NPASS Compound

Structure

NPC300657 OpenBabel07101718312D 54 62 0 0 1 0 0 0 0 0999 V2000 -6.0345 0.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5265 1.3713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3009 2.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4486 1.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5567 2.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 2.4086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5708 -3.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0503 -4.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6405 -1.2882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3918 -0.2123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 0.1880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0834 3.6753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2164 -5.3362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1532 0.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 2.2236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0546 0.0561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -1.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 0.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6405 -0.3041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4927 1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6082 -3.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1532 1.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0345 2.2236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3521 3.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0194 3.3712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8750 -4.6048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2538 -5.1316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4486 0.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5626 -0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 0.0561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3009 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0546 -1.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 -1.7803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4928 0.1880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5583 1.3713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5308 -0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9360 -0.3041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6973 0.7875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.5924 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9360 -1.2882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5963 0.3872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5785 -0.7962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0054 2.3554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5265 3.0759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4161 3.3209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7508 4.0297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8376 -4.8095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4047 -5.8629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3009 -0.5970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5626 -2.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 -2.7644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5957 1.1667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4935 -0.5916 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 1 2 2 0 0 0 0 1 18 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 22 1 0 0 0 0 4 28 1 0 0 0 0 5 20 2 0 0 0 0 5 24 1 0 0 0 0 6 20 1 0 0 0 0 6 25 2 0 0 0 0 7 21 2 0 0 0 0 7 26 1 0 0 0 0 8 21 1 0 0 0 0 8 27 2 0 0 0 0 9 19 2 0 0 0 0 9 33 1 0 0 0 0 10 18 1 0 0 0 0 10 34 2 0 0 0 0 11 19 1 0 0 0 0 11 37 2 0 0 0 0 12 24 2 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 13 27 1 0 0 0 0 14 22 2 0 0 0 0 14 31 1 0 0 0 0 15 23 2 0 0 0 0 15 35 1 0 0 0 0 16 29 2 0 0 0 0 16 30 1 0 0 0 0 17 32 2 0 0 0 0 17 36 1 0 0 0 0 18 35 2 0 0 0 0 19 34 1 0 0 0 0 22 43 1 0 0 0 0 23 44 1 0 0 0 0 24 45 1 0 0 0 0 25 46 1 0 0 0 0 26 47 1 0 0 0 0 27 48 1 0 0 0 0 28 31 2 0 0 0 0 29 32 1 0 0 0 0 30 36 2 0 0 0 0 30 38 1 0 0 0 0 31 49 1 0 0 0 0 32 50 1 0 0 0 0 33 40 2 0 0 0 0 33 51 1 0 0 0 0 34 52 1 0 0 0 0 35 52 1 0 0 0 0 36 53 1 0 0 0 0 37 40 1 0 0 0 0 37 54 1 0 0 0 0 38 20 1 1 0 0 0 38 41 1 0 0 0 0 39 21 1 6 0 0 0 39 40 1 0 0 0 0 39 42 1 0 0 0 0 41 28 1 6 0 0 0 41 53 1 0 0 0 0 42 29 1 1 0 0 0 42 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	726.17
Volume:	713.37
LogP:	6.54
LogD:	3.625
LogS:	-4.643
# Rotatable Bonds:	5
TPSA:	213.67
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	4.748
Fsp3:	0.095
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.411
MDCK Permeability:	5.561531907005701e-06
Pgp-inhibitor:	0.31
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.955
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	95.14875793457031%
Volume Distribution (VD):	0.403
Pgp-substrate:	4.581511974334717%

ADMET: Metabolism

CYP1A2-inhibitor:	0.579
CYP1A2-substrate:	0.564
CYP2C19-inhibitor:	0.889
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.768
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.423
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	6.698
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.932
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC300657

Natural Product ID:	NPC300657
*Common Name:**	Gneyulin B
IUPAC Name:	4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-5-[(2R,3R)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-(6-hydroxy-1-benzofuran-2-yl)-2,3-dihydro-1-benzofuran-2-yl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	HGGUGLARKRGHTC-IASBXJNJSA-N
Standard InCHI:	InChI=1S/C42H30O12/c43-22-3-4-28(31(49)14-22)41-38(20-5-24(45)12-25(46)6-20)30-16-29(32(50)17-36(30)53-41)42-39(21-7-26(47)13-27(48)8-21)40-33(51)9-19(11-37(40)54-42)34-10-18-1-2-23(44)15-35(18)52-34/h1-17,38-39,41-51H/t38-,39-,41+,42+/m1/s1
SMILES:	c1cc(cc2c1cc(c1cc(c3c(c1)O[C@@H](c1cc4c(cc1O)O[C@@H](c1ccc(cc1O)O)[C@@H]4c1cc(cc(c1)O)O)[C@@H]3c1cc(cc(c1)O)O)O)o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097908
PubChem CID:	46210600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO20232	Gnetum gnemonoides	Species	Gnetaceae	Eukaryota	bark	n.a.	n.a.	PMID[20192242]
NPO20232	Gnetum gnemonoides	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20232	Gnetum gnemonoides	Species	Gnetaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	IC50	=	18000.0	nM	PMID[518926]
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	IC50	=	37000.0	nM	PMID[518926]

☑ 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 NPC300657 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	465
0.1-0.2	1845
0.2-0.3	3712
0.3-0.4	10027
0.4-0.5	8796
0.5-0.6	3915
0.6-0.7	5804
0.7-0.8	5614
0.8-0.85	2063
0.85-0.9	412
0.9-0.95	43
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC286230
0.9333	High Similarity	NPC253730
0.9329	High Similarity	NPC169471
0.9152	High Similarity	NPC38591
0.9146	High Similarity	NPC301256
0.9146	High Similarity	NPC312273
0.9136	High Similarity	NPC137100
0.9091	High Similarity	NPC473012
0.9036	High Similarity	NPC159508
0.9036	High Similarity	NPC473009
0.9024	High Similarity	NPC40583
0.9006	High Similarity	NPC101991
0.9	High Similarity	NPC24748
0.9	High Similarity	NPC59491
0.8982	High Similarity	NPC474591
0.8982	High Similarity	NPC473010
0.8976	High Similarity	NPC473011
0.8971	High Similarity	NPC47905
0.8971	High Similarity	NPC139683
0.8971	High Similarity	NPC73929
0.897	High Similarity	NPC292863
0.897	High Similarity	NPC184326
0.8935	High Similarity	NPC53252
0.8929	High Similarity	NPC251336
0.8916	High Similarity	NPC137232
0.8916	High Similarity	NPC18380
0.8914	High Similarity	NPC304322
0.8909	High Similarity	NPC195167
0.8909	High Similarity	NPC105584
0.8909	High Similarity	NPC472877
0.8909	High Similarity	NPC51760
0.8902	High Similarity	NPC69531
0.8902	High Similarity	NPC121888
0.8902	High Similarity	NPC32867
0.8869	High Similarity	NPC469664
0.8862	High Similarity	NPC15374
0.8855	High Similarity	NPC472052
0.8855	High Similarity	NPC98023
0.8855	High Similarity	NPC470342
0.8855	High Similarity	NPC472060
0.8855	High Similarity	NPC226462
0.8855	High Similarity	NPC195136
0.8848	High Similarity	NPC246647
0.8848	High Similarity	NPC212967
0.8848	High Similarity	NPC164110
0.8848	High Similarity	NPC96342
0.8841	High Similarity	NPC66441
0.8841	High Similarity	NPC134171
0.8841	High Similarity	NPC300668
0.8841	High Similarity	NPC182555
0.8817	High Similarity	NPC82330
0.881	High Similarity	NPC290160
0.8802	High Similarity	NPC90822
0.8802	High Similarity	NPC189552
0.8802	High Similarity	NPC273467
0.8795	High Similarity	NPC15815
0.8795	High Similarity	NPC295090
0.8788	High Similarity	NPC309648
0.8788	High Similarity	NPC180924
0.878	High Similarity	NPC121568
0.878	High Similarity	NPC213608
0.878	High Similarity	NPC1477
0.8773	High Similarity	NPC170169
0.875	High Similarity	NPC261896
0.8743	High Similarity	NPC304839
0.8743	High Similarity	NPC220582
0.8743	High Similarity	NPC312993
0.8743	High Similarity	NPC42965
0.8743	High Similarity	NPC186325
0.8736	High Similarity	NPC478000
0.8735	High Similarity	NPC257166
0.8735	High Similarity	NPC65504
0.8735	High Similarity	NPC271741
0.8735	High Similarity	NPC208258
0.8735	High Similarity	NPC287789
0.8735	High Similarity	NPC1796
0.8735	High Similarity	NPC475184
0.8727	High Similarity	NPC100049
0.8727	High Similarity	NPC14606
0.8727	High Similarity	NPC205026
0.8727	High Similarity	NPC258474
0.8727	High Similarity	NPC150908
0.8727	High Similarity	NPC79375
0.8727	High Similarity	NPC201227
0.8727	High Similarity	NPC265624
0.8727	High Similarity	NPC158027
0.8727	High Similarity	NPC198490
0.8727	High Similarity	NPC186227
0.8727	High Similarity	NPC52611
0.8727	High Similarity	NPC148938
0.8727	High Similarity	NPC215203
0.8727	High Similarity	NPC159707
0.8727	High Similarity	NPC37253
0.8727	High Similarity	NPC121649
0.8727	High Similarity	NPC248739
0.8721	High Similarity	NPC477529
0.8721	High Similarity	NPC477836
0.872	High Similarity	NPC115601
0.872	High Similarity	NPC78324
0.872	High Similarity	NPC208011
0.872	High Similarity	NPC174086
0.872	High Similarity	NPC5871
0.872	High Similarity	NPC39154
0.8712	High Similarity	NPC78335
0.8712	High Similarity	NPC230713
0.8712	High Similarity	NPC167576
0.8706	High Similarity	NPC53640
0.8706	High Similarity	NPC477835
0.8706	High Similarity	NPC171985
0.8706	High Similarity	NPC320741
0.8706	High Similarity	NPC224851
0.8698	High Similarity	NPC109180
0.869	High Similarity	NPC304387
0.8683	High Similarity	NPC55443
0.8683	High Similarity	NPC226287
0.8683	High Similarity	NPC51247
0.8683	High Similarity	NPC324736
0.8683	High Similarity	NPC18699
0.8683	High Similarity	NPC177650
0.8675	High Similarity	NPC56049
0.8675	High Similarity	NPC61112
0.8675	High Similarity	NPC198489
0.8675	High Similarity	NPC54830
0.8667	High Similarity	NPC472462
0.8667	High Similarity	NPC194593
0.8667	High Similarity	NPC290830
0.8667	High Similarity	NPC71061
0.8667	High Similarity	NPC72425
0.8667	High Similarity	NPC235333
0.8667	High Similarity	NPC303485
0.8667	High Similarity	NPC72370
0.8667	High Similarity	NPC183874
0.8659	High Similarity	NPC111112
0.8659	High Similarity	NPC67322
0.8659	High Similarity	NPC138299
0.8659	High Similarity	NPC222713
0.8655	High Similarity	NPC476459
0.865	High Similarity	NPC226644
0.865	High Similarity	NPC178202
0.865	High Similarity	NPC37226
0.8639	High Similarity	NPC477239
0.8639	High Similarity	NPC3448
0.8631	High Similarity	NPC121647
0.8629	High Similarity	NPC475783
0.8623	High Similarity	NPC324358
0.8623	High Similarity	NPC268360
0.8623	High Similarity	NPC318527
0.8623	High Similarity	NPC323627
0.8623	High Similarity	NPC322459
0.8614	High Similarity	NPC254351
0.8614	High Similarity	NPC226656
0.8614	High Similarity	NPC66508
0.8614	High Similarity	NPC297531
0.8614	High Similarity	NPC213936
0.8613	High Similarity	NPC174700
0.8613	High Similarity	NPC28589
0.8613	High Similarity	NPC248593
0.8613	High Similarity	NPC478002
0.8606	High Similarity	NPC207624
0.8606	High Similarity	NPC43345
0.8605	High Similarity	NPC300307
0.8605	High Similarity	NPC107627
0.8589	High Similarity	NPC135325
0.8589	High Similarity	NPC122894
0.8588	High Similarity	NPC63438
0.858	High Similarity	NPC472261
0.858	High Similarity	NPC74854
0.858	High Similarity	NPC45124
0.858	High Similarity	NPC30655
0.8571	High Similarity	NPC324220
0.8571	High Similarity	NPC312630
0.8571	High Similarity	NPC476350
0.8571	High Similarity	NPC476349
0.8563	High Similarity	NPC65885
0.8563	High Similarity	NPC160015
0.8563	High Similarity	NPC247677
0.8555	High Similarity	NPC477571
0.8555	High Similarity	NPC477572
0.8555	High Similarity	NPC477573
0.8554	High Similarity	NPC122365
0.8554	High Similarity	NPC324447
0.8547	High Similarity	NPC50394
0.8547	High Similarity	NPC324522
0.8547	High Similarity	NPC472058
0.8547	High Similarity	NPC470341
0.8547	High Similarity	NPC105414
0.8547	High Similarity	NPC234497
0.8545	High Similarity	NPC178484
0.8545	High Similarity	NPC476553
0.8545	High Similarity	NPC58668
0.8545	High Similarity	NPC476552
0.8545	High Similarity	NPC193976
0.8545	High Similarity	NPC115324
0.8545	High Similarity	NPC106372
0.8545	High Similarity	NPC476551
0.8545	High Similarity	NPC23668
0.8539	High Similarity	NPC154527
0.8538	High Similarity	NPC136641
0.8537	High Similarity	NPC288840
0.8537	High Similarity	NPC317492

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 NPC300657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	988
0.2-0.3	1652
0.3-0.4	2679
0.4-0.5	1968
0.5-0.6	950
0.6-0.7	319
0.7-0.8	145
0.8-0.85	30
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8802	High Similarity	NPD6959	Discontinued
0.8503	High Similarity	NPD8443	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD3749	Approved
0.8249	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD7768	Phase 2
0.8182	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD4380	Phase 2
0.8121	Intermediate Similarity	NPD7390	Discontinued
0.8118	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD5494	Approved
0.8072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD8313	Approved
0.8056	Intermediate Similarity	NPD8312	Approved
0.8037	Intermediate Similarity	NPD1549	Phase 2
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD3818	Discontinued
0.7919	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD5844	Phase 1
0.7874	Intermediate Similarity	NPD7075	Discontinued
0.7874	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2534	Approved
0.7857	Intermediate Similarity	NPD2532	Approved
0.7853	Intermediate Similarity	NPD1510	Phase 2
0.7849	Intermediate Similarity	NPD1934	Approved
0.7838	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3882	Suspended
0.7805	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD920	Approved
0.7758	Intermediate Similarity	NPD2344	Approved
0.7751	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1607	Approved
0.7701	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD1511	Approved
0.7674	Intermediate Similarity	NPD3226	Approved
0.7665	Intermediate Similarity	NPD2800	Approved
0.766	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3926	Phase 2
0.7647	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6801	Discontinued
0.7637	Intermediate Similarity	NPD7074	Phase 3
0.7633	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1240	Approved
0.7602	Intermediate Similarity	NPD1512	Approved
0.7582	Intermediate Similarity	NPD7054	Approved
0.7574	Intermediate Similarity	NPD2309	Approved
0.7572	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1243	Approved
0.756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5402	Approved
0.7542	Intermediate Similarity	NPD1247	Approved
0.7541	Intermediate Similarity	NPD7472	Approved
0.753	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7525	Intermediate Similarity	NPD8151	Discontinued
0.7515	Intermediate Similarity	NPD3750	Approved
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD5404	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD5408	Approved
0.7485	Intermediate Similarity	NPD5406	Approved
0.7485	Intermediate Similarity	NPD5405	Approved
0.7459	Intermediate Similarity	NPD7251	Discontinued
0.7458	Intermediate Similarity	NPD3817	Phase 2
0.7432	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD919	Approved
0.7419	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7003	Approved
0.7411	Intermediate Similarity	NPD7871	Phase 2
0.7411	Intermediate Similarity	NPD7870	Phase 2
0.7403	Intermediate Similarity	NPD7229	Phase 3
0.7401	Intermediate Similarity	NPD5761	Phase 2
0.7401	Intermediate Similarity	NPD5760	Phase 2
0.7396	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6799	Approved
0.7381	Intermediate Similarity	NPD2935	Discontinued
0.7378	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD4287	Approved
0.7356	Intermediate Similarity	NPD5403	Approved
0.7354	Intermediate Similarity	NPD8434	Phase 2
0.7341	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.7321	Intermediate Similarity	NPD2799	Discontinued
0.7318	Intermediate Similarity	NPD4966	Approved
0.7318	Intermediate Similarity	NPD4967	Phase 2
0.7318	Intermediate Similarity	NPD4965	Approved
0.7312	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD5710	Approved
0.7308	Intermediate Similarity	NPD5711	Approved
0.7303	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD1465	Phase 2
0.7302	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6781	Approved
0.7296	Intermediate Similarity	NPD6777	Approved
0.7296	Intermediate Similarity	NPD6782	Approved
0.7296	Intermediate Similarity	NPD6776	Approved
0.7296	Intermediate Similarity	NPD6778	Approved
0.7296	Intermediate Similarity	NPD6779	Approved
0.7296	Intermediate Similarity	NPD6780	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7278	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7256	Intermediate Similarity	NPD4908	Phase 1
0.7243	Intermediate Similarity	NPD7177	Discontinued
0.7243	Intermediate Similarity	NPD3751	Discontinued
0.7243	Intermediate Similarity	NPD7228	Approved
0.7241	Intermediate Similarity	NPD5401	Approved
0.7219	Intermediate Similarity	NPD3748	Approved
0.7213	Intermediate Similarity	NPD3787	Discontinued
0.7209	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4628	Phase 3
0.7204	Intermediate Similarity	NPD7286	Phase 2
0.7202	Intermediate Similarity	NPD6651	Approved
0.7192	Intermediate Similarity	NPD7783	Phase 2
0.7192	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7435	Discontinued
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7701	Phase 2
0.7128	Intermediate Similarity	NPD4360	Phase 2
0.7128	Intermediate Similarity	NPD4363	Phase 3
0.7108	Intermediate Similarity	NPD7801	Approved
0.7102	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD943	Approved
0.7081	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2296	Approved
0.7066	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7874	Approved
0.705	Intermediate Similarity	NPD6823	Phase 2
0.7041	Intermediate Similarity	NPD6535	Approved
0.7041	Intermediate Similarity	NPD6534	Approved
0.7035	Intermediate Similarity	NPD1471	Phase 3
0.702	Intermediate Similarity	NPD7700	Phase 2
0.702	Intermediate Similarity	NPD7699	Phase 2
0.7011	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7005	Intermediate Similarity	NPD4361	Phase 2
0.7005	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8320	Phase 1
0.698	Remote Similarity	NPD8319	Approved
0.697	Remote Similarity	NPD1470	Approved
0.6964	Remote Similarity	NPD3764	Approved
0.6961	Remote Similarity	NPD6280	Approved
0.6961	Remote Similarity	NPD6279	Approved
0.695	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6808	Phase 2
0.6933	Remote Similarity	NPD1610	Phase 2
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7680	Approved
0.6911	Remote Similarity	NPD7240	Approved
0.6906	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1729	Discontinued
0.6893	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2861	Phase 2
0.6885	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD1203	Approved
0.6865	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7654	Discontinued
0.6845	Remote Similarity	NPD6832	Phase 2
0.6829	Remote Similarity	NPD1201	Approved
0.6826	Remote Similarity	NPD2798	Approved
0.6821	Remote Similarity	NPD7033	Discontinued
0.6818	Remote Similarity	NPD6213	Phase 3
0.6818	Remote Similarity	NPD6212	Phase 3
0.6818	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8285	Discontinued
0.6784	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1613	Approved
0.6776	Remote Similarity	NPD6844	Discontinued
0.6765	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3268	Approved
0.6748	Remote Similarity	NPD7584	Approved
0.6747	Remote Similarity	NPD4749	Approved
0.6744	Remote Similarity	NPD1899	Clinical (unspecified phase)

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