NPASS Compound

Structure

NPC107478 OpenBabel07101718312D 28 29 0 0 1 0 0 0 0 0999 V2000 -6.9282 -1.0000 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 -5.1962 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 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 1.7321 -0.0000 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 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 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 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 -3.4641 -1.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 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 8 1 0 0 0 0 4 7 1 0 0 0 0 4 9 2 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 13 2 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 26 1 0 0 0 0 10 5 1 6 0 0 0 10 12 1 0 0 0 0 10 27 1 0 0 0 0 11 6 1 1 0 0 0 11 14 1 0 0 0 0 11 28 1 0 0 0 0 12 20 1 1 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 27 1 1 0 0 0 17 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	126.03
Volume:	122.237
LogP:	0.148
LogD:	0.544
LogS:	-0.287
# Rotatable Bonds:	2
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	2.491
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	3.530283720465377e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.214
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.444
30% Bioavailability (F30%):	0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.787
Plasma Protein Binding (PPB):	50.35667419433594%
Volume Distribution (VD):	0.876
Pgp-substrate:	75.18346405029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.473
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.487
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.684
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	7.185
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.177
AMES Toxicity:	0.866
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.274
Carcinogencity:	0.922
Eye Corrosion:	0.198
Eye Irritation:	0.986
Respiratory Toxicity:	0.319

Download Data

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

Natural Product: NPC107478

Natural Product ID:	NPC107478
*Common Name:**	(+)-(7S,8S)-Syringylglycerol8-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	AAZJIDQNEUWCEO-FOWLYOOKSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-25-8-3-7(4-9(26-2)13(8)21)12(20)10(5-18)27-17-16(24)15(23)14(22)11(6-19)28-17/h3-4,10-12,14-24H,5-6H2,1-2H3/t10-,11+,12-,14+,15-,16+,17+/m0/s1
SMILES:	OC[C@@H]([C@H](c1cc(OC)c(c(c1)OC)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466928
PubChem CID:	44577288
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
NPO21454	Iodes cirrhosa	Species	Icacinaceae	Eukaryota	root	n.a.	n.a.	PMID[18327912]
NPO21454	Iodes cirrhosa	Species	Icacinaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	-28.4	%	PMID[502813]

☑ 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 NPC107478 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	1543
0.2-0.3	4532
0.3-0.4	10920
0.4-0.5	7471
0.5-0.6	5145
0.6-0.7	7347
0.7-0.8	3991
0.8-0.85	948
0.85-0.9	332
0.9-0.95	77
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC470270
0.9766	High Similarity	NPC132895
0.969	High Similarity	NPC13745
0.969	High Similarity	NPC251981
0.969	High Similarity	NPC48863
0.9612	High Similarity	NPC215833
0.9612	High Similarity	NPC69513
0.9609	High Similarity	NPC65942
0.9609	High Similarity	NPC248307
0.9535	High Similarity	NPC299144
0.9478	High Similarity	NPC5262
0.9478	High Similarity	NPC189115
0.9478	High Similarity	NPC469559
0.9478	High Similarity	NPC472714
0.947	High Similarity	NPC195196
0.9462	High Similarity	NPC49074
0.9453	High Similarity	NPC307110
0.9403	High Similarity	NPC469661
0.9398	High Similarity	NPC212770
0.9398	High Similarity	NPC98777
0.9389	High Similarity	NPC35731
0.9389	High Similarity	NPC470881
0.9385	High Similarity	NPC162093
0.9338	High Similarity	NPC118385
0.9338	High Similarity	NPC187774
0.9338	High Similarity	NPC473045
0.9338	High Similarity	NPC472712
0.9338	High Similarity	NPC472713
0.9338	High Similarity	NPC473046
0.9338	High Similarity	NPC25292
0.9333	High Similarity	NPC475084
0.9323	High Similarity	NPC65530
0.9323	High Similarity	NPC59324
0.9313	High Similarity	NPC6836
0.927	High Similarity	NPC277867
0.927	High Similarity	NPC475096
0.927	High Similarity	NPC161700
0.9265	High Similarity	NPC473044
0.9248	High Similarity	NPC164857
0.9248	High Similarity	NPC52277
0.9248	High Similarity	NPC203230
0.9248	High Similarity	NPC177035
0.9248	High Similarity	NPC199459
0.9248	High Similarity	NPC242028
0.9237	High Similarity	NPC252833
0.9231	High Similarity	NPC80600
0.9231	High Similarity	NPC472024
0.9203	High Similarity	NPC99515
0.9203	High Similarity	NPC190714
0.9203	High Similarity	NPC125755
0.9179	High Similarity	NPC304152
0.9179	High Similarity	NPC138738
0.9179	High Similarity	NPC474039
0.9179	High Similarity	NPC470413
0.9173	High Similarity	NPC470236
0.916	High Similarity	NPC470096
0.916	High Similarity	NPC470095
0.9154	High Similarity	NPC26653
0.9154	High Similarity	NPC248355
0.9154	High Similarity	NPC166040
0.9154	High Similarity	NPC270849
0.9137	High Similarity	NPC227902
0.9137	High Similarity	NPC39657
0.9134	High Similarity	NPC165375
0.9134	High Similarity	NPC220598
0.9124	High Similarity	NPC37793
0.9124	High Similarity	NPC252169
0.9104	High Similarity	NPC172818
0.9104	High Similarity	NPC25695
0.9104	High Similarity	NPC104167
0.9098	High Similarity	NPC170694
0.9091	High Similarity	NPC160991
0.9091	High Similarity	NPC201587
0.9091	High Similarity	NPC16208
0.9091	High Similarity	NPC7903
0.9091	High Similarity	NPC184447
0.9091	High Similarity	NPC35932
0.9091	High Similarity	NPC253105
0.9084	High Similarity	NPC262606
0.9077	High Similarity	NPC302378
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	NPC76176
0.9058	High Similarity	NPC297342
0.9058	High Similarity	NPC138227
0.9058	High Similarity	NPC469313
0.9044	High Similarity	NPC177868
0.9023	High Similarity	NPC294166
0.9023	High Similarity	NPC115022
0.9023	High Similarity	NPC25821
0.9015	High Similarity	NPC166168
0.9015	High Similarity	NPC9912
0.9015	High Similarity	NPC475067
0.9015	High Similarity	NPC472597
0.9008	High Similarity	NPC476968
0.9008	High Similarity	NPC170844
0.9007	High Similarity	NPC55158
0.9007	High Similarity	NPC286235
0.9007	High Similarity	NPC106138
0.9007	High Similarity	NPC51328
0.9	High Similarity	NPC15538
0.9	High Similarity	NPC473480
0.8992	High Similarity	NPC12308
0.8986	High Similarity	NPC12728
0.8986	High Similarity	NPC185071
0.8978	High Similarity	NPC472711
0.8976	High Similarity	NPC49341
0.8963	High Similarity	NPC157554
0.8955	High Similarity	NPC87696
0.8955	High Similarity	NPC187194
0.8955	High Similarity	NPC244983
0.8955	High Similarity	NPC310854
0.8955	High Similarity	NPC326095
0.8947	High Similarity	NPC85799
0.8947	High Similarity	NPC26080
0.8947	High Similarity	NPC303422
0.8947	High Similarity	NPC165686
0.8944	High Similarity	NPC218041
0.8944	High Similarity	NPC9933
0.8944	High Similarity	NPC182368
0.8944	High Similarity	NPC260781
0.8944	High Similarity	NPC145979
0.8944	High Similarity	NPC469707
0.8944	High Similarity	NPC472710
0.8944	High Similarity	NPC214326
0.8944	High Similarity	NPC225815
0.8944	High Similarity	NPC469706
0.8944	High Similarity	NPC185955
0.8944	High Similarity	NPC472709
0.8939	High Similarity	NPC469614
0.8939	High Similarity	NPC469612
0.8939	High Similarity	NPC472338
0.8931	High Similarity	NPC98631
0.8931	High Similarity	NPC206615
0.8931	High Similarity	NPC186843
0.8931	High Similarity	NPC470213
0.8929	High Similarity	NPC212890
0.8913	High Similarity	NPC140502
0.8913	High Similarity	NPC48309
0.8905	High Similarity	NPC106944
0.8905	High Similarity	NPC210478
0.8897	High Similarity	NPC283949
0.8889	High Similarity	NPC238243
0.8889	High Similarity	NPC236522
0.8889	High Similarity	NPC184938
0.8889	High Similarity	NPC234333
0.8889	High Similarity	NPC101624
0.8889	High Similarity	NPC260898
0.8889	High Similarity	NPC47398
0.8881	High Similarity	NPC471391
0.8881	High Similarity	NPC471390
0.8872	High Similarity	NPC121376
0.8872	High Similarity	NPC474017
0.8872	High Similarity	NPC469613
0.8872	High Similarity	NPC309787
0.8872	High Similarity	NPC469625
0.8872	High Similarity	NPC30043
0.8864	High Similarity	NPC222004
0.8864	High Similarity	NPC470258
0.8864	High Similarity	NPC210623
0.8864	High Similarity	NPC218856
0.8864	High Similarity	NPC190629
0.8864	High Similarity	NPC3439
0.8864	High Similarity	NPC226788
0.8864	High Similarity	NPC228769
0.8864	High Similarity	NPC285339
0.8864	High Similarity	NPC273295
0.8864	High Similarity	NPC470633
0.8864	High Similarity	NPC202582
0.8857	High Similarity	NPC477702
0.8849	High Similarity	NPC46092
0.8849	High Similarity	NPC255566
0.8849	High Similarity	NPC81638
0.8849	High Similarity	NPC185307
0.8849	High Similarity	NPC477898
0.8849	High Similarity	NPC470950
0.8849	High Similarity	NPC113680
0.8849	High Similarity	NPC278961
0.8849	High Similarity	NPC298317
0.8841	High Similarity	NPC210192
0.8832	High Similarity	NPC100389
0.8832	High Similarity	NPC226005
0.8828	High Similarity	NPC470804
0.8828	High Similarity	NPC266045
0.8824	High Similarity	NPC197723
0.8824	High Similarity	NPC306441
0.8824	High Similarity	NPC3293
0.8824	High Similarity	NPC138350
0.8824	High Similarity	NPC40664
0.8824	High Similarity	NPC165482
0.8824	High Similarity	NPC16435
0.8819	High Similarity	NPC21902
0.8815	High Similarity	NPC287745
0.8815	High Similarity	NPC476411
0.8815	High Similarity	NPC130496
0.8815	High Similarity	NPC188555
0.8806	High Similarity	NPC470752

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 NPC107478 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	874
0.2-0.3	2078
0.3-0.4	2810
0.4-0.5	1588
0.5-0.6	915
0.6-0.7	495
0.7-0.8	76
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9008	High Similarity	NPD3027	Phase 3
0.8611	High Similarity	NPD1653	Approved
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7266	Discontinued
0.8296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3705	Approved
0.8258	Intermediate Similarity	NPD1091	Approved
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6234	Discontinued
0.8089	Intermediate Similarity	NPD7228	Approved
0.8038	Intermediate Similarity	NPD7054	Approved
0.803	Intermediate Similarity	NPD1357	Approved
0.8013	Intermediate Similarity	NPD37	Approved
0.7987	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD7074	Phase 3
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4966	Approved
0.7969	Intermediate Similarity	NPD228	Approved
0.7931	Intermediate Similarity	NPD6674	Discontinued
0.7868	Intermediate Similarity	NPD2983	Phase 2
0.7868	Intermediate Similarity	NPD2982	Phase 2
0.7862	Intermediate Similarity	NPD3818	Discontinued
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7794	Intermediate Similarity	NPD2981	Phase 2
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD3018	Phase 2
0.773	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1934	Approved
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7240	Approved
0.7547	Intermediate Similarity	NPD7199	Phase 2
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	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2978	Approved
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4749	Approved
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1610	Phase 2
0.7448	Intermediate Similarity	NPD230	Phase 1
0.7444	Intermediate Similarity	NPD5283	Phase 1
0.7426	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD2801	Approved
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7843	Approved
0.7349	Intermediate Similarity	NPD7685	Pre-registration
0.7349	Intermediate Similarity	NPD6559	Discontinued
0.7346	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7328	Intermediate Similarity	NPD2684	Approved
0.7324	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7294	Intermediate Similarity	NPD6843	Phase 3
0.7294	Intermediate Similarity	NPD6841	Approved
0.7294	Intermediate Similarity	NPD6842	Approved
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.726	Intermediate Similarity	NPD1558	Phase 1
0.7237	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2219	Phase 1
0.7237	Intermediate Similarity	NPD6190	Approved
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7233	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4237	Approved
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD3060	Approved
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD422	Phase 1
0.72	Intermediate Similarity	NPD1375	Discontinued
0.72	Intermediate Similarity	NPD3540	Phase 1
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD4678	Approved
0.7197	Intermediate Similarity	NPD4675	Approved
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7134	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3539	Phase 1
0.7123	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD290	Approved
0.7118	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4538	Approved
0.7114	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5124	Phase 1
0.7095	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.707	Intermediate Similarity	NPD3687	Approved
0.707	Intermediate Similarity	NPD3686	Approved
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD8455	Phase 2
0.7056	Intermediate Similarity	NPD7680	Approved
0.7051	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7027	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD291	Approved
0.7	Intermediate Similarity	NPD6111	Discontinued
0.6993	Remote Similarity	NPD5177	Phase 3
0.6978	Remote Similarity	NPD5536	Phase 2
0.6974	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3787	Discontinued
0.697	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5773	Approved
0.6957	Remote Similarity	NPD5772	Approved
0.6954	Remote Similarity	NPD5588	Approved
0.6954	Remote Similarity	NPD5960	Phase 3
0.6954	Remote Similarity	NPD4108	Discontinued
0.695	Remote Similarity	NPD5125	Phase 3
0.695	Remote Similarity	NPD5126	Approved
0.6948	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8651	Approved
0.6933	Remote Similarity	NPD6653	Approved
0.6933	Remote Similarity	NPD7075	Discontinued
0.6928	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1242	Phase 1
0.6923	Remote Similarity	NPD1774	Approved
0.6918	Remote Similarity	NPD9494	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6913	Remote Similarity	NPD2238	Phase 2
0.6903	Remote Similarity	NPD2677	Approved
0.6892	Remote Similarity	NPD3145	Approved
0.6892	Remote Similarity	NPD3144	Approved
0.6889	Remote Similarity	NPD556	Approved
0.6889	Remote Similarity	NPD4750	Phase 3
0.6887	Remote Similarity	NPD7097	Phase 1
0.6883	Remote Similarity	NPD4162	Approved
0.6879	Remote Similarity	NPD4123	Phase 3
0.6875	Remote Similarity	NPD3685	Discontinued
0.687	Remote Similarity	NPD940	Approved
0.687	Remote Similarity	NPD846	Approved
0.6859	Remote Similarity	NPD7124	Phase 2
0.6846	Remote Similarity	NPD6233	Phase 2
0.6845	Remote Similarity	NPD7473	Discontinued
0.6839	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD4110	Phase 3
0.6839	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD9384	Approved
0.6831	Remote Similarity	NPD9381	Approved
0.6818	Remote Similarity	NPD2424	Discontinued
0.6815	Remote Similarity	NPD7212	Phase 2
0.6815	Remote Similarity	NPD7213	Phase 3
0.681	Remote Similarity	NPD5402	Approved
0.6806	Remote Similarity	NPD2231	Phase 2
0.6806	Remote Similarity	NPD2235	Phase 2
0.6805	Remote Similarity	NPD3751	Discontinued
0.6797	Remote Similarity	NPD6100	Approved
0.6797	Remote Similarity	NPD9296	Approved
0.6797	Remote Similarity	NPD6099	Approved
0.6791	Remote Similarity	NPD968	Approved
0.679	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3496	Discontinued
0.6776	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4739	Approved
0.6772	Remote Similarity	NPD7447	Phase 1
0.6772	Remote Similarity	NPD3158	Phase 1
0.6772	Remote Similarity	NPD3157	Approved
0.6759	Remote Similarity	NPD9622	Approved
0.6759	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5735	Approved
0.6753	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5763	Approved
0.6753	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5762	Approved
0.6752	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5494	Approved
0.6741	Remote Similarity	NPD1358	Approved
0.6735	Remote Similarity	NPD6584	Phase 3
0.673	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.673	Remote Similarity	NPD52	Approved
0.673	Remote Similarity	NPD7526	Approved
0.6713	Remote Similarity	NPD6516	Phase 2
0.6713	Remote Similarity	NPD5846	Approved
0.6711	Remote Similarity	NPD3179	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