NPASS Compound

Structure

CID86008 OpenBabel06191715422D 45 49 0 0 1 0 0 0 0 0999 V2000 -1.7321 -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 -0.8660 -3.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -7.7942 -0.5000 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 -4.3301 -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 -6.9282 -0.0000 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 -6.0622 -0.5000 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 -6.0622 -1.5000 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 -1.7321 -6.0000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -6.9282 -3.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 14 1 0 0 0 0 3 9 2 0 0 0 0 3 12 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 10 1 0 0 0 0 5 15 2 0 0 0 0 6 11 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 26 1 0 0 0 0 10 41 1 0 0 0 0 11 19 1 0 0 0 0 11 26 2 0 0 0 0 12 14 2 0 0 0 0 12 32 1 0 0 0 0 13 18 2 0 0 0 0 13 33 1 0 0 0 0 14 43 1 0 0 0 0 15 18 1 0 0 0 0 15 42 1 0 0 0 0 16 7 1 6 0 0 0 16 20 1 0 0 0 0 16 44 1 0 0 0 0 17 8 1 6 0 0 0 17 21 1 0 0 0 0 17 45 1 0 0 0 0 18 19 1 0 0 0 0 19 34 2 0 0 0 0 20 22 1 0 0 0 0 20 35 1 1 0 0 0 21 23 1 0 0 0 0 21 36 1 1 0 0 0 22 24 1 0 0 0 0 22 37 1 6 0 0 0 23 25 1 0 0 0 0 23 38 1 6 0 0 0 24 27 1 0 0 0 0 24 39 1 1 0 0 0 25 28 1 0 0 0 0 25 40 1 1 0 0 0 26 42 1 0 0 0 0 27 41 1 6 0 0 0 27 44 1 0 0 0 0 28 43 1 6 0 0 0 28 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	640.16
Volume:	578.404
LogP:	-0.883
LogD:	-0.575
LogS:	-3.532
# Rotatable Bonds:	8
TPSA:	289.66
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.115
Synthetic Accessibility Score:	4.865
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.534
MDCK Permeability:	4.839070970774628e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	76.76656341552734%
Volume Distribution (VD):	0.569
Pgp-substrate:	18.90641212463379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.076
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.266
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.782
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.076
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC86008

Natural Product ID:	NPC86008
*Common Name:**	Pedunculosumoside F
IUPAC Name:	5-hydroxy-3-(hydroxymethyl)-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Pedunculosumoside F
Standard InCHIKey:	VWMQUPAZXJVKFZ-KJBTZJKUSA-N
Standard InCHI:	InChI=1S/C28H32O17/c29-6-11-19(34)18-13(33)4-10(41-27-24(39)22(37)20(35)16(7-30)44-27)5-15(18)42-26(11)9-1-2-14(12(32)3-9)43-28-25(40)23(38)21(36)17(8-31)45-28/h1-5,16-17,20-25,27-33,35-40H,6-8H2/t16-,17-,20-,21-,22+,23+,24-,25-,27-,28-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(c(c3=O)CO)c2ccc(c(c2)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773607
PubChem CID:	52951748
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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	56700.0	nM	PMID[543902]

☑ 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 NPC86008 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	479
0.1-0.2	1885
0.2-0.3	4365
0.3-0.4	10005
0.4-0.5	8140
0.5-0.6	4462
0.6-0.7	5507
0.7-0.8	5253
0.8-0.85	1578
0.85-0.9	490
0.9-0.95	437
0.95-1	96

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC180918
0.9874	High Similarity	NPC209296
0.9874	High Similarity	NPC195257
0.9873	High Similarity	NPC8856
0.9812	High Similarity	NPC285197
0.9753	High Similarity	NPC16194
0.9753	High Similarity	NPC220173
0.9753	High Similarity	NPC476472
0.9753	High Similarity	NPC19108
0.9753	High Similarity	NPC294815
0.9753	High Similarity	NPC198199
0.9753	High Similarity	NPC473327
0.9752	High Similarity	NPC3583
0.9752	High Similarity	NPC259152
0.9752	High Similarity	NPC26230
0.9752	High Similarity	NPC60735
0.975	High Similarity	NPC105283
0.9748	High Similarity	NPC115674
0.9748	High Similarity	NPC210073
0.9747	High Similarity	NPC270335
0.9747	High Similarity	NPC191306
0.9693	High Similarity	NPC219043
0.9691	High Similarity	NPC208668
0.9691	High Similarity	NPC204693
0.9689	High Similarity	NPC105095
0.9689	High Similarity	NPC67105
0.9689	High Similarity	NPC44328
0.9689	High Similarity	NPC259896
0.9689	High Similarity	NPC156869
0.9689	High Similarity	NPC177731
0.9689	High Similarity	NPC255157
0.9689	High Similarity	NPC218488
0.9689	High Similarity	NPC254855
0.9689	High Similarity	NPC51326
0.9689	High Similarity	NPC136042
0.9689	High Similarity	NPC29958
0.9689	High Similarity	NPC79056
0.9689	High Similarity	NPC231194
0.9689	High Similarity	NPC67326
0.9688	High Similarity	NPC275454
0.9686	High Similarity	NPC284277
0.9686	High Similarity	NPC311830
0.9686	High Similarity	NPC475366
0.9686	High Similarity	NPC475497
0.9686	High Similarity	NPC15358
0.9686	High Similarity	NPC22832
0.9684	High Similarity	NPC189142
0.9684	High Similarity	NPC77660
0.9634	High Similarity	NPC89052
0.9634	High Similarity	NPC173837
0.9634	High Similarity	NPC120952
0.9634	High Similarity	NPC251417
0.963	High Similarity	NPC471725
0.963	High Similarity	NPC134532
0.963	High Similarity	NPC155877
0.963	High Similarity	NPC203259
0.963	High Similarity	NPC471748
0.963	High Similarity	NPC176740
0.963	High Similarity	NPC256760
0.963	High Similarity	NPC33054
0.9627	High Similarity	NPC43587
0.9627	High Similarity	NPC227508
0.9627	High Similarity	NPC293629
0.9625	High Similarity	NPC5778
0.9625	High Similarity	NPC21100
0.9625	High Similarity	NPC197285
0.9625	High Similarity	NPC236934
0.9623	High Similarity	NPC284960
0.9623	High Similarity	NPC88023
0.9623	High Similarity	NPC29830
0.9623	High Similarity	NPC309025
0.9623	High Similarity	NPC19709
0.9623	High Similarity	NPC222936
0.9623	High Similarity	NPC168822
0.9623	High Similarity	NPC243930
0.9576	High Similarity	NPC126784
0.9576	High Similarity	NPC470444
0.9576	High Similarity	NPC473571
0.9576	High Similarity	NPC470443
0.9576	High Similarity	NPC241423
0.9576	High Similarity	NPC192539
0.9576	High Similarity	NPC110941
0.9576	High Similarity	NPC473682
0.9573	High Similarity	NPC169733
0.9573	High Similarity	NPC8573
0.9573	High Similarity	NPC202908
0.9573	High Similarity	NPC122467
0.9573	High Similarity	NPC292019
0.9573	High Similarity	NPC89127
0.9573	High Similarity	NPC255799
0.9573	High Similarity	NPC48984
0.9573	High Similarity	NPC471669
0.9573	High Similarity	NPC14187
0.9571	High Similarity	NPC25724
0.9568	High Similarity	NPC150767
0.9568	High Similarity	NPC78734
0.9568	High Similarity	NPC95866
0.9565	High Similarity	NPC146792
0.9565	High Similarity	NPC229729
0.9565	High Similarity	NPC58716
0.9565	High Similarity	NPC45400
0.9565	High Similarity	NPC45618
0.9563	High Similarity	NPC277205
0.956	High Similarity	NPC473043
0.9512	High Similarity	NPC253685
0.9512	High Similarity	NPC102028
0.9512	High Similarity	NPC142996
0.9509	High Similarity	NPC261254
0.9506	High Similarity	NPC45638
0.9506	High Similarity	NPC475942
0.9506	High Similarity	NPC201292
0.9506	High Similarity	NPC58053
0.9506	High Similarity	NPC170675
0.9506	High Similarity	NPC225434
0.9506	High Similarity	NPC105025
0.9506	High Similarity	NPC203050
0.9506	High Similarity	NPC223747
0.9506	High Similarity	NPC219904
0.9506	High Similarity	NPC229687
0.9506	High Similarity	NPC120099
0.9506	High Similarity	NPC186807
0.9506	High Similarity	NPC93337
0.9506	High Similarity	NPC471457
0.9506	High Similarity	NPC112755
0.9506	High Similarity	NPC226294
0.9506	High Similarity	NPC469931
0.9503	High Similarity	NPC179950
0.9503	High Similarity	NPC88789
0.9503	High Similarity	NPC56077
0.9503	High Similarity	NPC276222
0.9503	High Similarity	NPC253662
0.9503	High Similarity	NPC308404
0.9503	High Similarity	NPC118284
0.9503	High Similarity	NPC274618
0.9503	High Similarity	NPC145038
0.9503	High Similarity	NPC281131
0.95	High Similarity	NPC88043
0.9497	High Similarity	NPC182045
0.9461	High Similarity	NPC473072
0.9461	High Similarity	NPC470718
0.9461	High Similarity	NPC470449
0.9461	High Similarity	NPC470447
0.9461	High Similarity	NPC470445
0.9461	High Similarity	NPC470446
0.9455	High Similarity	NPC473862
0.9455	High Similarity	NPC65563
0.9455	High Similarity	NPC470949
0.9451	High Similarity	NPC472993
0.9451	High Similarity	NPC51774
0.9451	High Similarity	NPC239549
0.9451	High Similarity	NPC236191
0.9448	High Similarity	NPC206123
0.9448	High Similarity	NPC22195
0.9448	High Similarity	NPC282987
0.9448	High Similarity	NPC471416
0.9448	High Similarity	NPC84265
0.9448	High Similarity	NPC183357
0.9448	High Similarity	NPC21190
0.9448	High Similarity	NPC34287
0.9448	High Similarity	NPC245014
0.9444	High Similarity	NPC160156
0.9444	High Similarity	NPC84362
0.9444	High Similarity	NPC317489
0.9444	High Similarity	NPC173637
0.9444	High Similarity	NPC325555
0.9444	High Similarity	NPC52550
0.9444	High Similarity	NPC223424
0.9444	High Similarity	NPC265530
0.9444	High Similarity	NPC226304
0.9444	High Similarity	NPC477502
0.9444	High Similarity	NPC92565
0.9444	High Similarity	NPC127546
0.9441	High Similarity	NPC165720
0.9441	High Similarity	NPC19388
0.9441	High Similarity	NPC55786
0.9441	High Similarity	NPC240431
0.9437	High Similarity	NPC127782
0.9437	High Similarity	NPC300537
0.9434	High Similarity	NPC110349
0.9405	High Similarity	NPC25946
0.9405	High Similarity	NPC460984
0.9405	High Similarity	NPC470720
0.9405	High Similarity	NPC148710
0.9405	High Similarity	NPC470713
0.9405	High Similarity	NPC470717
0.9405	High Similarity	NPC470451
0.9405	High Similarity	NPC21359
0.9405	High Similarity	NPC470455
0.9401	High Similarity	NPC473071
0.9401	High Similarity	NPC473073
0.9398	High Similarity	NPC241196
0.9394	High Similarity	NPC294629
0.939	High Similarity	NPC48773
0.939	High Similarity	NPC211594
0.939	High Similarity	NPC67134
0.939	High Similarity	NPC267254
0.939	High Similarity	NPC156977
0.939	High Similarity	NPC47140
0.939	High Similarity	NPC172807
0.939	High Similarity	NPC153755

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 NPC86008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	958
0.2-0.3	2008
0.3-0.4	2763
0.4-0.5	1750
0.5-0.6	849
0.6-0.7	270
0.7-0.8	100
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9937	High Similarity	NPD7472	Approved
0.9874	High Similarity	NPD7054	Approved
0.9691	High Similarity	NPD7251	Discontinued
0.9689	High Similarity	NPD7074	Phase 3
0.9632	High Similarity	NPD7808	Phase 3
0.963	High Similarity	NPD6797	Phase 2
0.9325	High Similarity	NPD3818	Discontinued
0.9277	High Similarity	NPD4338	Clinical (unspecified phase)
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9085	High Similarity	NPD6167	Clinical (unspecified phase)
0.9085	High Similarity	NPD6168	Clinical (unspecified phase)
0.9085	High Similarity	NPD6166	Phase 2
0.9036	High Similarity	NPD7804	Clinical (unspecified phase)
0.8938	High Similarity	NPD1934	Approved
0.8765	High Similarity	NPD2801	Approved
0.8765	High Similarity	NPD2393	Clinical (unspecified phase)
0.8671	High Similarity	NPD1511	Approved
0.8598	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1512	Approved
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5494	Approved
0.8155	Intermediate Similarity	NPD5402	Approved
0.8136	Intermediate Similarity	NPD8313	Approved
0.8136	Intermediate Similarity	NPD8312	Approved
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8103	Intermediate Similarity	NPD7228	Approved
0.8095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8061	Intermediate Similarity	NPD5403	Approved
0.8049	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6801	Discontinued
0.8023	Intermediate Similarity	NPD6959	Discontinued
0.8023	Intermediate Similarity	NPD7685	Pre-registration
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7955	Intermediate Similarity	NPD5844	Phase 1
0.7943	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD5401	Approved
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7923	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3751	Discontinued
0.7888	Intermediate Similarity	NPD2796	Approved
0.7882	Intermediate Similarity	NPD8455	Phase 2
0.7879	Intermediate Similarity	NPD6799	Approved
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7874	Intermediate Similarity	NPD6232	Discontinued
0.787	Intermediate Similarity	NPD7411	Suspended
0.7844	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7266	Discontinued
0.7831	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7199	Phase 2
0.7814	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1613	Approved
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7722	Intermediate Similarity	NPD7240	Approved
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7584	Approved
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD37	Approved
0.7602	Intermediate Similarity	NPD6599	Discontinued
0.759	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD4967	Phase 2
0.7586	Intermediate Similarity	NPD4966	Approved
0.7578	Intermediate Similarity	NPD943	Approved
0.7578	Intermediate Similarity	NPD1240	Approved
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD6777	Approved
0.7539	Intermediate Similarity	NPD6776	Approved
0.7539	Intermediate Similarity	NPD6780	Approved
0.7539	Intermediate Similarity	NPD6781	Approved
0.7539	Intermediate Similarity	NPD6782	Approved
0.7539	Intermediate Similarity	NPD6779	Approved
0.7539	Intermediate Similarity	NPD6778	Approved
0.7531	Intermediate Similarity	NPD1933	Approved
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD919	Approved
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD1607	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7701	Phase 2
0.7443	Intermediate Similarity	NPD3749	Approved
0.744	Intermediate Similarity	NPD6190	Approved
0.743	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7416	Intermediate Similarity	NPD1247	Approved
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7371	Intermediate Similarity	NPD6823	Phase 2
0.7344	Intermediate Similarity	NPD7700	Phase 2
0.7344	Intermediate Similarity	NPD7699	Phase 2
0.7317	Intermediate Similarity	NPD447	Suspended
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3748	Approved
0.7286	Intermediate Similarity	NPD7874	Approved
0.7286	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6535	Approved
0.7277	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7585	Approved
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7245	Intermediate Similarity	NPD7680	Approved
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD7583	Approved
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2532	Approved
0.7209	Intermediate Similarity	NPD2533	Approved
0.7209	Intermediate Similarity	NPD2534	Approved
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7186	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD920	Approved
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD2800	Approved
0.7117	Intermediate Similarity	NPD6832	Phase 2
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4360	Phase 2
0.7098	Intermediate Similarity	NPD4363	Phase 3
0.7097	Intermediate Similarity	NPD5953	Discontinued
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7066	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.7052	Intermediate Similarity	NPD7390	Discontinued
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7045	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1243	Approved
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7012	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2798	Approved
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1548	Phase 1
0.6952	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8127	Discontinued
0.6938	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3
0.6927	Remote Similarity	NPD6842	Approved
0.6905	Remote Similarity	NPD5124	Phase 1
0.6905	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2344	Approved
0.6901	Remote Similarity	NPD2346	Discontinued
0.6894	Remote Similarity	NPD1610	Phase 2
0.6893	Remote Similarity	NPD7930	Approved
0.6882	Remote Similarity	NPD2799	Discontinued
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6385	Approved
0.6872	Remote Similarity	NPD6386	Approved
0.6871	Remote Similarity	NPD3225	Approved
0.6865	Remote Similarity	NPD5242	Approved
0.6859	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9269	Phase 2
0.685	Remote Similarity	NPD5005	Approved
0.685	Remote Similarity	NPD5006	Approved
0.6842	Remote Similarity	NPD7549	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