NPASS Compound

Structure

NPC294629 OpenBabel07101718182D 41 45 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 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 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 1 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 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 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 4.3301 -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 5.1962 -0.0000 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 3.4641 -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 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 2.5981 0.5000 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 -0.0000 -1.0000 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 -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 6.0622 0.5000 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 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 6 15 2 0 0 0 0 7 14 2 0 0 0 0 7 16 1 0 0 0 0 8 1 1 6 0 0 0 8 20 1 0 0 0 0 8 38 1 0 0 0 0 9 2 1 1 0 0 0 9 19 1 0 0 0 0 9 39 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 17 1 0 0 0 0 13 30 2 0 0 0 0 14 18 1 0 0 0 0 14 31 1 0 0 0 0 15 40 1 0 0 0 0 16 17 2 0 0 0 0 16 40 1 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 19 32 1 6 0 0 0 20 23 1 0 0 0 0 20 33 1 1 0 0 0 21 34 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 26 1 0 0 0 0 23 36 2 0 0 0 0 24 27 1 0 0 0 0 24 37 1 1 0 0 0 25 18 1 6 0 0 0 25 26 1 0 0 0 0 25 38 1 0 0 0 0 26 41 1 1 0 0 0 27 39 1 0 0 0 0 27 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.15
Volume:	532.101
LogP:	1.365
LogD:	-0.092
LogS:	-2.738
# Rotatable Bonds:	4
TPSA:	236.81
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	4.919
Fsp3:	0.407
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.32
MDCK Permeability:	1.2695285477093421e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.846
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	91.9129409790039%
Volume Distribution (VD):	0.595
Pgp-substrate:	11.85041332244873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.381
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	1.679
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.892
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.616
Respiratory Toxicity:	0.341

Download Data

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

Natural Product: NPC294629

Natural Product ID:	NPC294629
*Common Name:**	2''-O-Alpha-Rhamnosyl-6-C-(6-Deoxy-Ribo-Hexos-3-Ulosyl)Luteolin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3S,5R,6R)-5-hydroxy-6-methyl-4-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]chromen-4-one
Synonyms:
Standard InCHIKey:	WGIMZJFXUGTVFX-FLCGOUAWSA-N
Standard InCHI:	InChI=1S/C27H28O14/c1-8-20(33)23(36)26(41-27-24(37)22(35)19(32)9(2)39-27)25(38-8)18-14(31)7-16-17(21(18)34)13(30)6-15(40-16)10-3-4-11(28)12(29)5-10/h3-9,19-20,22,24-29,31-35,37H,1-2H3/t8-,9+,19+,20-,22-,24-,25+,26-,27+/m1/s1
SMILES:	C[C@@H]1[C@H](C(=O)[C@H]([C@H](c2c(cc3c(c(=O)cc(c4ccc(c(c4)O)O)o3)c2O)O)O1)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224898
PubChem CID:	49800177
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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	=	5.7	n.a.	PMID[476687]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.646	n.a.	PMID[476687]

☑ 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 NPC294629 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	463
0.1-0.2	1852
0.2-0.3	4177
0.3-0.4	9640
0.4-0.5	8467
0.5-0.6	4674
0.6-0.7	5502
0.7-0.8	5154
0.8-0.85	1696
0.85-0.9	584
0.9-0.95	398
0.95-1	90

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC150767
0.9815	High Similarity	NPC95866
0.9815	High Similarity	NPC78734
0.9755	High Similarity	NPC134532
0.9755	High Similarity	NPC203259
0.9755	High Similarity	NPC471748
0.9755	High Similarity	NPC176740
0.9755	High Similarity	NPC256760
0.9755	High Similarity	NPC155877
0.9755	High Similarity	NPC33054
0.9755	High Similarity	NPC471725
0.9753	High Similarity	NPC270578
0.9753	High Similarity	NPC52382
0.9695	High Similarity	NPC208668
0.9693	High Similarity	NPC255157
0.9693	High Similarity	NPC218488
0.9693	High Similarity	NPC254855
0.9693	High Similarity	NPC29958
0.9693	High Similarity	NPC136042
0.9693	High Similarity	NPC67326
0.9693	High Similarity	NPC67105
0.9693	High Similarity	NPC259896
0.9693	High Similarity	NPC156869
0.9691	High Similarity	NPC52550
0.9691	High Similarity	NPC160156
0.9691	High Similarity	NPC84362
0.9691	High Similarity	NPC223424
0.9691	High Similarity	NPC317489
0.9691	High Similarity	NPC173637
0.9691	High Similarity	NPC127546
0.9691	High Similarity	NPC92565
0.9643	High Similarity	NPC148710
0.9639	High Similarity	NPC168584
0.9636	High Similarity	NPC294815
0.9636	High Similarity	NPC473327
0.9636	High Similarity	NPC16194
0.9636	High Similarity	NPC476472
0.9636	High Similarity	NPC19108
0.9636	High Similarity	NPC220173
0.9634	High Similarity	NPC60735
0.9634	High Similarity	NPC26230
0.9632	High Similarity	NPC219904
0.9632	High Similarity	NPC225434
0.9632	High Similarity	NPC223747
0.9632	High Similarity	NPC203050
0.9632	High Similarity	NPC227508
0.9632	High Similarity	NPC120099
0.963	High Similarity	NPC210073
0.963	High Similarity	NPC179950
0.963	High Similarity	NPC73855
0.963	High Similarity	NPC281131
0.963	High Similarity	NPC277174
0.963	High Similarity	NPC253662
0.963	High Similarity	NPC88789
0.963	High Similarity	NPC308404
0.963	High Similarity	NPC135599
0.963	High Similarity	NPC113968
0.963	High Similarity	NPC118284
0.963	High Similarity	NPC274618
0.963	High Similarity	NPC115674
0.963	High Similarity	NPC145038
0.963	High Similarity	NPC328940
0.963	High Similarity	NPC276222
0.963	High Similarity	NPC56077
0.9578	High Similarity	NPC292019
0.9578	High Similarity	NPC202908
0.9578	High Similarity	NPC122467
0.9578	High Similarity	NPC89127
0.9578	High Similarity	NPC65563
0.9578	High Similarity	NPC470949
0.9578	High Similarity	NPC14187
0.9578	High Similarity	NPC471669
0.9576	High Similarity	NPC25724
0.9573	High Similarity	NPC244776
0.9573	High Similarity	NPC51326
0.9573	High Similarity	NPC116864
0.9573	High Similarity	NPC206123
0.9573	High Similarity	NPC285197
0.9573	High Similarity	NPC231194
0.9571	High Similarity	NPC275454
0.9571	High Similarity	NPC325555
0.9571	High Similarity	NPC265530
0.9571	High Similarity	NPC226304
0.9571	High Similarity	NPC477502
0.9568	High Similarity	NPC240431
0.9568	High Similarity	NPC55786
0.9568	High Similarity	NPC19388
0.9568	High Similarity	NPC277205
0.9529	High Similarity	NPC64755
0.9521	High Similarity	NPC89052
0.9521	High Similarity	NPC173837
0.9521	High Similarity	NPC251417
0.9518	High Similarity	NPC253685
0.9518	High Similarity	NPC108202
0.9515	High Similarity	NPC153755
0.9515	High Similarity	NPC190003
0.9515	High Similarity	NPC175107
0.9515	High Similarity	NPC245452
0.9512	High Similarity	NPC195257
0.9512	High Similarity	NPC5319
0.9512	High Similarity	NPC209296
0.9512	High Similarity	NPC43587
0.9509	High Similarity	NPC21100
0.9509	High Similarity	NPC236934
0.9509	High Similarity	NPC5778
0.9509	High Similarity	NPC197285
0.9509	High Similarity	NPC8856
0.9506	High Similarity	NPC179198
0.9506	High Similarity	NPC66087
0.9506	High Similarity	NPC29830
0.9506	High Similarity	NPC19709
0.9506	High Similarity	NPC278419
0.9464	High Similarity	NPC192539
0.9464	High Similarity	NPC473682
0.9464	High Similarity	NPC126784
0.9464	High Similarity	NPC470443
0.9464	High Similarity	NPC470444
0.9464	High Similarity	NPC110941
0.9464	High Similarity	NPC473571
0.9464	High Similarity	NPC241423
0.9461	High Similarity	NPC255799
0.9461	High Similarity	NPC48984
0.9461	High Similarity	NPC8573
0.9461	High Similarity	NPC219043
0.9461	High Similarity	NPC169733
0.9461	High Similarity	NPC473862
0.9458	High Similarity	NPC101026
0.9458	High Similarity	NPC42773
0.9458	High Similarity	NPC4390
0.9458	High Similarity	NPC45522
0.9458	High Similarity	NPC21666
0.9458	High Similarity	NPC24043
0.9458	High Similarity	NPC169977
0.9455	High Similarity	NPC79056
0.9455	High Similarity	NPC105095
0.9455	High Similarity	NPC235260
0.9455	High Similarity	NPC20505
0.9455	High Similarity	NPC44328
0.9455	High Similarity	NPC177731
0.9455	High Similarity	NPC155763
0.9451	High Similarity	NPC229729
0.9448	High Similarity	NPC311830
0.9448	High Similarity	NPC22832
0.9444	High Similarity	NPC44947
0.9444	High Similarity	NPC127782
0.9444	High Similarity	NPC259834
0.9444	High Similarity	NPC300537
0.9444	High Similarity	NPC473043
0.9444	High Similarity	NPC77660
0.9444	High Similarity	NPC189142
0.9444	High Similarity	NPC131745
0.9408	High Similarity	NPC473071
0.9408	High Similarity	NPC473073
0.9405	High Similarity	NPC139571
0.9405	High Similarity	NPC217520
0.9405	High Similarity	NPC35167
0.9401	High Similarity	NPC214621
0.9401	High Similarity	NPC223426
0.9401	High Similarity	NPC81042
0.9401	High Similarity	NPC34267
0.9398	High Similarity	NPC301683
0.9398	High Similarity	NPC476405
0.9398	High Similarity	NPC117260
0.9394	High Similarity	NPC86008
0.9394	High Similarity	NPC138927
0.9394	High Similarity	NPC229687
0.9394	High Similarity	NPC293629
0.9394	High Similarity	NPC105283
0.939	High Similarity	NPC67037
0.939	High Similarity	NPC255615
0.9387	High Similarity	NPC88023
0.9387	High Similarity	NPC270335
0.9387	High Similarity	NPC183672
0.9387	High Similarity	NPC284960
0.9387	High Similarity	NPC168822
0.9387	High Similarity	NPC191306
0.9387	High Similarity	NPC309025
0.9387	High Similarity	NPC257566
0.9387	High Similarity	NPC222936
0.9387	High Similarity	NPC124155
0.9387	High Similarity	NPC243930
0.9383	High Similarity	NPC289771
0.9383	High Similarity	NPC276377
0.9383	High Similarity	NPC173582
0.9383	High Similarity	NPC116458
0.9383	High Similarity	NPC215710
0.9383	High Similarity	NPC47923
0.9383	High Similarity	NPC181465
0.9383	High Similarity	NPC249281
0.9383	High Similarity	NPC246943
0.9383	High Similarity	NPC139320
0.9383	High Similarity	NPC265885
0.9383	High Similarity	NPC253788
0.9383	High Similarity	NPC476215
0.9383	High Similarity	NPC473438
0.9383	High Similarity	NPC163242
0.9353	High Similarity	NPC156785
0.9353	High Similarity	NPC470447
0.9353	High Similarity	NPC470445
0.9353	High Similarity	NPC162394

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 NPC294629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	960
0.2-0.3	1974
0.3-0.4	2733
0.4-0.5	1818
0.5-0.6	856
0.6-0.7	256
0.7-0.8	108
0.8-0.85	23
0.85-0.9	6
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9755	High Similarity	NPD6797	Phase 2
0.9695	High Similarity	NPD7251	Discontinued
0.9518	High Similarity	NPD7808	Phase 3
0.9512	High Similarity	NPD7054	Approved
0.9512	High Similarity	NPD7804	Clinical (unspecified phase)
0.9455	High Similarity	NPD7472	Approved
0.9455	High Similarity	NPD7074	Phase 3
0.9286	High Similarity	NPD4338	Clinical (unspecified phase)
0.9212	High Similarity	NPD6167	Clinical (unspecified phase)
0.9212	High Similarity	NPD6168	Clinical (unspecified phase)
0.9212	High Similarity	NPD6166	Phase 2
0.9102	High Similarity	NPD3818	Discontinued
0.908	High Similarity	NPD4381	Clinical (unspecified phase)
0.9012	High Similarity	NPD2393	Clinical (unspecified phase)
0.8834	High Similarity	NPD1934	Approved
0.8735	High Similarity	NPD7075	Discontinued
0.8727	High Similarity	NPD3817	Phase 2
0.8712	High Similarity	NPD4380	Phase 2
0.8606	High Similarity	NPD6801	Discontinued
0.858	High Similarity	NPD1512	Approved
0.8563	High Similarity	NPD6559	Discontinued
0.8563	High Similarity	NPD3882	Suspended
0.8554	High Similarity	NPD7096	Clinical (unspecified phase)
0.8554	High Similarity	NPD2801	Approved
0.8519	High Similarity	NPD4378	Clinical (unspecified phase)
0.8506	High Similarity	NPD7993	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5494	Approved
0.8284	Intermediate Similarity	NPD5402	Approved
0.8256	Intermediate Similarity	NPD6959	Discontinued
0.8193	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6799	Approved
0.8118	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD7411	Suspended
0.8086	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5844	Phase 1
0.8072	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5401	Approved
0.8056	Intermediate Similarity	NPD8313	Approved
0.8056	Intermediate Similarity	NPD8312	Approved
0.8037	Intermediate Similarity	NPD1549	Phase 2
0.8023	Intermediate Similarity	NPD7228	Approved
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD3787	Discontinued
0.7966	Intermediate Similarity	NPD7473	Discontinued
0.7941	Intermediate Similarity	NPD6599	Discontinued
0.7937	Intermediate Similarity	NPD6781	Approved
0.7937	Intermediate Similarity	NPD6776	Approved
0.7937	Intermediate Similarity	NPD6778	Approved
0.7937	Intermediate Similarity	NPD6782	Approved
0.7937	Intermediate Similarity	NPD6777	Approved
0.7937	Intermediate Similarity	NPD6780	Approved
0.7937	Intermediate Similarity	NPD6779	Approved
0.7931	Intermediate Similarity	NPD919	Approved
0.7929	Intermediate Similarity	NPD1653	Approved
0.7914	Intermediate Similarity	NPD2796	Approved
0.791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1465	Phase 2
0.7906	Intermediate Similarity	NPD7435	Discontinued
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1510	Phase 2
0.7841	Intermediate Similarity	NPD1247	Approved
0.7838	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7698	Approved
0.7812	Intermediate Similarity	NPD7696	Phase 3
0.7812	Intermediate Similarity	NPD7697	Approved
0.7803	Intermediate Similarity	NPD8455	Phase 2
0.7795	Intermediate Similarity	NPD8151	Discontinued
0.7784	Intermediate Similarity	NPD7584	Approved
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7685	Pre-registration
0.7744	Intermediate Similarity	NPD7701	Phase 2
0.774	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7716	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1613	Approved
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7870	Phase 2
0.768	Intermediate Similarity	NPD7871	Phase 2
0.7672	Intermediate Similarity	NPD6534	Approved
0.7672	Intermediate Similarity	NPD6535	Approved
0.7665	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7874	Approved
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.7644	Intermediate Similarity	NPD7699	Phase 2
0.7644	Intermediate Similarity	NPD37	Approved
0.7644	Intermediate Similarity	NPD7700	Phase 2
0.7626	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7783	Phase 2
0.7614	Intermediate Similarity	NPD4967	Phase 2
0.7614	Intermediate Similarity	NPD4965	Approved
0.7614	Intermediate Similarity	NPD4966	Approved
0.7614	Intermediate Similarity	NPD7768	Phase 2
0.7607	Intermediate Similarity	NPD1240	Approved
0.759	Intermediate Similarity	NPD8320	Phase 1
0.759	Intermediate Similarity	NPD8319	Approved
0.7574	Intermediate Similarity	NPD6190	Approved
0.7556	Intermediate Similarity	NPD3926	Phase 2
0.7554	Intermediate Similarity	NPD7240	Approved
0.7538	Intermediate Similarity	NPD7801	Approved
0.7515	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD1607	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6823	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8150	Discontinued
0.7442	Intermediate Similarity	NPD2534	Approved
0.7442	Intermediate Similarity	NPD2533	Approved
0.7442	Intermediate Similarity	NPD2532	Approved
0.7423	Intermediate Similarity	NPD3027	Phase 3
0.7412	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7585	Approved
0.7374	Intermediate Similarity	NPD3749	Approved
0.7371	Intermediate Similarity	NPD7458	Discontinued
0.7356	Intermediate Similarity	NPD920	Approved
0.7353	Intermediate Similarity	NPD2800	Approved
0.7349	Intermediate Similarity	NPD1933	Approved
0.7349	Intermediate Similarity	NPD230	Phase 1
0.7337	Intermediate Similarity	NPD7583	Approved
0.7326	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5953	Discontinued
0.7306	Intermediate Similarity	NPD4360	Phase 2
0.7306	Intermediate Similarity	NPD4363	Phase 3
0.7296	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7254	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6212	Phase 3
0.7254	Intermediate Similarity	NPD6213	Phase 3
0.7251	Intermediate Similarity	NPD1243	Approved
0.7251	Intermediate Similarity	NPD6674	Discontinued
0.7245	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7286	Phase 2
0.7202	Intermediate Similarity	NPD6651	Approved
0.7186	Intermediate Similarity	NPD7680	Approved
0.7169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6798	Discontinued
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2346	Discontinued
0.7118	Intermediate Similarity	NPD2799	Discontinued
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.7114	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.7079	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6099	Approved
0.7076	Intermediate Similarity	NPD6100	Approved
0.7048	Intermediate Similarity	NPD4908	Phase 1
0.7045	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD1091	Approved
0.703	Intermediate Similarity	NPD2798	Approved
0.7027	Intermediate Similarity	NPD5710	Approved
0.7027	Intermediate Similarity	NPD5711	Approved
0.7024	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7930	Approved
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6844	Discontinued
0.6954	Remote Similarity	NPD1652	Phase 2
0.6946	Remote Similarity	NPD6832	Phase 2
0.6936	Remote Similarity	NPD2344	Approved
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4361	Phase 2
0.6919	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2424	Discontinued
0.6886	Remote Similarity	NPD9494	Approved
0.6884	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8059	Phase 3
0.6882	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD1203	Approved
0.6864	Remote Similarity	NPD3268	Approved
0.6862	Remote Similarity	NPD2403	Approved
0.686	Remote Similarity	NPD7097	Phase 1

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