NPASS Compound

Structure

NPC251981 OpenBabel07101719152D 28 29 0 0 1 0 0 0 0 0999 V2000 3.4641 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 3.4641 1.0000 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 3.4641 -2.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 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 1.7321 0.0000 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 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 -1.7321 -2.0000 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 5.1962 0.0000 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 2.5981 2.5000 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 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 10 2 0 0 0 0 5 8 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 12 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 1 0 0 0 9 16 2 0 0 0 0 9 25 1 0 0 0 0 10 16 1 0 0 0 0 10 26 1 0 0 0 0 11 6 1 6 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 21 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 1 0 0 0 14 15 1 0 0 0 0 14 23 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 1 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	374.258
LogP:	-1.434
LogD:	-1.34
LogS:	-0.878
# Rotatable Bonds:	8
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	4.018
Fsp3:	0.647
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.991
MDCK Permeability:	8.703662024345249e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.834
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	25.23561668395996%
Volume Distribution (VD):	0.375
Pgp-substrate:	52.174781799316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.584
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.126
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC251981

Natural Product ID:	NPC251981
*Common Name:**	(-)-(7R,8S)-Erythro-1-C-Syringylglycerol 4-O-Beta-D-Glucopyranoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2,6-dimethoxy-4-[(1R,2S)-1,2,3-trihydroxypropyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	VIKGCVPVRTWXMM-DTXLLHAPSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-25-9-3-7(12(21)8(20)5-18)4-10(26-2)16(9)28-17-15(24)14(23)13(22)11(6-19)27-17/h3-4,8,11-15,17-24H,5-6H2,1-2H3/t8-,11+,12+,13+,14-,15+,17-/m0/s1
SMILES:	OC[C@@H]([C@@H](c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228183
PubChem CID:	16681197
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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	3
Others	3
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[521848]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[521848]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[521848]
NPT2	Others	Unspecified		Inhibition	=	26.6	%	PMID[521848]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	>	10000.0	nM	PMID[521848]
NPT27	Others	Unspecified		IC50	>	5000.0	nM	PMID[521848]

☑ 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 NPC251981 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	379
0.1-0.2	1548
0.2-0.3	4519
0.3-0.4	10939
0.4-0.5	7442
0.5-0.6	5070
0.6-0.7	7369
0.7-0.8	4192
0.8-0.85	874
0.85-0.9	261
0.9-0.95	89
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48863
1.0	High Similarity	NPC13745
0.9921	High Similarity	NPC69513
0.9921	High Similarity	NPC215833
0.9843	High Similarity	NPC299144
0.9766	High Similarity	NPC49074
0.969	High Similarity	NPC107478
0.9688	High Similarity	NPC162093
0.9542	High Similarity	NPC164857
0.9535	High Similarity	NPC470270
0.9531	High Similarity	NPC80600
0.9531	High Similarity	NPC472024
0.9478	High Similarity	NPC189115
0.9478	High Similarity	NPC469559
0.9466	High Similarity	NPC470236
0.9462	High Similarity	NPC132895
0.9453	High Similarity	NPC26653
0.9453	High Similarity	NPC166040
0.9453	High Similarity	NPC270849
0.9453	High Similarity	NPC248355
0.9403	High Similarity	NPC469661
0.9398	High Similarity	NPC212770
0.9398	High Similarity	NPC98777
0.9394	High Similarity	NPC25695
0.9394	High Similarity	NPC172818
0.9394	High Similarity	NPC104167
0.9375	High Similarity	NPC302378
0.9338	High Similarity	NPC25292
0.9338	High Similarity	NPC473045
0.9333	High Similarity	NPC475084
0.9323	High Similarity	NPC65530
0.9323	High Similarity	NPC59324
0.9313	High Similarity	NPC25821
0.9308	High Similarity	NPC248307
0.9308	High Similarity	NPC9912
0.9308	High Similarity	NPC65942
0.927	High Similarity	NPC277867
0.927	High Similarity	NPC161700
0.927	High Similarity	NPC475096
0.9265	High Similarity	NPC473044
0.9248	High Similarity	NPC242028
0.9248	High Similarity	NPC203230
0.9242	High Similarity	NPC187194
0.9231	High Similarity	NPC262606
0.9231	High Similarity	NPC469614
0.9231	High Similarity	NPC469612
0.9203	High Similarity	NPC190714
0.9203	High Similarity	NPC125755
0.9203	High Similarity	NPC99515
0.9191	High Similarity	NPC5262
0.9191	High Similarity	NPC472714
0.9185	High Similarity	NPC210478
0.9179	High Similarity	NPC138738
0.9179	High Similarity	NPC195196
0.9179	High Similarity	NPC470413
0.9167	High Similarity	NPC115022
0.9167	High Similarity	NPC294166
0.916	High Similarity	NPC469625
0.916	High Similarity	NPC30043
0.916	High Similarity	NPC469613
0.9154	High Similarity	NPC222004
0.9154	High Similarity	NPC307110
0.9154	High Similarity	NPC202582
0.9154	High Similarity	NPC470258
0.9154	High Similarity	NPC3439
0.9154	High Similarity	NPC210623
0.9154	High Similarity	NPC218856
0.9154	High Similarity	NPC226788
0.9154	High Similarity	NPC273295
0.9154	High Similarity	NPC285339
0.9154	High Similarity	NPC190629
0.9141	High Similarity	NPC12308
0.9137	High Similarity	NPC227902
0.9137	High Similarity	NPC39657
0.9124	High Similarity	NPC37793
0.9124	High Similarity	NPC252169
0.9098	High Similarity	NPC35731
0.9098	High Similarity	NPC476411
0.9098	High Similarity	NPC470881
0.9098	High Similarity	NPC170694
0.9091	High Similarity	NPC160991
0.9091	High Similarity	NPC184447
0.9091	High Similarity	NPC26080
0.9091	High Similarity	NPC7903
0.9091	High Similarity	NPC85799
0.9091	High Similarity	NPC303422
0.9091	High Similarity	NPC16208
0.9091	High Similarity	NPC165686
0.9091	High Similarity	NPC35932
0.9071	High Similarity	NPC175976
0.9071	High Similarity	NPC248132
0.9071	High Similarity	NPC130449
0.907	High Similarity	NPC473960
0.9058	High Similarity	NPC168579
0.9058	High Similarity	NPC472712
0.9058	High Similarity	NPC118385
0.9058	High Similarity	NPC138227
0.9058	High Similarity	NPC469313
0.9058	High Similarity	NPC76176
0.9058	High Similarity	NPC187774
0.9058	High Similarity	NPC472713
0.9058	High Similarity	NPC473046
0.9044	High Similarity	NPC226547
0.903	High Similarity	NPC238243
0.9023	High Similarity	NPC6836
0.9015	High Similarity	NPC166168
0.9015	High Similarity	NPC473412
0.9015	High Similarity	NPC475067
0.9015	High Similarity	NPC472597
0.9015	High Similarity	NPC121376
0.9015	High Similarity	NPC469698
0.9007	High Similarity	NPC55158
0.9007	High Similarity	NPC51328
0.9007	High Similarity	NPC286235
0.9007	High Similarity	NPC106138
0.9	High Similarity	NPC15538
0.9	High Similarity	NPC474119
0.9	High Similarity	NPC473480
0.8978	High Similarity	NPC210192
0.8963	High Similarity	NPC37468
0.8963	High Similarity	NPC197723
0.8963	High Similarity	NPC52277
0.8963	High Similarity	NPC138350
0.8963	High Similarity	NPC40664
0.8963	High Similarity	NPC199459
0.8963	High Similarity	NPC165482
0.8963	High Similarity	NPC177035
0.8963	High Similarity	NPC471719
0.8963	High Similarity	NPC3293
0.8955	High Similarity	NPC130496
0.8955	High Similarity	NPC87696
0.8955	High Similarity	NPC188555
0.8955	High Similarity	NPC310854
0.8947	High Similarity	NPC252833
0.8944	High Similarity	NPC472710
0.8944	High Similarity	NPC472709
0.8939	High Similarity	NPC472338
0.8936	High Similarity	NPC270751
0.8936	High Similarity	NPC93924
0.8913	High Similarity	NPC60249
0.8905	High Similarity	NPC106944
0.8897	High Similarity	NPC124149
0.8897	High Similarity	NPC283949
0.8897	High Similarity	NPC304152
0.8897	High Similarity	NPC474039
0.8889	High Similarity	NPC236522
0.8889	High Similarity	NPC234333
0.8889	High Similarity	NPC61946
0.8889	High Similarity	NPC55040
0.8889	High Similarity	NPC260898
0.8889	High Similarity	NPC47398
0.8881	High Similarity	NPC263064
0.8873	High Similarity	NPC95392
0.8873	High Similarity	NPC35877
0.8873	High Similarity	NPC55715
0.8872	High Similarity	NPC470095
0.8872	High Similarity	NPC309787
0.8872	High Similarity	NPC470096
0.8864	High Similarity	NPC218003
0.8849	High Similarity	NPC46092
0.8849	High Similarity	NPC470950
0.8849	High Similarity	NPC81638
0.8849	High Similarity	NPC185307
0.8841	High Similarity	NPC76871
0.8837	High Similarity	NPC220598
0.8837	High Similarity	NPC165375
0.8832	High Similarity	NPC292487
0.8832	High Similarity	NPC100389
0.8824	High Similarity	NPC306441
0.8824	High Similarity	NPC16435
0.8819	High Similarity	NPC21902
0.8815	High Similarity	NPC309744
0.8806	High Similarity	NPC470752
0.8806	High Similarity	NPC201587
0.8806	High Similarity	NPC253105
0.8803	High Similarity	NPC280945
0.8803	High Similarity	NPC96294
0.8803	High Similarity	NPC478237
0.8786	High Similarity	NPC297342
0.8786	High Similarity	NPC470235
0.8786	High Similarity	NPC283995
0.8786	High Similarity	NPC129417
0.8777	High Similarity	NPC476356
0.8777	High Similarity	NPC246947
0.8769	High Similarity	NPC94276
0.8769	High Similarity	NPC109822
0.8768	High Similarity	NPC56091
0.8768	High Similarity	NPC177868
0.8768	High Similarity	NPC46591
0.8759	High Similarity	NPC78809
0.8759	High Similarity	NPC185908
0.8759	High Similarity	NPC150442
0.8759	High Similarity	NPC134260
0.8759	High Similarity	NPC87777
0.8759	High Similarity	NPC262328
0.875	High Similarity	NPC112246
0.875	High Similarity	NPC213197
0.875	High Similarity	NPC121812
0.875	High Similarity	NPC473621
0.875	High Similarity	NPC185778

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 NPC251981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	876
0.2-0.3	2074
0.3-0.4	2764
0.4-0.5	1592
0.5-0.6	912
0.6-0.7	532
0.7-0.8	88
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8722	High Similarity	NPD3027	Phase 3
0.8611	High Similarity	NPD1653	Approved
0.8538	High Similarity	NPD1091	Approved
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3705	Approved
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6674	Discontinued
0.8042	Intermediate Similarity	NPD7266	Discontinued
0.8038	Intermediate Similarity	NPD7054	Approved
0.803	Intermediate Similarity	NPD1357	Approved
0.8013	Intermediate Similarity	NPD37	Approved
0.7987	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD7472	Approved
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4966	Approved
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7868	Intermediate Similarity	NPD2983	Phase 2
0.7868	Intermediate Similarity	NPD2982	Phase 2
0.7862	Intermediate Similarity	NPD7228	Approved
0.7862	Intermediate Similarity	NPD3818	Discontinued
0.784	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7794	Intermediate Similarity	NPD2981	Phase 2
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.777	Intermediate Similarity	NPD3018	Phase 2
0.773	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD228	Approved
0.7662	Intermediate Similarity	NPD1934	Approved
0.7634	Intermediate Similarity	NPD7843	Approved
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4749	Approved
0.7606	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2684	Approved
0.7594	Intermediate Similarity	NPD7157	Approved
0.7591	Intermediate Similarity	NPD1610	Phase 2
0.7568	Intermediate Similarity	NPD1652	Phase 2
0.7562	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7240	Approved
0.7556	Intermediate Similarity	NPD1548	Phase 1
0.7533	Intermediate Similarity	NPD5058	Phase 3
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6843	Phase 3
0.75	Intermediate Similarity	NPD6842	Approved
0.75	Intermediate Similarity	NPD6841	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD3817	Phase 2
0.7452	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5283	Phase 1
0.7432	Intermediate Similarity	NPD1375	Discontinued
0.7419	Intermediate Similarity	NPD4675	Approved
0.7419	Intermediate Similarity	NPD4678	Approved
0.7394	Intermediate Similarity	NPD2861	Phase 2
0.7389	Intermediate Similarity	NPD2801	Approved
0.7385	Intermediate Similarity	NPD290	Approved
0.7378	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4538	Approved
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7324	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7292	Intermediate Similarity	NPD4625	Phase 3
0.729	Intermediate Similarity	NPD3686	Approved
0.729	Intermediate Similarity	NPD3687	Approved
0.7278	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD2978	Approved
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7266	Intermediate Similarity	NPD291	Approved
0.726	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3620	Phase 2
0.726	Intermediate Similarity	NPD1558	Phase 1
0.7237	Intermediate Similarity	NPD2219	Phase 1
0.7237	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD4237	Approved
0.7211	Intermediate Similarity	NPD230	Phase 1
0.7206	Intermediate Similarity	NPD6671	Approved
0.72	Intermediate Similarity	NPD3540	Phase 1
0.7192	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD8651	Approved
0.7181	Intermediate Similarity	NPD5588	Approved
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7178	Intermediate Similarity	NPD3787	Discontinued
0.717	Intermediate Similarity	NPD5773	Approved
0.717	Intermediate Similarity	NPD5772	Approved
0.7162	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD1774	Approved
0.7143	Intermediate Similarity	NPD556	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7133	Intermediate Similarity	NPD3539	Phase 1
0.7124	Intermediate Similarity	NPD2677	Approved
0.7114	Intermediate Similarity	NPD7097	Phase 1
0.7113	Intermediate Similarity	NPD3685	Discontinued
0.7105	Intermediate Similarity	NPD4162	Approved
0.7105	Intermediate Similarity	NPD3060	Approved
0.7097	Intermediate Similarity	NPD4123	Phase 3
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7075	Intermediate Similarity	NPD6233	Phase 2
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7051	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2231	Phase 2
0.7042	Intermediate Similarity	NPD2235	Phase 2
0.7039	Intermediate Similarity	NPD2424	Discontinued
0.7037	Intermediate Similarity	NPD7075	Discontinued
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7022	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3496	Discontinued
0.7019	Intermediate Similarity	NPD5402	Approved
0.7013	Intermediate Similarity	NPD6190	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD6111	Discontinued
0.6993	Remote Similarity	NPD5177	Phase 3
0.6986	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5735	Approved
0.6978	Remote Similarity	NPD5536	Phase 2
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4108	Discontinued
0.6951	Remote Similarity	NPD5494	Approved
0.695	Remote Similarity	NPD6516	Phase 2
0.695	Remote Similarity	NPD5125	Phase 3
0.695	Remote Similarity	NPD5846	Approved
0.695	Remote Similarity	NPD5126	Approved
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7526	Approved
0.6943	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD52	Approved
0.6939	Remote Similarity	NPD3180	Approved
0.6939	Remote Similarity	NPD3179	Approved
0.6939	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD7212	Phase 2
0.6923	Remote Similarity	NPD7213	Phase 3
0.6923	Remote Similarity	NPD6799	Approved
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD968	Approved
0.6914	Remote Similarity	NPD2563	Approved
0.6914	Remote Similarity	NPD2560	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6913	Remote Similarity	NPD2238	Phase 2
0.6908	Remote Similarity	NPD6099	Approved
0.6908	Remote Similarity	NPD6100	Approved
0.6908	Remote Similarity	NPD2161	Phase 2
0.6901	Remote Similarity	NPD7549	Discontinued
0.6899	Remote Similarity	NPD5403	Approved
0.6899	Remote Similarity	NPD2122	Discontinued
0.6894	Remote Similarity	NPD3384	Approved
0.6894	Remote Similarity	NPD6801	Discontinued
0.6894	Remote Similarity	NPD3383	Approved
0.6894	Remote Similarity	NPD3382	Approved
0.6892	Remote Similarity	NPD6798	Discontinued
0.6889	Remote Similarity	NPD3022	Approved
0.6889	Remote Similarity	NPD3021	Approved
0.6879	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7447	Phase 1
0.6868	Remote Similarity	NPD7680	Approved
0.6867	Remote Similarity	NPD6232	Discontinued
0.6867	Remote Similarity	NPD6355	Discontinued
0.6867	Remote Similarity	NPD447	Suspended
0.6867	Remote Similarity	NPD4340	Discontinued
0.6863	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD821	Approved
0.6859	Remote Similarity	NPD7124	Phase 2
0.6857	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7819	Suspended
0.6849	Remote Similarity	NPD6584	Phase 3
0.6846	Remote Similarity	NPD4062	Phase 3
0.6846	Remote Similarity	NPD2674	Phase 3
0.6839	Remote Similarity	NPD4535	Phase 3
0.6839	Remote Similarity	NPD6331	Phase 2
0.6839	Remote Similarity	NPD1878	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