NPASS Compound

Structure

NPC97326 OpenBabel07101718192D 24 25 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 2.5981 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 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 -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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 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 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 4 1 0 0 0 0 3 9 2 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 10 12 1 0 0 0 0 11 19 1 0 0 0 0 12 23 1 0 0 0 0 13 8 1 6 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 16 1 0 0 0 0 15 21 1 6 0 0 0 16 17 1 0 0 0 0 16 22 1 1 0 0 0 17 23 1 6 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.15
Volume:	336.461
LogP:	1.277
LogD:	1.118
LogS:	-2.169
# Rotatable Bonds:	5
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	3.772
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.596
MDCK Permeability:	2.445132122375071e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.678
Human Intestinal Absorption (HIA):	0.233
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.781

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	87.0600814819336%
Volume Distribution (VD):	0.627
Pgp-substrate:	13.789328575134277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.323
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	7.237
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.255
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.594
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.157
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC97326

Natural Product ID:	NPC97326
*Common Name:**	1-O-Beta-D-Glucopyranosyl-1,4-Dihydroxy-2-Dimethylallylbenzene
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-hydroxy-2-(3-methylbut-2-enyl)phenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	TZABDPRGZVHMRW-NQNKBUKLSA-N
Standard InCHI:	InChI=1S/C17H24O7/c1-9(2)3-4-10-7-11(19)5-6-12(10)23-17-16(22)15(21)14(20)13(8-18)24-17/h3,5-7,13-22H,4,8H2,1-2H3/t13-,14-,15+,16-,17-/m1/s1
SMILES:	CC(=CCc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1938591
PubChem CID:	11078329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	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
Others	10

Activity Type	# Activity
Cell Line	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	10.0	%	PMID[455623]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	72.0	%	PMID[455623]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	86.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	53.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	50.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	30.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	43.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	>	50.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	60.0	%	PMID[455623]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	2.0	n.a.	PMID[455623]

☑ 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 NPC97326 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	337
0.1-0.2	1436
0.2-0.3	3963
0.3-0.4	10313
0.4-0.5	8309
0.5-0.6	5176
0.6-0.7	9129
0.7-0.8	3480
0.8-0.85	435
0.85-0.9	105
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC40377
0.9457	High Similarity	NPC475628
0.9187	High Similarity	NPC226712
0.916	High Similarity	NPC104167
0.9141	High Similarity	NPC262606
0.9091	High Similarity	NPC134260
0.907	High Similarity	NPC166168
0.9062	High Similarity	NPC270849
0.9062	High Similarity	NPC26653
0.9048	High Similarity	NPC12308
0.9048	High Similarity	NPC470510
0.9008	High Similarity	NPC87696
0.8992	High Similarity	NPC472024
0.8992	High Similarity	NPC80600
0.8952	High Similarity	NPC198734
0.8952	High Similarity	NPC269242
0.8952	High Similarity	NPC469412
0.8952	High Similarity	NPC473875
0.8923	High Similarity	NPC248307
0.8923	High Similarity	NPC65942
0.8915	High Similarity	NPC166040
0.8915	High Similarity	NPC248355
0.8915	High Similarity	NPC218003
0.8889	High Similarity	NPC210192
0.8871	High Similarity	NPC60589
0.8871	High Similarity	NPC469708
0.8837	High Similarity	NPC302378
0.8824	High Similarity	NPC145319
0.8824	High Similarity	NPC164599
0.881	High Similarity	NPC476142
0.8806	High Similarity	NPC138738
0.8806	High Similarity	NPC470413
0.8797	High Similarity	NPC79957
0.8788	High Similarity	NPC115022
0.8788	High Similarity	NPC25821
0.8788	High Similarity	NPC294166
0.8779	High Similarity	NPC9912
0.8779	High Similarity	NPC121376
0.8779	High Similarity	NPC475067
0.8777	High Similarity	NPC227902
0.8769	High Similarity	NPC307110
0.8768	High Similarity	NPC138915
0.8759	High Similarity	NPC252169
0.8741	High Similarity	NPC183781
0.874	High Similarity	NPC474130
0.8722	High Similarity	NPC35731
0.8722	High Similarity	NPC187194
0.8722	High Similarity	NPC251981
0.8722	High Similarity	NPC48863
0.8722	High Similarity	NPC470881
0.8722	High Similarity	NPC13745
0.8714	High Similarity	NPC175976
0.8712	High Similarity	NPC26080
0.8712	High Similarity	NPC303422
0.8712	High Similarity	NPC165686
0.8712	High Similarity	NPC85799
0.8692	High Similarity	NPC146540
0.8689	High Similarity	NPC142319
0.8686	High Similarity	NPC475084
0.8672	High Similarity	NPC287429
0.8667	High Similarity	NPC87777
0.8667	High Similarity	NPC262328
0.8661	High Similarity	NPC46586
0.8661	High Similarity	NPC204535
0.8657	High Similarity	NPC238243
0.8657	High Similarity	NPC185778
0.8651	High Similarity	NPC475529
0.8647	High Similarity	NPC49074
0.8647	High Similarity	NPC6836
0.8647	High Similarity	NPC215833
0.8647	High Similarity	NPC69513
0.8633	High Similarity	NPC475096
0.8603	High Similarity	NPC472151
0.8593	High Similarity	NPC165482
0.8593	High Similarity	NPC3293
0.8593	High Similarity	NPC199459
0.8593	High Similarity	NPC197723
0.8593	High Similarity	NPC138350
0.8593	High Similarity	NPC40664
0.8593	High Similarity	NPC52277
0.8593	High Similarity	NPC177035
0.8582	High Similarity	NPC107478
0.8582	High Similarity	NPC130496
0.8582	High Similarity	NPC476411
0.8582	High Similarity	NPC188555
0.8582	High Similarity	NPC34456
0.8571	High Similarity	NPC99515
0.8571	High Similarity	NPC252833
0.8571	High Similarity	NPC299144
0.8571	High Similarity	NPC125755
0.8571	High Similarity	NPC162093
0.8571	High Similarity	NPC190714
0.8561	High Similarity	NPC138227
0.8561	High Similarity	NPC474491
0.8561	High Similarity	NPC76176
0.8561	High Similarity	NPC168579
0.8561	High Similarity	NPC469313
0.8561	High Similarity	NPC325003
0.856	High Similarity	NPC283616
0.8551	High Similarity	NPC469559
0.8551	High Similarity	NPC189115
0.8551	High Similarity	NPC253878
0.8548	High Similarity	NPC175771
0.8548	High Similarity	NPC154256
0.8548	High Similarity	NPC148055
0.8548	High Similarity	NPC290470
0.854	High Similarity	NPC106944
0.8529	High Similarity	NPC124149
0.8529	High Similarity	NPC304152
0.8519	High Similarity	NPC472337
0.8511	High Similarity	NPC193473
0.8511	High Similarity	NPC275284
0.8511	High Similarity	NPC213074
0.8511	High Similarity	NPC31325
0.8511	High Similarity	NPC474422
0.8511	High Similarity	NPC15538
0.8511	High Similarity	NPC114505
0.8511	High Similarity	NPC224674
0.8511	High Similarity	NPC15956
0.8511	High Similarity	NPC473480
0.8507	High Similarity	NPC132895
0.85	High Similarity	NPC23807
0.85	High Similarity	NPC43508
0.85	High Similarity	NPC161700
0.85	High Similarity	NPC277867
0.85	High Similarity	NPC476301
0.8489	Intermediate Similarity	NPC470950
0.8489	Intermediate Similarity	NPC46092
0.8489	Intermediate Similarity	NPC185307
0.8489	Intermediate Similarity	NPC37793
0.8489	Intermediate Similarity	NPC473044
0.8485	Intermediate Similarity	NPC5851
0.8485	Intermediate Similarity	NPC86030
0.8478	Intermediate Similarity	NPC471414
0.8478	Intermediate Similarity	NPC469661
0.8473	Intermediate Similarity	NPC147821
0.8473	Intermediate Similarity	NPC198798
0.8473	Intermediate Similarity	NPC163332
0.8473	Intermediate Similarity	NPC111247
0.8473	Intermediate Similarity	NPC41706
0.8473	Intermediate Similarity	NPC292056
0.8473	Intermediate Similarity	NPC319625
0.8473	Intermediate Similarity	NPC118787
0.8473	Intermediate Similarity	NPC183181
0.8467	Intermediate Similarity	NPC100389
0.8467	Intermediate Similarity	NPC212770
0.8467	Intermediate Similarity	NPC98777
0.8456	Intermediate Similarity	NPC172818
0.8456	Intermediate Similarity	NPC37468
0.8456	Intermediate Similarity	NPC166180
0.8456	Intermediate Similarity	NPC472334
0.8456	Intermediate Similarity	NPC25695
0.8456	Intermediate Similarity	NPC203230
0.8456	Intermediate Similarity	NPC472336
0.8456	Intermediate Similarity	NPC242028
0.8456	Intermediate Similarity	NPC164857
0.8456	Intermediate Similarity	NPC469383
0.8451	Intermediate Similarity	NPC140722
0.8451	Intermediate Similarity	NPC92054
0.8451	Intermediate Similarity	NPC4958
0.844	Intermediate Similarity	NPC199928
0.8433	Intermediate Similarity	NPC269421
0.8433	Intermediate Similarity	NPC51262
0.8433	Intermediate Similarity	NPC470270
0.8429	Intermediate Similarity	NPC79429
0.8429	Intermediate Similarity	NPC292443
0.8429	Intermediate Similarity	NPC25292
0.8429	Intermediate Similarity	NPC232228
0.8429	Intermediate Similarity	NPC217635
0.8429	Intermediate Similarity	NPC129417
0.8429	Intermediate Similarity	NPC283995
0.8429	Intermediate Similarity	NPC470235
0.8429	Intermediate Similarity	NPC471667
0.8429	Intermediate Similarity	NPC473045
0.8425	Intermediate Similarity	NPC232295
0.8421	Intermediate Similarity	NPC220935
0.8417	Intermediate Similarity	NPC128337
0.8417	Intermediate Similarity	NPC84207
0.8417	Intermediate Similarity	NPC5253
0.8417	Intermediate Similarity	NPC49542
0.8417	Intermediate Similarity	NPC139976
0.8417	Intermediate Similarity	NPC472353
0.8417	Intermediate Similarity	NPC230718
0.8417	Intermediate Similarity	NPC476356
0.8417	Intermediate Similarity	NPC60249
0.8414	Intermediate Similarity	NPC78809
0.8409	Intermediate Similarity	NPC72529
0.8403	Intermediate Similarity	NPC213197
0.8397	Intermediate Similarity	NPC178284
0.8397	Intermediate Similarity	NPC58607
0.8397	Intermediate Similarity	NPC191037
0.8394	Intermediate Similarity	NPC474282
0.8394	Intermediate Similarity	NPC107551
0.8394	Intermediate Similarity	NPC59324
0.8394	Intermediate Similarity	NPC176051
0.8394	Intermediate Similarity	NPC103976
0.8394	Intermediate Similarity	NPC102904
0.8394	Intermediate Similarity	NPC326797
0.8394	Intermediate Similarity	NPC65530
0.8387	Intermediate Similarity	NPC313193

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 NPC97326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	834
0.2-0.3	1816
0.3-0.4	2733
0.4-0.5	1716
0.5-0.6	1044
0.6-0.7	639
0.7-0.8	77
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9187	High Similarity	NPD1091	Approved
0.832	Intermediate Similarity	NPD6671	Approved
0.8264	Intermediate Similarity	NPD1653	Approved
0.8195	Intermediate Similarity	NPD2861	Phase 2
0.8162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1613	Approved
0.8115	Intermediate Similarity	NPD290	Approved
0.7958	Intermediate Similarity	NPD6674	Discontinued
0.7941	Intermediate Similarity	NPD3027	Phase 3
0.7939	Intermediate Similarity	NPD3496	Discontinued
0.7868	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD7266	Discontinued
0.7794	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4749	Approved
0.776	Intermediate Similarity	NPD2684	Approved
0.7754	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3705	Approved
0.7742	Intermediate Similarity	NPD968	Approved
0.7737	Intermediate Similarity	NPD4908	Phase 1
0.7708	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD5058	Phase 3
0.7656	Intermediate Similarity	NPD7843	Approved
0.7652	Intermediate Similarity	NPD1357	Approved
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7626	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7157	Approved
0.7612	Intermediate Similarity	NPD1610	Phase 2
0.7597	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1548	Phase 1
0.7574	Intermediate Similarity	NPD6696	Suspended
0.7574	Intermediate Similarity	NPD8651	Approved
0.7569	Intermediate Similarity	NPD5762	Approved
0.7569	Intermediate Similarity	NPD5763	Approved
0.7554	Intermediate Similarity	NPD4625	Phase 3
0.7535	Intermediate Similarity	NPD6653	Approved
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD7054	Approved
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7483	Intermediate Similarity	NPD2677	Approved
0.7466	Intermediate Similarity	NPD1652	Phase 2
0.7463	Intermediate Similarity	NPD1778	Approved
0.7453	Intermediate Similarity	NPD7472	Approved
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7447	Intermediate Similarity	NPD6233	Phase 2
0.7442	Intermediate Similarity	NPD228	Approved
0.7426	Intermediate Similarity	NPD2235	Phase 2
0.7426	Intermediate Similarity	NPD2231	Phase 2
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6797	Phase 2
0.7362	Intermediate Similarity	NPD7251	Discontinued
0.7362	Intermediate Similarity	NPD6559	Discontinued
0.7353	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5125	Phase 3
0.7333	Intermediate Similarity	NPD5126	Approved
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7328	Intermediate Similarity	NPD1398	Phase 1
0.7317	Intermediate Similarity	NPD7808	Phase 3
0.731	Intermediate Similarity	NPD5960	Phase 3
0.731	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD5588	Approved
0.7296	Intermediate Similarity	NPD3787	Discontinued
0.7293	Intermediate Similarity	NPD7340	Approved
0.7284	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD1774	Approved
0.726	Intermediate Similarity	NPD6032	Approved
0.7254	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3685	Discontinued
0.7244	Intermediate Similarity	NPD5402	Approved
0.7241	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7097	Phase 1
0.7234	Intermediate Similarity	NPD596	Approved
0.7234	Intermediate Similarity	NPD600	Approved
0.7226	Intermediate Similarity	NPD1934	Approved
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6002	Phase 3
0.7211	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6005	Phase 3
0.7211	Intermediate Similarity	NPD6004	Phase 3
0.7203	Intermediate Similarity	NPD839	Approved
0.7203	Intermediate Similarity	NPD840	Approved
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD2801	Approved
0.7179	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD8313	Approved
0.7169	Intermediate Similarity	NPD8312	Approved
0.7153	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD291	Approved
0.7133	Intermediate Similarity	NPD7985	Registered
0.7125	Intermediate Similarity	NPD7199	Phase 2
0.7122	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7228	Approved
0.7117	Intermediate Similarity	NPD3751	Discontinued
0.7115	Intermediate Similarity	NPD37	Approved
0.7107	Intermediate Similarity	NPD6234	Discontinued
0.7103	Intermediate Similarity	NPD5735	Approved
0.7101	Intermediate Similarity	NPD1611	Approved
0.7095	Intermediate Similarity	NPD1375	Discontinued
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7092	Intermediate Similarity	NPD558	Phase 2
0.709	Intermediate Similarity	NPD709	Approved
0.7089	Intermediate Similarity	NPD4967	Phase 2
0.7089	Intermediate Similarity	NPD4966	Approved
0.7089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4965	Approved
0.708	Intermediate Similarity	NPD5846	Approved
0.708	Intermediate Similarity	NPD6516	Phase 2
0.7075	Intermediate Similarity	NPD4108	Discontinued
0.7075	Intermediate Similarity	NPD2154	Approved
0.7075	Intermediate Similarity	NPD2155	Approved
0.7075	Intermediate Similarity	NPD2156	Approved
0.707	Intermediate Similarity	NPD2977	Approved
0.707	Intermediate Similarity	NPD2978	Approved
0.7068	Intermediate Similarity	NPD5283	Phase 1
0.7067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3179	Approved
0.7063	Intermediate Similarity	NPD3180	Approved
0.7063	Intermediate Similarity	NPD7095	Approved
0.705	Intermediate Similarity	NPD1608	Approved
0.7042	Intermediate Similarity	NPD3018	Phase 2
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1558	Phase 1
0.7027	Intermediate Similarity	NPD2935	Discontinued
0.7027	Intermediate Similarity	NPD6100	Approved
0.7027	Intermediate Similarity	NPD6099	Approved
0.7023	Intermediate Similarity	NPD556	Approved
0.7021	Intermediate Similarity	NPD1794	Approved
0.7014	Intermediate Similarity	NPD1048	Approved
0.7014	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5177	Phase 3
0.6994	Remote Similarity	NPD6166	Phase 2
0.6994	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1138	Approved
0.6992	Remote Similarity	NPD821	Approved
0.6987	Remote Similarity	NPD4380	Phase 2
0.6986	Remote Similarity	NPD4340	Discontinued
0.6978	Remote Similarity	NPD776	Approved
0.6978	Remote Similarity	NPD1535	Discovery
0.6977	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3122	Phase 3
0.6972	Remote Similarity	NPD5647	Approved
0.6972	Remote Similarity	NPD3690	Phase 2
0.6972	Remote Similarity	NPD3691	Phase 2
0.697	Remote Similarity	NPD5844	Phase 1
0.6968	Remote Similarity	NPD3686	Approved
0.6968	Remote Similarity	NPD3687	Approved
0.6967	Remote Similarity	NPD9365	Approved
0.6966	Remote Similarity	NPD4062	Phase 3
0.6957	Remote Similarity	NPD4626	Approved
0.6954	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4535	Phase 3
0.6954	Remote Similarity	NPD3892	Phase 2
0.695	Remote Similarity	NPD3225	Approved
0.6948	Remote Similarity	NPD2676	Approved
0.6948	Remote Similarity	NPD2675	Approved
0.6937	Remote Similarity	NPD7075	Discontinued
0.6933	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2233	Approved
0.6929	Remote Similarity	NPD2232	Approved
0.6929	Remote Similarity	NPD2230	Approved
0.6929	Remote Similarity	NPD1481	Phase 2
0.6928	Remote Similarity	NPD7213	Phase 3
0.6928	Remote Similarity	NPD7212	Phase 2
0.6923	Remote Similarity	NPD2237	Approved
0.6918	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4140	Approved
0.6918	Remote Similarity	NPD3620	Phase 2
0.6918	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1139	Approved
0.6917	Remote Similarity	NPD1137	Approved
0.6903	Remote Similarity	NPD5403	Approved
0.6901	Remote Similarity	NPD2797	Approved
0.6901	Remote Similarity	NPD6362	Approved
0.6894	Remote Similarity	NPD4750	Phase 3
0.6887	Remote Similarity	NPD5061	Approved
0.6887	Remote Similarity	NPD4237	Approved
0.6887	Remote Similarity	NPD5062	Approved
0.6887	Remote Similarity	NPD4236	Phase 3
0.6887	Remote Similarity	NPD3060	Approved
0.6884	Remote Similarity	NPD5691	Approved
0.6883	Remote Similarity	NPD7447	Phase 1
0.6883	Remote Similarity	NPD3536	Discontinued
0.688	Remote Similarity	NPD844	Approved
0.6879	Remote Similarity	NPD6582	Phase 2
0.6879	Remote Similarity	NPD2982	Phase 2
0.6879	Remote Similarity	NPD2983	Phase 2
0.6879	Remote Similarity	NPD6583	Phase 3

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