NPASS Compound

Structure

NPC15358 OpenBabel07101718192D 46 50 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 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 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -1.7321 -2.0000 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 -8.6603 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 12 2 0 0 0 0 5 19 1 0 0 0 0 6 12 1 0 0 0 0 6 20 2 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 18 2 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 15 1 0 0 0 0 10 42 1 0 0 0 0 11 43 1 0 0 0 0 12 16 1 0 0 0 0 13 38 1 0 0 0 0 14 22 1 0 0 0 0 14 31 2 0 0 0 0 15 23 1 0 0 0 0 15 32 1 1 0 0 0 16 44 1 0 0 0 0 17 22 2 0 0 0 0 17 44 1 0 0 0 0 18 22 1 0 0 0 0 18 45 1 0 0 0 0 19 28 2 0 0 0 0 19 39 1 0 0 0 0 20 28 1 0 0 0 0 20 40 1 0 0 0 0 21 11 1 6 0 0 0 21 24 1 0 0 0 0 21 46 1 0 0 0 0 23 26 1 0 0 0 0 23 33 1 6 0 0 0 24 25 1 0 0 0 0 24 34 1 1 0 0 0 25 27 1 0 0 0 0 25 35 1 6 0 0 0 26 29 1 0 0 0 0 26 36 1 1 0 0 0 27 30 1 0 0 0 0 27 37 1 1 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 29 43 1 6 0 0 0 30 45 1 6 0 0 0 30 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.2
Volume:	604.206
LogP:	0.954
LogD:	0.602
LogS:	-4.026
# Rotatable Bonds:	10
TPSA:	225.43
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	4.664
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.199
MDCK Permeability:	5.253808558336459e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.708
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	59.804222106933594%
Volume Distribution (VD):	0.601
Pgp-substrate:	26.96828842163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	1.801
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.683
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.385
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.591
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC15358

Natural Product ID:	NPC15358
*Common Name:**	Lethedioside B
IUPAC Name:	7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	YCCFHELFYKTGSO-VQLIQGKVSA-N
Standard InCHI:	InChI=1S/C30H36O16/c1-38-13-7-17-22(14(31)9-16(44-17)12-5-19(39-2)28(41-4)20(6-12)40-3)18(8-13)45-30-27(37)25(35)24(34)21(46-30)11-43-29-26(36)23(33)15(32)10-42-29/h5-9,15,21,23-27,29-30,32-37H,10-11H2,1-4H3/t15-,21-,23+,24-,25+,26-,27-,29+,30-/m1/s1
SMILES:	COc1cc(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)c2c(c1)oc(cc2=O)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510037
PubChem CID:	10439249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]

☑ 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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	32.0	ug.mL-1	PMID[511196]

☑ 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 NPC15358 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	439
0.1-0.2	1820
0.2-0.3	3940
0.3-0.4	9576
0.4-0.5	8759
0.5-0.6	4707
0.6-0.7	5616
0.7-0.8	5372
0.8-0.85	1523
0.85-0.9	537
0.9-0.95	349
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC475366
0.9872	High Similarity	NPC475497
0.9872	High Similarity	NPC284277
0.9742	High Similarity	NPC110349
0.9686	High Similarity	NPC86008
0.9686	High Similarity	NPC209296
0.9686	High Similarity	NPC195257
0.9679	High Similarity	NPC182045
0.9625	High Similarity	NPC52353
0.9568	High Similarity	NPC473327
0.9568	High Similarity	NPC294815
0.9568	High Similarity	NPC198199
0.9568	High Similarity	NPC476472
0.9568	High Similarity	NPC19108
0.9568	High Similarity	NPC220173
0.9568	High Similarity	NPC16194
0.9565	High Similarity	NPC180918
0.9565	High Similarity	NPC475155
0.9563	High Similarity	NPC61791
0.9563	High Similarity	NPC293629
0.9563	High Similarity	NPC227508
0.956	High Similarity	NPC210073
0.956	High Similarity	NPC8856
0.956	High Similarity	NPC115674
0.9557	High Similarity	NPC284960
0.9557	High Similarity	NPC243930
0.9557	High Similarity	NPC309025
0.9557	High Similarity	NPC88023
0.9557	High Similarity	NPC222936
0.9509	High Similarity	NPC255799
0.9509	High Similarity	NPC48984
0.9506	High Similarity	NPC25724
0.9506	High Similarity	NPC208668
0.9506	High Similarity	NPC204693
0.9503	High Similarity	NPC67105
0.9503	High Similarity	NPC285197
0.9503	High Similarity	NPC177731
0.9503	High Similarity	NPC231194
0.9503	High Similarity	NPC194483
0.9503	High Similarity	NPC79056
0.9503	High Similarity	NPC293004
0.9503	High Similarity	NPC105095
0.9503	High Similarity	NPC51326
0.9503	High Similarity	NPC44328
0.95	High Similarity	NPC275454
0.9497	High Similarity	NPC311830
0.9497	High Similarity	NPC22832
0.9494	High Similarity	NPC473043
0.9451	High Similarity	NPC173837
0.9451	High Similarity	NPC475261
0.9451	High Similarity	NPC251417
0.9451	High Similarity	NPC89052
0.9451	High Similarity	NPC120952
0.9448	High Similarity	NPC102028
0.9444	High Similarity	NPC60735
0.9444	High Similarity	NPC203259
0.9444	High Similarity	NPC33054
0.9444	High Similarity	NPC471748
0.9444	High Similarity	NPC176740
0.9444	High Similarity	NPC256760
0.9444	High Similarity	NPC471725
0.9444	High Similarity	NPC3583
0.9444	High Similarity	NPC26230
0.9444	High Similarity	NPC155877
0.9444	High Similarity	NPC259152
0.9444	High Similarity	NPC134532
0.9441	High Similarity	NPC105283
0.9441	High Similarity	NPC43587
0.9437	High Similarity	NPC236934
0.9437	High Similarity	NPC5778
0.9434	High Similarity	NPC19709
0.9434	High Similarity	NPC191306
0.9434	High Similarity	NPC270335
0.9423	High Similarity	NPC295613
0.9423	High Similarity	NPC473657
0.9394	High Similarity	NPC473571
0.9394	High Similarity	NPC192539
0.9394	High Similarity	NPC126784
0.9394	High Similarity	NPC470444
0.9394	High Similarity	NPC470443
0.9394	High Similarity	NPC473895
0.9394	High Similarity	NPC473682
0.9394	High Similarity	NPC110941
0.9394	High Similarity	NPC241423
0.939	High Similarity	NPC89127
0.939	High Similarity	NPC14187
0.939	High Similarity	NPC202908
0.939	High Similarity	NPC219043
0.939	High Similarity	NPC292019
0.939	High Similarity	NPC169733
0.939	High Similarity	NPC471669
0.939	High Similarity	NPC122467
0.9383	High Similarity	NPC255157
0.9383	High Similarity	NPC150767
0.9383	High Similarity	NPC254855
0.9383	High Similarity	NPC136042
0.9383	High Similarity	NPC67326
0.9383	High Similarity	NPC259896
0.9383	High Similarity	NPC95866
0.9383	High Similarity	NPC218488
0.9383	High Similarity	NPC156869
0.9383	High Similarity	NPC78734
0.9383	High Similarity	NPC29958
0.9379	High Similarity	NPC265530
0.9379	High Similarity	NPC477502
0.9379	High Similarity	NPC135345
0.9379	High Similarity	NPC226304
0.9379	High Similarity	NPC229729
0.9379	High Similarity	NPC325555
0.9371	High Similarity	NPC77660
0.9371	High Similarity	NPC189142
0.9329	High Similarity	NPC142996
0.9325	High Similarity	NPC267254
0.9325	High Similarity	NPC261254
0.9325	High Similarity	NPC156977
0.9321	High Similarity	NPC229687
0.9321	High Similarity	NPC226294
0.9321	High Similarity	NPC120099
0.9321	High Similarity	NPC219904
0.9321	High Similarity	NPC45638
0.9321	High Similarity	NPC203050
0.9321	High Similarity	NPC93337
0.9321	High Similarity	NPC186807
0.9321	High Similarity	NPC475942
0.9321	High Similarity	NPC58053
0.9321	High Similarity	NPC472383
0.9321	High Similarity	NPC105025
0.9321	High Similarity	NPC472381
0.9321	High Similarity	NPC225434
0.9321	High Similarity	NPC469931
0.9321	High Similarity	NPC223747
0.9321	High Similarity	NPC201292
0.9317	High Similarity	NPC21100
0.9317	High Similarity	NPC113968
0.9317	High Similarity	NPC73855
0.9317	High Similarity	NPC277174
0.9317	High Similarity	NPC328940
0.9317	High Similarity	NPC135599
0.9317	High Similarity	NPC99957
0.9317	High Similarity	NPC181616
0.9317	High Similarity	NPC197285
0.9313	High Similarity	NPC29830
0.9313	High Similarity	NPC168822
0.9304	High Similarity	NPC138811
0.9304	High Similarity	NPC22062
0.9304	High Similarity	NPC473634
0.9299	High Similarity	NPC261866
0.9281	High Similarity	NPC470449
0.9281	High Similarity	NPC470446
0.9281	High Similarity	NPC470447
0.9281	High Similarity	NPC473072
0.9281	High Similarity	NPC470445
0.9273	High Similarity	NPC473862
0.9273	High Similarity	NPC470949
0.9273	High Similarity	NPC65563
0.9273	High Similarity	NPC8573
0.9268	High Similarity	NPC236191
0.9268	High Similarity	NPC51774
0.9268	High Similarity	NPC472993
0.9268	High Similarity	NPC239549
0.9264	High Similarity	NPC21190
0.9264	High Similarity	NPC206123
0.9264	High Similarity	NPC183357
0.9264	High Similarity	NPC22195
0.9264	High Similarity	NPC224462
0.9264	High Similarity	NPC44558
0.9264	High Similarity	NPC105511
0.9259	High Similarity	NPC223424
0.9259	High Similarity	NPC317489
0.9259	High Similarity	NPC173637
0.9259	High Similarity	NPC58716
0.9259	High Similarity	NPC127546
0.9259	High Similarity	NPC52550
0.9259	High Similarity	NPC45618
0.9259	High Similarity	NPC45400
0.9259	High Similarity	NPC146792
0.9259	High Similarity	NPC93099
0.9259	High Similarity	NPC84362
0.9255	High Similarity	NPC277205
0.9255	High Similarity	NPC240431
0.9255	High Similarity	NPC55786
0.9255	High Similarity	NPC19388
0.925	High Similarity	NPC127782
0.925	High Similarity	NPC300537
0.925	High Similarity	NPC244875
0.925	High Similarity	NPC475382
0.925	High Similarity	NPC298171
0.925	High Similarity	NPC414831
0.9245	High Similarity	NPC473623
0.9241	High Similarity	NPC129827
0.9241	High Similarity	NPC44931
0.9241	High Similarity	NPC65003
0.9241	High Similarity	NPC473512
0.9226	High Similarity	NPC148710
0.9226	High Similarity	NPC470451
0.9226	High Similarity	NPC470455
0.9226	High Similarity	NPC470713
0.9226	High Similarity	NPC460984
0.9226	High Similarity	NPC470717
0.9226	High Similarity	NPC25946

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 NPC15358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	955
0.2-0.3	1945
0.3-0.4	2751
0.4-0.5	1812
0.5-0.6	879
0.6-0.7	280
0.7-0.8	112
0.8-0.85	17
0.85-0.9	4
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9748	High Similarity	NPD7472	Approved
0.9686	High Similarity	NPD7054	Approved
0.9568	High Similarity	NPD7808	Phase 3
0.9506	High Similarity	NPD7251	Discontinued
0.9503	High Similarity	NPD7074	Phase 3
0.9444	High Similarity	NPD6797	Phase 2
0.9024	High Similarity	NPD3818	Discontinued
0.9	High Similarity	NPD4381	Clinical (unspecified phase)
0.8982	High Similarity	NPD4338	Clinical (unspecified phase)
0.897	High Similarity	NPD7804	Clinical (unspecified phase)
0.8902	High Similarity	NPD6167	Clinical (unspecified phase)
0.8902	High Similarity	NPD6168	Clinical (unspecified phase)
0.8902	High Similarity	NPD6166	Phase 2
0.8758	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD1934	Approved
0.858	High Similarity	NPD2801	Approved
0.858	High Similarity	NPD2393	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8365	Intermediate Similarity	NPD1511	Approved
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5494	Approved
0.8314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6559	Discontinued
0.8261	Intermediate Similarity	NPD1512	Approved
0.8253	Intermediate Similarity	NPD3882	Suspended
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8084	Intermediate Similarity	NPD5402	Approved
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD6959	Discontinued
0.8038	Intermediate Similarity	NPD2796	Approved
0.8035	Intermediate Similarity	NPD7228	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.7989	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD5403	Approved
0.7988	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5401	Approved
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8313	Approved
0.7966	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD7240	Approved
0.7953	Intermediate Similarity	NPD7199	Phase 2
0.7939	Intermediate Similarity	NPD1653	Approved
0.7937	Intermediate Similarity	NPD1549	Phase 2
0.7917	Intermediate Similarity	NPD8455	Phase 2
0.7917	Intermediate Similarity	NPD1465	Phase 2
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7904	Intermediate Similarity	NPD7411	Suspended
0.7874	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7803	Intermediate Similarity	NPD6232	Discontinued
0.7801	Intermediate Similarity	NPD8151	Discontinued
0.7759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD37	Approved
0.775	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4965	Approved
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7673	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD7266	Discontinued
0.765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD919	Approved
0.7614	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7584	Approved
0.7595	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3926	Phase 2
0.7543	Intermediate Similarity	NPD1247	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7455	Intermediate Similarity	NPD6674	Discontinued
0.7449	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7783	Phase 2
0.7448	Intermediate Similarity	NPD7696	Phase 3
0.7448	Intermediate Similarity	NPD7435	Discontinued
0.7448	Intermediate Similarity	NPD7697	Approved
0.7448	Intermediate Similarity	NPD7698	Approved
0.7414	Intermediate Similarity	NPD7768	Phase 2
0.741	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD3750	Approved
0.7407	Intermediate Similarity	NPD1607	Approved
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7346	Intermediate Similarity	NPD230	Phase 1
0.7346	Intermediate Similarity	NPD447	Suspended
0.732	Intermediate Similarity	NPD7871	Phase 2
0.732	Intermediate Similarity	NPD7870	Phase 2
0.7317	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD3027	Phase 3
0.7306	Intermediate Similarity	NPD6823	Phase 2
0.7296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD943	Approved
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7257	Intermediate Similarity	NPD5353	Approved
0.7251	Intermediate Similarity	NPD920	Approved
0.725	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1243	Approved
0.7245	Intermediate Similarity	NPD7583	Approved
0.7241	Intermediate Similarity	NPD6844	Discontinued
0.724	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2532	Approved
0.7235	Intermediate Similarity	NPD2534	Approved
0.7235	Intermediate Similarity	NPD2533	Approved
0.7225	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7874	Approved
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7208	Intermediate Similarity	NPD7585	Approved
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7801	Approved
0.7169	Intermediate Similarity	NPD6099	Approved
0.7169	Intermediate Similarity	NPD6100	Approved
0.7169	Intermediate Similarity	NPD2935	Discontinued
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD2800	Approved
0.7135	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1091	Approved
0.7128	Intermediate Similarity	NPD6841	Approved
0.7128	Intermediate Similarity	NPD6843	Phase 3
0.7128	Intermediate Similarity	NPD6842	Approved
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2798	Approved
0.7118	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7092	Intermediate Similarity	NPD7680	Approved
0.7091	Intermediate Similarity	NPD6651	Approved
0.7076	Intermediate Similarity	NPD7390	Discontinued
0.7074	Intermediate Similarity	NPD8150	Discontinued
0.7069	Intermediate Similarity	NPD3226	Approved
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7043	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4360	Phase 2
0.7031	Intermediate Similarity	NPD4363	Phase 3
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5953	Discontinued
0.7025	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2346	Discontinued
0.7011	Intermediate Similarity	NPD7286	Phase 2
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6385	Approved
0.6989	Remote Similarity	NPD6386	Approved
0.6979	Remote Similarity	NPD6213	Phase 3
0.6979	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6212	Phase 3
0.6978	Remote Similarity	NPD5242	Approved
0.6954	Remote Similarity	NPD5006	Approved
0.6954	Remote Similarity	NPD5005	Approved
0.6951	Remote Similarity	NPD6798	Discontinued
0.6946	Remote Similarity	NPD7097	Phase 1
0.6933	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5124	Phase 1
0.6909	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD9494	Approved
0.6871	Remote Similarity	NPD3018	Phase 2
0.6862	Remote Similarity	NPD7549	Discontinued
0.6852	Remote Similarity	NPD1203	Approved
0.6848	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2654	Approved
0.6837	Remote Similarity	NPD4420	Approved
0.6832	Remote Similarity	NPD4379	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