NPASS Compound

Structure

NPC472129 OpenBabel07101718322D 59 64 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 3.4641 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 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 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 -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 1.0000 0.0000 C 0 0 1 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 1.7321 3.0000 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 -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 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 3 2 0 0 0 0 2 15 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 21 2 0 0 0 0 9 22 2 0 0 0 0 10 11 1 0 0 0 0 11 51 1 0 0 0 0 12 39 1 0 0 0 0 13 20 2 0 0 0 0 13 53 1 0 0 0 0 14 52 1 0 0 0 0 15 40 2 0 0 0 0 15 54 1 0 0 0 0 16 3 1 1 0 0 0 16 17 1 0 0 0 0 16 36 1 0 0 0 0 17 10 1 1 0 0 0 17 20 1 0 0 0 0 18 25 2 0 0 0 0 18 35 1 0 0 0 0 19 30 2 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 25 1 0 0 0 0 21 41 1 0 0 0 0 22 30 1 0 0 0 0 22 42 1 0 0 0 0 23 12 1 1 0 0 0 23 26 1 0 0 0 0 23 55 1 0 0 0 0 24 14 1 6 0 0 0 24 27 1 0 0 0 0 24 56 1 0 0 0 0 25 43 1 0 0 0 0 26 28 1 0 0 0 0 26 44 1 6 0 0 0 27 31 1 0 0 0 0 27 45 1 1 0 0 0 28 29 1 0 0 0 0 28 46 1 1 0 0 0 29 37 1 0 0 0 0 29 47 1 6 0 0 0 30 58 1 0 0 0 0 31 32 1 0 0 0 0 31 54 1 6 0 0 0 32 38 1 0 0 0 0 32 57 1 1 0 0 0 33 48 2 0 0 0 0 33 52 1 0 0 0 0 34 49 2 0 0 0 0 34 51 1 0 0 0 0 35 50 2 0 0 0 0 35 57 1 0 0 0 0 36 53 1 0 0 0 0 36 59 1 6 0 0 0 37 55 1 0 0 0 0 37 58 1 1 0 0 0 38 56 1 0 0 0 0 38 59 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	834.22
Volume:	767.422
LogP:	1.516
LogD:	0.482
LogS:	-2.495
# Rotatable Bonds:	15
TPSA:	313.19
# H-Bond Aceptor:	21
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	5.63
Fsp3:	0.474
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:	-6.618
MDCK Permeability:	0.00012425793102011085
Pgp-inhibitor:	0.001
Pgp-substrate:	0.693
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	72.00243377685547%
Volume Distribution (VD):	0.438
Pgp-substrate:	16.4810848236084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.325
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	1.119
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.123
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC472129

Natural Product ID:	NPC472129
*Common Name:**	IEDLYUUSVPCGLY-KPXIVHIRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEDLYUUSVPCGLY-KPXIVHIRSA-N
Standard InCHI:	InChI=1S/C38H42O21/c1-3-16-17-10-11-51-34(49)20(17)13-53-36(16)59-38-32(57-35(50)18-6-4-8-21(41)25(18)43)31(54-15(2)40)27(45)24(56-38)14-52-33(48)19-7-5-9-22(42)30(19)58-37-29(47)28(46)26(44)23(12-39)55-37/h3-9,13,16-17,23-24,26-29,31-32,36-39,41-47H,1,10-12,14H2,2H3/t16-,17+,23-,24-,26-,27-,28+,29-,31+,32-,36+,37+,38+/m1/s1
SMILES:	CC(=O)OC1C(C(OC(C1OC(=O)C2=C(C(=CC=C2)O)O)OC3C(C4CCOC(=O)C4=CO3)C=C)COC(=O)C5=C(C(=CC=C5)O)OC6C(C(C(C(O6)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338641
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[485518]

☑ 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 NPC472129 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	393
0.1-0.2	1606
0.2-0.3	3545
0.3-0.4	8224
0.4-0.5	9274
0.5-0.6	5974
0.6-0.7	6831
0.7-0.8	5601
0.8-0.85	997
0.85-0.9	244
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43434
0.9937	High Similarity	NPC472133
0.9748	High Similarity	NPC472130
0.9748	High Similarity	NPC472131
0.9226	High Similarity	NPC120952
0.9182	High Similarity	NPC472127
0.9182	High Similarity	NPC472128
0.9107	High Similarity	NPC198199
0.9102	High Similarity	NPC180918
0.907	High Similarity	NPC295625
0.907	High Similarity	NPC473554
0.907	High Similarity	NPC470719
0.9048	High Similarity	NPC163165
0.9036	High Similarity	NPC298847
0.9012	High Similarity	NPC470713
0.9012	High Similarity	NPC223860
0.9012	High Similarity	NPC470717
0.9012	High Similarity	NPC470451
0.9012	High Similarity	NPC460984
0.9012	High Similarity	NPC25946
0.9012	High Similarity	NPC470720
0.9012	High Similarity	NPC249560
0.9012	High Similarity	NPC21359
0.9012	High Similarity	NPC275977
0.9012	High Similarity	NPC470455
0.9	High Similarity	NPC89052
0.9	High Similarity	NPC251417
0.9	High Similarity	NPC173837
0.8982	High Similarity	NPC209296
0.8982	High Similarity	NPC658
0.8982	High Similarity	NPC197708
0.8982	High Similarity	NPC195257
0.8982	High Similarity	NPC86008
0.8963	High Similarity	NPC217950
0.896	High Similarity	NPC33083
0.8953	High Similarity	NPC35924
0.8953	High Similarity	NPC470447
0.8953	High Similarity	NPC470445
0.8953	High Similarity	NPC470718
0.8953	High Similarity	NPC156785
0.8953	High Similarity	NPC470449
0.8953	High Similarity	NPC470446
0.8953	High Similarity	NPC162394
0.8953	High Similarity	NPC241781
0.8953	High Similarity	NPC199172
0.8947	High Similarity	NPC192539
0.8947	High Similarity	NPC471030
0.8941	High Similarity	NPC471669
0.8941	High Similarity	NPC255799
0.8941	High Similarity	NPC292019
0.8941	High Similarity	NPC473862
0.8941	High Similarity	NPC89127
0.8941	High Similarity	NPC202908
0.8941	High Similarity	NPC219043
0.8941	High Similarity	NPC48984
0.8941	High Similarity	NPC122467
0.8941	High Similarity	NPC14187
0.8935	High Similarity	NPC204693
0.8935	High Similarity	NPC172033
0.8935	High Similarity	NPC88560
0.8935	High Similarity	NPC472993
0.8935	High Similarity	NPC175230
0.8929	High Similarity	NPC177731
0.8929	High Similarity	NPC105095
0.8929	High Similarity	NPC231194
0.8929	High Similarity	NPC51326
0.8929	High Similarity	NPC79056
0.8929	High Similarity	NPC44328
0.8922	High Similarity	NPC116745
0.8916	High Similarity	NPC99216
0.8908	High Similarity	NPC30011
0.8908	High Similarity	NPC97817
0.8908	High Similarity	NPC72554
0.8889	High Similarity	NPC475261
0.8882	High Similarity	NPC102028
0.8882	High Similarity	NPC253685
0.8882	High Similarity	NPC142996
0.8882	High Similarity	NPC19108
0.8882	High Similarity	NPC294815
0.8882	High Similarity	NPC16194
0.8882	High Similarity	NPC476472
0.8882	High Similarity	NPC220173
0.8882	High Similarity	NPC473327
0.8876	High Similarity	NPC172807
0.8876	High Similarity	NPC3583
0.8876	High Similarity	NPC211594
0.8876	High Similarity	NPC259152
0.8876	High Similarity	NPC102851
0.8876	High Similarity	NPC254540
0.8876	High Similarity	NPC5786
0.8869	High Similarity	NPC43587
0.8869	High Similarity	NPC229687
0.8869	High Similarity	NPC293629
0.8869	High Similarity	NPC61791
0.8869	High Similarity	NPC105283
0.8862	High Similarity	NPC210073
0.8862	High Similarity	NPC115674
0.8862	High Similarity	NPC8856
0.8851	High Similarity	NPC474093
0.8851	High Similarity	NPC104910
0.8848	High Similarity	NPC132737
0.8848	High Similarity	NPC71780
0.8837	High Similarity	NPC110941
0.8837	High Similarity	NPC470443
0.8837	High Similarity	NPC126784
0.8837	High Similarity	NPC473571
0.8837	High Similarity	NPC473682
0.8837	High Similarity	NPC241423
0.8837	High Similarity	NPC473895
0.8837	High Similarity	NPC470444
0.883	High Similarity	NPC472991
0.883	High Similarity	NPC233994
0.883	High Similarity	NPC472992
0.883	High Similarity	NPC211532
0.883	High Similarity	NPC169733
0.8827	High Similarity	NPC191046
0.8827	High Similarity	NPC194095
0.8827	High Similarity	NPC327032
0.8824	High Similarity	NPC239549
0.8824	High Similarity	NPC25724
0.8824	High Similarity	NPC208668
0.8824	High Similarity	NPC316539
0.8824	High Similarity	NPC236191
0.8824	High Similarity	NPC4390
0.8824	High Similarity	NPC51774
0.8817	High Similarity	NPC204937
0.8817	High Similarity	NPC285197
0.8817	High Similarity	NPC149011
0.8817	High Similarity	NPC67105
0.881	High Similarity	NPC229729
0.881	High Similarity	NPC45400
0.8802	High Similarity	NPC22832
0.8802	High Similarity	NPC475366
0.8802	High Similarity	NPC15358
0.8802	High Similarity	NPC284277
0.8802	High Similarity	NPC311830
0.8802	High Similarity	NPC475497
0.88	High Similarity	NPC475179
0.8795	High Similarity	NPC22324
0.8795	High Similarity	NPC246024
0.8793	High Similarity	NPC470416
0.8786	High Similarity	NPC469371
0.878	High Similarity	NPC133984
0.8779	High Similarity	NPC217520
0.8779	High Similarity	NPC267680
0.8779	High Similarity	NPC477895
0.8779	High Similarity	NPC476618
0.8779	High Similarity	NPC476621
0.8779	High Similarity	NPC293626
0.8779	High Similarity	NPC476622
0.8779	High Similarity	NPC35167
0.8779	High Similarity	NPC113836
0.8779	High Similarity	NPC253521
0.8779	High Similarity	NPC217387
0.8779	High Similarity	NPC476623
0.8779	High Similarity	NPC37668
0.8779	High Similarity	NPC196127
0.8779	High Similarity	NPC472387
0.8779	High Similarity	NPC476620
0.8779	High Similarity	NPC139571
0.8779	High Similarity	NPC476619
0.8779	High Similarity	NPC258044
0.8772	High Similarity	NPC84482
0.8772	High Similarity	NPC477848
0.8772	High Similarity	NPC169645
0.8765	High Similarity	NPC472386
0.8765	High Similarity	NPC60735
0.8765	High Similarity	NPC67134
0.8765	High Similarity	NPC307518
0.8765	High Similarity	NPC471748
0.8765	High Similarity	NPC9002
0.8765	High Similarity	NPC26230
0.8765	High Similarity	NPC134532
0.8765	High Similarity	NPC155877
0.8765	High Similarity	NPC175107
0.8765	High Similarity	NPC190003
0.8765	High Similarity	NPC47140
0.8765	High Similarity	NPC288152
0.8765	High Similarity	NPC153755
0.8765	High Similarity	NPC257011
0.8765	High Similarity	NPC267254
0.8765	High Similarity	NPC301683
0.8765	High Similarity	NPC33054
0.8765	High Similarity	NPC176740
0.8765	High Similarity	NPC205076
0.8765	High Similarity	NPC256760
0.8765	High Similarity	NPC156977
0.8765	High Similarity	NPC137871
0.8765	High Similarity	NPC203259
0.8765	High Similarity	NPC475155
0.8765	High Similarity	NPC48773
0.8765	High Similarity	NPC471725
0.8757	High Similarity	NPC226294
0.8757	High Similarity	NPC264302
0.8757	High Similarity	NPC58053
0.8757	High Similarity	NPC469931
0.8757	High Similarity	NPC93337
0.8757	High Similarity	NPC45638
0.8757	High Similarity	NPC186807
0.8757	High Similarity	NPC475942

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 NPC472129 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	918
0.2-0.3	1918
0.3-0.4	2656
0.4-0.5	1910
0.5-0.6	966
0.6-0.7	318
0.7-0.8	109
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9042	High Similarity	NPD7472	Approved
0.8982	High Similarity	NPD7054	Approved
0.8929	High Similarity	NPD7074	Phase 3
0.8882	High Similarity	NPD7808	Phase 3
0.8824	High Similarity	NPD7251	Discontinued
0.8765	High Similarity	NPD6797	Phase 2
0.8663	High Similarity	NPD4338	Clinical (unspecified phase)
0.8613	High Similarity	NPD8313	Approved
0.8613	High Similarity	NPD8312	Approved
0.8588	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD7685	Pre-registration
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6166	Phase 2
0.8256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7228	Approved
0.8047	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7964	Intermediate Similarity	NPD1653	Approved
0.7941	Intermediate Similarity	NPD8455	Phase 2
0.7941	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1933	Approved
0.7901	Intermediate Similarity	NPD7266	Discontinued
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.7849	Intermediate Similarity	NPD3882	Suspended
0.7836	Intermediate Similarity	NPD1465	Phase 2
0.7816	Intermediate Similarity	NPD5494	Approved
0.7812	Intermediate Similarity	NPD447	Suspended
0.7803	Intermediate Similarity	NPD7075	Discontinued
0.7802	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5403	Approved
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7733	Intermediate Similarity	NPD7819	Suspended
0.7725	Intermediate Similarity	NPD1511	Approved
0.7709	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.768	Intermediate Similarity	NPD7240	Approved
0.7679	Intermediate Similarity	NPD5401	Approved
0.7657	Intermediate Similarity	NPD6234	Discontinued
0.7653	Intermediate Similarity	NPD7783	Phase 2
0.7653	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD8151	Discontinued
0.7633	Intermediate Similarity	NPD1512	Approved
0.763	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6232	Discontinued
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD6801	Discontinued
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7568	Intermediate Similarity	NPD8150	Discontinued
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7556	Intermediate Similarity	NPD3751	Discontinued
0.7545	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7526	Intermediate Similarity	NPD8320	Phase 1
0.7526	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7698	Approved
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7444	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD4628	Phase 3
0.743	Intermediate Similarity	NPD3787	Discontinued
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7411	Suspended
0.7412	Intermediate Similarity	NPD6799	Approved
0.7412	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7701	Phase 2
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7399	Intermediate Similarity	NPD3226	Approved
0.7396	Intermediate Similarity	NPD6190	Approved
0.7391	Intermediate Similarity	NPD6832	Phase 2
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8434	Phase 2
0.7374	Intermediate Similarity	NPD6959	Discontinued
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD6823	Phase 2
0.7321	Intermediate Similarity	NPD1549	Phase 2
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1203	Approved
0.7306	Intermediate Similarity	NPD7700	Phase 2
0.7306	Intermediate Similarity	NPD7699	Phase 2
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.73	Intermediate Similarity	NPD7801	Approved
0.7299	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD7680	Approved
0.7278	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.7257	Intermediate Similarity	NPD6599	Discontinued
0.7235	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD2796	Approved
0.7195	Intermediate Similarity	NPD2313	Discontinued
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7175	Intermediate Similarity	NPD6844	Discontinued
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2798	Approved
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD9717	Approved
0.7111	Intermediate Similarity	NPD3749	Approved
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7584	Approved
0.7099	Intermediate Similarity	NPD2797	Approved
0.7098	Intermediate Similarity	NPD6212	Phase 3
0.7098	Intermediate Similarity	NPD6213	Phase 3
0.7098	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD919	Approved
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3225	Approved
0.7024	Intermediate Similarity	NPD7930	Approved
0.7012	Intermediate Similarity	NPD9494	Approved
0.7011	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD5353	Approved
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD411	Approved
0.6982	Remote Similarity	NPD7097	Phase 1
0.698	Remote Similarity	NPD7585	Approved
0.6973	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2532	Approved
0.6971	Remote Similarity	NPD2534	Approved
0.6971	Remote Similarity	NPD2533	Approved
0.6964	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD4308	Phase 3
0.6941	Remote Similarity	NPD3748	Approved
0.6936	Remote Similarity	NPD8166	Discontinued
0.6931	Remote Similarity	NPD7583	Approved
0.6928	Remote Similarity	NPD3027	Phase 3
0.6927	Remote Similarity	NPD6386	Approved
0.6927	Remote Similarity	NPD6385	Approved
0.6919	Remote Similarity	NPD8285	Discontinued
0.6914	Remote Similarity	NPD1608	Approved
0.6905	Remote Similarity	NPD1240	Approved
0.6905	Remote Similarity	NPD943	Approved
0.6902	Remote Similarity	NPD1247	Approved
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4420	Approved
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1019	Discontinued
0.6842	Remote Similarity	NPD7038	Approved
0.6842	Remote Similarity	NPD7039	Approved
0.6836	Remote Similarity	NPD6273	Approved
0.6824	Remote Similarity	NPD1607	Approved
0.6824	Remote Similarity	NPD6653	Approved
0.6823	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7549	Discontinued
0.6802	Remote Similarity	NPD6099	Approved
0.6802	Remote Similarity	NPD6100	Approved
0.6798	Remote Similarity	NPD920	Approved
0.6792	Remote Similarity	NPD9493	Approved
0.6789	Remote Similarity	NPD5953	Discontinued
0.6788	Remote Similarity	NPD3267	Approved
0.6788	Remote Similarity	NPD3266	Approved
0.6786	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD7286	Phase 2
0.6763	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2344	Approved
0.6747	Remote Similarity	NPD5647	Approved
0.6746	Remote Similarity	NPD6233	Phase 2
0.6744	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