NPASS Compound

Structure

CID236934 OpenBabel06191716032D 33 36 0 0 1 0 0 0 0 0999 V2000 -8.6603 0.0000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -5.1962 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 -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 -7.7942 -2.5000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 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 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 1.7321 -0.0000 0.0000 C 0 0 2 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 -8.6603 -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 -4.3301 1.5000 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 -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 -1.0000 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 -4.3301 -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 30 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 10 31 1 0 0 0 0 11 15 2 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 26 2 0 0 0 0 14 9 1 6 0 0 0 14 32 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 17 8 1 6 0 0 0 17 19 1 0 0 0 0 17 33 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.13
Volume:	433.08
LogP:	0.791
LogD:	0.543
LogS:	-4.267
# Rotatable Bonds:	5
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	4.064
Fsp3:	0.409
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.447
MDCK Permeability:	2.165410842280835e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.395
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	81.57767486572266%
Volume Distribution (VD):	0.625
Pgp-substrate:	15.14267349243164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.455
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	9.134
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.501
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.665
Carcinogencity:	0.779
Eye Corrosion:	0.003
Eye Irritation:	0.148
Respiratory Toxicity:	0.413

Download Data

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

Natural Product: NPC236934

Natural Product ID:	NPC236934
*Common Name:**	Homoeriodictyol 7-O-Beta-D-Glucopyranoside
IUPAC Name:	(2S)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	KZQCCKUDYVSOLC-YMTXFHFDSA-N
Standard InCHI:	InChI=1S/C22H24O11/c1-30-15-4-9(2-3-11(15)24)14-7-13(26)18-12(25)5-10(6-16(18)32-14)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-6,14,17,19-25,27-29H,7-8H2,1H3/t14-,17+,19+,20-,21+,22+/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CC(=O)c2c(cc(cc2O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086150
PubChem CID:	21629877
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
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00231-5]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12377236]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121165]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO539	Picea vulgaris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14062	Oophaga speciosa	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23400.0	nM	PMID[553306]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	88.7	%	PMID[553306]
NPT1	Others	Radical scavenging activity		ED50	=	100.0	uM	PMID[553306]

☑ 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 NPC236934 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	402
0.1-0.2	1628
0.2-0.3	3802
0.3-0.4	9277
0.4-0.5	8942
0.5-0.6	3926
0.6-0.7	4855
0.7-0.8	5885
0.8-0.85	2561
0.85-0.9	1020
0.9-0.95	360
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC5778
0.9873	High Similarity	NPC229687
0.9872	High Similarity	NPC29830
0.9811	High Similarity	NPC231194
0.9811	High Similarity	NPC21190
0.9811	High Similarity	NPC105095
0.9811	High Similarity	NPC44328
0.9811	High Similarity	NPC177731
0.9811	High Similarity	NPC22195
0.9811	High Similarity	NPC183357
0.9811	High Similarity	NPC79056
0.9811	High Similarity	NPC51326
0.981	High Similarity	NPC45400
0.981	High Similarity	NPC477502
0.981	High Similarity	NPC229729
0.9809	High Similarity	NPC22832
0.9809	High Similarity	NPC311830
0.9808	High Similarity	NPC127782
0.9808	High Similarity	NPC300537
0.975	High Similarity	NPC256760
0.975	High Similarity	NPC261254
0.9748	High Similarity	NPC270578
0.9748	High Similarity	NPC43587
0.9748	High Similarity	NPC209296
0.9748	High Similarity	NPC472383
0.9748	High Similarity	NPC112755
0.9748	High Similarity	NPC471457
0.9748	High Similarity	NPC293629
0.9748	High Similarity	NPC95855
0.9748	High Similarity	NPC210042
0.9748	High Similarity	NPC472381
0.9748	High Similarity	NPC170675
0.9748	High Similarity	NPC52382
0.9748	High Similarity	NPC195257
0.9747	High Similarity	NPC115674
0.9747	High Similarity	NPC210073
0.9745	High Similarity	NPC222936
0.9745	High Similarity	NPC309025
0.9745	High Similarity	NPC270335
0.9745	High Similarity	NPC243930
0.9745	High Similarity	NPC19709
0.9745	High Similarity	NPC284960
0.9745	High Similarity	NPC88023
0.9745	High Similarity	NPC191306
0.9689	High Similarity	NPC208668
0.9689	High Similarity	NPC239549
0.9689	High Similarity	NPC51774
0.9689	High Similarity	NPC236191
0.9688	High Similarity	NPC78734
0.9688	High Similarity	NPC34287
0.9688	High Similarity	NPC474434
0.9688	High Similarity	NPC44558
0.9688	High Similarity	NPC471416
0.9688	High Similarity	NPC150767
0.9686	High Similarity	NPC93099
0.9686	High Similarity	NPC160156
0.9686	High Similarity	NPC92565
0.9684	High Similarity	NPC165720
0.9682	High Similarity	NPC189142
0.9682	High Similarity	NPC473043
0.9682	High Similarity	NPC77660
0.9627	High Similarity	NPC48773
0.9627	High Similarity	NPC472386
0.9627	High Similarity	NPC235575
0.9627	High Similarity	NPC205076
0.9627	High Similarity	NPC267254
0.9627	High Similarity	NPC301683
0.9627	High Similarity	NPC307518
0.9625	High Similarity	NPC226294
0.9625	High Similarity	NPC219904
0.9625	High Similarity	NPC223747
0.9625	High Similarity	NPC120099
0.9625	High Similarity	NPC86008
0.9625	High Similarity	NPC201292
0.9625	High Similarity	NPC183036
0.9625	High Similarity	NPC58053
0.9625	High Similarity	NPC475942
0.9625	High Similarity	NPC45638
0.9625	High Similarity	NPC105283
0.9625	High Similarity	NPC186807
0.9625	High Similarity	NPC93337
0.9625	High Similarity	NPC225434
0.9625	High Similarity	NPC469931
0.9625	High Similarity	NPC105025
0.9625	High Similarity	NPC203050
0.9623	High Similarity	NPC197285
0.9623	High Similarity	NPC8856
0.9623	High Similarity	NPC21100
0.962	High Similarity	NPC168822
0.962	High Similarity	NPC88043
0.9618	High Similarity	NPC182045
0.9568	High Similarity	NPC204693
0.9565	High Similarity	NPC67105
0.9565	High Similarity	NPC206123
0.9565	High Similarity	NPC285197
0.9565	High Similarity	NPC105511
0.9565	High Similarity	NPC212748
0.9565	High Similarity	NPC224462
0.9565	High Similarity	NPC218488
0.9565	High Similarity	NPC95866
0.9563	High Similarity	NPC173637
0.9563	High Similarity	NPC84362
0.9563	High Similarity	NPC52550
0.9563	High Similarity	NPC226304
0.9563	High Similarity	NPC58716
0.9563	High Similarity	NPC116745
0.9563	High Similarity	NPC127546
0.9563	High Similarity	NPC265530
0.9563	High Similarity	NPC317489
0.9563	High Similarity	NPC146792
0.9563	High Similarity	NPC45618
0.9563	High Similarity	NPC325555
0.9563	High Similarity	NPC223424
0.956	High Similarity	NPC277205
0.956	High Similarity	NPC284277
0.956	High Similarity	NPC475366
0.956	High Similarity	NPC475497
0.9554	High Similarity	NPC110349
0.9512	High Similarity	NPC241196
0.9509	High Similarity	NPC198199
0.9509	High Similarity	NPC108202
0.9509	High Similarity	NPC102028
0.9509	High Similarity	NPC476472
0.9509	High Similarity	NPC294815
0.9509	High Similarity	NPC19108
0.9509	High Similarity	NPC220173
0.9509	High Similarity	NPC142996
0.9509	High Similarity	NPC294629
0.9509	High Similarity	NPC473327
0.9509	High Similarity	NPC16194
0.9506	High Similarity	NPC33054
0.9506	High Similarity	NPC203259
0.9506	High Similarity	NPC471748
0.9506	High Similarity	NPC259152
0.9506	High Similarity	NPC67134
0.9506	High Similarity	NPC176740
0.9506	High Similarity	NPC47140
0.9506	High Similarity	NPC476405
0.9506	High Similarity	NPC254540
0.9506	High Similarity	NPC156977
0.9506	High Similarity	NPC26230
0.9506	High Similarity	NPC153755
0.9506	High Similarity	NPC172807
0.9506	High Similarity	NPC180918
0.9506	High Similarity	NPC155877
0.9506	High Similarity	NPC211594
0.9506	High Similarity	NPC471725
0.9506	High Similarity	NPC60735
0.9506	High Similarity	NPC3583
0.9506	High Similarity	NPC117260
0.9506	High Similarity	NPC134532
0.9503	High Similarity	NPC61791
0.9503	High Similarity	NPC227508
0.95	High Similarity	NPC135599
0.95	High Similarity	NPC145038
0.95	High Similarity	NPC281131
0.95	High Similarity	NPC56077
0.95	High Similarity	NPC118284
0.95	High Similarity	NPC99957
0.95	High Similarity	NPC276222
0.95	High Similarity	NPC181616
0.95	High Similarity	NPC113968
0.95	High Similarity	NPC274618
0.95	High Similarity	NPC88789
0.95	High Similarity	NPC308404
0.95	High Similarity	NPC253662
0.95	High Similarity	NPC179950
0.95	High Similarity	NPC277174
0.95	High Similarity	NPC73855
0.95	High Similarity	NPC328940
0.9487	High Similarity	NPC206378
0.9451	High Similarity	NPC472380
0.9451	High Similarity	NPC255799
0.9451	High Similarity	NPC472384
0.9451	High Similarity	NPC268533
0.9451	High Similarity	NPC169733
0.9451	High Similarity	NPC472382
0.9448	High Similarity	NPC45522
0.9448	High Similarity	NPC88560
0.9448	High Similarity	NPC175230
0.9448	High Similarity	NPC169977
0.9448	High Similarity	NPC172033
0.9448	High Similarity	NPC101026
0.9448	High Similarity	NPC472993
0.9448	High Similarity	NPC42773
0.9448	High Similarity	NPC25724
0.9448	High Similarity	NPC24043
0.9448	High Similarity	NPC4390
0.9448	High Similarity	NPC21666
0.9444	High Similarity	NPC245014
0.9444	High Similarity	NPC259896
0.9444	High Similarity	NPC293004
0.9444	High Similarity	NPC67326
0.9444	High Similarity	NPC255157
0.9444	High Similarity	NPC282987
0.9444	High Similarity	NPC244776
0.9444	High Similarity	NPC204937
0.9444	High Similarity	NPC254855
0.9444	High Similarity	NPC156869
0.9444	High Similarity	NPC84265

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 NPC236934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	896
0.2-0.3	1831
0.3-0.4	2666
0.4-0.5	1836
0.5-0.6	975
0.6-0.7	413
0.7-0.8	135
0.8-0.85	25
0.85-0.9	10
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9811	High Similarity	NPD7074	Phase 3
0.9748	High Similarity	NPD7054	Approved
0.9688	High Similarity	NPD7472	Approved
0.9506	High Similarity	NPD6797	Phase 2
0.9448	High Similarity	NPD7251	Discontinued
0.9441	High Similarity	NPD3818	Discontinued
0.939	High Similarity	NPD7808	Phase 3
0.9317	High Similarity	NPD6167	Clinical (unspecified phase)
0.9317	High Similarity	NPD6168	Clinical (unspecified phase)
0.9317	High Similarity	NPD6166	Phase 2
0.9304	High Similarity	NPD4381	Clinical (unspecified phase)
0.9295	High Similarity	NPD1934	Approved
0.9273	High Similarity	NPD4338	Clinical (unspecified phase)
0.9114	High Similarity	NPD2393	Clinical (unspecified phase)
0.903	High Similarity	NPD7804	Clinical (unspecified phase)
0.8875	High Similarity	NPD2801	Approved
0.8765	High Similarity	NPD4868	Clinical (unspecified phase)
0.8704	High Similarity	NPD3817	Phase 2
0.8688	High Similarity	NPD4380	Phase 2
0.8662	High Similarity	NPD1511	Approved
0.865	High Similarity	NPD3882	Suspended
0.8647	High Similarity	NPD6559	Discontinued
0.8553	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD5494	Approved
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.848	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD1465	Phase 2
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD5844	Phase 1
0.8253	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8225	Intermediate Similarity	NPD6959	Discontinued
0.8221	Intermediate Similarity	NPD1653	Approved
0.8198	Intermediate Similarity	NPD7228	Approved
0.8193	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.816	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5402	Approved
0.814	Intermediate Similarity	NPD7473	Discontinued
0.8118	Intermediate Similarity	NPD7199	Phase 2
0.8101	Intermediate Similarity	NPD2796	Approved
0.8086	Intermediate Similarity	NPD6799	Approved
0.8049	Intermediate Similarity	NPD5403	Approved
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD8312	Approved
0.8013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1613	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7937	Intermediate Similarity	NPD7266	Discontinued
0.7927	Intermediate Similarity	NPD5401	Approved
0.7919	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD37	Approved
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7901	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1240	Approved
0.7886	Intermediate Similarity	NPD3751	Discontinued
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4965	Approved
0.7882	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3787	Discontinued
0.7833	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3027	Phase 3
0.7799	Intermediate Similarity	NPD1607	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7765	Intermediate Similarity	NPD8455	Phase 2
0.776	Intermediate Similarity	NPD8151	Discontinued
0.7756	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD7584	Approved
0.7736	Intermediate Similarity	NPD1933	Approved
0.7714	Intermediate Similarity	NPD3926	Phase 2
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7709	Intermediate Similarity	NPD7240	Approved
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD919	Approved
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD3750	Approved
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7669	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3749	Approved
0.7625	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD1247	Approved
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7592	Intermediate Similarity	NPD7696	Phase 3
0.7592	Intermediate Similarity	NPD7698	Approved
0.7592	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7783	Phase 2
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2935	Discontinued
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.753	Intermediate Similarity	NPD6190	Approved
0.7526	Intermediate Similarity	NPD7701	Phase 2
0.7516	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7435	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7699	Phase 2
0.7421	Intermediate Similarity	NPD7700	Phase 2
0.741	Intermediate Similarity	NPD2800	Approved
0.741	Intermediate Similarity	NPD6674	Discontinued
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5953	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7585	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7326	Intermediate Similarity	NPD3226	Approved
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7323	Intermediate Similarity	NPD7801	Approved
0.732	Intermediate Similarity	NPD7680	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD920	Approved
0.7308	Intermediate Similarity	NPD1091	Approved
0.7296	Intermediate Similarity	NPD7583	Approved
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7256	Intermediate Similarity	NPD6651	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.725	Intermediate Similarity	NPD9494	Approved
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7215	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6212	Phase 3
0.7211	Intermediate Similarity	NPD6213	Phase 3
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7202	Intermediate Similarity	NPD1243	Approved
0.7197	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2798	Approved
0.7186	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD2344	Approved
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5242	Approved
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1203	Approved
0.7119	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7117	Intermediate Similarity	NPD6798	Discontinued
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.7102	Intermediate Similarity	NPD6844	Discontinued
0.7101	Intermediate Similarity	NPD1652	Phase 2
0.7101	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5005	Approved
0.7092	Intermediate Similarity	NPD5006	Approved
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6842	Approved
0.709	Intermediate Similarity	NPD6841	Approved
0.709	Intermediate Similarity	NPD6843	Phase 3
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7072	Intermediate Similarity	NPD5711	Approved
0.7072	Intermediate Similarity	NPD5710	Approved
0.7066	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7930	Approved
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2309	Approved
0.7012	Intermediate Similarity	NPD3268	Approved
0.7005	Intermediate Similarity	NPD8155	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data