NPASS Compound

Structure

NPC470236 OpenBabel07101719132D 37 39 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 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 3.0000 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 6.9282 6.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 1 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 7.7942 4.5000 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 7.7942 3.5000 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 6.9282 3.0000 0.0000 C 0 0 1 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 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 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 6.0622 4.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 34 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 11 21 2 0 0 0 0 11 32 1 0 0 0 0 12 21 1 0 0 0 0 12 33 1 0 0 0 0 13 8 1 1 0 0 0 13 15 1 0 0 0 0 13 35 1 0 0 0 0 14 9 1 6 0 0 0 14 16 1 0 0 0 0 14 36 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 6 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 20 1 0 0 0 0 18 29 1 6 0 0 0 19 22 1 0 0 0 0 19 30 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 1 0 0 0 21 37 1 0 0 0 0 22 34 1 1 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 23 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.19
Volume:	493.212
LogP:	-1.226
LogD:	-1.349
LogS:	-1.554
# Rotatable Bonds:	10
TPSA:	217.22
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.148
Synthetic Accessibility Score:	4.493
Fsp3:	0.652
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.218
MDCK Permeability:	8.58226339914836e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	30.61803436279297%
Volume Distribution (VD):	0.361
Pgp-substrate:	27.217992782592773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.516
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.136
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	1.016
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.371
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.562
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC470236

Natural Product ID:	NPC470236
*Common Name:**	Isosyringinoside
IUPAC Name:	(2S,3S,4R,5R,6S)-2-[(E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Isosyringinoside
Standard InCHIKey:	RYVGCUJETSKZDU-NXJCARKOSA-N
Standard InCHI:	InChI=1S/C23H34O14/c1-32-11-6-10(4-3-5-34-22-19(30)17(28)15(26)13(8-24)35-22)7-12(33-2)21(11)37-23-20(31)18(29)16(27)14(9-25)36-23/h3-4,6-7,13-20,22-31H,5,8-9H2,1-2H3/b4-3+/t13-,14+,15-,16+,17+,18-,19-,20+,22-,23-/m0/s1
SMILES:	COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CCOC3C(C(C(C(O3)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911059
PubChem CID:	57399043
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
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO16259	Syringa reticulata	Species	Oleaceae	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
EC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	14140.0	nM	PMID[491857]
NPT1	Others	Radical scavenging activity		EC50	>	100000.0	nM	PMID[491857]

☑ 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 NPC470236 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	394
0.1-0.2	1594
0.2-0.3	4522
0.3-0.4	10754
0.4-0.5	7761
0.5-0.6	5515
0.6-0.7	7653
0.7-0.8	3740
0.8-0.85	522
0.85-0.9	170
0.9-0.95	67
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC164857
0.9766	High Similarity	NPC162093
0.969	High Similarity	NPC49074
0.9538	High Similarity	NPC69513
0.9538	High Similarity	NPC215833
0.9474	High Similarity	NPC98777
0.9474	High Similarity	NPC212770
0.9466	High Similarity	NPC13745
0.9466	High Similarity	NPC251981
0.9466	High Similarity	NPC48863
0.9462	High Similarity	NPC299144
0.9453	High Similarity	NPC302378
0.9407	High Similarity	NPC469559
0.9398	High Similarity	NPC59324
0.9398	High Similarity	NPC65530
0.9389	High Similarity	NPC132895
0.9385	High Similarity	NPC469698
0.9385	High Similarity	NPC473412
0.9385	High Similarity	NPC9912
0.938	High Similarity	NPC248355
0.9323	High Similarity	NPC242028
0.9323	High Similarity	NPC197723
0.9323	High Similarity	NPC3293
0.9323	High Similarity	NPC165482
0.9323	High Similarity	NPC203230
0.9323	High Similarity	NPC40664
0.9323	High Similarity	NPC138350
0.9318	High Similarity	NPC187194
0.9308	High Similarity	NPC472024
0.9308	High Similarity	NPC80600
0.9265	High Similarity	NPC475084
0.9265	High Similarity	NPC189115
0.9259	High Similarity	NPC210478
0.9254	High Similarity	NPC195196
0.9248	High Similarity	NPC238243
0.9242	High Similarity	NPC115022
0.9242	High Similarity	NPC294166
0.9231	High Similarity	NPC166040
0.9231	High Similarity	NPC26653
0.9231	High Similarity	NPC270849
0.9203	High Similarity	NPC475096
0.9191	High Similarity	NPC469661
0.9179	High Similarity	NPC104167
0.9173	High Similarity	NPC130496
0.9173	High Similarity	NPC476411
0.9173	High Similarity	NPC107478
0.9173	High Similarity	NPC188555
0.9173	High Similarity	NPC35731
0.9167	High Similarity	NPC470270
0.9167	High Similarity	NPC165686
0.9167	High Similarity	NPC26080
0.9167	High Similarity	NPC85799
0.9167	High Similarity	NPC303422
0.9137	High Similarity	NPC125755
0.913	High Similarity	NPC25292
0.913	High Similarity	NPC473045
0.9111	High Similarity	NPC138738
0.9111	High Similarity	NPC470413
0.9098	High Similarity	NPC25821
0.9091	High Similarity	NPC121376
0.9084	High Similarity	NPC307110
0.9071	High Similarity	NPC227902
0.9071	High Similarity	NPC39657
0.9065	High Similarity	NPC277867
0.9065	High Similarity	NPC161700
0.9058	High Similarity	NPC473044
0.9058	High Similarity	NPC252169
0.9051	High Similarity	NPC257095
0.9051	High Similarity	NPC273932
0.9051	High Similarity	NPC89686
0.9037	High Similarity	NPC25695
0.9037	High Similarity	NPC172818
0.903	High Similarity	NPC87696
0.9007	High Similarity	NPC270751
0.9	High Similarity	NPC99515
0.9	High Similarity	NPC190714
0.8993	High Similarity	NPC469313
0.8993	High Similarity	NPC168579
0.8993	High Similarity	NPC138227
0.8993	High Similarity	NPC76176
0.8986	High Similarity	NPC5262
0.8986	High Similarity	NPC472714
0.8978	High Similarity	NPC106944
0.8971	High Similarity	NPC124149
0.8971	High Similarity	NPC304152
0.8963	High Similarity	NPC55040
0.8947	High Similarity	NPC469613
0.8947	High Similarity	NPC469625
0.8947	High Similarity	NPC30043
0.8947	High Similarity	NPC248307
0.8947	High Similarity	NPC65942
0.8944	High Similarity	NPC286235
0.8944	High Similarity	NPC106138
0.8944	High Similarity	NPC55158
0.8944	High Similarity	NPC95392
0.8944	High Similarity	NPC55715
0.8944	High Similarity	NPC35877
0.8944	High Similarity	NPC51328
0.8939	High Similarity	NPC218003
0.8936	High Similarity	NPC473480
0.8936	High Similarity	NPC15538
0.8936	High Similarity	NPC52740
0.8923	High Similarity	NPC12308
0.8921	High Similarity	NPC37793
0.8897	High Similarity	NPC52277
0.8897	High Similarity	NPC199459
0.8897	High Similarity	NPC37468
0.8897	High Similarity	NPC177035
0.8889	High Similarity	NPC170694
0.8881	High Similarity	NPC114740
0.8881	High Similarity	NPC252833
0.8873	High Similarity	NPC280945
0.8873	High Similarity	NPC130449
0.8873	High Similarity	NPC93924
0.8873	High Similarity	NPC175976
0.8873	High Similarity	NPC478237
0.8873	High Similarity	NPC248132
0.8873	High Similarity	NPC96294
0.8872	High Similarity	NPC469614
0.8872	High Similarity	NPC262606
0.8872	High Similarity	NPC469612
0.8857	High Similarity	NPC471063
0.8857	High Similarity	NPC472712
0.8857	High Similarity	NPC187774
0.8857	High Similarity	NPC297342
0.8857	High Similarity	NPC472713
0.8857	High Similarity	NPC118385
0.8857	High Similarity	NPC473046
0.8849	High Similarity	NPC246947
0.8846	High Similarity	NPC25817
0.8841	High Similarity	NPC202700
0.8828	High Similarity	NPC246893
0.8819	High Similarity	NPC473621
0.8815	High Similarity	NPC263064
0.8815	High Similarity	NPC6836
0.8806	High Similarity	NPC166168
0.8806	High Similarity	NPC475067
0.8797	High Similarity	NPC190629
0.8797	High Similarity	NPC202582
0.8797	High Similarity	NPC3439
0.8797	High Similarity	NPC210623
0.8797	High Similarity	NPC218856
0.8797	High Similarity	NPC470258
0.8797	High Similarity	NPC285339
0.8797	High Similarity	NPC273295
0.8797	High Similarity	NPC226788
0.8797	High Similarity	NPC222004
0.8788	High Similarity	NPC474119
0.8786	High Similarity	NPC470950
0.8786	High Similarity	NPC46092
0.8786	High Similarity	NPC185307
0.8777	High Similarity	NPC76871
0.8777	High Similarity	NPC210192
0.8769	High Similarity	NPC217854
0.8768	High Similarity	NPC100389
0.8759	High Similarity	NPC215060
0.8759	High Similarity	NPC471719
0.8759	High Similarity	NPC476352
0.8759	High Similarity	NPC302610
0.875	High Similarity	NPC472709
0.875	High Similarity	NPC472710
0.875	High Similarity	NPC238140
0.875	High Similarity	NPC470881
0.8741	High Similarity	NPC16208
0.8741	High Similarity	NPC35932
0.8741	High Similarity	NPC7903
0.8741	High Similarity	NPC184447
0.8741	High Similarity	NPC160991
0.8732	High Similarity	NPC276753
0.8732	High Similarity	NPC476865
0.8732	High Similarity	NPC205796
0.8723	High Similarity	NPC217635
0.8723	High Similarity	NPC470235
0.8723	High Similarity	NPC471667
0.8723	High Similarity	NPC79429
0.8723	High Similarity	NPC283995
0.8723	High Similarity	NPC129417
0.8722	High Similarity	NPC247146
0.8714	High Similarity	NPC157816
0.8714	High Similarity	NPC60249
0.8714	High Similarity	NPC476356
0.8712	High Similarity	NPC298845
0.8705	High Similarity	NPC226547
0.8696	High Similarity	NPC262328
0.8696	High Similarity	NPC87777
0.8692	High Similarity	NPC476142
0.869	High Similarity	NPC213197
0.8686	High Similarity	NPC185778
0.8686	High Similarity	NPC236522
0.8686	High Similarity	NPC61946
0.8682	High Similarity	NPC198734
0.8682	High Similarity	NPC469412
0.8682	High Similarity	NPC199023
0.8681	High Similarity	NPC283839
0.8681	High Similarity	NPC90896
0.8671	High Similarity	NPC41844
0.8667	High Similarity	NPC470096
0.8667	High Similarity	NPC472597
0.8667	High Similarity	NPC470095
0.8662	High Similarity	NPC22150

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 NPC470236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	860
0.2-0.3	2021
0.3-0.4	2871
0.4-0.5	1631
0.5-0.6	900
0.6-0.7	479
0.7-0.8	65
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8552	High Similarity	NPD1653	Approved
0.8382	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD1091	Approved
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6674	Discontinued
0.8112	Intermediate Similarity	NPD7266	Discontinued
0.8101	Intermediate Similarity	NPD7054	Approved
0.805	Intermediate Similarity	NPD7472	Approved
0.805	Intermediate Similarity	NPD7074	Phase 3
0.8043	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD1357	Approved
0.7941	Intermediate Similarity	NPD2983	Phase 2
0.7941	Intermediate Similarity	NPD2982	Phase 2
0.7926	Intermediate Similarity	NPD3705	Approved
0.7901	Intermediate Similarity	NPD7808	Phase 3
0.7868	Intermediate Similarity	NPD2981	Phase 2
0.784	Intermediate Similarity	NPD7251	Discontinued
0.7812	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD37	Approved
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7714	Intermediate Similarity	NPD3018	Phase 2
0.7702	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD7240	Approved
0.7595	Intermediate Similarity	NPD6234	Discontinued
0.7576	Intermediate Similarity	NPD7843	Approved
0.7576	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD7157	Approved
0.7535	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1652	Phase 2
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD5058	Phase 3
0.7469	Intermediate Similarity	NPD6166	Phase 2
0.7469	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8455	Phase 2
0.7439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD2684	Approved
0.7405	Intermediate Similarity	NPD3817	Phase 2
0.7372	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD228	Approved
0.7358	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6841	Approved
0.7353	Intermediate Similarity	NPD6843	Phase 3
0.7353	Intermediate Similarity	NPD6842	Approved
0.7344	Intermediate Similarity	NPD291	Approved
0.7342	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD290	Approved
0.731	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4749	Approved
0.7305	Intermediate Similarity	NPD6559	Discontinued
0.7297	Intermediate Similarity	NPD4536	Approved
0.7297	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4538	Approved
0.7296	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1375	Discontinued
0.7261	Intermediate Similarity	NPD4675	Approved
0.7261	Intermediate Similarity	NPD4678	Approved
0.7259	Intermediate Similarity	NPD5283	Phase 1
0.7254	Intermediate Similarity	NPD8651	Approved
0.7233	Intermediate Similarity	NPD2801	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7218	Intermediate Similarity	NPD556	Approved
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7097	Phase 1
0.7162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD3787	Discontinued
0.7133	Intermediate Similarity	NPD5588	Approved
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7123	Intermediate Similarity	NPD4625	Phase 3
0.7086	Intermediate Similarity	NPD3539	Phase 1
0.7078	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4236	Phase 3
0.7059	Intermediate Similarity	NPD4237	Approved
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7047	Intermediate Similarity	NPD5735	Approved
0.7042	Intermediate Similarity	NPD422	Phase 1
0.7041	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3882	Suspended
0.7034	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6671	Approved
0.7027	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.7025	Intermediate Similarity	NPD3687	Approved
0.7025	Intermediate Similarity	NPD3686	Approved
0.7019	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5773	Approved
0.7019	Intermediate Similarity	NPD2978	Approved
0.7019	Intermediate Similarity	NPD5772	Approved
0.7019	Intermediate Similarity	NPD2977	Approved
0.7012	Intermediate Similarity	NPD5494	Approved
0.7007	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD6653	Approved
0.6994	Remote Similarity	NPD7075	Discontinued
0.6987	Remote Similarity	NPD1511	Approved
0.6987	Remote Similarity	NPD4357	Discontinued
0.6987	Remote Similarity	NPD1774	Approved
0.6983	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4005	Discontinued
0.698	Remote Similarity	NPD1558	Phase 1
0.698	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3620	Phase 2
0.6974	Remote Similarity	NPD3454	Phase 3
0.6968	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD2677	Approved
0.6968	Remote Similarity	NPD2219	Phase 1
0.6962	Remote Similarity	NPD2122	Discontinued
0.6948	Remote Similarity	NPD4162	Approved
0.6944	Remote Similarity	NPD3685	Discontinued
0.6943	Remote Similarity	NPD4123	Phase 3
0.6939	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4380	Phase 2
0.6933	Remote Similarity	NPD230	Phase 1
0.6929	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5762	Approved
0.6928	Remote Similarity	NPD5763	Approved
0.6923	Remote Similarity	NPD7680	Approved
0.6914	Remote Similarity	NPD1465	Phase 2
0.6914	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD4108	Discontinued
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD6516	Phase 2
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD5846	Approved
0.6901	Remote Similarity	NPD5125	Phase 3
0.6899	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD52	Approved
0.6899	Remote Similarity	NPD7526	Approved
0.6899	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1512	Approved
0.6892	Remote Similarity	NPD3180	Approved
0.6892	Remote Similarity	NPD3179	Approved
0.6883	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD7533	Approved
0.6879	Remote Similarity	NPD7534	Approved
0.6871	Remote Similarity	NPD5402	Approved
0.6871	Remote Similarity	NPD5353	Approved
0.6867	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD4060	Phase 1
0.6864	Remote Similarity	NPD3751	Discontinued
0.6852	Remote Similarity	NPD3382	Approved
0.6852	Remote Similarity	NPD3383	Approved
0.6852	Remote Similarity	NPD3384	Approved
0.6846	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD6111	Discontinued
0.6839	Remote Similarity	NPD3060	Approved
0.6839	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5177	Phase 3
0.6835	Remote Similarity	NPD7447	Phase 1
0.6824	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6355	Discontinued
0.6821	Remote Similarity	NPD1933	Approved
0.6815	Remote Similarity	NPD1358	Approved
0.6815	Remote Similarity	NPD5756	Phase 2
0.6815	Remote Similarity	NPD7124	Phase 2
0.6807	Remote Similarity	NPD5677	Discontinued
0.6797	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4535	Phase 3
0.6795	Remote Similarity	NPD4628	Phase 3
0.6795	Remote Similarity	NPD6331	Phase 2
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1778	Approved
0.6782	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6799	Approved
0.6772	Remote Similarity	NPD5297	Approved
0.6772	Remote Similarity	NPD7213	Phase 3
0.6772	Remote Similarity	NPD7212	Phase 2
0.6763	Remote Similarity	NPD7549	Discontinued
0.6759	Remote Similarity	NPD2231	Phase 2
0.6759	Remote Similarity	NPD2235	Phase 2
0.6755	Remote Similarity	NPD4140	Approved
0.6753	Remote Similarity	NPD6099	Approved
0.6753	Remote Similarity	NPD2161	Phase 2
0.6753	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD5403	Approved
0.6748	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD1242	Phase 1

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