NPASS Compound

Structure

NPC476448 OpenBabel07101718312D 32 34 0 0 1 0 0 0 0 0999 V2000 -5.2437 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 3.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8417 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 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 -4.3776 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 29 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 21 1 0 0 0 0 10 30 1 0 0 0 0 11 1 1 6 0 0 0 11 31 1 0 0 0 0 13 23 1 0 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 18 27 1 0 0 0 0 19 31 1 6 0 0 0 19 32 1 0 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 21 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.19
Volume:	434.886
LogP:	-0.19
LogD:	-0.899
LogS:	-2.375
# Rotatable Bonds:	9
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.536
Fsp3:	0.714
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.378
MDCK Permeability:	2.6075182177009992e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.929
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	57.167198181152344%
Volume Distribution (VD):	0.334
Pgp-substrate:	35.836631774902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	1.235
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.651
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.931
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC476448

Natural Product ID:	NPC476448
*Common Name:**	2-(3,4-Dihydroxy-4-Hydroxymethyl-Tetrahydro-Furan-2-Yloxymethyl)-6-[(S)-3-(4-Hydroxy-Phenyl)-1-Methyl-Propoxy]-Tetrahydro-Pyran-3,4,5-Triol
IUPAC Name:	(2R,3R,4R,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QJVVGCSWIOLQDG-RQBDADRMSA-N
Standard InCHI:	InChI=1S/C21H32O11/c1-11(2-3-12-4-6-13(23)7-5-12)31-19-17(26)16(25)15(24)14(32-19)8-29-20-18(27)21(28,9-22)10-30-20/h4-7,11,14-20,22-28H,2-3,8-10H2,1H3/t11-,14+,15-,16+,17+,18-,19+,20+,21+/m0/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](O[C@H](CCc2ccc(cc2)O)C)[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL610676
PubChem CID:	46875817
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	3.6	%	PMID[547063]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	1.7	%	PMID[547063]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	0.7	%	PMID[547063]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	-4.5	%	PMID[547063]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	10.8	%	PMID[547063]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	21.8	%	PMID[547063]

☑ 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 NPC476448 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	248
0.1-0.2	1092
0.2-0.3	2886
0.3-0.4	8254
0.4-0.5	10943
0.5-0.6	10362
0.6-0.7	7191
0.7-0.8	1523
0.8-0.85	140
0.85-0.9	39
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476445
1.0	High Similarity	NPC469548
0.9912	High Similarity	NPC469702
0.9912	High Similarity	NPC282409
0.9573	High Similarity	NPC470907
0.9573	High Similarity	NPC232454
0.9573	High Similarity	NPC178449
0.9558	High Similarity	NPC148055
0.9487	High Similarity	NPC471067
0.9402	High Similarity	NPC55608
0.9381	High Similarity	NPC157338
0.9316	High Similarity	NPC469704
0.9316	High Similarity	NPC201402
0.9316	High Similarity	NPC469703
0.9316	High Similarity	NPC160854
0.9256	High Similarity	NPC469687
0.925	High Similarity	NPC90318
0.9237	High Similarity	NPC469686
0.9052	High Similarity	NPC175771
0.9043	High Similarity	NPC313193
0.896	High Similarity	NPC478255
0.8952	High Similarity	NPC469549
0.8943	High Similarity	NPC471881
0.8943	High Similarity	NPC35288
0.8943	High Similarity	NPC471882
0.8943	High Similarity	NPC156692
0.8943	High Similarity	NPC45224
0.8943	High Similarity	NPC173150
0.8917	High Similarity	NPC266045
0.8862	High Similarity	NPC61181
0.8852	High Similarity	NPC287429
0.8819	High Similarity	NPC164172
0.879	High Similarity	NPC106677
0.879	High Similarity	NPC108659
0.879	High Similarity	NPC231607
0.879	High Similarity	NPC264900
0.879	High Similarity	NPC103533
0.879	High Similarity	NPC79715
0.875	High Similarity	NPC470881
0.874	High Similarity	NPC471095
0.874	High Similarity	NPC471066
0.872	High Similarity	NPC225307
0.871	High Similarity	NPC94179
0.8689	High Similarity	NPC52097
0.8689	High Similarity	NPC476142
0.8672	High Similarity	NPC6836
0.8661	High Similarity	NPC235294
0.8661	High Similarity	NPC46137
0.8651	High Similarity	NPC184092
0.864	High Similarity	NPC288416
0.8629	High Similarity	NPC470510
0.8618	High Similarity	NPC212176
0.8607	High Similarity	NPC11724
0.8594	High Similarity	NPC252833
0.8583	High Similarity	NPC17968
0.8583	High Similarity	NPC469705
0.8583	High Similarity	NPC470122
0.8571	High Similarity	NPC148982
0.856	High Similarity	NPC252114
0.856	High Similarity	NPC471157
0.855	High Similarity	NPC469696
0.8534	High Similarity	NPC264784
0.8527	High Similarity	NPC254398
0.8527	High Similarity	NPC25821
0.8525	High Similarity	NPC269242
0.8525	High Similarity	NPC476872
0.8525	High Similarity	NPC469412
0.8525	High Similarity	NPC198734
0.8516	High Similarity	NPC475824
0.8516	High Similarity	NPC246869
0.8516	High Similarity	NPC65942
0.8516	High Similarity	NPC225384
0.8516	High Similarity	NPC248307
0.8516	High Similarity	NPC138777
0.8516	High Similarity	NPC281798
0.8496	Intermediate Similarity	NPC47286
0.8485	Intermediate Similarity	NPC328273
0.8485	Intermediate Similarity	NPC171134
0.8485	Intermediate Similarity	NPC321638
0.8485	Intermediate Similarity	NPC321184
0.848	Intermediate Similarity	NPC83218
0.848	Intermediate Similarity	NPC126991
0.8462	Intermediate Similarity	NPC471883
0.8462	Intermediate Similarity	NPC169398
0.8462	Intermediate Similarity	NPC35731
0.845	Intermediate Similarity	NPC254275
0.845	Intermediate Similarity	NPC473924
0.8443	Intermediate Similarity	NPC60589
0.8443	Intermediate Similarity	NPC469708
0.8425	Intermediate Similarity	NPC158673
0.8417	Intermediate Similarity	NPC301651
0.8417	Intermediate Similarity	NPC473556
0.8409	Intermediate Similarity	NPC304152
0.8409	Intermediate Similarity	NPC195196
0.8397	Intermediate Similarity	NPC263829
0.8385	Intermediate Similarity	NPC28637
0.8372	Intermediate Similarity	NPC219677
0.837	Intermediate Similarity	NPC46092
0.8359	Intermediate Similarity	NPC307110
0.8358	Intermediate Similarity	NPC472711
0.8333	Intermediate Similarity	NPC52277
0.8333	Intermediate Similarity	NPC177035
0.8333	Intermediate Similarity	NPC123704
0.8333	Intermediate Similarity	NPC199459
0.8309	Intermediate Similarity	NPC470235
0.8309	Intermediate Similarity	NPC300894
0.8309	Intermediate Similarity	NPC141455
0.8309	Intermediate Similarity	NPC84181
0.8309	Intermediate Similarity	NPC196063
0.8309	Intermediate Similarity	NPC129417
0.8309	Intermediate Similarity	NPC296954
0.8309	Intermediate Similarity	NPC283995
0.8295	Intermediate Similarity	NPC472024
0.8295	Intermediate Similarity	NPC80600
0.8295	Intermediate Similarity	NPC474491
0.8271	Intermediate Similarity	NPC470413
0.8271	Intermediate Similarity	NPC101686
0.8271	Intermediate Similarity	NPC65262
0.8271	Intermediate Similarity	NPC138738
0.8271	Intermediate Similarity	NPC469364
0.8248	Intermediate Similarity	NPC18979
0.8235	Intermediate Similarity	NPC477898
0.8235	Intermediate Similarity	NPC478250
0.8235	Intermediate Similarity	NPC105005
0.8235	Intermediate Similarity	NPC185307
0.8235	Intermediate Similarity	NPC40305
0.8235	Intermediate Similarity	NPC470950
0.8231	Intermediate Similarity	NPC254819
0.8231	Intermediate Similarity	NPC476407
0.822	Intermediate Similarity	NPC30563
0.8217	Intermediate Similarity	NPC97326
0.8217	Intermediate Similarity	NPC270849
0.8217	Intermediate Similarity	NPC477294
0.8217	Intermediate Similarity	NPC248355
0.8217	Intermediate Similarity	NPC253595
0.8217	Intermediate Similarity	NPC166040
0.8217	Intermediate Similarity	NPC477293
0.8217	Intermediate Similarity	NPC26653
0.8217	Intermediate Similarity	NPC229784
0.8211	Intermediate Similarity	NPC477803
0.8209	Intermediate Similarity	NPC49597
0.8209	Intermediate Similarity	NPC81515
0.8209	Intermediate Similarity	NPC476383
0.8209	Intermediate Similarity	NPC64141
0.8209	Intermediate Similarity	NPC472350
0.8209	Intermediate Similarity	NPC68092
0.8209	Intermediate Similarity	NPC197316
0.8209	Intermediate Similarity	NPC89105
0.8197	Intermediate Similarity	NPC476266
0.8195	Intermediate Similarity	NPC469383
0.8188	Intermediate Similarity	NPC112861
0.8188	Intermediate Similarity	NPC229505
0.8182	Intermediate Similarity	NPC34293
0.8182	Intermediate Similarity	NPC287597
0.8182	Intermediate Similarity	NPC886
0.8182	Intermediate Similarity	NPC187194
0.8182	Intermediate Similarity	NPC107478
0.8175	Intermediate Similarity	NPC184464
0.8175	Intermediate Similarity	NPC251062
0.8168	Intermediate Similarity	NPC473285
0.8162	Intermediate Similarity	NPC472353
0.8162	Intermediate Similarity	NPC476356
0.816	Intermediate Similarity	NPC226712
0.8154	Intermediate Similarity	NPC262606
0.814	Intermediate Similarity	NPC302378
0.814	Intermediate Similarity	NPC232880
0.8136	Intermediate Similarity	NPC276061
0.8136	Intermediate Similarity	NPC474148
0.8134	Intermediate Similarity	NPC476376
0.8134	Intermediate Similarity	NPC260425
0.8134	Intermediate Similarity	NPC87777
0.8134	Intermediate Similarity	NPC262328
0.812	Intermediate Similarity	NPC101624
0.812	Intermediate Similarity	NPC79957
0.812	Intermediate Similarity	NPC123988
0.812	Intermediate Similarity	NPC184938
0.8116	Intermediate Similarity	NPC22150
0.8116	Intermediate Similarity	NPC38041
0.8116	Intermediate Similarity	NPC279298
0.8106	Intermediate Similarity	NPC294166
0.8106	Intermediate Similarity	NPC215037
0.8106	Intermediate Similarity	NPC115022
0.8106	Intermediate Similarity	NPC132895
0.8103	Intermediate Similarity	NPC37714
0.8103	Intermediate Similarity	NPC152384
0.8102	Intermediate Similarity	NPC186296
0.8095	Intermediate Similarity	NPC469927
0.8092	Intermediate Similarity	NPC9912
0.8092	Intermediate Similarity	NPC475067
0.8088	Intermediate Similarity	NPC159387
0.8088	Intermediate Similarity	NPC476385
0.8088	Intermediate Similarity	NPC7518
0.8088	Intermediate Similarity	NPC134405
0.8088	Intermediate Similarity	NPC47471
0.8088	Intermediate Similarity	NPC476377
0.8088	Intermediate Similarity	NPC154262
0.8088	Intermediate Similarity	NPC137501
0.8083	Intermediate Similarity	NPC42911
0.8083	Intermediate Similarity	NPC153795
0.8083	Intermediate Similarity	NPC290353

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 NPC476448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	692
0.2-0.3	1496
0.3-0.4	3042
0.4-0.5	2050
0.5-0.6	1272
0.6-0.7	354
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8209	Intermediate Similarity	NPD7266	Discontinued
0.816	Intermediate Similarity	NPD1091	Approved
0.7578	Intermediate Similarity	NPD5125	Phase 3
0.7578	Intermediate Similarity	NPD5126	Approved
0.7535	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD7843	Approved
0.7478	Intermediate Similarity	NPD2933	Approved
0.7478	Intermediate Similarity	NPD2934	Approved
0.7462	Intermediate Similarity	NPD3705	Approved
0.7414	Intermediate Similarity	NPD2860	Approved
0.7414	Intermediate Similarity	NPD2859	Approved
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7364	Intermediate Similarity	NPD1357	Approved
0.7323	Intermediate Similarity	NPD7157	Approved
0.7317	Intermediate Similarity	NPD2684	Approved
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7239	Intermediate Similarity	NPD3094	Phase 2
0.7227	Intermediate Similarity	NPD3020	Approved
0.7162	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD969	Suspended
0.7122	Intermediate Similarity	NPD1613	Approved
0.7122	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3021	Approved
0.712	Intermediate Similarity	NPD3022	Approved
0.7097	Intermediate Similarity	NPD290	Approved
0.7092	Intermediate Similarity	NPD7097	Phase 1
0.7092	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7068	Intermediate Similarity	NPD3092	Approved
0.7045	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5588	Approved
0.7039	Intermediate Similarity	NPD8455	Phase 2
0.7034	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2861	Phase 2
0.6991	Remote Similarity	NPD111	Approved
0.6986	Remote Similarity	NPD6190	Approved
0.6984	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7228	Approved
0.6972	Remote Similarity	NPD4538	Approved
0.6972	Remote Similarity	NPD4536	Approved
0.6972	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4908	Phase 1
0.6923	Remote Similarity	NPD6671	Approved
0.6912	Remote Similarity	NPD8651	Approved
0.6894	Remote Similarity	NPD1548	Phase 1
0.6894	Remote Similarity	NPD3091	Approved
0.6885	Remote Similarity	NPD1242	Phase 1
0.6885	Remote Similarity	NPD3028	Approved
0.6875	Remote Similarity	NPD228	Approved
0.6863	Remote Similarity	NPD37	Approved
0.6861	Remote Similarity	NPD4103	Phase 2
0.6861	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6234	Discontinued
0.6857	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1652	Phase 2
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD4966	Approved
0.6838	Remote Similarity	NPD3685	Discontinued
0.6838	Remote Similarity	NPD4659	Approved
0.6835	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7054	Approved
0.6818	Remote Similarity	NPD2978	Approved
0.6818	Remote Similarity	NPD2977	Approved
0.6818	Remote Similarity	NPD856	Approved
0.6818	Remote Similarity	NPD16	Approved
0.6815	Remote Similarity	NPD1610	Phase 2
0.681	Remote Similarity	NPD6559	Discontinued
0.681	Remote Similarity	NPD7685	Pre-registration
0.6809	Remote Similarity	NPD6407	Approved
0.6809	Remote Similarity	NPD6233	Phase 2
0.6809	Remote Similarity	NPD6405	Approved
0.6806	Remote Similarity	NPD5960	Phase 3
0.6791	Remote Similarity	NPD9384	Approved
0.6791	Remote Similarity	NPD9381	Approved
0.679	Remote Similarity	NPD7074	Phase 3
0.679	Remote Similarity	NPD7472	Approved
0.6783	Remote Similarity	NPD6653	Approved
0.6781	Remote Similarity	NPD2424	Discontinued
0.6779	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3818	Discontinued
0.6769	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7741	Discontinued
0.6767	Remote Similarity	NPD9545	Approved
0.6765	Remote Similarity	NPD2561	Approved
0.6765	Remote Similarity	NPD2562	Approved
0.6763	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5736	Approved
0.6761	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD968	Approved
0.6744	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4750	Phase 3
0.6715	Remote Similarity	NPD9622	Approved
0.6713	Remote Similarity	NPD5124	Phase 1
0.6713	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6355	Discontinued
0.6707	Remote Similarity	NPD7251	Discontinued
0.6694	Remote Similarity	NPD1809	Phase 2
0.6694	Remote Similarity	NPD844	Approved
0.6693	Remote Similarity	NPD1358	Approved
0.6692	Remote Similarity	NPD317	Approved
0.6692	Remote Similarity	NPD318	Approved
0.6691	Remote Similarity	NPD422	Phase 1
0.669	Remote Similarity	NPD7033	Discontinued
0.6689	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD5314	Approved
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD3179	Approved
0.6667	Remote Similarity	NPD3180	Approved
0.6646	Remote Similarity	NPD6797	Phase 2
0.6643	Remote Similarity	NPD4060	Phase 1
0.6643	Remote Similarity	NPD3059	Approved
0.6643	Remote Similarity	NPD3062	Approved
0.6643	Remote Similarity	NPD3061	Approved
0.6641	Remote Similarity	NPD2229	Approved
0.6641	Remote Similarity	NPD2234	Approved
0.6641	Remote Similarity	NPD2228	Approved
0.6623	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4380	Phase 2
0.6622	Remote Similarity	NPD4236	Phase 3
0.6622	Remote Similarity	NPD4237	Approved
0.662	Remote Similarity	NPD6798	Discontinued
0.662	Remote Similarity	NPD3764	Approved
0.6619	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7240	Approved
0.6599	Remote Similarity	NPD1375	Discontinued
0.6599	Remote Similarity	NPD5763	Approved
0.6599	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5762	Approved
0.6597	Remote Similarity	NPD4340	Discontinued
0.6597	Remote Similarity	NPD5735	Approved
0.6594	Remote Similarity	NPD4749	Approved
0.6575	Remote Similarity	NPD4108	Discontinued
0.6573	Remote Similarity	NPD4062	Phase 3
0.6573	Remote Similarity	NPD6663	Approved
0.6571	Remote Similarity	NPD9621	Approved
0.6571	Remote Similarity	NPD9620	Approved
0.6571	Remote Similarity	NPD9619	Approved
0.6569	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD821	Approved
0.6562	Remote Similarity	NPD7199	Phase 2
0.6552	Remote Similarity	NPD2568	Approved
0.6549	Remote Similarity	NPD7095	Approved
0.6548	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6696	Suspended
0.6538	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2238	Phase 2
0.6528	Remote Similarity	NPD3620	Phase 2
0.6515	Remote Similarity	NPD5283	Phase 1
0.6513	Remote Similarity	NPD3536	Discontinued
0.6504	Remote Similarity	NPD288	Approved
0.6503	Remote Similarity	NPD597	Approved
0.6503	Remote Similarity	NPD598	Approved
0.6503	Remote Similarity	NPD601	Approved
0.65	Remote Similarity	NPD1135	Approved
0.65	Remote Similarity	NPD1129	Approved
0.65	Remote Similarity	NPD1131	Approved
0.65	Remote Similarity	NPD6362	Approved
0.65	Remote Similarity	NPD1133	Approved
0.65	Remote Similarity	NPD1134	Approved
0.6497	Remote Similarity	NPD5772	Approved
0.6497	Remote Similarity	NPD5773	Approved
0.6493	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6004	Phase 3
0.6486	Remote Similarity	NPD6002	Phase 3
0.6486	Remote Similarity	NPD6005	Phase 3
0.6486	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3134	Approved
0.6483	Remote Similarity	NPD230	Phase 1
0.6478	Remote Similarity	NPD7075	Discontinued
0.6478	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6582	Phase 2
0.6475	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6583	Phase 3
0.6475	Remote Similarity	NPD2982	Phase 2
0.6475	Remote Similarity	NPD2983	Phase 2
0.6467	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4535	Phase 3
0.6466	Remote Similarity	NPD9618	Approved
0.6466	Remote Similarity	NPD9614	Approved
0.6466	Remote Similarity	NPD2629	Approved
0.6458	Remote Similarity	NPD1130	Approved
0.6458	Remote Similarity	NPD1136	Approved
0.6458	Remote Similarity	NPD1132	Approved
0.6457	Remote Similarity	NPD9610	Approved
0.6457	Remote Similarity	NPD9608	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