NPASS Compound

Structure

NPC469364 OpenBabel07101719152D 48 51 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 3.4641 -4.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 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 0.5000 0.0000 C 0 0 1 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 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 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 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -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 3 0 0 0 0 0 0 0 0 0 2.5981 -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 1 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 42 1 0 0 0 0 3 16 2 0 0 0 0 4 6 1 0 0 0 0 4 14 2 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 43 1 0 0 0 0 10 21 1 0 0 0 0 11 32 1 0 0 0 0 12 18 2 0 0 0 0 12 44 1 0 0 0 0 13 45 1 0 0 0 0 15 33 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 18 28 1 0 0 0 0 19 11 1 1 0 0 0 19 22 1 0 0 0 0 19 46 1 0 0 0 0 20 13 1 1 0 0 0 20 23 1 0 0 0 0 20 47 1 0 0 0 0 21 34 2 0 0 0 0 21 43 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 37 1 1 0 0 0 25 27 1 0 0 0 0 25 38 1 1 0 0 0 26 30 1 0 0 0 0 26 39 1 6 0 0 0 27 31 1 0 0 0 0 27 40 1 6 0 0 0 28 41 2 0 0 0 0 28 42 1 0 0 0 0 29 44 1 0 0 0 0 29 48 1 0 0 0 0 30 45 1 1 0 0 0 30 46 1 0 0 0 0 31 47 1 0 0 0 0 31 48 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	686.24
Volume:	641.485
LogP:	-0.228
LogD:	-0.494
LogS:	-2.382
# Rotatable Bonds:	14
TPSA:	260.59
# H-Bond Aceptor:	17
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.062
Synthetic Accessibility Score:	5.237
Fsp3:	0.613
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:	-6.207
MDCK Permeability:	0.000253310747211799
Pgp-inhibitor:	0.011
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	42.56897735595703%
Volume Distribution (VD):	0.363
Pgp-substrate:	18.8214111328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.023
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.183
Carcinogencity:	0.874
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC469364

Natural Product ID:	NPC469364
*Common Name:**	Excelside B
IUPAC Name:	methyl (4S,5E)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:	excelside B
Standard InCHIKey:	FVQYDVAAZIXQID-AZCYGJOYSA-N
Standard InCHI:	InChI=1S/C31H42O17/c1-3-16-17(10-21(34)43-9-8-14-4-6-15(33)7-5-14)18(28(41)42-2)12-44-29(16)48-31-27(40)25(38)23(36)20(47-31)13-45-30-26(39)24(37)22(35)19(11-32)46-30/h3-7,12,17,19-20,22-27,29-33,35-40H,8-11,13H2,1-2H3/b16-3+/t17-,19+,20+,22+,23+,24-,25-,26+,27+,29?,30+,31-/m0/s1
SMILES:	C/C=C1/C(OC=C([C@H]1CC(=O)OCCc1ccc(cc1)O)C(=O)OC)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076843
PubChem CID:	46881042
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000781]
NPO19884	Fraxinus excelsior	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
Others	5

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-30.8	%	PMID[509867]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-16.7	%	PMID[509867]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-22.7	%	PMID[509867]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-24.3	%	PMID[509867]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Activity	=	24.8	%	PMID[509867]

☑ 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 NPC469364 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	288
0.1-0.2	1077
0.2-0.3	2696
0.3-0.4	6288
0.4-0.5	10601
0.5-0.6	8287
0.6-0.7	10656
0.7-0.8	2531
0.8-0.85	183
0.85-0.9	73
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65262
1.0	High Similarity	NPC101686
0.9769	High Similarity	NPC169398
0.9343	High Similarity	NPC469367
0.9286	High Similarity	NPC23677
0.9281	High Similarity	NPC212808
0.927	High Similarity	NPC296643
0.9203	High Similarity	NPC293154
0.9185	High Similarity	NPC472132
0.9098	High Similarity	NPC46137
0.9098	High Similarity	NPC235294
0.9	High Similarity	NPC202391
0.9	High Similarity	NPC296659
0.8971	High Similarity	NPC263829
0.8955	High Similarity	NPC138777
0.8955	High Similarity	NPC246869
0.8955	High Similarity	NPC225384
0.8947	High Similarity	NPC469549
0.8939	High Similarity	NPC106677
0.8913	High Similarity	NPC220936
0.8913	High Similarity	NPC31745
0.8797	High Similarity	NPC471881
0.8797	High Similarity	NPC35288
0.8797	High Similarity	NPC471882
0.8797	High Similarity	NPC156692
0.8797	High Similarity	NPC45224
0.8797	High Similarity	NPC288416
0.8797	High Similarity	NPC173150
0.8759	High Similarity	NPC69367
0.8741	High Similarity	NPC474268
0.8741	High Similarity	NPC119773
0.8741	High Similarity	NPC475539
0.8741	High Similarity	NPC143246
0.8732	High Similarity	NPC251062
0.8732	High Similarity	NPC63304
0.8732	High Similarity	NPC184464
0.8722	High Similarity	NPC61181
0.8722	High Similarity	NPC471157
0.8705	High Similarity	NPC476376
0.8702	High Similarity	NPC52097
0.869	High Similarity	NPC96599
0.8676	High Similarity	NPC254819
0.8676	High Similarity	NPC478255
0.8676	High Similarity	NPC281798
0.8671	High Similarity	NPC475528
0.8667	High Similarity	NPC253595
0.8662	High Similarity	NPC186296
0.8662	High Similarity	NPC475213
0.8662	High Similarity	NPC152796
0.8657	High Similarity	NPC103533
0.8652	High Similarity	NPC476385
0.8652	High Similarity	NPC47471
0.8652	High Similarity	NPC134405
0.8652	High Similarity	NPC476377
0.8647	High Similarity	NPC83218
0.8647	High Similarity	NPC126991
0.8643	High Similarity	NPC68092
0.8643	High Similarity	NPC205195
0.8643	High Similarity	NPC89105
0.8643	High Similarity	NPC197316
0.8643	High Similarity	NPC81515
0.8643	High Similarity	NPC472350
0.8643	High Similarity	NPC476383
0.8643	High Similarity	NPC64141
0.8633	High Similarity	NPC471345
0.863	High Similarity	NPC240592
0.863	High Similarity	NPC117346
0.8626	High Similarity	NPC11724
0.8626	High Similarity	NPC55608
0.8601	High Similarity	NPC77922
0.8601	High Similarity	NPC473281
0.8593	High Similarity	NPC225307
0.8582	High Similarity	NPC252114
0.8582	High Similarity	NPC475530
0.8582	High Similarity	NPC473799
0.8581	High Similarity	NPC246893
0.8571	High Similarity	NPC260425
0.8551	High Similarity	NPC28637
0.8551	High Similarity	NPC114116
0.855	High Similarity	NPC476872
0.8531	High Similarity	NPC298257
0.8531	High Similarity	NPC476384
0.8531	High Similarity	NPC119537
0.8531	High Similarity	NPC205864
0.8531	High Similarity	NPC247032
0.8531	High Similarity	NPC478250
0.8531	High Similarity	NPC476375
0.8531	High Similarity	NPC476381
0.8531	High Similarity	NPC269141
0.8531	High Similarity	NPC96795
0.8531	High Similarity	NPC112
0.8531	High Similarity	NPC476397
0.8531	High Similarity	NPC175214
0.8531	High Similarity	NPC264632
0.8531	High Similarity	NPC76406
0.8531	High Similarity	NPC476378
0.8531	High Similarity	NPC476380
0.8521	High Similarity	NPC137501
0.8521	High Similarity	NPC159387
0.8521	High Similarity	NPC154262
0.8521	High Similarity	NPC7518
0.8511	High Similarity	NPC49597
0.8503	High Similarity	NPC182350
0.8489	Intermediate Similarity	NPC471029
0.8483	Intermediate Similarity	NPC473147
0.8483	Intermediate Similarity	NPC37838
0.8478	Intermediate Similarity	NPC473285
0.8472	Intermediate Similarity	NPC64195
0.8472	Intermediate Similarity	NPC300894
0.8472	Intermediate Similarity	NPC141455
0.8472	Intermediate Similarity	NPC196063
0.8472	Intermediate Similarity	NPC471028
0.8472	Intermediate Similarity	NPC296954
0.8462	Intermediate Similarity	NPC265648
0.8462	Intermediate Similarity	NPC222433
0.8446	Intermediate Similarity	NPC158546
0.8446	Intermediate Similarity	NPC289021
0.8446	Intermediate Similarity	NPC474620
0.844	Intermediate Similarity	NPC78363
0.8435	Intermediate Similarity	NPC478234
0.8429	Intermediate Similarity	NPC476870
0.8425	Intermediate Similarity	NPC473149
0.8414	Intermediate Similarity	NPC252292
0.8414	Intermediate Similarity	NPC476382
0.8414	Intermediate Similarity	NPC34587
0.8414	Intermediate Similarity	NPC100998
0.8414	Intermediate Similarity	NPC34927
0.8403	Intermediate Similarity	NPC204644
0.8403	Intermediate Similarity	NPC105005
0.8394	Intermediate Similarity	NPC295970
0.8392	Intermediate Similarity	NPC80098
0.8389	Intermediate Similarity	NPC106818
0.837	Intermediate Similarity	NPC123704
0.8357	Intermediate Similarity	NPC287597
0.8357	Intermediate Similarity	NPC34293
0.8357	Intermediate Similarity	NPC886
0.8357	Intermediate Similarity	NPC471883
0.8356	Intermediate Similarity	NPC229505
0.8356	Intermediate Similarity	NPC291153
0.8346	Intermediate Similarity	NPC469686
0.8345	Intermediate Similarity	NPC194938
0.8344	Intermediate Similarity	NPC475484
0.8333	Intermediate Similarity	NPC148080
0.8333	Intermediate Similarity	NPC469705
0.8333	Intermediate Similarity	NPC282409
0.8333	Intermediate Similarity	NPC319995
0.8333	Intermediate Similarity	NPC17968
0.8333	Intermediate Similarity	NPC289415
0.8333	Intermediate Similarity	NPC469623
0.8333	Intermediate Similarity	NPC87403
0.8333	Intermediate Similarity	NPC470122
0.8333	Intermediate Similarity	NPC469702
0.8322	Intermediate Similarity	NPC475379
0.8311	Intermediate Similarity	NPC470933
0.8311	Intermediate Similarity	NPC476398
0.8311	Intermediate Similarity	NPC259347
0.8311	Intermediate Similarity	NPC476386
0.8311	Intermediate Similarity	NPC94871
0.8311	Intermediate Similarity	NPC473427
0.8311	Intermediate Similarity	NPC306890
0.8311	Intermediate Similarity	NPC471062
0.8311	Intermediate Similarity	NPC478242
0.8311	Intermediate Similarity	NPC478236
0.8308	Intermediate Similarity	NPC148055
0.8299	Intermediate Similarity	NPC97240
0.8299	Intermediate Similarity	NPC232992
0.8299	Intermediate Similarity	NPC175275
0.8284	Intermediate Similarity	NPC476142
0.8276	Intermediate Similarity	NPC263397
0.8276	Intermediate Similarity	NPC302286
0.8276	Intermediate Similarity	NPC88754
0.8276	Intermediate Similarity	NPC116104
0.8276	Intermediate Similarity	NPC237872
0.8271	Intermediate Similarity	NPC476445
0.8271	Intermediate Similarity	NPC469548
0.8271	Intermediate Similarity	NPC201402
0.8271	Intermediate Similarity	NPC469704
0.8271	Intermediate Similarity	NPC469703
0.8271	Intermediate Similarity	NPC476448
0.8271	Intermediate Similarity	NPC160854
0.8267	Intermediate Similarity	NPC203664
0.8264	Intermediate Similarity	NPC46644
0.8264	Intermediate Similarity	NPC79908
0.8261	Intermediate Similarity	NPC477293
0.8261	Intermediate Similarity	NPC477294
0.8261	Intermediate Similarity	NPC229784
0.8255	Intermediate Similarity	NPC470927
0.8255	Intermediate Similarity	NPC188393
0.8255	Intermediate Similarity	NPC35097
0.8255	Intermediate Similarity	NPC257970
0.8255	Intermediate Similarity	NPC470934
0.8255	Intermediate Similarity	NPC107197
0.8252	Intermediate Similarity	NPC220942
0.8252	Intermediate Similarity	NPC324262
0.8252	Intermediate Similarity	NPC171134
0.8252	Intermediate Similarity	NPC321638
0.8252	Intermediate Similarity	NPC321184
0.8252	Intermediate Similarity	NPC328273
0.8252	Intermediate Similarity	NPC62800
0.8243	Intermediate Similarity	NPC220282

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 NPC469364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	710
0.2-0.3	1564
0.3-0.4	2769
0.4-0.5	2191
0.5-0.6	1239
0.6-0.7	400
0.7-0.8	36
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8643	High Similarity	NPD7266	Discontinued
0.7806	Intermediate Similarity	NPD8455	Phase 2
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD7472	Approved
0.7597	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD7054	Approved
0.7561	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1091	Approved
0.7551	Intermediate Similarity	NPD7097	Phase 1
0.755	Intermediate Similarity	NPD6190	Approved
0.753	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.747	Intermediate Similarity	NPD6797	Phase 2
0.7432	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7337	Intermediate Similarity	NPD8313	Approved
0.7337	Intermediate Similarity	NPD8312	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD37	Approved
0.7186	Intermediate Similarity	NPD3818	Discontinued
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7179	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6234	Discontinued
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.716	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4966	Approved
0.7153	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6653	Approved
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7089	Intermediate Similarity	NPD5403	Approved
0.7081	Intermediate Similarity	NPD6801	Discontinued
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD230	Phase 1
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8166	Discontinued
0.7019	Intermediate Similarity	NPD7411	Suspended
0.6988	Remote Similarity	NPD7199	Phase 2
0.698	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD6674	Discontinued
0.6963	Remote Similarity	NPD1358	Approved
0.6962	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7843	Approved
0.6954	Remote Similarity	NPD4340	Discontinued
0.6944	Remote Similarity	NPD422	Phase 1
0.6933	Remote Similarity	NPD4062	Phase 3
0.6913	Remote Similarity	NPD3027	Phase 3
0.6899	Remote Similarity	NPD6799	Approved
0.6892	Remote Similarity	NPD5736	Approved
0.689	Remote Similarity	NPD5402	Approved
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3134	Approved
0.6884	Remote Similarity	NPD969	Suspended
0.6875	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD6362	Approved
0.6867	Remote Similarity	NPD3764	Approved
0.6864	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6166	Phase 2
0.6864	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4908	Phase 1
0.6835	Remote Similarity	NPD5058	Phase 3
0.6824	Remote Similarity	NPD5647	Approved
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3750	Approved
0.681	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7157	Approved
0.6806	Remote Similarity	NPD5125	Phase 3
0.6806	Remote Similarity	NPD5126	Approved
0.6805	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7095	Approved
0.6795	Remote Similarity	NPD1549	Phase 2
0.6795	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD3817	Phase 2
0.6786	Remote Similarity	NPD8127	Discontinued
0.6776	Remote Similarity	NPD1613	Approved
0.6776	Remote Similarity	NPD4060	Phase 1
0.6776	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1934	Approved
0.6759	Remote Similarity	NPD3847	Discontinued
0.6755	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5844	Phase 1
0.6742	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6005	Phase 3
0.6731	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6004	Phase 3
0.6731	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6002	Phase 3
0.6727	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7819	Suspended
0.6721	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8319	Approved
0.672	Remote Similarity	NPD8320	Phase 1
0.6715	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3705	Approved
0.6712	Remote Similarity	NPD1535	Discovery
0.6711	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6663	Approved
0.671	Remote Similarity	NPD1510	Phase 2
0.6702	Remote Similarity	NPD7585	Approved
0.669	Remote Similarity	NPD1778	Approved
0.6688	Remote Similarity	NPD2424	Discontinued
0.6686	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD1481	Phase 2
0.6649	Remote Similarity	NPD7583	Approved
0.6647	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD3787	Discontinued
0.6646	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6599	Discontinued
0.6646	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4538	Approved
0.6645	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4536	Approved
0.6644	Remote Similarity	NPD3267	Approved
0.6644	Remote Similarity	NPD3266	Approved
0.6643	Remote Similarity	NPD9493	Approved
0.6629	Remote Similarity	NPD8434	Phase 2
0.6629	Remote Similarity	NPD8150	Discontinued
0.6627	Remote Similarity	NPD2801	Approved
0.6627	Remote Similarity	NPD1465	Phase 2
0.6625	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5763	Approved
0.6624	Remote Similarity	NPD5762	Approved
0.6623	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD6832	Phase 2
0.6621	Remote Similarity	NPD1357	Approved
0.662	Remote Similarity	NPD2629	Approved
0.6599	Remote Similarity	NPD1610	Phase 2
0.6596	Remote Similarity	NPD5535	Approved
0.6594	Remote Similarity	NPD290	Approved
0.6577	Remote Similarity	NPD8651	Approved
0.6576	Remote Similarity	NPD7699	Phase 2
0.6576	Remote Similarity	NPD7700	Phase 2
0.6569	Remote Similarity	NPD5048	Discontinued
0.6561	Remote Similarity	NPD2239	Approved
0.6561	Remote Similarity	NPD2438	Suspended
0.6561	Remote Similarity	NPD2796	Approved
0.6561	Remote Similarity	NPD2240	Approved
0.6561	Remote Similarity	NPD7584	Approved
0.6558	Remote Similarity	NPD1240	Approved
0.6552	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1241	Discontinued
0.6543	Remote Similarity	NPD3536	Discontinued
0.6533	Remote Similarity	NPD3094	Phase 2
0.6532	Remote Similarity	NPD7473	Discontinued
0.6531	Remote Similarity	NPD3496	Discontinued
0.6528	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7440	Discontinued
0.6515	Remote Similarity	NPD2934	Approved
0.6515	Remote Similarity	NPD2933	Approved
0.6513	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7783	Phase 2
0.651	Remote Similarity	NPD3685	Discontinued
0.651	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5585	Approved
0.6506	Remote Similarity	NPD6677	Suspended
0.6505	Remote Similarity	NPD6778	Approved
0.6505	Remote Similarity	NPD6779	Approved
0.6505	Remote Similarity	NPD6780	Approved
0.6505	Remote Similarity	NPD6782	Approved
0.6505	Remote Similarity	NPD6777	Approved
0.6505	Remote Similarity	NPD6781	Approved
0.6505	Remote Similarity	NPD6776	Approved
0.6503	Remote Similarity	NPD6273	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