NPASS Compound

Structure

NPC208769 OpenBabel07101719152D 45 48 0 0 1 0 0 0 0 0999 V2000 -1.7321 -5.0000 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 -1.7321 -3.0000 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 8.6603 3.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 6.9282 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 6.0622 2.5000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 4.3301 4.5000 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 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 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 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -4.5000 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 5.1962 3.0000 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 6.9282 3.0000 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 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 10 2 0 0 0 0 5 27 1 0 0 0 0 6 40 1 0 0 0 0 7 41 1 0 0 0 0 8 42 1 0 0 0 0 9 14 2 0 0 0 0 9 38 1 0 0 0 0 10 14 1 0 0 0 0 10 39 1 0 0 0 0 11 5 1 6 0 0 0 11 15 1 0 0 0 0 11 43 1 0 0 0 0 12 6 1 1 0 0 0 12 16 1 0 0 0 0 12 44 1 0 0 0 0 13 7 1 1 0 0 0 13 17 1 0 0 0 0 13 45 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 1 0 0 0 16 19 1 0 0 0 0 16 30 1 6 0 0 0 17 20 1 0 0 0 0 17 31 1 6 0 0 0 18 21 1 0 0 0 0 18 32 1 6 0 0 0 19 22 1 0 0 0 0 19 33 1 1 0 0 0 20 23 1 0 0 0 0 20 34 1 1 0 0 0 21 24 1 0 0 0 0 21 35 1 1 0 0 0 22 25 1 0 0 0 0 22 36 1 6 0 0 0 23 26 1 0 0 0 0 23 37 1 6 0 0 0 24 40 1 6 0 0 0 24 43 1 0 0 0 0 25 41 1 1 0 0 0 25 44 1 0 0 0 0 26 42 1 1 0 0 0 26 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.22
Volume:	583.131
LogP:	-2.274
LogD:	-2.148
LogS:	-0.807
# Rotatable Bonds:	11
TPSA:	296.37
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	4.955
Fsp3:	0.769
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.703
MDCK Permeability:	0.00015467741468455642
Pgp-inhibitor:	0.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	30.68624496459961%
Volume Distribution (VD):	0.446
Pgp-substrate:	31.056102752685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.759
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.587
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.818
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC208769

Natural Product ID:	NPC208769
*Common Name:**	4-Hydroxy-3,5-Dimethoxyphenyl Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3,5-dimethoxyphenoxy)oxan-2-yl]methoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	XSZKQQFUCZZITK-XVWRWHHWSA-N
Standard InCHI:	InChI=1S/C26H40O19/c1-38-9-3-8(4-10(39-2)14(9)28)42-26-23(37)20(34)17(31)13(45-26)7-41-25-22(36)19(33)16(30)12(44-25)6-40-24-21(35)18(32)15(29)11(5-27)43-24/h3-4,11-13,15-37H,5-7H2,1-2H3/t11-,12-,13-,15-,16-,17-,18+,19+,20+,21-,22-,23-,24-,25-,26-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC[C@H]3O[C@@H](Oc4cc(OC)c(c(c4)OC)O)[C@@H]([C@H]([C@@H]3O)O)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:	CHEMBL541965
PubChem CID:	42638456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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	=	0.8	n.a.	PMID[523803]

☑ 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 NPC208769 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	429
0.1-0.2	2305
0.2-0.3	7867
0.3-0.4	10768
0.4-0.5	7300
0.5-0.6	8228
0.6-0.7	4692
0.7-0.8	1038
0.8-0.85	49
0.85-0.9	5
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC287780
0.9839	High Similarity	NPC60756
0.9762	High Similarity	NPC60982
0.9675	High Similarity	NPC189589
0.9675	High Similarity	NPC469622
0.9597	High Similarity	NPC37074
0.9516	High Similarity	NPC298845
0.944	High Similarity	NPC469621
0.9431	High Similarity	NPC192810
0.9431	High Similarity	NPC217854
0.9365	High Similarity	NPC247146
0.9355	High Similarity	NPC25817
0.9355	High Similarity	NPC221090
0.935	High Similarity	NPC152722
0.9187	High Similarity	NPC276195
0.9113	High Similarity	NPC57751
0.8906	High Similarity	NPC171533
0.879	High Similarity	NPC228907
0.871	High Similarity	NPC9248
0.8529	High Similarity	NPC164857
0.8468	Intermediate Similarity	NPC142319
0.8456	Intermediate Similarity	NPC470236
0.8438	Intermediate Similarity	NPC205850
0.8425	Intermediate Similarity	NPC214289
0.8406	Intermediate Similarity	NPC212770
0.8406	Intermediate Similarity	NPC98777
0.8394	Intermediate Similarity	NPC104167
0.8357	Intermediate Similarity	NPC469559
0.8333	Intermediate Similarity	NPC59324
0.8333	Intermediate Similarity	NPC65530
0.8333	Intermediate Similarity	NPC110677
0.8322	Intermediate Similarity	NPC227902
0.831	Intermediate Similarity	NPC277867
0.831	Intermediate Similarity	NPC161700
0.8309	Intermediate Similarity	NPC132895
0.8309	Intermediate Similarity	NPC49074
0.8308	Intermediate Similarity	NPC228875
0.8308	Intermediate Similarity	NPC126216
0.8308	Intermediate Similarity	NPC105147
0.8298	Intermediate Similarity	NPC252169
0.8286	Intermediate Similarity	NPC273932
0.8286	Intermediate Similarity	NPC89686
0.8286	Intermediate Similarity	NPC257095
0.8268	Intermediate Similarity	NPC151617
0.8268	Intermediate Similarity	NPC76915
0.8264	Intermediate Similarity	NPC280945
0.8261	Intermediate Similarity	NPC40664
0.8261	Intermediate Similarity	NPC197723
0.8261	Intermediate Similarity	NPC3293
0.8261	Intermediate Similarity	NPC138350
0.8261	Intermediate Similarity	NPC165482
0.8261	Intermediate Similarity	NPC242028
0.8261	Intermediate Similarity	NPC203230
0.8252	Intermediate Similarity	NPC125755
0.8248	Intermediate Similarity	NPC251981
0.8248	Intermediate Similarity	NPC87696
0.8248	Intermediate Similarity	NPC48863
0.8248	Intermediate Similarity	NPC107478
0.8248	Intermediate Similarity	NPC13745
0.8235	Intermediate Similarity	NPC162093
0.8235	Intermediate Similarity	NPC470270
0.8235	Intermediate Similarity	NPC299144
0.8227	Intermediate Similarity	NPC189115
0.8227	Intermediate Similarity	NPC475084
0.8219	Intermediate Similarity	NPC473621
0.8201	Intermediate Similarity	NPC195196
0.8194	Intermediate Similarity	NPC15538
0.8194	Intermediate Similarity	NPC473480
0.8188	Intermediate Similarity	NPC238243
0.8182	Intermediate Similarity	NPC475096
0.8175	Intermediate Similarity	NPC69513
0.8175	Intermediate Similarity	NPC215833
0.8169	Intermediate Similarity	NPC37793
0.8156	Intermediate Similarity	NPC469661
0.8138	Intermediate Similarity	NPC175976
0.8138	Intermediate Similarity	NPC478237
0.812	Intermediate Similarity	NPC12308
0.8116	Intermediate Similarity	NPC188555
0.8116	Intermediate Similarity	NPC130496
0.8116	Intermediate Similarity	NPC35731
0.8112	Intermediate Similarity	NPC225445
0.8112	Intermediate Similarity	NPC168579
0.8112	Intermediate Similarity	NPC76176
0.8112	Intermediate Similarity	NPC138227
0.8112	Intermediate Similarity	NPC25292
0.8112	Intermediate Similarity	NPC469313
0.8112	Intermediate Similarity	NPC473045
0.8099	Intermediate Similarity	NPC5262
0.8099	Intermediate Similarity	NPC472714
0.8088	Intermediate Similarity	NPC262606
0.8085	Intermediate Similarity	NPC106944
0.8071	Intermediate Similarity	NPC138738
0.8071	Intermediate Similarity	NPC470413
0.8071	Intermediate Similarity	NPC262328
0.8071	Intermediate Similarity	NPC87777
0.8069	Intermediate Similarity	NPC39657
0.8043	Intermediate Similarity	NPC115022
0.8043	Intermediate Similarity	NPC294166
0.8042	Intermediate Similarity	NPC473044
0.8042	Intermediate Similarity	NPC116922
0.8029	Intermediate Similarity	NPC166168
0.8015	Intermediate Similarity	NPC218003
0.8015	Intermediate Similarity	NPC248355
0.8015	Intermediate Similarity	NPC307110
0.8014	Intermediate Similarity	NPC130449
0.8014	Intermediate Similarity	NPC248132
0.8	Intermediate Similarity	NPC99515
0.8	Intermediate Similarity	NPC476865
0.8	Intermediate Similarity	NPC140750
0.8	Intermediate Similarity	NPC190714
0.7987	Intermediate Similarity	NPC78809
0.7986	Intermediate Similarity	NPC472713
0.7986	Intermediate Similarity	NPC187774
0.7986	Intermediate Similarity	NPC473046
0.7986	Intermediate Similarity	NPC472712
0.7986	Intermediate Similarity	NPC118385
0.7973	Intermediate Similarity	NPC213197
0.7971	Intermediate Similarity	NPC165686
0.7971	Intermediate Similarity	NPC26080
0.7971	Intermediate Similarity	NPC85799
0.7971	Intermediate Similarity	NPC303422
0.7967	Intermediate Similarity	NPC232654
0.7959	Intermediate Similarity	NPC55158
0.7959	Intermediate Similarity	NPC106138
0.7959	Intermediate Similarity	NPC286235
0.7959	Intermediate Similarity	NPC35877
0.7959	Intermediate Similarity	NPC95392
0.7959	Intermediate Similarity	NPC51328
0.7959	Intermediate Similarity	NPC55715
0.7956	Intermediate Similarity	NPC470079
0.7943	Intermediate Similarity	NPC304152
0.7941	Intermediate Similarity	NPC302378
0.7931	Intermediate Similarity	NPC476868
0.7931	Intermediate Similarity	NPC476866
0.7931	Intermediate Similarity	NPC476869
0.7931	Intermediate Similarity	NPC476864
0.7926	Intermediate Similarity	NPC233559
0.7917	Intermediate Similarity	NPC113680
0.7917	Intermediate Similarity	NPC278961
0.7908	Intermediate Similarity	NPC100936
0.7908	Intermediate Similarity	NPC1253
0.7905	Intermediate Similarity	NPC472709
0.7905	Intermediate Similarity	NPC472710
0.7905	Intermediate Similarity	NPC114740
0.7903	Intermediate Similarity	NPC124712
0.7899	Intermediate Similarity	NPC9912
0.7899	Intermediate Similarity	NPC65942
0.7899	Intermediate Similarity	NPC473412
0.7899	Intermediate Similarity	NPC121376
0.7899	Intermediate Similarity	NPC248307
0.7899	Intermediate Similarity	NPC469698
0.7883	Intermediate Similarity	NPC166040
0.7872	Intermediate Similarity	NPC469383
0.7872	Intermediate Similarity	NPC52277
0.7872	Intermediate Similarity	NPC199459
0.7872	Intermediate Similarity	NPC177035
0.7867	Intermediate Similarity	NPC246893
0.7862	Intermediate Similarity	NPC297342
0.7862	Intermediate Similarity	NPC177597
0.7862	Intermediate Similarity	NPC476867
0.7857	Intermediate Similarity	NPC310854
0.7857	Intermediate Similarity	NPC170694
0.7857	Intermediate Similarity	NPC247871
0.7857	Intermediate Similarity	NPC187194
0.7847	Intermediate Similarity	NPC84207
0.7847	Intermediate Similarity	NPC128337
0.7847	Intermediate Similarity	NPC5253
0.7847	Intermediate Similarity	NPC139976
0.7847	Intermediate Similarity	NPC49542
0.7847	Intermediate Similarity	NPC230718
0.7842	Intermediate Similarity	NPC252833
0.7838	Intermediate Similarity	NPC313334
0.7838	Intermediate Similarity	NPC283839
0.7838	Intermediate Similarity	NPC90896
0.7838	Intermediate Similarity	NPC206264
0.7838	Intermediate Similarity	NPC212670
0.7832	Intermediate Similarity	NPC210478
0.7832	Intermediate Similarity	NPC202700
0.7826	Intermediate Similarity	NPC80600
0.7826	Intermediate Similarity	NPC472024
0.7817	Intermediate Similarity	NPC124149
0.781	Intermediate Similarity	NPC40377
0.781	Intermediate Similarity	NPC198487
0.7808	Intermediate Similarity	NPC307466
0.7801	Intermediate Similarity	NPC185778
0.78	Intermediate Similarity	NPC472612
0.78	Intermediate Similarity	NPC289967
0.78	Intermediate Similarity	NPC472611
0.78	Intermediate Similarity	NPC21902
0.7793	Intermediate Similarity	NPC46092
0.7793	Intermediate Similarity	NPC472451
0.7793	Intermediate Similarity	NPC185307
0.7793	Intermediate Similarity	NPC470950
0.7786	Intermediate Similarity	NPC6836
0.7786	Intermediate Similarity	NPC25821
0.7785	Intermediate Similarity	NPC225815
0.7785	Intermediate Similarity	NPC260781
0.7785	Intermediate Similarity	NPC218041
0.7785	Intermediate Similarity	NPC238140
0.7785	Intermediate Similarity	NPC469707

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 NPC208769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	1113
0.2-0.3	3014
0.3-0.4	2562
0.4-0.5	1372
0.5-0.6	638
0.6-0.7	111
0.7-0.8	9
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
0.7838	Intermediate Similarity	NPD1653	Approved
0.7687	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD291	Approved
0.7407	Intermediate Similarity	NPD7472	Approved
0.7407	Intermediate Similarity	NPD7074	Phase 3
0.7376	Intermediate Similarity	NPD3027	Phase 3
0.7364	Intermediate Similarity	NPD556	Approved
0.7346	Intermediate Similarity	NPD7054	Approved
0.7343	Intermediate Similarity	NPD1613	Approved
0.7343	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3454	Phase 3
0.7279	Intermediate Similarity	NPD7266	Discontinued
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7178	Intermediate Similarity	NPD7228	Approved
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7113	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6674	Discontinued
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9296	Approved
0.7007	Intermediate Similarity	NPD7534	Approved
0.7007	Intermediate Similarity	NPD7533	Approved
0.6944	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3818	Discontinued
0.6852	Remote Similarity	NPD6234	Discontinued
0.6828	Remote Similarity	NPD4908	Phase 1
0.6826	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7240	Approved
0.6774	Remote Similarity	NPD9365	Approved
0.675	Remote Similarity	NPD37	Approved
0.6747	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6166	Phase 2
0.6735	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6714	Remote Similarity	NPD1357	Approved
0.6708	Remote Similarity	NPD8455	Phase 2
0.669	Remote Similarity	NPD3705	Approved
0.6646	Remote Similarity	NPD1934	Approved
0.6643	Remote Similarity	NPD1548	Phase 1
0.6623	Remote Similarity	NPD1652	Phase 2
0.6613	Remote Similarity	NPD9295	Approved
0.6605	Remote Similarity	NPD2801	Approved
0.6597	Remote Similarity	NPD2983	Phase 2
0.6597	Remote Similarity	NPD4749	Approved
0.6597	Remote Similarity	NPD2982	Phase 2
0.6573	Remote Similarity	NPD1610	Phase 2
0.6569	Remote Similarity	NPD7843	Approved
0.6567	Remote Similarity	NPD290	Approved
0.6566	Remote Similarity	NPD7199	Phase 2
0.655	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD9094	Approved
0.6528	Remote Similarity	NPD2981	Phase 2
0.6512	Remote Similarity	NPD7685	Pre-registration
0.6503	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5058	Phase 3
0.6494	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD968	Approved
0.649	Remote Similarity	NPD5124	Phase 1
0.649	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD9552	Approved
0.6442	Remote Similarity	NPD3384	Approved
0.6442	Remote Similarity	NPD3382	Approved
0.6442	Remote Similarity	NPD3383	Approved
0.6433	Remote Similarity	NPD5844	Phase 1
0.6429	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6671	Approved
0.6429	Remote Similarity	NPD7157	Approved
0.6429	Remote Similarity	NPD191	Approved
0.6419	Remote Similarity	NPD2861	Phase 2
0.6419	Remote Similarity	NPD3018	Phase 2
0.6416	Remote Similarity	NPD6559	Discontinued
0.6405	Remote Similarity	NPD7097	Phase 1
0.64	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD2684	Approved
0.6395	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6841	Approved
0.6384	Remote Similarity	NPD6843	Phase 3
0.6384	Remote Similarity	NPD6842	Approved
0.6377	Remote Similarity	NPD228	Approved
0.6364	Remote Similarity	NPD1798	Approved
0.6364	Remote Similarity	NPD1797	Approved
0.6364	Remote Similarity	NPD5402	Approved
0.6358	Remote Similarity	NPD6233	Phase 2
0.6345	Remote Similarity	NPD422	Phase 1
0.6335	Remote Similarity	NPD5403	Approved
0.6333	Remote Similarity	NPD4625	Phase 3
0.6331	Remote Similarity	NPD3787	Discontinued
0.6319	Remote Similarity	NPD4380	Phase 2
0.6303	Remote Similarity	NPD1465	Phase 2
0.6299	Remote Similarity	NPD4538	Approved
0.6299	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4536	Approved
0.629	Remote Similarity	NPD7680	Approved
0.6287	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7075	Discontinued
0.6271	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3817	Phase 2
0.6265	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7212	Phase 2
0.625	Remote Similarity	NPD8312	Approved
0.625	Remote Similarity	NPD7213	Phase 3
0.625	Remote Similarity	NPD8313	Approved
0.6242	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD9299	Approved
0.6234	Remote Similarity	NPD2224	Approved
0.6234	Remote Similarity	NPD2223	Approved
0.6228	Remote Similarity	NPD3882	Suspended
0.6226	Remote Similarity	NPD6190	Approved
0.6224	Remote Similarity	NPD1103	Approved
0.6224	Remote Similarity	NPD1102	Approved
0.6222	Remote Similarity	NPD9501	Approved
0.622	Remote Similarity	NPD4675	Approved
0.622	Remote Similarity	NPD4678	Approved
0.6216	Remote Similarity	NPD8651	Approved
0.6213	Remote Similarity	NPD5494	Approved
0.6211	Remote Similarity	NPD5401	Approved
0.6211	Remote Similarity	NPD7447	Phase 1
0.6209	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3620	Phase 2
0.6205	Remote Similarity	NPD2977	Approved
0.6205	Remote Similarity	NPD2978	Approved
0.62	Remote Similarity	NPD2250	Discontinued
0.62	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD2671	Approved
0.6187	Remote Similarity	NPD2673	Approved
0.6185	Remote Similarity	NPD3751	Discontinued
0.6169	Remote Similarity	NPD230	Phase 1
0.6169	Remote Similarity	NPD1933	Approved
0.6164	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5588	Approved
0.6154	Remote Similarity	NPD5960	Phase 3
0.6149	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1511	Approved
0.6135	Remote Similarity	NPD2122	Discontinued
0.6135	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5647	Approved
0.6129	Remote Similarity	NPD6653	Approved
0.6124	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6099	Approved
0.6115	Remote Similarity	NPD6100	Approved
0.6108	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD1558	Phase 1
0.6102	Remote Similarity	NPD7549	Discontinued
0.6101	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD9093	Approved
0.6096	Remote Similarity	NPD5125	Phase 3
0.6096	Remote Similarity	NPD5126	Approved
0.609	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD1375	Discontinued
0.6076	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD1512	Approved
0.6071	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6362	Approved
0.6062	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD915	Approved
0.6054	Remote Similarity	NPD3496	Discontinued
0.6051	Remote Similarity	NPD7033	Discontinued
0.6049	Remote Similarity	NPD1774	Approved
0.6048	Remote Similarity	NPD9089	Approved
0.6048	Remote Similarity	NPD6801	Discontinued
0.604	Remote Similarity	NPD3685	Discontinued
0.6038	Remote Similarity	NPD1549	Phase 2
0.6034	Remote Similarity	NPD8054	Approved
0.6034	Remote Similarity	NPD8053	Approved
0.6025	Remote Similarity	NPD2219	Phase 1
0.6022	Remote Similarity	NPD7906	Approved
0.6013	Remote Similarity	NPD3180	Approved
0.6013	Remote Similarity	NPD3179	Approved
0.6012	Remote Similarity	NPD5773	Approved
0.6012	Remote Similarity	NPD5772	Approved
0.6	Remote Similarity	NPD3686	Approved
0.6	Remote Similarity	NPD6696	Suspended
0.6	Remote Similarity	NPD3687	Approved
0.6	Remote Similarity	NPD5177	Phase 3
0.6	Remote Similarity	NPD3225	Approved
0.5989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD7007	Discovery
0.5988	Remote Similarity	NPD5756	Phase 2
0.5988	Remote Similarity	NPD7411	Suspended
0.5986	Remote Similarity	NPD6516	Phase 2
0.5986	Remote Similarity	NPD5846	Approved
0.5976	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD3540	Phase 1
0.5975	Remote Similarity	NPD5763	Approved
0.5975	Remote Similarity	NPD5762	Approved
0.5974	Remote Similarity	NPD6798	Discontinued

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