NPASS Compound

Structure

NPC470270 OpenBabel07101718192D 24 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 -2.5981 -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 -1.0000 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 -1.5000 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 2 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 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 -5.1962 -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 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 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 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 16 1 0 0 0 0 6 7 1 0 0 0 0 6 23 1 0 0 0 0 8 11 2 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 5 1 6 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 1 0 0 0 13 14 1 0 0 0 0 13 19 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 23 1 6 0 0 0 15 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.13
Volume:	322.086
LogP:	-0.686
LogD:	-0.478
LogS:	-0.82
# Rotatable Bonds:	6
TPSA:	138.07
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	3.516
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.691
MDCK Permeability:	7.536746852565557e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.469
Human Intestinal Absorption (HIA):	0.839
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	32.98691940307617%
Volume Distribution (VD):	0.612
Pgp-substrate:	43.02908706665039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.498
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	3.789
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.308
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.687
Carcinogencity:	0.039
Eye Corrosion:	0.004
Eye Irritation:	0.132
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC470270

Natural Product ID:	NPC470270
*Common Name:**	3,5-Dimethoxy-4-Hydroxybenzyl-1-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	VZSGMNVXQXYFPI-TVKJYDDYSA-N
Standard InCHI:	InChI=1S/C15H22O9/c1-21-8-3-7(4-9(22-2)11(8)17)6-23-15-14(20)13(19)12(18)10(5-16)24-15/h3-4,10,12-20H,5-6H2,1-2H3/t10-,12-,13+,14-,15-/m1/s1
SMILES:	COC1=CC(=CC(=C1O)OC)COC2C(C(C(C(O2)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939390
PubChem CID:	57395395
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:0002207] O-glycosyl compounds

*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
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[561850]

☑ 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 NPC470270 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	381
0.1-0.2	1608
0.2-0.3	4834
0.3-0.4	11113
0.4-0.5	7102
0.5-0.6	5293
0.6-0.7	7335
0.7-0.8	3777
0.8-0.85	893
0.85-0.9	278
0.9-0.95	69
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC107478
0.9764	High Similarity	NPC132895
0.9685	High Similarity	NPC299144
0.9535	High Similarity	NPC48863
0.9535	High Similarity	NPC13745
0.9535	High Similarity	NPC251981
0.9466	High Similarity	NPC195196
0.9457	High Similarity	NPC69513
0.9457	High Similarity	NPC49074
0.9457	High Similarity	NPC215833
0.9453	High Similarity	NPC65942
0.9453	High Similarity	NPC248307
0.9449	High Similarity	NPC307110
0.9394	High Similarity	NPC212770
0.9394	High Similarity	NPC98777
0.938	High Similarity	NPC162093
0.9328	High Similarity	NPC472714
0.9328	High Similarity	NPC475084
0.9328	High Similarity	NPC469559
0.9328	High Similarity	NPC5262
0.9328	High Similarity	NPC189115
0.9318	High Similarity	NPC59324
0.9318	High Similarity	NPC65530
0.9308	High Similarity	NPC6836
0.9297	High Similarity	NPC166040
0.9254	High Similarity	NPC469661
0.9242	High Similarity	NPC164857
0.9242	High Similarity	NPC203230
0.9242	High Similarity	NPC242028
0.9237	High Similarity	NPC35731
0.9237	High Similarity	NPC470881
0.9231	High Similarity	NPC252833
0.9191	High Similarity	NPC118385
0.9191	High Similarity	NPC473046
0.9191	High Similarity	NPC472713
0.9191	High Similarity	NPC25292
0.9191	High Similarity	NPC472712
0.9191	High Similarity	NPC473045
0.9191	High Similarity	NPC187774
0.9167	High Similarity	NPC470236
0.9154	High Similarity	NPC166168
0.9147	High Similarity	NPC248355
0.9134	High Similarity	NPC12308
0.9127	High Similarity	NPC165375
0.9127	High Similarity	NPC220598
0.9124	High Similarity	NPC277867
0.9124	High Similarity	NPC475096
0.9124	High Similarity	NPC161700
0.9118	High Similarity	NPC473044
0.9118	High Similarity	NPC252169
0.9098	High Similarity	NPC104167
0.9098	High Similarity	NPC177035
0.9098	High Similarity	NPC199459
0.9098	High Similarity	NPC52277
0.9077	High Similarity	NPC80600
0.9077	High Similarity	NPC472024
0.907	High Similarity	NPC302378
0.9062	High Similarity	NPC473960
0.9058	High Similarity	NPC125755
0.9058	High Similarity	NPC190714
0.9058	High Similarity	NPC99515
0.9051	High Similarity	NPC297342
0.903	High Similarity	NPC304152
0.903	High Similarity	NPC470413
0.903	High Similarity	NPC138738
0.903	High Similarity	NPC474039
0.9015	High Similarity	NPC115022
0.9015	High Similarity	NPC25821
0.9015	High Similarity	NPC294166
0.9008	High Similarity	NPC470096
0.9008	High Similarity	NPC470095
0.9	High Similarity	NPC270849
0.9	High Similarity	NPC26653
0.8993	High Similarity	NPC39657
0.8993	High Similarity	NPC227902
0.8978	High Similarity	NPC37793
0.8968	High Similarity	NPC49341
0.8955	High Similarity	NPC25695
0.8955	High Similarity	NPC172818
0.8955	High Similarity	NPC157554
0.8947	High Similarity	NPC170694
0.8947	High Similarity	NPC87696
0.8939	High Similarity	NPC35932
0.8939	High Similarity	NPC165686
0.8939	High Similarity	NPC160991
0.8939	High Similarity	NPC16208
0.8939	High Similarity	NPC253105
0.8939	High Similarity	NPC7903
0.8939	High Similarity	NPC85799
0.8939	High Similarity	NPC184447
0.8939	High Similarity	NPC26080
0.8939	High Similarity	NPC303422
0.8939	High Similarity	NPC201587
0.8931	High Similarity	NPC262606
0.8929	High Similarity	NPC130449
0.8929	High Similarity	NPC248132
0.8929	High Similarity	NPC175976
0.8913	High Similarity	NPC168579
0.8913	High Similarity	NPC469313
0.8913	High Similarity	NPC138227
0.8913	High Similarity	NPC76176
0.8897	High Similarity	NPC210478
0.8897	High Similarity	NPC177868
0.8881	High Similarity	NPC238243
0.8865	High Similarity	NPC55158
0.8865	High Similarity	NPC286235
0.8865	High Similarity	NPC51328
0.8865	High Similarity	NPC106138
0.8864	High Similarity	NPC121376
0.8864	High Similarity	NPC9912
0.8864	High Similarity	NPC475067
0.8864	High Similarity	NPC472597
0.8857	High Similarity	NPC15538
0.8857	High Similarity	NPC473480
0.8857	High Similarity	NPC41844
0.8855	High Similarity	NPC228769
0.8855	High Similarity	NPC470633
0.8855	High Similarity	NPC170844
0.8855	High Similarity	NPC476968
0.8841	High Similarity	NPC12728
0.8841	High Similarity	NPC185071
0.8832	High Similarity	NPC472711
0.8824	High Similarity	NPC226005
0.8824	High Similarity	NPC100389
0.8819	High Similarity	NPC266045
0.8819	High Similarity	NPC470804
0.8815	High Similarity	NPC3293
0.8815	High Similarity	NPC138350
0.8815	High Similarity	NPC40664
0.8815	High Similarity	NPC165482
0.8815	High Similarity	NPC197723
0.8815	High Similarity	NPC186418
0.881	High Similarity	NPC229401
0.8806	High Similarity	NPC244983
0.8806	High Similarity	NPC187194
0.8806	High Similarity	NPC310854
0.8806	High Similarity	NPC188555
0.8806	High Similarity	NPC326095
0.8806	High Similarity	NPC130496
0.8803	High Similarity	NPC214326
0.8803	High Similarity	NPC469706
0.8803	High Similarity	NPC260781
0.8803	High Similarity	NPC218041
0.8803	High Similarity	NPC472710
0.8803	High Similarity	NPC182368
0.8803	High Similarity	NPC145979
0.8803	High Similarity	NPC9933
0.8803	High Similarity	NPC469707
0.8803	High Similarity	NPC472709
0.8803	High Similarity	NPC185955
0.8803	High Similarity	NPC225815
0.8794	High Similarity	NPC478237
0.8788	High Similarity	NPC469612
0.8788	High Similarity	NPC469614
0.8788	High Similarity	NPC472338
0.8786	High Similarity	NPC212890
0.8779	High Similarity	NPC186843
0.8779	High Similarity	NPC470213
0.8779	High Similarity	NPC98631
0.8779	High Similarity	NPC206615
0.8768	High Similarity	NPC48309
0.8768	High Similarity	NPC140502
0.8759	High Similarity	NPC106944
0.875	High Similarity	NPC124149
0.875	High Similarity	NPC283949
0.8741	High Similarity	NPC236522
0.8741	High Similarity	NPC234333
0.8741	High Similarity	NPC213197
0.8741	High Similarity	NPC101624
0.8741	High Similarity	NPC260898
0.8741	High Similarity	NPC184938
0.8741	High Similarity	NPC47398
0.8732	High Similarity	NPC313334
0.8732	High Similarity	NPC90896
0.8732	High Similarity	NPC212670
0.8732	High Similarity	NPC283839
0.8732	High Similarity	NPC206264
0.8731	High Similarity	NPC471390
0.8731	High Similarity	NPC471391
0.8731	High Similarity	NPC58585
0.8722	High Similarity	NPC469698
0.8722	High Similarity	NPC30043
0.8722	High Similarity	NPC469613
0.8722	High Similarity	NPC473412
0.8722	High Similarity	NPC309787
0.8722	High Similarity	NPC474017
0.8722	High Similarity	NPC469625
0.8714	High Similarity	NPC477702
0.8712	High Similarity	NPC3439
0.8712	High Similarity	NPC210623
0.8712	High Similarity	NPC470258
0.8712	High Similarity	NPC285339
0.8712	High Similarity	NPC226788
0.8712	High Similarity	NPC218003
0.8712	High Similarity	NPC222004
0.8712	High Similarity	NPC273295
0.8712	High Similarity	NPC218856
0.8712	High Similarity	NPC190629
0.8712	High Similarity	NPC202582
0.8705	High Similarity	NPC298317

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 NPC470270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	875
0.2-0.3	2149
0.3-0.4	2794
0.4-0.5	1572
0.5-0.6	924
0.6-0.7	456
0.7-0.8	69
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD3027	Phase 3
0.8732	High Similarity	NPD1653	Approved
0.8519	High Similarity	NPD1613	Approved
0.8519	High Similarity	NPD1612	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1091	Approved
0.8284	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7266	Discontinued
0.8154	Intermediate Similarity	NPD1357	Approved
0.8106	Intermediate Similarity	NPD3705	Approved
0.7974	Intermediate Similarity	NPD6234	Discontinued
0.7962	Intermediate Similarity	NPD7228	Approved
0.7953	Intermediate Similarity	NPD228	Approved
0.7911	Intermediate Similarity	NPD7054	Approved
0.7881	Intermediate Similarity	NPD37	Approved
0.7862	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD7074	Phase 3
0.7852	Intermediate Similarity	NPD2982	Phase 2
0.7852	Intermediate Similarity	NPD2983	Phase 2
0.7843	Intermediate Similarity	NPD4965	Approved
0.7843	Intermediate Similarity	NPD4966	Approved
0.7843	Intermediate Similarity	NPD4967	Phase 2
0.7793	Intermediate Similarity	NPD6674	Discontinued
0.7778	Intermediate Similarity	NPD2981	Phase 2
0.7754	Intermediate Similarity	NPD3018	Phase 2
0.7736	Intermediate Similarity	NPD3818	Discontinued
0.7702	Intermediate Similarity	NPD6797	Phase 2
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7808	Phase 3
0.7552	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4908	Phase 1
0.7445	Intermediate Similarity	NPD1610	Phase 2
0.7439	Intermediate Similarity	NPD7240	Approved
0.7421	Intermediate Similarity	NPD7199	Phase 2
0.7407	Intermediate Similarity	NPD1548	Phase 1
0.7391	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6166	Phase 2
0.7391	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2977	Approved
0.7372	Intermediate Similarity	NPD2978	Approved
0.7361	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3620	Phase 2
0.7343	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7315	Intermediate Similarity	NPD1652	Phase 2
0.7293	Intermediate Similarity	NPD5283	Phase 1
0.7261	Intermediate Similarity	NPD2801	Approved
0.7241	Intermediate Similarity	NPD1558	Phase 1
0.7237	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD290	Approved
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2219	Phase 1
0.7219	Intermediate Similarity	NPD6190	Approved
0.7218	Intermediate Similarity	NPD7843	Approved
0.7208	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD422	Phase 1
0.7185	Intermediate Similarity	NPD7157	Approved
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1375	Discontinued
0.7181	Intermediate Similarity	NPD3540	Phase 1
0.7179	Intermediate Similarity	NPD4675	Approved
0.7179	Intermediate Similarity	NPD4678	Approved
0.7176	Intermediate Similarity	NPD2684	Approved
0.7176	Intermediate Similarity	NPD6841	Approved
0.7176	Intermediate Similarity	NPD6843	Phase 3
0.7176	Intermediate Similarity	NPD6842	Approved
0.7171	Intermediate Similarity	NPD5058	Phase 3
0.717	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7124	Intermediate Similarity	NPD1511	Approved
0.7114	Intermediate Similarity	NPD3539	Phase 1
0.7109	Intermediate Similarity	NPD291	Approved
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7107	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4237	Approved
0.7086	Intermediate Similarity	NPD3060	Approved
0.7086	Intermediate Similarity	NPD4236	Phase 3
0.707	Intermediate Similarity	NPD4380	Phase 2
0.7066	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1465	Phase 2
0.7034	Intermediate Similarity	NPD4625	Phase 3
0.7032	Intermediate Similarity	NPD1512	Approved
0.7031	Intermediate Similarity	NPD1242	Phase 1
0.7014	Intermediate Similarity	NPD9494	Approved
0.7013	Intermediate Similarity	NPD4357	Discontinued
0.7006	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3021	Approved
0.6992	Remote Similarity	NPD3022	Approved
0.6992	Remote Similarity	NPD556	Approved
0.6986	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4536	Approved
0.698	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4538	Approved
0.6974	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5536	Phase 2
0.6946	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD7680	Approved
0.6943	Remote Similarity	NPD3687	Approved
0.6943	Remote Similarity	NPD3686	Approved
0.6939	Remote Similarity	NPD2674	Phase 3
0.6939	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8455	Phase 2
0.6934	Remote Similarity	NPD6671	Approved
0.6908	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD9296	Approved
0.6903	Remote Similarity	NPD1774	Approved
0.6894	Remote Similarity	NPD5353	Approved
0.6894	Remote Similarity	NPD968	Approved
0.6892	Remote Similarity	NPD4060	Phase 1
0.6871	Remote Similarity	NPD3145	Approved
0.6871	Remote Similarity	NPD3144	Approved
0.6867	Remote Similarity	NPD6111	Discontinued
0.6863	Remote Similarity	NPD5177	Phase 3
0.6859	Remote Similarity	NPD4123	Phase 3
0.6848	Remote Similarity	NPD3787	Discontinued
0.6848	Remote Similarity	NPD6232	Discontinued
0.6846	Remote Similarity	NPD846	Approved
0.6846	Remote Similarity	NPD940	Approved
0.6842	Remote Similarity	NPD1358	Approved
0.6842	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5772	Approved
0.6832	Remote Similarity	NPD5773	Approved
0.6821	Remote Similarity	NPD5960	Phase 3
0.6821	Remote Similarity	NPD4108	Discontinued
0.6821	Remote Similarity	NPD5588	Approved
0.6818	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7075	Discontinued
0.6809	Remote Similarity	NPD5125	Phase 3
0.6809	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD9384	Approved
0.6809	Remote Similarity	NPD5126	Approved
0.6806	Remote Similarity	NPD8651	Approved
0.68	Remote Similarity	NPD6653	Approved
0.6783	Remote Similarity	NPD9269	Phase 2
0.6779	Remote Similarity	NPD2238	Phase 2
0.6774	Remote Similarity	NPD2677	Approved
0.6755	Remote Similarity	NPD7097	Phase 1
0.6753	Remote Similarity	NPD4162	Approved
0.6741	Remote Similarity	NPD4750	Phase 3
0.6736	Remote Similarity	NPD3685	Discontinued
0.6736	Remote Similarity	NPD9622	Approved
0.6733	Remote Similarity	NPD447	Suspended
0.6732	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7124	Phase 2
0.6726	Remote Similarity	NPD7473	Discontinued
0.6714	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6233	Phase 2
0.671	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4628	Phase 3
0.671	Remote Similarity	NPD4110	Phase 3
0.671	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1778	Approved
0.6689	Remote Similarity	NPD3180	Approved
0.6689	Remote Similarity	NPD3179	Approved
0.6688	Remote Similarity	NPD7213	Phase 3
0.6688	Remote Similarity	NPD5297	Approved
0.6688	Remote Similarity	NPD7212	Phase 2
0.6688	Remote Similarity	NPD1549	Phase 2
0.6688	Remote Similarity	NPD2424	Discontinued
0.6687	Remote Similarity	NPD5402	Approved
0.6686	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD2122	Discontinued
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD2231	Phase 2
0.6667	Remote Similarity	NPD2235	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD3158	Phase 1
0.6646	Remote Similarity	NPD7447	Phase 1
0.6646	Remote Similarity	NPD4739	Approved
0.6646	Remote Similarity	NPD1424	Approved
0.6646	Remote Similarity	NPD3157	Approved
0.6645	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3496	Discontinued
0.6627	Remote Similarity	NPD5494	Approved
0.6626	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5762	Approved

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