NPASS Compound

Structure

CID25724 OpenBabel06191715352D 50 54 0 0 1 0 0 0 0 0999 V2000 -8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 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 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 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 -7.7942 -2.5000 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 3.4641 -4.0000 0.0000 C 0 0 2 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 -4.5000 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 1.7321 -4.0000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 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 -6.0622 1.5000 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 1.7321 2.0000 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 -8.6603 -1.0000 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 -4.3301 1.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 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 0.8660 -4.5000 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 13 2 0 0 0 0 5 14 1 0 0 0 0 6 14 2 0 0 0 0 6 18 1 0 0 0 0 7 15 2 0 0 0 0 7 17 1 0 0 0 0 8 15 1 0 0 0 0 8 19 2 0 0 0 0 9 16 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 36 1 0 0 0 0 13 23 1 0 0 0 0 14 30 1 0 0 0 0 15 46 1 0 0 0 0 16 24 1 0 0 0 0 16 30 2 0 0 0 0 17 22 2 0 0 0 0 17 37 1 0 0 0 0 18 23 2 0 0 0 0 18 38 1 0 0 0 0 19 22 1 0 0 0 0 19 47 1 0 0 0 0 20 10 1 6 0 0 0 20 25 1 0 0 0 0 20 48 1 0 0 0 0 21 11 1 6 0 0 0 21 26 1 0 0 0 0 21 49 1 0 0 0 0 22 24 1 0 0 0 0 23 39 1 0 0 0 0 24 40 2 0 0 0 0 25 27 1 0 0 0 0 25 41 1 1 0 0 0 26 28 1 0 0 0 0 26 42 1 1 0 0 0 27 29 1 0 0 0 0 27 43 1 6 0 0 0 28 31 1 0 0 0 0 28 44 1 6 0 0 0 29 32 1 0 0 0 0 29 45 1 1 0 0 0 30 47 1 0 0 0 0 31 33 1 0 0 0 0 31 50 1 1 0 0 0 32 48 1 0 0 0 0 32 50 1 6 0 0 0 33 46 1 6 0 0 0 33 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	708.23
Volume:	662.247
LogP:	1.098
LogD:	0.595
LogS:	-3.491
# Rotatable Bonds:	11
TPSA:	286.5
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	5.129
Fsp3:	0.515
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407
MDCK Permeability:	3.0008011890458874e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	92.87419891357422%
Volume Distribution (VD):	0.677
Pgp-substrate:	6.452377796173096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.218
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.51
Carcinogencity:	0.108
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC25724

Natural Product ID:	NPC25724
*Common Name:**	Pedunculosumoside C
IUPAC Name:	7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-3-(hydroxymethyl)chromen-4-one
Synonyms:	Pedunculosumoside C
Standard InCHIKey:	ZDGISMQFYIDRSP-KZGGGLRYSA-N
Standard InCHI:	InChI=1S/C33H40O17/c1-12(2)3-4-13-5-14(6-18(38)23(13)39)30-16(9-34)24(40)22-17(37)7-15(8-19(22)47-30)46-33-31(28(44)26(42)21(11-36)49-33)50-32-29(45)27(43)25(41)20(10-35)48-32/h3,5-8,20-21,25-29,31-39,41-45H,4,9-11H2,1-2H3/t20-,21-,25-,26-,27+,28+,29-,31-,32+,33-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)CO)c2cc(O)c(c(c2)CC=C(C)C)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773497
PubChem CID:	52951629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO31176	Ophioglossum pedunculosum	Species	Ophioglossaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21401115]

☑ 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
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	70500.0	nM	PMID[527816]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[527816]

☑ 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 NPC25724 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	457
0.1-0.2	1844
0.2-0.3	3965
0.3-0.4	9491
0.4-0.5	8707
0.5-0.6	4852
0.6-0.7	5474
0.7-0.8	5357
0.8-0.85	1550
0.85-0.9	643
0.9-0.95	327
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC255799
0.9755	High Similarity	NPC208668
0.9753	High Similarity	NPC150767
0.9753	High Similarity	NPC78734
0.9753	High Similarity	NPC218488
0.9693	High Similarity	NPC256760
0.963	High Similarity	NPC477502
0.9576	High Similarity	NPC294629
0.9576	High Similarity	NPC198199
0.9573	High Similarity	NPC180918
0.9571	High Similarity	NPC105283
0.9571	High Similarity	NPC195257
0.9571	High Similarity	NPC227508
0.9571	High Similarity	NPC86008
0.9571	High Similarity	NPC209296
0.9571	High Similarity	NPC43587
0.9568	High Similarity	NPC8856
0.9568	High Similarity	NPC210073
0.9568	High Similarity	NPC115674
0.9518	High Similarity	NPC292019
0.9518	High Similarity	NPC202908
0.9518	High Similarity	NPC122467
0.9518	High Similarity	NPC14187
0.9512	High Similarity	NPC79056
0.9512	High Similarity	NPC105095
0.9512	High Similarity	NPC51326
0.9512	High Similarity	NPC44328
0.9512	High Similarity	NPC67105
0.9512	High Similarity	NPC177731
0.9512	High Similarity	NPC231194
0.9509	High Similarity	NPC275454
0.9506	High Similarity	NPC15358
0.9503	High Similarity	NPC473043
0.9471	High Similarity	NPC64755
0.9467	High Similarity	NPC148710
0.9461	High Similarity	NPC89052
0.9461	High Similarity	NPC120952
0.9461	High Similarity	NPC251417
0.9458	High Similarity	NPC473327
0.9458	High Similarity	NPC220173
0.9458	High Similarity	NPC294815
0.9458	High Similarity	NPC19108
0.9458	High Similarity	NPC476472
0.9458	High Similarity	NPC16194
0.9455	High Similarity	NPC471725
0.9455	High Similarity	NPC155877
0.9455	High Similarity	NPC134532
0.9455	High Similarity	NPC203259
0.9455	High Similarity	NPC33054
0.9455	High Similarity	NPC471748
0.9455	High Similarity	NPC176740
0.9451	High Similarity	NPC293629
0.9448	High Similarity	NPC236934
0.9448	High Similarity	NPC5778
0.9444	High Similarity	NPC124155
0.9444	High Similarity	NPC222936
0.9444	High Similarity	NPC284960
0.9444	High Similarity	NPC29830
0.9444	High Similarity	NPC19709
0.9444	High Similarity	NPC257566
0.9408	High Similarity	NPC132111
0.9405	High Similarity	NPC192539
0.9401	High Similarity	NPC89127
0.9401	High Similarity	NPC471669
0.9401	High Similarity	NPC219043
0.9401	High Similarity	NPC473862
0.9401	High Similarity	NPC48984
0.9398	High Similarity	NPC204693
0.9394	High Similarity	NPC67326
0.9394	High Similarity	NPC156869
0.9394	High Similarity	NPC285197
0.9394	High Similarity	NPC259896
0.9394	High Similarity	NPC95866
0.9394	High Similarity	NPC29958
0.9394	High Similarity	NPC255157
0.9394	High Similarity	NPC254855
0.9394	High Similarity	NPC136042
0.939	High Similarity	NPC229729
0.9387	High Similarity	NPC475366
0.9387	High Similarity	NPC475497
0.9387	High Similarity	NPC22832
0.9387	High Similarity	NPC284277
0.9387	High Similarity	NPC311830
0.9383	High Similarity	NPC77660
0.9383	High Similarity	NPC189142
0.9383	High Similarity	NPC300537
0.9383	High Similarity	NPC44947
0.9383	High Similarity	NPC127782
0.9353	High Similarity	NPC49690
0.9353	High Similarity	NPC318119
0.9345	High Similarity	NPC241196
0.9345	High Similarity	NPC173837
0.9341	High Similarity	NPC142996
0.9341	High Similarity	NPC102028
0.9337	High Similarity	NPC301683
0.9337	High Similarity	NPC3583
0.9337	High Similarity	NPC26230
0.9337	High Similarity	NPC60735
0.9337	High Similarity	NPC259152
0.9337	High Similarity	NPC261254
0.9333	High Similarity	NPC5319
0.9333	High Similarity	NPC52382
0.9333	High Similarity	NPC229687
0.9333	High Similarity	NPC270578
0.9329	High Similarity	NPC73855
0.9329	High Similarity	NPC328940
0.9329	High Similarity	NPC135599
0.9329	High Similarity	NPC113968
0.9329	High Similarity	NPC277174
0.9325	High Similarity	NPC88023
0.9325	High Similarity	NPC191306
0.9325	High Similarity	NPC270335
0.9325	High Similarity	NPC309025
0.9325	High Similarity	NPC168822
0.9325	High Similarity	NPC243930
0.9321	High Similarity	NPC47923
0.9294	High Similarity	NPC321916
0.9294	High Similarity	NPC162394
0.9294	High Similarity	NPC241781
0.9294	High Similarity	NPC156785
0.929	High Similarity	NPC470444
0.929	High Similarity	NPC473571
0.929	High Similarity	NPC470443
0.929	High Similarity	NPC473682
0.929	High Similarity	NPC110941
0.929	High Similarity	NPC126784
0.929	High Similarity	NPC241423
0.9286	High Similarity	NPC65563
0.9286	High Similarity	NPC169733
0.9286	High Similarity	NPC470949
0.9281	High Similarity	NPC236191
0.9281	High Similarity	NPC213052
0.9281	High Similarity	NPC51774
0.9281	High Similarity	NPC239549
0.9277	High Similarity	NPC22195
0.9277	High Similarity	NPC224462
0.9277	High Similarity	NPC52353
0.9277	High Similarity	NPC21190
0.9277	High Similarity	NPC183357
0.9273	High Similarity	NPC325555
0.9273	High Similarity	NPC265530
0.9273	High Similarity	NPC223424
0.9273	High Similarity	NPC317489
0.9273	High Similarity	NPC127546
0.9273	High Similarity	NPC52550
0.9273	High Similarity	NPC160156
0.9273	High Similarity	NPC45400
0.9273	High Similarity	NPC92565
0.9273	High Similarity	NPC226304
0.9273	High Similarity	NPC84362
0.9273	High Similarity	NPC173637
0.9268	High Similarity	NPC19388
0.9268	High Similarity	NPC55786
0.9268	High Similarity	NPC277205
0.9268	High Similarity	NPC240431
0.9264	High Similarity	NPC475382
0.9264	High Similarity	NPC190450
0.9259	High Similarity	NPC110349
0.924	High Similarity	NPC21359
0.924	High Similarity	NPC275977
0.924	High Similarity	NPC223860
0.924	High Similarity	NPC470455
0.924	High Similarity	NPC470713
0.924	High Similarity	NPC25946
0.924	High Similarity	NPC460984
0.924	High Similarity	NPC470717
0.924	High Similarity	NPC470451
0.924	High Similarity	NPC470720
0.924	High Similarity	NPC249560
0.9235	High Similarity	NPC469371
0.9231	High Similarity	NPC475261
0.9231	High Similarity	NPC168584
0.9226	High Similarity	NPC108202
0.9226	High Similarity	NPC253685
0.9226	High Similarity	NPC472607
0.9222	High Similarity	NPC288152
0.9222	High Similarity	NPC267254
0.9222	High Similarity	NPC47140
0.9222	High Similarity	NPC9002
0.9222	High Similarity	NPC307518
0.9222	High Similarity	NPC235575
0.9222	High Similarity	NPC475155
0.9222	High Similarity	NPC156977
0.9222	High Similarity	NPC67134
0.9222	High Similarity	NPC257011
0.9222	High Similarity	NPC137871
0.9222	High Similarity	NPC205076
0.9222	High Similarity	NPC48773
0.9217	High Similarity	NPC186807
0.9217	High Similarity	NPC225434
0.9217	High Similarity	NPC210042
0.9217	High Similarity	NPC45638
0.9217	High Similarity	NPC469931
0.9217	High Similarity	NPC93337
0.9217	High Similarity	NPC475942
0.9217	High Similarity	NPC201292
0.9217	High Similarity	NPC477165
0.9217	High Similarity	NPC105025
0.9217	High Similarity	NPC472381
0.9217	High Similarity	NPC58053

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 NPC25724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	964
0.2-0.3	2009
0.3-0.4	2757
0.4-0.5	1801
0.5-0.6	825
0.6-0.7	242
0.7-0.8	113
0.8-0.85	22
0.85-0.9	3
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD7472	Approved
0.9571	High Similarity	NPD7054	Approved
0.9515	High Similarity	NPD7251	Discontinued
0.9512	High Similarity	NPD7074	Phase 3
0.9458	High Similarity	NPD7808	Phase 3
0.9455	High Similarity	NPD6797	Phase 2
0.9333	High Similarity	NPD7804	Clinical (unspecified phase)
0.9042	High Similarity	NPD3818	Discontinued
0.9018	High Similarity	NPD4381	Clinical (unspecified phase)
0.8951	High Similarity	NPD2393	Clinical (unspecified phase)
0.8922	High Similarity	NPD6168	Clinical (unspecified phase)
0.8922	High Similarity	NPD6167	Clinical (unspecified phase)
0.8922	High Similarity	NPD6166	Phase 2
0.8889	High Similarity	NPD4338	Clinical (unspecified phase)
0.8773	High Similarity	NPD1934	Approved
0.865	High Similarity	NPD4380	Phase 2
0.8555	High Similarity	NPD7993	Clinical (unspecified phase)
0.8506	High Similarity	NPD6559	Discontinued
0.8503	High Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD2801	Approved
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8395	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD8312	Approved
0.8305	Intermediate Similarity	NPD8313	Approved
0.8304	Intermediate Similarity	NPD6959	Discontinued
0.8293	Intermediate Similarity	NPD1512	Approved
0.8274	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7819	Suspended
0.8246	Intermediate Similarity	NPD5494	Approved
0.8232	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6801	Discontinued
0.8187	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3882	Suspended
0.8171	Intermediate Similarity	NPD7228	Approved
0.8115	Intermediate Similarity	NPD8151	Discontinued
0.8059	Intermediate Similarity	NPD8455	Phase 2
0.8047	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1549	Phase 2
0.7955	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD1465	Phase 2
0.7943	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD5402	Approved
0.7889	Intermediate Similarity	NPD7685	Pre-registration
0.787	Intermediate Similarity	NPD1653	Approved
0.7853	Intermediate Similarity	NPD2796	Approved
0.7824	Intermediate Similarity	NPD7584	Approved
0.7811	Intermediate Similarity	NPD5403	Approved
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.779	Intermediate Similarity	NPD7240	Approved
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.776	Intermediate Similarity	NPD7696	Phase 3
0.776	Intermediate Similarity	NPD7697	Approved
0.776	Intermediate Similarity	NPD7698	Approved
0.7759	Intermediate Similarity	NPD7768	Phase 2
0.7755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7783	Phase 2
0.7738	Intermediate Similarity	NPD6799	Approved
0.7717	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7266	Discontinued
0.7696	Intermediate Similarity	NPD6782	Approved
0.7696	Intermediate Similarity	NPD6779	Approved
0.7696	Intermediate Similarity	NPD6780	Approved
0.7696	Intermediate Similarity	NPD6776	Approved
0.7696	Intermediate Similarity	NPD6778	Approved
0.7696	Intermediate Similarity	NPD6777	Approved
0.7696	Intermediate Similarity	NPD6781	Approved
0.7692	Intermediate Similarity	NPD7701	Phase 2
0.7692	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD37	Approved
0.7684	Intermediate Similarity	NPD7199	Phase 2
0.7668	Intermediate Similarity	NPD7435	Discontinued
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7657	Intermediate Similarity	NPD4967	Phase 2
0.7657	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD4966	Approved
0.7654	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1613	Approved
0.764	Intermediate Similarity	NPD3787	Discontinued
0.7629	Intermediate Similarity	NPD7871	Phase 2
0.7629	Intermediate Similarity	NPD7870	Phase 2
0.7592	Intermediate Similarity	NPD7700	Phase 2
0.7592	Intermediate Similarity	NPD7699	Phase 2
0.7572	Intermediate Similarity	NPD6599	Discontinued
0.7571	Intermediate Similarity	NPD919	Approved
0.7546	Intermediate Similarity	NPD1240	Approved
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6823	Phase 2
0.7525	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7874	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7801	Approved
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD3750	Approved
0.7456	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1607	Approved
0.7453	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD8320	Phase 1
0.7449	Intermediate Similarity	NPD8319	Approved
0.7439	Intermediate Similarity	NPD943	Approved
0.7435	Intermediate Similarity	NPD6534	Approved
0.7435	Intermediate Similarity	NPD6535	Approved
0.7427	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2935	Discontinued
0.7424	Intermediate Similarity	NPD7585	Approved
0.7414	Intermediate Similarity	NPD7458	Discontinued
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6674	Discontinued
0.7396	Intermediate Similarity	NPD2800	Approved
0.7396	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD8150	Discontinued
0.7374	Intermediate Similarity	NPD7583	Approved
0.7371	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3027	Phase 3
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7349	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7390	Discontinued
0.7318	Intermediate Similarity	NPD3749	Approved
0.7317	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7680	Approved
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7302	Intermediate Similarity	NPD8434	Phase 2
0.7299	Intermediate Similarity	NPD920	Approved
0.7294	Intermediate Similarity	NPD1243	Approved
0.7289	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5953	Discontinued
0.7254	Intermediate Similarity	NPD4363	Phase 3
0.7254	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7216	Intermediate Similarity	NPD3226	Approved
0.7209	Intermediate Similarity	NPD6190	Approved
0.7202	Intermediate Similarity	NPD6213	Phase 3
0.7202	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6212	Phase 3
0.7184	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7930	Approved
0.7108	Intermediate Similarity	NPD2313	Discontinued
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD5124	Phase 1
0.7076	Intermediate Similarity	NPD2346	Discontinued
0.7065	Intermediate Similarity	NPD5710	Approved
0.7065	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD6844	Discontinued
0.6995	Remote Similarity	NPD8059	Phase 3
0.6995	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6832	Phase 2
0.6988	Remote Similarity	NPD4908	Phase 1
0.6975	Remote Similarity	NPD1091	Approved
0.697	Remote Similarity	NPD2798	Approved
0.6959	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5353	Approved
0.6907	Remote Similarity	NPD6842	Approved
0.6907	Remote Similarity	NPD6841	Approved
0.6907	Remote Similarity	NPD6843	Phase 3
0.6901	Remote Similarity	NPD7097	Phase 1
0.6897	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1652	Phase 2
0.6882	Remote Similarity	NPD7229	Phase 3
0.6879	Remote Similarity	NPD2344	Approved
0.6871	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4361	Phase 2
0.6857	Remote Similarity	NPD8166	Discontinued
0.685	Remote Similarity	NPD8285	Discontinued
0.6839	Remote Similarity	NPD2424	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data