NPASS Compound

Structure

NPC189589 OpenBabel07101719522D 34 36 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -4.3301 -2.5000 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 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 3.4641 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 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -6.0622 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 -4.3301 1.5000 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 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -3.4641 -1.0000 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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 9 2 0 0 0 0 5 21 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 12 2 0 0 0 0 8 29 1 0 0 0 0 9 12 1 0 0 0 0 9 30 1 0 0 0 0 10 5 1 6 0 0 0 10 13 1 0 0 0 0 10 33 1 0 0 0 0 11 6 1 6 0 0 0 11 14 1 0 0 0 0 11 34 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 6 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 20 1 0 0 0 0 18 28 1 1 0 0 0 19 31 1 6 0 0 0 19 33 1 0 0 0 0 20 32 1 6 0 0 0 20 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.16
Volume:	443.961
LogP:	-1.652
LogD:	-1.306
LogS:	-0.922
# Rotatable Bonds:	8
TPSA:	217.22
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	4.343
Fsp3:	0.7
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:	-6.589
MDCK Permeability:	9.92040877463296e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	33.57700729370117%
Volume Distribution (VD):	0.378
Pgp-substrate:	30.48798370361328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.484
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.234
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.732
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.038
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC189589

Natural Product ID:	NPC189589
*Common Name:**	4-Hydroxy-3,5-Dimethoxyphenyl Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3,5-dimethoxyphenoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	BMQJMZFDNFDQNP-JFRFVCMESA-N
Standard InCHI:	InChI=1S/C20H30O14/c1-29-8-3-7(4-9(30-2)12(8)22)32-20-18(28)16(26)14(24)11(34-20)6-31-19-17(27)15(25)13(23)10(5-21)33-19/h3-4,10-11,13-28H,5-6H2,1-2H3/t10-,11-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(OC)c(c(c3)OC)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562563
PubChem CID:	42638298
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
NPO33268	wheat	n.a.	n.a.	n.a.	wheat germ	n.a.	n.a.	PMID[19284743]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat bran	n.a.	n.a.	PMID[21658963]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.85	n.a.	PMID[486899]

☑ 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 NPC189589 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	388
0.1-0.2	2261
0.2-0.3	7897
0.3-0.4	11591
0.4-0.5	5827
0.5-0.6	7750
0.6-0.7	5456
0.7-0.8	1405
0.8-0.85	88
0.85-0.9	14
0.9-0.95	9
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469622
0.9917	High Similarity	NPC37074
0.9833	High Similarity	NPC298845
0.9752	High Similarity	NPC469621
0.9748	High Similarity	NPC192810
0.9748	High Similarity	NPC217854
0.9675	High Similarity	NPC208769
0.9667	High Similarity	NPC25817
0.9667	High Similarity	NPC221090
0.9664	High Similarity	NPC152722
0.9597	High Similarity	NPC287780
0.9516	High Similarity	NPC60756
0.9496	High Similarity	NPC276195
0.9444	High Similarity	NPC60982
0.9355	High Similarity	NPC247146
0.9194	High Similarity	NPC171533
0.9083	High Similarity	NPC228907
0.9	High Similarity	NPC9248
0.879	High Similarity	NPC57751
0.875	High Similarity	NPC142319
0.8657	High Similarity	NPC98777
0.8657	High Similarity	NPC212770
0.8647	High Similarity	NPC164857
0.8647	High Similarity	NPC104167
0.8582	High Similarity	NPC65530
0.8582	High Similarity	NPC59324
0.8571	High Similarity	NPC470236
0.8561	High Similarity	NPC49074
0.8561	High Similarity	NPC132895
0.856	High Similarity	NPC205850
0.8548	High Similarity	NPC214289
0.854	High Similarity	NPC252169
0.8537	High Similarity	NPC76915
0.8537	High Similarity	NPC151617
0.8507	High Similarity	NPC203230
0.8507	High Similarity	NPC242028
0.8496	Intermediate Similarity	NPC48863
0.8496	Intermediate Similarity	NPC251981
0.8496	Intermediate Similarity	NPC107478
0.8496	Intermediate Similarity	NPC87696
0.8496	Intermediate Similarity	NPC13745
0.8485	Intermediate Similarity	NPC299144
0.8485	Intermediate Similarity	NPC470270
0.8485	Intermediate Similarity	NPC162093
0.8467	Intermediate Similarity	NPC475084
0.8467	Intermediate Similarity	NPC189115
0.8467	Intermediate Similarity	NPC469559
0.8429	Intermediate Similarity	NPC227902
0.8425	Intermediate Similarity	NPC228875
0.8425	Intermediate Similarity	NPC105147
0.8425	Intermediate Similarity	NPC126216
0.8421	Intermediate Similarity	NPC215833
0.8421	Intermediate Similarity	NPC69513
0.8417	Intermediate Similarity	NPC161700
0.8417	Intermediate Similarity	NPC277867
0.8394	Intermediate Similarity	NPC469661
0.8372	Intermediate Similarity	NPC12308
0.8369	Intermediate Similarity	NPC175976
0.8369	Intermediate Similarity	NPC478237
0.8357	Intermediate Similarity	NPC125755
0.8345	Intermediate Similarity	NPC473045
0.8345	Intermediate Similarity	NPC25292
0.8309	Intermediate Similarity	NPC195196
0.8308	Intermediate Similarity	NPC110677
0.8296	Intermediate Similarity	NPC238243
0.8286	Intermediate Similarity	NPC475096
0.8284	Intermediate Similarity	NPC294166
0.8284	Intermediate Similarity	NPC115022
0.8273	Intermediate Similarity	NPC37793
0.8273	Intermediate Similarity	NPC473044
0.8271	Intermediate Similarity	NPC166168
0.8258	Intermediate Similarity	NPC307110
0.8258	Intermediate Similarity	NPC218003
0.8258	Intermediate Similarity	NPC248355
0.8244	Intermediate Similarity	NPC140750
0.8235	Intermediate Similarity	NPC40664
0.8235	Intermediate Similarity	NPC197723
0.8235	Intermediate Similarity	NPC232654
0.8235	Intermediate Similarity	NPC165482
0.8235	Intermediate Similarity	NPC138350
0.8235	Intermediate Similarity	NPC3293
0.8227	Intermediate Similarity	NPC190714
0.8227	Intermediate Similarity	NPC99515
0.8222	Intermediate Similarity	NPC130496
0.8222	Intermediate Similarity	NPC188555
0.8222	Intermediate Similarity	NPC35731
0.8214	Intermediate Similarity	NPC469313
0.8214	Intermediate Similarity	NPC168579
0.8214	Intermediate Similarity	NPC76176
0.8214	Intermediate Similarity	NPC138227
0.8209	Intermediate Similarity	NPC85799
0.8209	Intermediate Similarity	NPC26080
0.8209	Intermediate Similarity	NPC165686
0.8209	Intermediate Similarity	NPC303422
0.8201	Intermediate Similarity	NPC472714
0.8201	Intermediate Similarity	NPC5262
0.8195	Intermediate Similarity	NPC262606
0.8194	Intermediate Similarity	NPC213197
0.8182	Intermediate Similarity	NPC302378
0.8175	Intermediate Similarity	NPC470413
0.8175	Intermediate Similarity	NPC87777
0.8175	Intermediate Similarity	NPC262328
0.8175	Intermediate Similarity	NPC138738
0.8169	Intermediate Similarity	NPC15538
0.8169	Intermediate Similarity	NPC473480
0.8169	Intermediate Similarity	NPC39657
0.8168	Intermediate Similarity	NPC233559
0.8167	Intermediate Similarity	NPC124712
0.8134	Intermediate Similarity	NPC9912
0.8134	Intermediate Similarity	NPC248307
0.8134	Intermediate Similarity	NPC65942
0.8134	Intermediate Similarity	NPC121376
0.812	Intermediate Similarity	NPC166040
0.8115	Intermediate Similarity	NPC247871
0.8112	Intermediate Similarity	NPC130449
0.8112	Intermediate Similarity	NPC248132
0.8088	Intermediate Similarity	NPC310854
0.8088	Intermediate Similarity	NPC170694
0.8085	Intermediate Similarity	NPC187774
0.8085	Intermediate Similarity	NPC472713
0.8085	Intermediate Similarity	NPC473046
0.8085	Intermediate Similarity	NPC118385
0.8085	Intermediate Similarity	NPC472712
0.8082	Intermediate Similarity	NPC78809
0.8074	Intermediate Similarity	NPC252833
0.806	Intermediate Similarity	NPC472024
0.806	Intermediate Similarity	NPC470079
0.806	Intermediate Similarity	NPC80600
0.8058	Intermediate Similarity	NPC202700
0.8058	Intermediate Similarity	NPC210478
0.8058	Intermediate Similarity	NPC106944
0.8056	Intermediate Similarity	NPC313334
0.8056	Intermediate Similarity	NPC212670
0.8056	Intermediate Similarity	NPC206264
0.8056	Intermediate Similarity	NPC106138
0.8056	Intermediate Similarity	NPC286235
0.8056	Intermediate Similarity	NPC51328
0.8056	Intermediate Similarity	NPC55158
0.8045	Intermediate Similarity	NPC198487
0.8045	Intermediate Similarity	NPC40377
0.8043	Intermediate Similarity	NPC304152
0.8043	Intermediate Similarity	NPC124149
0.8029	Intermediate Similarity	NPC185778
0.8028	Intermediate Similarity	NPC307466
0.8015	Intermediate Similarity	NPC6836
0.8015	Intermediate Similarity	NPC25821
0.8	Intermediate Similarity	NPC257095
0.8	Intermediate Similarity	NPC307875
0.8	Intermediate Similarity	NPC273932
0.8	Intermediate Similarity	NPC469698
0.8	Intermediate Similarity	NPC475067
0.8	Intermediate Similarity	NPC89686
0.8	Intermediate Similarity	NPC473412
0.8	Intermediate Similarity	NPC114740
0.8	Intermediate Similarity	NPC472710
0.8	Intermediate Similarity	NPC472709
0.7986	Intermediate Similarity	NPC96294
0.7986	Intermediate Similarity	NPC280945
0.7986	Intermediate Similarity	NPC100389
0.7985	Intermediate Similarity	NPC270849
0.7985	Intermediate Similarity	NPC97326
0.7985	Intermediate Similarity	NPC26653
0.7971	Intermediate Similarity	NPC25695
0.7971	Intermediate Similarity	NPC52277
0.7971	Intermediate Similarity	NPC199459
0.7971	Intermediate Similarity	NPC177035
0.7971	Intermediate Similarity	NPC172818
0.7958	Intermediate Similarity	NPC297342
0.7956	Intermediate Similarity	NPC187194
0.7956	Intermediate Similarity	NPC470881
0.7945	Intermediate Similarity	NPC473621
0.7943	Intermediate Similarity	NPC157816
0.7943	Intermediate Similarity	NPC84207
0.7943	Intermediate Similarity	NPC5253
0.7943	Intermediate Similarity	NPC139976
0.7943	Intermediate Similarity	NPC230718
0.7943	Intermediate Similarity	NPC49542
0.7943	Intermediate Similarity	NPC128337
0.7941	Intermediate Similarity	NPC7903
0.7941	Intermediate Similarity	NPC16208
0.7941	Intermediate Similarity	NPC35932
0.7941	Intermediate Similarity	NPC160991
0.7941	Intermediate Similarity	NPC184447
0.7923	Intermediate Similarity	NPC226712
0.7917	Intermediate Similarity	NPC41844
0.7914	Intermediate Similarity	NPC326797
0.7914	Intermediate Similarity	NPC107551
0.7914	Intermediate Similarity	NPC103976
0.7914	Intermediate Similarity	NPC134260
0.7914	Intermediate Similarity	NPC102904
0.7914	Intermediate Similarity	NPC176051
0.7914	Intermediate Similarity	NPC474282
0.7899	Intermediate Similarity	NPC472337
0.7899	Intermediate Similarity	NPC234333
0.7899	Intermediate Similarity	NPC260898
0.7899	Intermediate Similarity	NPC47398
0.7891	Intermediate Similarity	NPC21902
0.7887	Intermediate Similarity	NPC470950
0.7887	Intermediate Similarity	NPC478239
0.7887	Intermediate Similarity	NPC81638

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 NPC189589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	1076
0.2-0.3	2927
0.3-0.4	2579
0.4-0.5	1361
0.5-0.6	731
0.6-0.7	158
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8056	Intermediate Similarity	NPD1653	Approved
0.7923	Intermediate Similarity	NPD1091	Approved
0.775	Intermediate Similarity	NPD291	Approved
0.76	Intermediate Similarity	NPD556	Approved
0.7591	Intermediate Similarity	NPD3027	Phase 3
0.7554	Intermediate Similarity	NPD1613	Approved
0.7554	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3454	Phase 3
0.7319	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD7472	Approved
0.7266	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD9296	Approved
0.7241	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.709	Intermediate Similarity	NPD7534	Approved
0.709	Intermediate Similarity	NPD7533	Approved
0.7073	Intermediate Similarity	NPD7251	Discontinued
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.703	Intermediate Similarity	NPD7808	Phase 3
0.7027	Intermediate Similarity	NPD6674	Discontinued
0.7025	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD9365	Approved
0.6962	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD37	Approved
0.6912	Remote Similarity	NPD1357	Approved
0.6901	Remote Similarity	NPD4908	Phase 1
0.6899	Remote Similarity	NPD4967	Phase 2
0.6899	Remote Similarity	NPD4965	Approved
0.6899	Remote Similarity	NPD4966	Approved
0.6884	Remote Similarity	NPD3705	Approved
0.6838	Remote Similarity	NPD1548	Phase 1
0.6833	Remote Similarity	NPD9295	Approved
0.6815	Remote Similarity	NPD1934	Approved
0.681	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6166	Phase 2
0.6806	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1652	Phase 2
0.6792	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2983	Phase 2
0.6786	Remote Similarity	NPD4749	Approved
0.6786	Remote Similarity	NPD2982	Phase 2
0.6772	Remote Similarity	NPD2801	Approved
0.6769	Remote Similarity	NPD290	Approved
0.6763	Remote Similarity	NPD1610	Phase 2
0.675	Remote Similarity	NPD9094	Approved
0.6728	Remote Similarity	NPD7199	Phase 2
0.6714	Remote Similarity	NPD2981	Phase 2
0.6692	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD7240	Approved
0.6642	Remote Similarity	NPD7843	Approved
0.6641	Remote Similarity	NPD9552	Approved
0.6618	Remote Similarity	NPD191	Approved
0.6604	Remote Similarity	NPD3384	Approved
0.6604	Remote Similarity	NPD3383	Approved
0.6604	Remote Similarity	NPD3382	Approved
0.6597	Remote Similarity	NPD3018	Phase 2
0.6597	Remote Similarity	NPD2861	Phase 2
0.6591	Remote Similarity	NPD2684	Approved
0.6573	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6559	Discontinued
0.6567	Remote Similarity	NPD228	Approved
0.6562	Remote Similarity	NPD8455	Phase 2
0.6554	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5124	Phase 1
0.6547	Remote Similarity	NPD1798	Approved
0.6547	Remote Similarity	NPD1797	Approved
0.6545	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6233	Phase 2
0.6525	Remote Similarity	NPD422	Phase 1
0.6509	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4625	Phase 3
0.6496	Remote Similarity	NPD6671	Approved
0.6496	Remote Similarity	NPD7157	Approved
0.6488	Remote Similarity	NPD5844	Phase 1
0.6471	Remote Similarity	NPD7685	Pre-registration
0.6467	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4538	Approved
0.6467	Remote Similarity	NPD4536	Approved
0.6463	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6842	Approved
0.6437	Remote Similarity	NPD6841	Approved
0.6437	Remote Similarity	NPD6843	Phase 3
0.6434	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD9299	Approved
0.642	Remote Similarity	NPD5402	Approved
0.642	Remote Similarity	NPD3817	Phase 2
0.6412	Remote Similarity	NPD9501	Approved
0.6403	Remote Similarity	NPD1103	Approved
0.6403	Remote Similarity	NPD1102	Approved
0.64	Remote Similarity	NPD2224	Approved
0.64	Remote Similarity	NPD2223	Approved
0.6392	Remote Similarity	NPD5403	Approved
0.6389	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6190	Approved
0.6386	Remote Similarity	NPD3787	Discontinued
0.638	Remote Similarity	NPD3882	Suspended
0.6376	Remote Similarity	NPD3620	Phase 2
0.6376	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4675	Approved
0.6375	Remote Similarity	NPD4380	Phase 2
0.6375	Remote Similarity	NPD4678	Approved
0.637	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2671	Approved
0.637	Remote Similarity	NPD2250	Discontinued
0.637	Remote Similarity	NPD2673	Approved
0.6358	Remote Similarity	NPD7097	Phase 1
0.6358	Remote Similarity	NPD2977	Approved
0.6358	Remote Similarity	NPD1465	Phase 2
0.6358	Remote Similarity	NPD2978	Approved
0.6341	Remote Similarity	NPD7075	Discontinued
0.6341	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1933	Approved
0.6333	Remote Similarity	NPD230	Phase 1
0.6319	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5960	Phase 3
0.6316	Remote Similarity	NPD5588	Approved
0.6306	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7212	Phase 2
0.6306	Remote Similarity	NPD7213	Phase 3
0.6306	Remote Similarity	NPD1511	Approved
0.6303	Remote Similarity	NPD9093	Approved
0.6301	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5647	Approved
0.6289	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD8651	Approved
0.6268	Remote Similarity	NPD5126	Approved
0.6268	Remote Similarity	NPD5125	Phase 3
0.6267	Remote Similarity	NPD1558	Phase 1
0.6266	Remote Similarity	NPD5401	Approved
0.6265	Remote Similarity	NPD5494	Approved
0.6258	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7680	Approved
0.625	Remote Similarity	NPD9089	Approved
0.6235	Remote Similarity	NPD3751	Discontinued
0.6234	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD1375	Discontinued
0.6234	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1512	Approved
0.6224	Remote Similarity	NPD915	Approved
0.6224	Remote Similarity	NPD3496	Discontinued
0.6218	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD7033	Discontinued
0.6207	Remote Similarity	NPD3685	Discontinued
0.6203	Remote Similarity	NPD1774	Approved
0.6196	Remote Similarity	NPD6801	Discontinued
0.6194	Remote Similarity	NPD1549	Phase 2
0.6184	Remote Similarity	NPD6653	Approved
0.6178	Remote Similarity	NPD2219	Phase 1
0.6174	Remote Similarity	NPD3179	Approved
0.6174	Remote Similarity	NPD3180	Approved
0.6171	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6099	Approved
0.6169	Remote Similarity	NPD6100	Approved
0.6164	Remote Similarity	NPD7447	Phase 1
0.6159	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5177	Phase 3
0.6154	Remote Similarity	NPD6516	Phase 2
0.6154	Remote Similarity	NPD5846	Approved
0.6149	Remote Similarity	NPD3686	Approved
0.6149	Remote Similarity	NPD7549	Discontinued
0.6149	Remote Similarity	NPD3687	Approved
0.6135	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6798	Discontinued
0.6129	Remote Similarity	NPD3540	Phase 1
0.6127	Remote Similarity	NPD7007	Discovery
0.6125	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6362	Approved
0.6118	Remote Similarity	NPD4340	Discontinued
0.6115	Remote Similarity	NPD4628	Phase 3
0.6115	Remote Similarity	NPD5283	Phase 1
0.6114	Remote Similarity	NPD8312	Approved
0.6114	Remote Similarity	NPD8313	Approved
0.6111	Remote Similarity	NPD4005	Discontinued
0.6101	Remote Similarity	NPD6799	Approved
0.6101	Remote Similarity	NPD4357	Discontinued
0.609	Remote Similarity	NPD2424	Discontinued
0.6087	Remote Similarity	NPD2122	Discontinued
0.6081	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD2677	Approved
0.6076	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5677	Discontinued
0.6065	Remote Similarity	NPD3539	Phase 1
0.6065	Remote Similarity	NPD1551	Phase 2
0.6062	Remote Similarity	NPD1754	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