NPASS Compound

Structure

NPC256760 OpenBabel07101718232D 41 45 0 0 1 0 0 0 0 0999 V2000 9.5263 -4.5000 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 1.7321 -0.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 C 0 0 1 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -1.7321 -2.0000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -3.5000 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 6.9282 -3.0000 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 -0.8660 2.5000 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 5.1962 -0.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 15 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 5 16 2 0 0 0 0 6 13 2 0 0 0 0 6 18 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 28 1 0 0 0 0 9 1 1 1 0 0 0 9 22 1 0 0 0 0 9 38 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 29 1 0 0 0 0 12 21 1 0 0 0 0 12 30 2 0 0 0 0 13 20 1 0 0 0 0 13 31 1 0 0 0 0 14 22 1 0 0 0 0 14 32 1 6 0 0 0 15 40 1 0 0 0 0 16 39 1 0 0 0 0 17 20 1 1 0 0 0 17 38 1 0 0 0 0 18 21 2 0 0 0 0 18 39 1 0 0 0 0 19 8 1 6 0 0 0 19 23 1 0 0 0 0 19 41 1 0 0 0 0 20 24 2 0 0 0 0 21 24 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 0 0 0 0 23 34 1 1 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 40 1 6 0 0 0 27 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	0.557
LogD:	-0.127
LogS:	-3.536
# Rotatable Bonds:	5
TPSA:	239.97
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.182
Synthetic Accessibility Score:	4.821
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.395
MDCK Permeability:	1.730748772388324e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	88.03534698486328%
Volume Distribution (VD):	0.659
Pgp-substrate:	12.669974327087402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	1.564
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.502
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.78
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.828
Skin Sensitization:	0.798
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC256760

Natural Product ID:	NPC256760
*Common Name:**	Farobin B
IUPAC Name:	6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:	farobin B
Standard InCHIKey:	NJNUVWMGNSDFQJ-GIZWKEFHSA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-9-22(33)14(32)7-17(38-9)20-13(31)6-18-21(24(20)35)12(30)5-16(39-18)10-2-3-15(11(29)4-10)40-27-26(37)25(36)23(34)19(8-28)41-27/h2-6,9,14,17,19,22-23,25-29,31-37H,7-8H2,1H3/t9-,14+,17-,19-,22+,23-,25+,26-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2O)c2cc(=O)c3c(o2)cc(c(c3O)[C@H]2C[C@H](O)[C@H]([C@H](O2)C)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224896
PubChem CID:	46938450
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
NPO33290	fargesia robusta	Species	Poaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20863141]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Activity	=	8.3	n.a.	PMID[458470]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.075	n.a.	PMID[458470]

☑ 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 NPC256760 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	450
0.1-0.2	1849
0.2-0.3	4084
0.3-0.4	9660
0.4-0.5	8560
0.5-0.6	4449
0.6-0.7	5342
0.7-0.8	5345
0.8-0.85	1769
0.85-0.9	698
0.9-0.95	405
0.95-1	86

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC150767
0.9938	High Similarity	NPC208668
0.9938	High Similarity	NPC78734
0.9814	High Similarity	NPC218488
0.9814	High Similarity	NPC231194
0.9814	High Similarity	NPC51326
0.9812	High Similarity	NPC477502
0.9755	High Similarity	NPC294629
0.9752	High Similarity	NPC209296
0.9752	High Similarity	NPC195257
0.975	High Similarity	NPC5778
0.975	High Similarity	NPC115674
0.975	High Similarity	NPC236934
0.975	High Similarity	NPC210073
0.9695	High Similarity	NPC255799
0.9693	High Similarity	NPC25724
0.9691	High Similarity	NPC79056
0.9691	High Similarity	NPC105095
0.9691	High Similarity	NPC44328
0.9691	High Similarity	NPC177731
0.9689	High Similarity	NPC229729
0.9688	High Similarity	NPC311830
0.9688	High Similarity	NPC22832
0.963	High Similarity	NPC229687
0.963	High Similarity	NPC43587
0.963	High Similarity	NPC293629
0.963	High Similarity	NPC86008
0.9627	High Similarity	NPC8856
0.9625	High Similarity	NPC284960
0.9625	High Similarity	NPC88023
0.9625	High Similarity	NPC191306
0.9625	High Similarity	NPC29830
0.9625	High Similarity	NPC309025
0.9625	High Similarity	NPC19709
0.9625	High Similarity	NPC270335
0.9625	High Similarity	NPC222936
0.9625	High Similarity	NPC243930
0.9573	High Similarity	NPC204693
0.9573	High Similarity	NPC236191
0.9573	High Similarity	NPC51774
0.9573	High Similarity	NPC239549
0.9571	High Similarity	NPC183357
0.9571	High Similarity	NPC22195
0.9571	High Similarity	NPC95866
0.9571	High Similarity	NPC67105
0.9571	High Similarity	NPC285197
0.9571	High Similarity	NPC21190
0.9568	High Similarity	NPC45400
0.9565	High Similarity	NPC475497
0.9565	High Similarity	NPC284277
0.9565	High Similarity	NPC475366
0.9563	High Similarity	NPC189142
0.9563	High Similarity	NPC127782
0.9563	High Similarity	NPC44947
0.9563	High Similarity	NPC300537
0.9563	High Similarity	NPC473043
0.9563	High Similarity	NPC77660
0.9524	High Similarity	NPC148710
0.9518	High Similarity	NPC168584
0.9515	High Similarity	NPC19108
0.9515	High Similarity	NPC472607
0.9515	High Similarity	NPC220173
0.9515	High Similarity	NPC473327
0.9515	High Similarity	NPC16194
0.9515	High Similarity	NPC198199
0.9515	High Similarity	NPC108202
0.9515	High Similarity	NPC476472
0.9515	High Similarity	NPC294815
0.9512	High Similarity	NPC235575
0.9512	High Similarity	NPC205076
0.9512	High Similarity	NPC180918
0.9512	High Similarity	NPC155877
0.9512	High Similarity	NPC471725
0.9512	High Similarity	NPC301683
0.9512	High Similarity	NPC267254
0.9512	High Similarity	NPC60735
0.9512	High Similarity	NPC48773
0.9512	High Similarity	NPC3583
0.9512	High Similarity	NPC261254
0.9512	High Similarity	NPC134532
0.9512	High Similarity	NPC307518
0.9512	High Similarity	NPC259152
0.9512	High Similarity	NPC33054
0.9512	High Similarity	NPC203259
0.9512	High Similarity	NPC471748
0.9512	High Similarity	NPC176740
0.9512	High Similarity	NPC26230
0.9509	High Similarity	NPC45638
0.9509	High Similarity	NPC95855
0.9509	High Similarity	NPC201292
0.9509	High Similarity	NPC226294
0.9509	High Similarity	NPC58053
0.9509	High Similarity	NPC170675
0.9509	High Similarity	NPC225434
0.9509	High Similarity	NPC105025
0.9509	High Similarity	NPC203050
0.9509	High Similarity	NPC475942
0.9509	High Similarity	NPC223747
0.9509	High Similarity	NPC52382
0.9509	High Similarity	NPC210042
0.9509	High Similarity	NPC472381
0.9509	High Similarity	NPC105283
0.9509	High Similarity	NPC186807
0.9509	High Similarity	NPC270578
0.9509	High Similarity	NPC93337
0.9509	High Similarity	NPC471457
0.9509	High Similarity	NPC472383
0.9509	High Similarity	NPC112755
0.9509	High Similarity	NPC120099
0.9509	High Similarity	NPC219904
0.9509	High Similarity	NPC227508
0.9509	High Similarity	NPC469931
0.9506	High Similarity	NPC21100
0.9506	High Similarity	NPC197285
0.9503	High Similarity	NPC124155
0.9503	High Similarity	NPC257566
0.9503	High Similarity	NPC168822
0.95	High Similarity	NPC182045
0.95	High Similarity	NPC26326
0.95	High Similarity	NPC47923
0.9458	High Similarity	NPC169733
0.9455	High Similarity	NPC472993
0.9451	High Similarity	NPC254855
0.9451	High Similarity	NPC224462
0.9451	High Similarity	NPC29958
0.9451	High Similarity	NPC474434
0.9451	High Similarity	NPC156869
0.9451	High Similarity	NPC259896
0.9451	High Similarity	NPC136042
0.9451	High Similarity	NPC44558
0.9451	High Similarity	NPC34287
0.9451	High Similarity	NPC206123
0.9451	High Similarity	NPC67326
0.9451	High Similarity	NPC255157
0.9451	High Similarity	NPC105511
0.9451	High Similarity	NPC471416
0.9448	High Similarity	NPC93099
0.9448	High Similarity	NPC84362
0.9448	High Similarity	NPC317489
0.9448	High Similarity	NPC325555
0.9448	High Similarity	NPC52550
0.9448	High Similarity	NPC223424
0.9448	High Similarity	NPC160156
0.9448	High Similarity	NPC265530
0.9448	High Similarity	NPC226304
0.9448	High Similarity	NPC58716
0.9448	High Similarity	NPC92565
0.9448	High Similarity	NPC45618
0.9448	High Similarity	NPC127546
0.9448	High Similarity	NPC275454
0.9448	High Similarity	NPC146792
0.9448	High Similarity	NPC173637
0.9444	High Similarity	NPC165720
0.9444	High Similarity	NPC15358
0.9444	High Similarity	NPC277205
0.9444	High Similarity	NPC470773
0.9437	High Similarity	NPC110349
0.9401	High Similarity	NPC469600
0.9401	High Similarity	NPC89052
0.9401	High Similarity	NPC120952
0.9401	High Similarity	NPC173837
0.9401	High Similarity	NPC251417
0.9398	High Similarity	NPC102028
0.9398	High Similarity	NPC142996
0.9394	High Similarity	NPC47140
0.9394	High Similarity	NPC472386
0.9394	High Similarity	NPC67134
0.9394	High Similarity	NPC153755
0.9394	High Similarity	NPC254540
0.9394	High Similarity	NPC172807
0.9394	High Similarity	NPC156977
0.9394	High Similarity	NPC476405
0.9394	High Similarity	NPC211594
0.9394	High Similarity	NPC475155
0.9394	High Similarity	NPC117260
0.939	High Similarity	NPC183036
0.939	High Similarity	NPC61791
0.939	High Similarity	NPC471287
0.9387	High Similarity	NPC274618
0.9387	High Similarity	NPC56077
0.9387	High Similarity	NPC118284
0.9387	High Similarity	NPC99957
0.9387	High Similarity	NPC181616
0.9387	High Similarity	NPC113968
0.9387	High Similarity	NPC145038
0.9387	High Similarity	NPC73855
0.9387	High Similarity	NPC281131
0.9387	High Similarity	NPC308404
0.9387	High Similarity	NPC88789
0.9387	High Similarity	NPC328940
0.9387	High Similarity	NPC135599
0.9387	High Similarity	NPC179950
0.9387	High Similarity	NPC253662
0.9387	High Similarity	NPC276222
0.9387	High Similarity	NPC277174
0.9383	High Similarity	NPC88043
0.9383	High Similarity	NPC470772
0.9379	High Similarity	NPC303913
0.9379	High Similarity	NPC472632
0.9379	High Similarity	NPC474038

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 NPC256760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	945
0.2-0.3	1941
0.3-0.4	2745
0.4-0.5	1818
0.5-0.6	863
0.6-0.7	279
0.7-0.8	119
0.8-0.85	19
0.85-0.9	9
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9752	High Similarity	NPD7054	Approved
0.9691	High Similarity	NPD7074	Phase 3
0.9691	High Similarity	NPD7472	Approved
0.9512	High Similarity	NPD6797	Phase 2
0.9455	High Similarity	NPD7251	Discontinued
0.9398	High Similarity	NPD7808	Phase 3
0.9329	High Similarity	NPD3818	Discontinued
0.9273	High Similarity	NPD7804	Clinical (unspecified phase)
0.9207	High Similarity	NPD6166	Phase 2
0.9207	High Similarity	NPD6168	Clinical (unspecified phase)
0.9207	High Similarity	NPD6167	Clinical (unspecified phase)
0.9193	High Similarity	NPD4381	Clinical (unspecified phase)
0.9167	High Similarity	NPD4338	Clinical (unspecified phase)
0.9125	High Similarity	NPD2393	Clinical (unspecified phase)
0.9062	High Similarity	NPD1934	Approved
0.882	High Similarity	NPD4380	Phase 2
0.8773	High Similarity	NPD2801	Approved
0.8663	High Similarity	NPD6559	Discontinued
0.8606	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1511	Approved
0.8554	High Similarity	NPD4868	Clinical (unspecified phase)
0.8512	High Similarity	NPD5494	Approved
0.8503	High Similarity	NPD7075	Discontinued
0.8457	Intermediate Similarity	NPD1512	Approved
0.8443	Intermediate Similarity	NPD3882	Suspended
0.8395	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6801	Discontinued
0.8353	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8274	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7228	Approved
0.8214	Intermediate Similarity	NPD7819	Suspended
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8198	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD8312	Approved
0.8146	Intermediate Similarity	NPD8313	Approved
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8133	Intermediate Similarity	NPD1653	Approved
0.8132	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8059	Intermediate Similarity	NPD5402	Approved
0.8022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5403	Approved
0.7964	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7933	Intermediate Similarity	NPD7685	Pre-registration
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7895	Intermediate Similarity	NPD8455	Phase 2
0.7892	Intermediate Similarity	NPD6799	Approved
0.7876	Intermediate Similarity	NPD8151	Discontinued
0.7865	Intermediate Similarity	NPD7584	Approved
0.7844	Intermediate Similarity	NPD5401	Approved
0.7836	Intermediate Similarity	NPD37	Approved
0.7831	Intermediate Similarity	NPD6781	Approved
0.7831	Intermediate Similarity	NPD6782	Approved
0.7831	Intermediate Similarity	NPD6778	Approved
0.7831	Intermediate Similarity	NPD6776	Approved
0.7831	Intermediate Similarity	NPD6777	Approved
0.7831	Intermediate Similarity	NPD6780	Approved
0.7831	Intermediate Similarity	NPD6779	Approved
0.7816	Intermediate Similarity	NPD919	Approved
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD3751	Discontinued
0.7803	Intermediate Similarity	NPD4966	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7803	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7240	Approved
0.7727	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD6599	Discontinued
0.7708	Intermediate Similarity	NPD7435	Discontinued
0.7708	Intermediate Similarity	NPD7696	Phase 3
0.7708	Intermediate Similarity	NPD7697	Approved
0.7708	Intermediate Similarity	NPD7698	Approved
0.7704	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD7783	Phase 2
0.7702	Intermediate Similarity	NPD1240	Approved
0.7701	Intermediate Similarity	NPD7768	Phase 2
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7701	Phase 2
0.7625	Intermediate Similarity	NPD3027	Phase 3
0.7607	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7566	Intermediate Similarity	NPD6535	Approved
0.7566	Intermediate Similarity	NPD6534	Approved
0.7565	Intermediate Similarity	NPD6823	Phase 2
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1933	Approved
0.7545	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3926	Phase 2
0.7539	Intermediate Similarity	NPD7699	Phase 2
0.7539	Intermediate Similarity	NPD7700	Phase 2
0.7529	Intermediate Similarity	NPD2533	Approved
0.7529	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7585	Approved
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3749	Approved
0.7457	Intermediate Similarity	NPD7458	Discontinued
0.7442	Intermediate Similarity	NPD920	Approved
0.744	Intermediate Similarity	NPD2800	Approved
0.744	Intermediate Similarity	NPD6674	Discontinued
0.7439	Intermediate Similarity	NPD230	Phase 1
0.7437	Intermediate Similarity	NPD7801	Approved
0.7411	Intermediate Similarity	NPD7583	Approved
0.7409	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD8319	Approved
0.7398	Intermediate Similarity	NPD8320	Phase 1
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7382	Intermediate Similarity	NPD4360	Phase 2
0.7382	Intermediate Similarity	NPD4363	Phase 3
0.7368	Intermediate Similarity	NPD7390	Discontinued
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD6190	Approved
0.7347	Intermediate Similarity	NPD7680	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD1243	Approved
0.7333	Intermediate Similarity	NPD447	Suspended
0.733	Intermediate Similarity	NPD6212	Phase 3
0.733	Intermediate Similarity	NPD6213	Phase 3
0.733	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3748	Approved
0.7289	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7256	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5124	Phase 1
0.7229	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7202	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.7159	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1091	Approved
0.7117	Intermediate Similarity	NPD2798	Approved
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5710	Approved
0.7104	Intermediate Similarity	NPD5711	Approved
0.7101	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7930	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD6832	Phase 2
0.7019	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2344	Approved
0.7015	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4361	Phase 2
0.699	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2424	Discontinued
0.6973	Remote Similarity	NPD5242	Approved
0.6963	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD1203	Approved
0.695	Remote Similarity	NPD5005	Approved
0.695	Remote Similarity	NPD5006	Approved
0.6948	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8059	Phase 3
0.6947	Remote Similarity	NPD7549	Discontinued
0.6946	Remote Similarity	NPD3268	Approved

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