NPASS Compound

Structure

NPC470881 OpenBabel07101719522D 32 34 0 0 1 0 0 0 0 0999 V2000 8.7078 -6.0933 0.0000 C 0 0 0 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 8.7078 -3.0933 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 5.2437 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -4.0933 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 6.9757 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7078 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8417 -4.5933 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 2 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 C 0 0 1 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 9.5738 -4.5933 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 7.8417 -5.5933 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 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 3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 29 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 30 1 0 0 0 0 8 20 1 0 0 0 0 8 21 1 0 0 0 0 9 20 1 0 0 0 0 9 31 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 7 1 6 0 0 0 13 14 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 18 32 1 0 0 0 0 19 30 1 6 0 0 0 19 31 1 0 0 0 0 20 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.17
Volume:	426.38
LogP:	-0.982
LogD:	-1.147
LogS:	-1.513
# Rotatable Bonds:	9
TPSA:	187.76
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.2
Synthetic Accessibility Score:	4.391
Fsp3:	0.7
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.328
MDCK Permeability:	2.658594530657865e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.849
Human Intestinal Absorption (HIA):	0.973
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	40.5060920715332%
Volume Distribution (VD):	0.323
Pgp-substrate:	42.89747619628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.324
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.311
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.909
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC470881

Natural Product ID:	NPC470881
*Common Name:**	2-(4-Hydroxy-3-Methoxyphenyl)Ethanol 1-O-[Beta-D-Apiofuranosyl-(1-6)-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	MYOINCYRVGGFRT-LTRJMQNCSA-N
Standard InCHI:	InChI=1S/C20H30O12/c1-28-12-6-10(2-3-11(12)22)4-5-29-18-16(25)15(24)14(23)13(32-18)7-30-19-17(26)20(27,8-21)9-31-19/h2-3,6,13-19,21-27H,4-5,7-9H2,1H3/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1
SMILES:	COC1=C(C=CC(=C1)CCOC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227742
PubChem CID:	16681196
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
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	7
Others	1

Activity Type	# Activity
Cell Line	3
Others	4
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[496105]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[496105]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[496105]
NPT2	Others	Unspecified		Inhibition	=	44.3	%	PMID[496105]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	>	10000.0	nM	PMID[496105]
NPT27	Others	Unspecified		IC50	>	5000.0	nM	PMID[496105]
NPT2	Others	Unspecified		IC50	=	1600.0	nM	PMID[496105]

☑ 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 NPC470881 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	355
0.1-0.2	1353
0.2-0.3	3521
0.3-0.4	9302
0.4-0.5	9431
0.5-0.6	6217
0.6-0.7	8329
0.7-0.8	3200
0.8-0.85	636
0.85-0.9	298
0.9-0.95	49
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC6836
0.9843	High Similarity	NPC252833
0.9764	High Similarity	NPC65942
0.9764	High Similarity	NPC248307
0.9612	High Similarity	NPC25821
0.9606	High Similarity	NPC307110
0.9538	High Similarity	NPC35731
0.947	High Similarity	NPC195196
0.947	High Similarity	NPC304152
0.9407	High Similarity	NPC46092
0.9403	High Similarity	NPC472711
0.9394	High Similarity	NPC52277
0.9394	High Similarity	NPC177035
0.9394	High Similarity	NPC199459
0.9389	High Similarity	NPC107478
0.938	High Similarity	NPC80600
0.938	High Similarity	NPC472024
0.9338	High Similarity	NPC129417
0.9338	High Similarity	NPC84181
0.9338	High Similarity	NPC470235
0.9338	High Similarity	NPC283995
0.9323	High Similarity	NPC470413
0.9323	High Similarity	NPC138738
0.9318	High Similarity	NPC101624
0.9318	High Similarity	NPC184938
0.9313	High Similarity	NPC132895
0.9302	High Similarity	NPC248355
0.9302	High Similarity	NPC270849
0.9302	High Similarity	NPC166040
0.9302	High Similarity	NPC26653
0.9291	High Similarity	NPC90318
0.927	High Similarity	NPC18979
0.9265	High Similarity	NPC477898
0.9265	High Similarity	NPC470950
0.9265	High Similarity	NPC185307
0.9254	High Similarity	NPC226005
0.9237	High Similarity	NPC470270
0.9225	High Similarity	NPC302378
0.9203	High Similarity	NPC112861
0.9191	High Similarity	NPC476356
0.916	High Similarity	NPC9912
0.913	High Similarity	NPC22150
0.913	High Similarity	NPC38041
0.913	High Similarity	NPC279298
0.913	High Similarity	NPC469586
0.9104	High Similarity	NPC157554
0.9098	High Similarity	NPC13745
0.9098	High Similarity	NPC48863
0.9098	High Similarity	NPC187194
0.9098	High Similarity	NPC251981
0.9091	High Similarity	NPC106739
0.9091	High Similarity	NPC471505
0.9058	High Similarity	NPC472712
0.9058	High Similarity	NPC118385
0.9058	High Similarity	NPC473046
0.9058	High Similarity	NPC110063
0.9058	High Similarity	NPC187774
0.9058	High Similarity	NPC472713
0.9051	High Similarity	NPC140502
0.9051	High Similarity	NPC189115
0.9051	High Similarity	NPC48309
0.9051	High Similarity	NPC469559
0.9044	High Similarity	NPC106944
0.9037	High Similarity	NPC477797
0.9037	High Similarity	NPC477798
0.903	High Similarity	NPC135777
0.903	High Similarity	NPC142547
0.903	High Similarity	NPC174191
0.9023	High Similarity	NPC69513
0.9023	High Similarity	NPC215833
0.9023	High Similarity	NPC49074
0.9015	High Similarity	NPC166168
0.9015	High Similarity	NPC277804
0.9	High Similarity	NPC193473
0.9	High Similarity	NPC114505
0.9	High Similarity	NPC275284
0.9	High Similarity	NPC213074
0.9	High Similarity	NPC39657
0.9	High Similarity	NPC224674
0.9	High Similarity	NPC15956
0.9	High Similarity	NPC31325
0.8986	High Similarity	NPC278961
0.8986	High Similarity	NPC113680
0.8978	High Similarity	NPC469661
0.8976	High Similarity	NPC470804
0.8976	High Similarity	NPC266045
0.8971	High Similarity	NPC156376
0.8971	High Similarity	NPC98777
0.8971	High Similarity	NPC100389
0.8971	High Similarity	NPC123526
0.8971	High Similarity	NPC212770
0.8971	High Similarity	NPC193666
0.8971	High Similarity	NPC88640
0.8963	High Similarity	NPC25695
0.8963	High Similarity	NPC172818
0.8955	High Similarity	NPC87696
0.8955	High Similarity	NPC476411
0.8947	High Similarity	NPC299144
0.8947	High Similarity	NPC4940
0.8947	High Similarity	NPC162093
0.8944	High Similarity	NPC470934
0.8944	High Similarity	NPC98624
0.8944	High Similarity	NPC475224
0.8944	High Similarity	NPC188393
0.8939	High Similarity	NPC187998
0.8939	High Similarity	NPC77040
0.8939	High Similarity	NPC174495
0.8939	High Similarity	NPC42300
0.8939	High Similarity	NPC242807
0.8939	High Similarity	NPC173308
0.8939	High Similarity	NPC145305
0.8939	High Similarity	NPC181079
0.8939	High Similarity	NPC153739
0.8939	High Similarity	NPC257582
0.8939	High Similarity	NPC92164
0.8939	High Similarity	NPC241522
0.8939	High Similarity	NPC64201
0.8939	High Similarity	NPC275950
0.8931	High Similarity	NPC474178
0.8931	High Similarity	NPC252307
0.8931	High Similarity	NPC245826
0.8929	High Similarity	NPC474234
0.8921	High Similarity	NPC297342
0.8921	High Similarity	NPC473045
0.8921	High Similarity	NPC25292
0.8915	High Similarity	NPC287429
0.8913	High Similarity	NPC246947
0.8913	High Similarity	NPC253878
0.8913	High Similarity	NPC5262
0.8913	High Similarity	NPC475084
0.8913	High Similarity	NPC472714
0.8897	High Similarity	NPC65530
0.8897	High Similarity	NPC59324
0.8897	High Similarity	NPC474039
0.8881	High Similarity	NPC254398
0.8881	High Similarity	NPC169973
0.8873	High Similarity	NPC51328
0.8873	High Similarity	NPC55158
0.8873	High Similarity	NPC286235
0.8872	High Similarity	NPC476345
0.8864	High Similarity	NPC475875
0.8864	High Similarity	NPC86030
0.8864	High Similarity	NPC5851
0.8857	High Similarity	NPC272619
0.8857	High Similarity	NPC287615
0.8857	High Similarity	NPC286245
0.8857	High Similarity	NPC43508
0.8857	High Similarity	NPC100998
0.8857	High Similarity	NPC83743
0.8857	High Similarity	NPC252292
0.8857	High Similarity	NPC262182
0.8857	High Similarity	NPC34587
0.8857	High Similarity	NPC34927
0.8857	High Similarity	NPC476301
0.8857	High Similarity	NPC476382
0.8857	High Similarity	NPC216819
0.8857	High Similarity	NPC475096
0.8855	High Similarity	NPC183181
0.8855	High Similarity	NPC118787
0.8855	High Similarity	NPC41706
0.8855	High Similarity	NPC111247
0.8855	High Similarity	NPC163332
0.8855	High Similarity	NPC319625
0.8855	High Similarity	NPC147821
0.8855	High Similarity	NPC292056
0.8849	High Similarity	NPC81638
0.8849	High Similarity	NPC473044
0.8849	High Similarity	NPC478239
0.8841	High Similarity	NPC471414
0.8841	High Similarity	NPC471908
0.8824	High Similarity	NPC164857
0.8824	High Similarity	NPC203230
0.8824	High Similarity	NPC186418
0.8824	High Similarity	NPC37468
0.8824	High Similarity	NPC242028
0.8824	High Similarity	NPC471988
0.8819	High Similarity	NPC35071
0.8819	High Similarity	NPC177475
0.8819	High Similarity	NPC148615
0.8806	High Similarity	NPC181049
0.8806	High Similarity	NPC104077
0.8806	High Similarity	NPC219671
0.8806	High Similarity	NPC147616
0.8806	High Similarity	NPC254275
0.8806	High Similarity	NPC473924
0.8806	High Similarity	NPC207400
0.8806	High Similarity	NPC259742
0.8803	High Similarity	NPC248132
0.8803	High Similarity	NPC130449
0.8794	High Similarity	NPC125755
0.8794	High Similarity	NPC190714
0.8794	High Similarity	NPC99515
0.8788	High Similarity	NPC128208
0.8788	High Similarity	NPC470084
0.8788	High Similarity	NPC129570
0.8788	High Similarity	NPC282703
0.8788	High Similarity	NPC21867
0.8788	High Similarity	NPC45774
0.8788	High Similarity	NPC72529
0.8788	High Similarity	NPC11258

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 NPC470881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	787
0.2-0.3	1822
0.3-0.4	2845
0.4-0.5	1772
0.5-0.6	1057
0.6-0.7	516
0.7-0.8	73
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8582	High Similarity	NPD3027	Phase 3
0.8538	High Similarity	NPD3705	Approved
0.845	Intermediate Similarity	NPD1357	Approved
0.8429	Intermediate Similarity	NPD7266	Discontinued
0.8258	Intermediate Similarity	NPD1091	Approved
0.8231	Intermediate Similarity	NPD1653	Approved
0.8129	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1613	Approved
0.811	Intermediate Similarity	NPD228	Approved
0.7931	Intermediate Similarity	NPD6674	Discontinued
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7862	Intermediate Similarity	NPD7228	Approved
0.7843	Intermediate Similarity	NPD2978	Approved
0.7843	Intermediate Similarity	NPD2977	Approved
0.7842	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD37	Approved
0.777	Intermediate Similarity	NPD5058	Phase 3
0.777	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7742	Intermediate Similarity	NPD4966	Approved
0.7742	Intermediate Similarity	NPD4967	Phase 2
0.7742	Intermediate Similarity	NPD4965	Approved
0.7718	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7054	Approved
0.7669	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7654	Intermediate Similarity	NPD7472	Approved
0.7622	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3620	Phase 2
0.7609	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5283	Phase 1
0.7568	Intermediate Similarity	NPD4237	Approved
0.7568	Intermediate Similarity	NPD4236	Phase 3
0.7551	Intermediate Similarity	NPD1375	Discontinued
0.7518	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7482	Intermediate Similarity	NPD2982	Phase 2
0.7482	Intermediate Similarity	NPD2983	Phase 2
0.7463	Intermediate Similarity	NPD7157	Approved
0.7462	Intermediate Similarity	NPD2684	Approved
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.7438	Intermediate Similarity	NPD7199	Phase 2
0.741	Intermediate Similarity	NPD2981	Phase 2
0.741	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3018	Phase 2
0.7381	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1558	Phase 1
0.7351	Intermediate Similarity	NPD6190	Approved
0.7349	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD6671	Approved
0.7333	Intermediate Similarity	NPD3060	Approved
0.7325	Intermediate Similarity	NPD1934	Approved
0.7319	Intermediate Similarity	NPD5126	Approved
0.7319	Intermediate Similarity	NPD5125	Phase 3
0.7297	Intermediate Similarity	NPD5588	Approved
0.7278	Intermediate Similarity	NPD5773	Approved
0.7278	Intermediate Similarity	NPD5772	Approved
0.7273	Intermediate Similarity	NPD3021	Approved
0.7273	Intermediate Similarity	NPD3022	Approved
0.7252	Intermediate Similarity	NPD290	Approved
0.725	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6559	Discontinued
0.7239	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4536	Approved
0.723	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6166	Phase 2
0.7195	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7188	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3882	Suspended
0.7179	Intermediate Similarity	NPD3687	Approved
0.7179	Intermediate Similarity	NPD3686	Approved
0.717	Intermediate Similarity	NPD8455	Phase 2
0.717	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7132	Intermediate Similarity	NPD291	Approved
0.7123	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7097	Phase 1
0.7113	Intermediate Similarity	NPD4749	Approved
0.7101	Intermediate Similarity	NPD5536	Phase 2
0.7092	Intermediate Similarity	NPD1610	Phase 2
0.7086	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5960	Phase 3
0.7067	Intermediate Similarity	NPD4108	Discontinued
0.7063	Intermediate Similarity	NPD8651	Approved
0.7063	Intermediate Similarity	NPD2801	Approved
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1548	Phase 1
0.7039	Intermediate Similarity	NPD2424	Discontinued
0.7034	Intermediate Similarity	NPD9494	Approved
0.7032	Intermediate Similarity	NPD1774	Approved
0.7027	Intermediate Similarity	NPD2238	Phase 2
0.7022	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2563	Approved
0.7019	Intermediate Similarity	NPD2560	Approved
0.7015	Intermediate Similarity	NPD556	Approved
0.7013	Intermediate Similarity	NPD2677	Approved
0.7007	Intermediate Similarity	NPD3145	Approved
0.7007	Intermediate Similarity	NPD3144	Approved
0.6993	Remote Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD3685	Discontinued
0.6993	Remote Similarity	NPD5177	Phase 3
0.6993	Remote Similarity	NPD4162	Approved
0.6987	Remote Similarity	NPD4123	Phase 3
0.6981	Remote Similarity	NPD7028	Phase 2
0.698	Remote Similarity	NPD5735	Approved
0.698	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD5763	Approved
0.6964	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7680	Approved
0.6959	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6233	Phase 2
0.6957	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.695	Remote Similarity	NPD9381	Approved
0.695	Remote Similarity	NPD9384	Approved
0.6948	Remote Similarity	NPD4628	Phase 3
0.6944	Remote Similarity	NPD6696	Suspended
0.6939	Remote Similarity	NPD7095	Approved
0.6939	Remote Similarity	NPD4625	Phase 3
0.6933	Remote Similarity	NPD5604	Discontinued
0.6933	Remote Similarity	NPD2492	Phase 1
0.6929	Remote Similarity	NPD9296	Approved
0.6923	Remote Similarity	NPD2231	Phase 2
0.6923	Remote Similarity	NPD2235	Phase 2
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD968	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6908	Remote Similarity	NPD2161	Phase 2
0.6903	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD6841	Approved
0.6897	Remote Similarity	NPD6843	Phase 3
0.6897	Remote Similarity	NPD7906	Approved
0.6897	Remote Similarity	NPD3094	Phase 2
0.6897	Remote Similarity	NPD6842	Approved
0.6894	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD27	Approved
0.6886	Remote Similarity	NPD2489	Approved
0.6879	Remote Similarity	NPD4739	Approved
0.6875	Remote Similarity	NPD4675	Approved
0.6875	Remote Similarity	NPD9622	Approved
0.6875	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4380	Phase 2
0.6875	Remote Similarity	NPD4678	Approved
0.6871	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6355	Discontinued
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5124	Phase 1
0.6867	Remote Similarity	NPD3787	Discontinued
0.6867	Remote Similarity	NPD6071	Discontinued
0.6866	Remote Similarity	NPD1358	Approved
0.6863	Remote Similarity	NPD3540	Phase 1
0.686	Remote Similarity	NPD7313	Approved
0.686	Remote Similarity	NPD7311	Approved
0.686	Remote Similarity	NPD7310	Approved
0.686	Remote Similarity	NPD7312	Approved
0.6855	Remote Similarity	NPD4210	Discontinued
0.6853	Remote Similarity	NPD422	Phase 1
0.6852	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD558	Phase 2
0.6849	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6584	Phase 3
0.6842	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD6331	Phase 2
0.6839	Remote Similarity	NPD4663	Approved
0.6835	Remote Similarity	NPD52	Approved
0.6835	Remote Similarity	NPD7526	Approved
0.6835	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5846	Approved
0.6831	Remote Similarity	NPD6516	Phase 2
0.6826	Remote Similarity	NPD2970	Approved
0.6826	Remote Similarity	NPD2969	Approved
0.6824	Remote Similarity	NPD3179	Approved
0.6824	Remote Similarity	NPD3180	Approved
0.6821	Remote Similarity	NPD7309	Approved
0.6815	Remote Similarity	NPD1511	Approved
0.6815	Remote Similarity	NPD4357	Discontinued
0.6807	Remote Similarity	NPD8127	Discontinued
0.68	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3059	Approved
0.68	Remote Similarity	NPD4140	Approved
0.68	Remote Similarity	NPD3062	Approved
0.68	Remote Similarity	NPD3061	Approved
0.6797	Remote Similarity	NPD3539	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data