0.8660 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 2 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 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 3.4641 -3.0000 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 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -6.9282 3.0000 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 -6.0622 2.5000 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 1.7321 0.0000 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -6.9282 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 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 -6.0622 1.5000 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 5.1962 -3.0000 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 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -5.1962 4.0000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 1 2 2 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 19 2 0 0 0 0 8 20 2 0 0 0 0 9 10 1 0 0 0 0 10 49 1 0 0 0 0 11 37 1 0 0 0 0 12 18 2 0 0 0 0 12 51 1 0 0 0 0 13 50 1 0 0 0 0 14 2 1 1 0 0 0 14 15 1 0 0 0 0 14 34 1 0 0 0 0 15 9 1 1 0 0 0 15 18 1 0 0 0 0 16 23 2 0 0 0 0 16 33 1 0 0 0 0 17 29 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 23 1 0 0 0 0 19 38 1 0 0 0 0 20 29 1 0 0 0 0 20 39 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 52 1 0 0 0 0 22 13 1 6 0 0 0 22 25 1 0 0 0 0 22 53 1 0 0 0 0 23 40 1 0 0 0 0 24 26 1 0 0 0 0 24 41 1 6 0 0 0 25 27 1 0 0 0 0 25 42 1 1 0 0 0 26 28 1 0 0 0 0 26 43 1 1 0 0 0 27 30 1 0 0 0 0 27 44 1 6 0 0 0 28 35 1 0 0 0 0 28 45 1 6 0 0 0 29 55 1 0 0 0 0 30 36 1 0 0 0 0 30 54 1 1 0 0 0 31 46 2 0 0 0 0 31 50 1 0 0 0 0 32 47 2 0 0 0 0 32 49 1 0 0 0 0 33 48 2 0 0 0 0 33 54 1 0 0 0 0 34 51 1 0 0 0 0 34 56 1 6 0 0 0 35 52 1 0 0 0 0 35 55 1 1 0 0 0 36 53 1 0 0 0 0 36 56 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	792.21
Volume:	726.677
LogP:	1.364
LogD:	0.399
LogS:	-2.519
# Rotatable Bonds:	13
TPSA:	307.12
# H-Bond Aceptor:	20
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	5.546
Fsp3:	0.472
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.7
MDCK Permeability:	7.733629900030792e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.495
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	75.06156158447266%
Volume Distribution (VD):	0.562
Pgp-substrate:	13.136967658996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.247
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.229
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	1.001
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.259
Carcinogencity:	0.365
Eye Corrosion:	0.003
Eye Irritation:	0.27
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC472133

Natural Product ID:	NPC472133
*Common Name:**	IXZFPRBKGLVTKP-DEOFNSNRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IXZFPRBKGLVTKP-DEOFNSNRSA-N
Standard InCHI:	InChI=1S/C36H40O20/c1-2-14-15-9-10-49-32(47)18(15)12-51-34(14)56-36-30(54-33(48)16-5-3-7-19(38)23(16)40)27(44)25(42)22(53-36)13-50-31(46)17-6-4-8-20(39)29(17)55-35-28(45)26(43)24(41)21(11-37)52-35/h2-8,12,14-15,21-22,24-28,30,34-45H,1,9-11,13H2/t14-,15+,21-,22-,24-,25-,26+,27+,28-,30-,34+,35+,36+/m1/s1
SMILES:	C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)COC(=O)C4=C(C(=CC=C4)O)OC5C(C(C(C(O5)CO)O)O)O)O)O)OC(=O)C6=C(C(=CC=C6)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338645
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24806310]
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25442320]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[455069]

☑ 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 NPC472133 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	413
0.1-0.2	1670
0.2-0.3	3712
0.3-0.4	8493
0.4-0.5	9099
0.5-0.6	5858
0.6-0.7	7044
0.7-0.8	5225
0.8-0.85	957
0.85-0.9	219
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC43434
0.9937	High Similarity	NPC472129
0.981	High Similarity	NPC472131
0.981	High Similarity	NPC472130
0.9167	High Similarity	NPC120952
0.9157	High Similarity	NPC180918
0.9119	High Similarity	NPC472127
0.9119	High Similarity	NPC472128
0.9048	High Similarity	NPC198199
0.9036	High Similarity	NPC86008
0.9012	High Similarity	NPC470719
0.9012	High Similarity	NPC295625
0.9012	High Similarity	NPC473554
0.9006	High Similarity	NPC470718
0.8994	High Similarity	NPC219043
0.8988	High Similarity	NPC163165
0.8976	High Similarity	NPC298847
0.8953	High Similarity	NPC25946
0.8953	High Similarity	NPC470720
0.8953	High Similarity	NPC223860
0.8953	High Similarity	NPC275977
0.8953	High Similarity	NPC470455
0.8953	High Similarity	NPC249560
0.8953	High Similarity	NPC21359
0.8953	High Similarity	NPC470451
0.8953	High Similarity	NPC460984
0.8953	High Similarity	NPC470717
0.8953	High Similarity	NPC470713
0.8941	High Similarity	NPC89052
0.8941	High Similarity	NPC173837
0.8941	High Similarity	NPC251417
0.8935	High Similarity	NPC253685
0.8929	High Similarity	NPC259152
0.8929	High Similarity	NPC3583
0.8922	High Similarity	NPC658
0.8922	High Similarity	NPC105283
0.8922	High Similarity	NPC197708
0.8922	High Similarity	NPC195257
0.8922	High Similarity	NPC209296
0.8916	High Similarity	NPC8856
0.8902	High Similarity	NPC33083
0.8902	High Similarity	NPC132737
0.8902	High Similarity	NPC71780
0.8902	High Similarity	NPC217950
0.8895	High Similarity	NPC470449
0.8895	High Similarity	NPC470446
0.8895	High Similarity	NPC470445
0.8895	High Similarity	NPC470447
0.8895	High Similarity	NPC35924
0.8895	High Similarity	NPC199172
0.8895	High Similarity	NPC162394
0.8895	High Similarity	NPC241781
0.8895	High Similarity	NPC156785
0.8889	High Similarity	NPC192539
0.8889	High Similarity	NPC471030
0.8882	High Similarity	NPC472991
0.8882	High Similarity	NPC255799
0.8882	High Similarity	NPC471669
0.8882	High Similarity	NPC122467
0.8882	High Similarity	NPC473862
0.8882	High Similarity	NPC202908
0.8882	High Similarity	NPC14187
0.8882	High Similarity	NPC89127
0.8882	High Similarity	NPC48984
0.8882	High Similarity	NPC292019
0.8882	High Similarity	NPC472992
0.8876	High Similarity	NPC88560
0.8876	High Similarity	NPC204693
0.8876	High Similarity	NPC172033
0.8876	High Similarity	NPC472993
0.8876	High Similarity	NPC175230
0.8869	High Similarity	NPC285197
0.8869	High Similarity	NPC44328
0.8869	High Similarity	NPC79056
0.8869	High Similarity	NPC105095
0.8869	High Similarity	NPC51326
0.8869	High Similarity	NPC231194
0.8869	High Similarity	NPC177731
0.8869	High Similarity	NPC149011
0.8869	High Similarity	NPC204937
0.8862	High Similarity	NPC45400
0.8862	High Similarity	NPC116745
0.8855	High Similarity	NPC99216
0.8851	High Similarity	NPC72554
0.8851	High Similarity	NPC97817
0.8851	High Similarity	NPC30011
0.8848	High Similarity	NPC22324
0.8837	High Similarity	NPC469371
0.883	High Similarity	NPC113836
0.883	High Similarity	NPC476620
0.883	High Similarity	NPC476622
0.883	High Similarity	NPC37668
0.883	High Similarity	NPC475261
0.883	High Similarity	NPC476618
0.883	High Similarity	NPC476623
0.883	High Similarity	NPC476619
0.883	High Similarity	NPC253521
0.883	High Similarity	NPC476621
0.8824	High Similarity	NPC102028
0.8824	High Similarity	NPC476472
0.8824	High Similarity	NPC19108
0.8824	High Similarity	NPC294815
0.8824	High Similarity	NPC16194
0.8824	High Similarity	NPC473327
0.8824	High Similarity	NPC142996
0.8824	High Similarity	NPC220173
0.8817	High Similarity	NPC172807
0.8817	High Similarity	NPC211594
0.8817	High Similarity	NPC60735
0.8817	High Similarity	NPC67134
0.8817	High Similarity	NPC47140
0.8817	High Similarity	NPC5786
0.8817	High Similarity	NPC26230
0.8817	High Similarity	NPC102851
0.8817	High Similarity	NPC254540
0.881	High Similarity	NPC43587
0.881	High Similarity	NPC229687
0.881	High Similarity	NPC293629
0.881	High Similarity	NPC61791
0.8802	High Similarity	NPC210073
0.8802	High Similarity	NPC115674
0.8795	High Similarity	NPC191306
0.8795	High Similarity	NPC127415
0.8795	High Similarity	NPC168822
0.8795	High Similarity	NPC88043
0.8795	High Similarity	NPC270335
0.8793	High Similarity	NPC104910
0.8793	High Similarity	NPC474093
0.8786	High Similarity	NPC97119
0.8786	High Similarity	NPC297503
0.8786	High Similarity	NPC135831
0.8786	High Similarity	NPC132111
0.8779	High Similarity	NPC473571
0.8779	High Similarity	NPC473682
0.8779	High Similarity	NPC470443
0.8779	High Similarity	NPC473895
0.8779	High Similarity	NPC470444
0.8779	High Similarity	NPC110941
0.8779	High Similarity	NPC126784
0.8779	High Similarity	NPC241423
0.8772	High Similarity	NPC8573
0.8772	High Similarity	NPC169733
0.8772	High Similarity	NPC233994
0.8772	High Similarity	NPC61904
0.8772	High Similarity	NPC144097
0.8772	High Similarity	NPC211532
0.8765	High Similarity	NPC327032
0.8765	High Similarity	NPC299761
0.8765	High Similarity	NPC230439
0.8765	High Similarity	NPC4390
0.8765	High Similarity	NPC316539
0.8765	High Similarity	NPC51774
0.8765	High Similarity	NPC92153
0.8765	High Similarity	NPC239549
0.8765	High Similarity	NPC236191
0.8765	High Similarity	NPC279281
0.8765	High Similarity	NPC25724
0.8765	High Similarity	NPC208668
0.8765	High Similarity	NPC194095
0.8765	High Similarity	NPC191046
0.8757	High Similarity	NPC471416
0.8757	High Similarity	NPC259896
0.8757	High Similarity	NPC255157
0.8757	High Similarity	NPC136042
0.8757	High Similarity	NPC254855
0.8757	High Similarity	NPC67105
0.8757	High Similarity	NPC155763
0.8757	High Similarity	NPC67326
0.8757	High Similarity	NPC156869
0.8757	High Similarity	NPC235260
0.8757	High Similarity	NPC34287
0.8757	High Similarity	NPC218488
0.8757	High Similarity	NPC29958
0.8757	High Similarity	NPC20505
0.875	High Similarity	NPC275454
0.875	High Similarity	NPC469652
0.875	High Similarity	NPC229729
0.875	High Similarity	NPC58716
0.875	High Similarity	NPC45618
0.875	High Similarity	NPC472720
0.875	High Similarity	NPC472721
0.875	High Similarity	NPC31208
0.875	High Similarity	NPC472724
0.875	High Similarity	NPC160543
0.875	High Similarity	NPC146792
0.875	High Similarity	NPC93065
0.875	High Similarity	NPC187632
0.8743	High Similarity	NPC65489
0.8743	High Similarity	NPC475366
0.8743	High Similarity	NPC475179
0.8743	High Similarity	NPC284277
0.8743	High Similarity	NPC311830
0.8743	High Similarity	NPC15358
0.8743	High Similarity	NPC165720
0.8743	High Similarity	NPC475497
0.8743	High Similarity	NPC22832
0.8736	High Similarity	NPC470416
0.8736	High Similarity	NPC318119
0.8736	High Similarity	NPC231254
0.8735	High Similarity	NPC77660

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 NPC472133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	926
0.2-0.3	1942
0.3-0.4	2686
0.4-0.5	1868
0.5-0.6	945
0.6-0.7	301
0.7-0.8	105
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8982	High Similarity	NPD7472	Approved
0.8922	High Similarity	NPD7054	Approved
0.8869	High Similarity	NPD7074	Phase 3
0.8824	High Similarity	NPD7808	Phase 3
0.8765	High Similarity	NPD7251	Discontinued
0.8713	High Similarity	NPD4338	Clinical (unspecified phase)
0.8706	High Similarity	NPD6797	Phase 2
0.8663	High Similarity	NPD8312	Approved
0.8663	High Similarity	NPD8313	Approved
0.8639	High Similarity	NPD3818	Discontinued
0.8439	Intermediate Similarity	NPD7685	Pre-registration
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD6166	Phase 2
0.8171	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD1934	Approved
0.8022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1653	Approved
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD8455	Phase 2
0.7941	Intermediate Similarity	NPD3817	Phase 2
0.7882	Intermediate Similarity	NPD1465	Phase 2
0.7882	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1933	Approved
0.7844	Intermediate Similarity	NPD5403	Approved
0.784	Intermediate Similarity	NPD7266	Discontinued
0.7821	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD3882	Suspended
0.7771	Intermediate Similarity	NPD1511	Approved
0.7759	Intermediate Similarity	NPD5494	Approved
0.775	Intermediate Similarity	NPD447	Suspended
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7075	Discontinued
0.7725	Intermediate Similarity	NPD5401	Approved
0.7679	Intermediate Similarity	NPD1512	Approved
0.7674	Intermediate Similarity	NPD7819	Suspended
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD7473	Discontinued
0.7624	Intermediate Similarity	NPD7240	Approved
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6234	Discontinued
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.759	Intermediate Similarity	NPD8151	Discontinued
0.7572	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4966	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD8319	Approved
0.7472	Intermediate Similarity	NPD3787	Discontinued
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.744	Intermediate Similarity	NPD6190	Approved
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD7697	Approved
0.7412	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7374	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7874	Approved
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7358	Intermediate Similarity	NPD6781	Approved
0.7358	Intermediate Similarity	NPD1203	Approved
0.7358	Intermediate Similarity	NPD6778	Approved
0.7358	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD6782	Approved
0.7358	Intermediate Similarity	NPD6776	Approved
0.7358	Intermediate Similarity	NPD6777	Approved
0.7358	Intermediate Similarity	NPD6780	Approved
0.7356	Intermediate Similarity	NPD7411	Suspended
0.7353	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6799	Approved
0.7341	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7871	Phase 2
0.7296	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD3750	Approved
0.7262	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7699	Phase 2
0.7254	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7245	Intermediate Similarity	NPD7680	Approved
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1091	Approved
0.7212	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.72	Intermediate Similarity	NPD6599	Discontinued
0.7186	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD6674	Discontinued
0.711	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2798	Approved
0.7098	Intermediate Similarity	NPD6534	Approved
0.7098	Intermediate Similarity	NPD6535	Approved
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD3225	Approved
0.7076	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9717	Approved
0.705	Intermediate Similarity	NPD7584	Approved
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7037	Intermediate Similarity	NPD2797	Approved
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3268	Approved
0.7019	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD919	Approved
0.6982	Remote Similarity	NPD3748	Approved
0.6976	Remote Similarity	NPD7930	Approved
0.6957	Remote Similarity	NPD3926	Phase 2
0.6951	Remote Similarity	NPD9494	Approved
0.6946	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD5353	Approved
0.6939	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7585	Approved
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD411	Approved
0.6923	Remote Similarity	NPD7097	Phase 1
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2533	Approved
0.6914	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6355	Discontinued
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4308	Phase 3
0.6881	Remote Similarity	NPD7583	Approved
0.6879	Remote Similarity	NPD8166	Discontinued
0.6872	Remote Similarity	NPD6385	Approved
0.6872	Remote Similarity	NPD6386	Approved
0.6869	Remote Similarity	NPD8285	Discontinued
0.6867	Remote Similarity	NPD3027	Phase 3
0.6852	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD1247	Approved
0.6848	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1240	Approved
0.6834	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4420	Approved
0.681	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7038	Approved
0.6789	Remote Similarity	NPD7039	Approved
0.6788	Remote Similarity	NPD1019	Discontinued
0.678	Remote Similarity	NPD6273	Approved
0.6771	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6653	Approved
0.6765	Remote Similarity	NPD1607	Approved
0.6754	Remote Similarity	NPD7549	Discontinued
0.6744	Remote Similarity	NPD6100	Approved
0.6744	Remote Similarity	NPD6099	Approved
0.6742	Remote Similarity	NPD920	Approved
0.6737	Remote Similarity	NPD5953	Discontinued
0.673	Remote Similarity	NPD9493	Approved
0.6727	Remote Similarity	NPD3267	Approved
0.6727	Remote Similarity	NPD3266	Approved
0.6726	Remote Similarity	NPD6798	Discontinued
0.6725	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD642	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7286	Phase 2
0.6705	Remote Similarity	NPD2344	Approved
0.6705	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8059	Phase 3

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