NPASS Compound

Structure

NPC470235 OpenBabel07101719132D 38 41 0 0 1 0 0 0 0 0999 V2000 8.3923 -7.9494 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 7.8969 -4.3780 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 8.7059 -4.9658 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 6.8788 -5.7793 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 6.1743 -4.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5575 -3.6637 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 6.7788 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9833 -4.7847 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 5.3007 -2.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6014 -5.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6878 -6.3670 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -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 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 1 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 6.2788 -3.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7654 -4.6418 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 9.4104 -6.5481 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 7.0878 -3.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5833 -7.3616 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 6.1097 -1.5933 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 34 1 0 0 0 0 2 35 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 26 1 0 0 0 0 10 15 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 26 1 0 0 0 0 12 36 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 1 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 19 2 0 0 0 0 17 37 1 0 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 11 1 6 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 25 1 0 0 0 0 23 32 1 1 0 0 0 24 14 1 6 0 0 0 24 36 1 0 0 0 0 25 37 1 6 0 0 0 25 38 1 0 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.21
Volume:	513.69
LogP:	0.249
LogD:	0.036
LogS:	-3.084
# Rotatable Bonds:	9
TPSA:	187.76
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	4.491
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.412
MDCK Permeability:	1.9981987861683592e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.881
20% Bioavailability (F20%):	0.199
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	67.94391632080078%
Volume Distribution (VD):	0.312
Pgp-substrate:	18.425127029418945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.516
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	3.581
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.485
Carcinogencity:	0.432
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC470235

Natural Product ID:	NPC470235
*Common Name:**	Olivil 4-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4R,5R,6S)-2-[4-[(2R,3S,4R)-4-hydroxy-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	OXHVZEZYYQQCRJ-DXYSKKKFSA-N
Standard InCHI:	InChI=1S/C26H34O12/c1-34-18-7-13(3-5-16(18)29)9-26(33)12-36-24(15(26)10-27)14-4-6-17(19(8-14)35-2)37-25-23(32)22(31)21(30)20(11-28)38-25/h3-8,15,20-25,27-33H,9-12H2,1-2H3/t15-,20-,21-,22+,23-,24-,25-,26-/m0/s1
SMILES:	OC[C@H]1[C@@H](OC[C@@]1(O)Cc1ccc(c(c1)OC)O)c1ccc(c(c1)OC)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1911055
PubChem CID:	57395551
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO16259	Syringa reticulata	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
EC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[569204]
NPT1	Others	Radical scavenging activity		EC50	>	100000.0	nM	PMID[569204]

☑ 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 NPC470235 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	404
0.1-0.2	1364
0.2-0.3	3392
0.3-0.4	8835
0.4-0.5	9798
0.5-0.6	5819
0.6-0.7	8293
0.7-0.8	3637
0.8-0.85	755
0.85-0.9	297
0.9-0.95	89
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283995
1.0	High Similarity	NPC129417
0.9926	High Similarity	NPC46092
0.9926	High Similarity	NPC185307
0.9926	High Similarity	NPC470950
0.9855	High Similarity	NPC112861
0.9853	High Similarity	NPC476356
0.9783	High Similarity	NPC18979
0.9783	High Similarity	NPC22150
0.9783	High Similarity	NPC38041
0.9783	High Similarity	NPC279298
0.9779	High Similarity	NPC472711
0.971	High Similarity	NPC84181
0.9643	High Similarity	NPC213074
0.9643	High Similarity	NPC224674
0.9643	High Similarity	NPC31325
0.9643	High Similarity	NPC15956
0.9643	High Similarity	NPC193473
0.9643	High Similarity	NPC39657
0.9643	High Similarity	NPC114505
0.9643	High Similarity	NPC275284
0.9638	High Similarity	NPC477898
0.9577	High Similarity	NPC98624
0.9577	High Similarity	NPC475224
0.9565	High Similarity	NPC246947
0.9559	High Similarity	NPC470413
0.9559	High Similarity	NPC138738
0.9507	High Similarity	NPC286235
0.9507	High Similarity	NPC55158
0.9507	High Similarity	NPC51328
0.95	High Similarity	NPC469586
0.95	High Similarity	NPC476301
0.95	High Similarity	NPC43508
0.9485	High Similarity	NPC199459
0.9485	High Similarity	NPC177035
0.9485	High Similarity	NPC52277
0.9437	High Similarity	NPC248132
0.9437	High Similarity	NPC130449
0.9429	High Similarity	NPC472713
0.9429	High Similarity	NPC472712
0.9429	High Similarity	NPC79429
0.9429	High Similarity	NPC118385
0.9429	High Similarity	NPC471063
0.9429	High Similarity	NPC471667
0.9429	High Similarity	NPC217635
0.9429	High Similarity	NPC473046
0.9429	High Similarity	NPC187774
0.942	High Similarity	NPC106944
0.9416	High Similarity	NPC304152
0.9412	High Similarity	NPC101624
0.9412	High Similarity	NPC184938
0.9371	High Similarity	NPC44452
0.9357	High Similarity	NPC278961
0.9357	High Similarity	NPC113680
0.9348	High Similarity	NPC156376
0.9338	High Similarity	NPC470881
0.9338	High Similarity	NPC187194
0.9338	High Similarity	NPC476411
0.9306	High Similarity	NPC472710
0.9306	High Similarity	NPC472709
0.9296	High Similarity	NPC205796
0.9296	High Similarity	NPC276753
0.9291	High Similarity	NPC25292
0.9291	High Similarity	NPC473045
0.9286	High Similarity	NPC253878
0.9286	High Similarity	NPC469559
0.9286	High Similarity	NPC5262
0.9286	High Similarity	NPC189115
0.9286	High Similarity	NPC472714
0.9286	High Similarity	NPC302506
0.9265	High Similarity	NPC25821
0.9265	High Similarity	NPC6836
0.9247	High Similarity	NPC61604
0.9247	High Similarity	NPC299706
0.9247	High Similarity	NPC245615
0.9247	High Similarity	NPC115466
0.9225	High Similarity	NPC286245
0.9225	High Similarity	NPC272619
0.9225	High Similarity	NPC475096
0.922	High Similarity	NPC473044
0.9214	High Similarity	NPC469661
0.9214	High Similarity	NPC471414
0.9214	High Similarity	NPC471908
0.9203	High Similarity	NPC77861
0.9197	High Similarity	NPC35731
0.9191	High Similarity	NPC252833
0.9191	High Similarity	NPC106739
0.9191	High Similarity	NPC471505
0.9189	High Similarity	NPC163635
0.9167	High Similarity	NPC270751
0.9167	High Similarity	NPC226153
0.9167	High Similarity	NPC304048
0.9161	High Similarity	NPC190714
0.9161	High Similarity	NPC99515
0.9155	High Similarity	NPC179521
0.9155	High Similarity	NPC253015
0.9155	High Similarity	NPC471065
0.9149	High Similarity	NPC60249
0.9149	High Similarity	NPC48309
0.913	High Similarity	NPC135777
0.913	High Similarity	NPC142547
0.9118	High Similarity	NPC277804
0.9118	High Similarity	NPC65942
0.9118	High Similarity	NPC248307
0.9118	High Similarity	NPC476345
0.9097	High Similarity	NPC227902
0.9097	High Similarity	NPC99183
0.9085	High Similarity	NPC81638
0.9078	High Similarity	NPC76871
0.9071	High Similarity	NPC193666
0.9071	High Similarity	NPC88640
0.9071	High Similarity	NPC98777
0.9071	High Similarity	NPC123526
0.9071	High Similarity	NPC212770
0.906	High Similarity	NPC11411
0.906	High Similarity	NPC228357
0.9048	High Similarity	NPC478268
0.9044	High Similarity	NPC174495
0.9044	High Similarity	NPC80600
0.9044	High Similarity	NPC181079
0.9044	High Similarity	NPC153739
0.9044	High Similarity	NPC42300
0.9044	High Similarity	NPC275950
0.9044	High Similarity	NPC472024
0.9044	High Similarity	NPC173308
0.9044	High Similarity	NPC145305
0.9044	High Similarity	NPC92164
0.9044	High Similarity	NPC257582
0.9044	High Similarity	NPC242807
0.9044	High Similarity	NPC77040
0.9044	High Similarity	NPC241522
0.9044	High Similarity	NPC64201
0.9044	High Similarity	NPC187998
0.9041	High Similarity	NPC229882
0.9041	High Similarity	NPC158635
0.9034	High Similarity	NPC175976
0.9028	High Similarity	NPC93610
0.9028	High Similarity	NPC125755
0.9028	High Similarity	NPC241846
0.9021	High Similarity	NPC110063
0.9014	High Similarity	NPC475084
0.9007	High Similarity	NPC55793
0.9	High Similarity	NPC477798
0.9	High Similarity	NPC195196
0.9	High Similarity	NPC477797
0.9	High Similarity	NPC65530
0.9	High Similarity	NPC59324
0.9	High Similarity	NPC474039
0.8993	High Similarity	NPC38699
0.8993	High Similarity	NPC93783
0.8986	High Similarity	NPC169973
0.8978	High Similarity	NPC9912
0.8973	High Similarity	NPC55715
0.8973	High Similarity	NPC35877
0.8973	High Similarity	NPC95392
0.8971	High Similarity	NPC86030
0.8971	High Similarity	NPC166040
0.8971	High Similarity	NPC26653
0.8971	High Similarity	NPC248355
0.8971	High Similarity	NPC5851
0.8971	High Similarity	NPC475875
0.8971	High Similarity	NPC270849
0.8971	High Similarity	NPC307110
0.8958	High Similarity	NPC307466
0.8958	High Similarity	NPC277867
0.8958	High Similarity	NPC161700
0.8951	High Similarity	NPC478239
0.8944	High Similarity	NPC470372
0.894	High Similarity	NPC478269
0.8933	High Similarity	NPC478055
0.8929	High Similarity	NPC172818
0.8929	High Similarity	NPC29799
0.8929	High Similarity	NPC209985
0.8929	High Similarity	NPC477939
0.8929	High Similarity	NPC177160
0.8929	High Similarity	NPC471988
0.8929	High Similarity	NPC54743
0.8929	High Similarity	NPC242028
0.8929	High Similarity	NPC156502
0.8929	High Similarity	NPC263367
0.8929	High Similarity	NPC25695
0.8929	High Similarity	NPC10737
0.8929	High Similarity	NPC203230
0.8921	High Similarity	NPC478085
0.8919	High Similarity	NPC302610
0.8913	High Similarity	NPC147616
0.8913	High Similarity	NPC254275
0.8913	High Similarity	NPC4940
0.8913	High Similarity	NPC181049
0.8913	High Similarity	NPC207400
0.8913	High Similarity	NPC219671
0.8913	High Similarity	NPC259742
0.8913	High Similarity	NPC104077
0.8912	High Similarity	NPC188393
0.8912	High Similarity	NPC470934
0.8904	High Similarity	NPC166584
0.8904	High Similarity	NPC301961
0.8904	High Similarity	NPC116229
0.8897	High Similarity	NPC184733
0.8897	High Similarity	NPC21867

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 NPC470235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	761
0.2-0.3	1713
0.3-0.4	2782
0.4-0.5	1862
0.5-0.6	1074
0.6-0.7	540
0.7-0.8	94
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8429	Intermediate Similarity	NPD3027	Phase 3
0.8425	Intermediate Similarity	NPD6674	Discontinued
0.8414	Intermediate Similarity	NPD7266	Discontinued
0.838	Intermediate Similarity	NPD1613	Approved
0.838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7228	Approved
0.8116	Intermediate Similarity	NPD3705	Approved
0.8105	Intermediate Similarity	NPD1653	Approved
0.8101	Intermediate Similarity	NPD6234	Discontinued
0.8099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2861	Phase 2
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5058	Phase 3
0.8013	Intermediate Similarity	NPD37	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7986	Intermediate Similarity	NPD1091	Approved
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD4967	Phase 2
0.7975	Intermediate Similarity	NPD4966	Approved
0.7927	Intermediate Similarity	NPD7054	Approved
0.7899	Intermediate Similarity	NPD1357	Approved
0.7892	Intermediate Similarity	NPD7685	Pre-registration
0.7888	Intermediate Similarity	NPD7199	Phase 2
0.7879	Intermediate Similarity	NPD7472	Approved
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7706	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7251	Discontinued
0.7679	Intermediate Similarity	NPD7240	Approved
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7625	Intermediate Similarity	NPD2978	Approved
0.7625	Intermediate Similarity	NPD8455	Phase 2
0.7625	Intermediate Similarity	NPD2977	Approved
0.7619	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7609	Intermediate Similarity	NPD7157	Approved
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD228	Approved
0.7566	Intermediate Similarity	NPD1375	Discontinued
0.7562	Intermediate Similarity	NPD1934	Approved
0.755	Intermediate Similarity	NPD5588	Approved
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD7843	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7483	Intermediate Similarity	NPD4538	Approved
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7467	Intermediate Similarity	NPD5735	Approved
0.7465	Intermediate Similarity	NPD5125	Phase 3
0.7465	Intermediate Similarity	NPD5126	Approved
0.7432	Intermediate Similarity	NPD7095	Approved
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7425	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6166	Phase 2
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1558	Phase 1
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4749	Approved
0.7378	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6671	Approved
0.7353	Intermediate Similarity	NPD2684	Approved
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD5762	Approved
0.7338	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD8651	Approved
0.732	Intermediate Similarity	NPD5960	Phase 3
0.732	Intermediate Similarity	NPD4108	Discontinued
0.7315	Intermediate Similarity	NPD4625	Phase 3
0.7308	Intermediate Similarity	NPD6331	Phase 2
0.7308	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4110	Phase 3
0.7303	Intermediate Similarity	NPD6653	Approved
0.7294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7310	Approved
0.7283	Intermediate Similarity	NPD7313	Approved
0.7283	Intermediate Similarity	NPD7312	Approved
0.7283	Intermediate Similarity	NPD7311	Approved
0.7268	Intermediate Similarity	NPD7680	Approved
0.7261	Intermediate Similarity	NPD6190	Approved
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.7256	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7244	Intermediate Similarity	NPD4237	Approved
0.7241	Intermediate Similarity	NPD7309	Approved
0.7241	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD27	Approved
0.7219	Intermediate Similarity	NPD2489	Approved
0.7216	Intermediate Similarity	NPD7906	Approved
0.7212	Intermediate Similarity	NPD3882	Suspended
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7195	Intermediate Similarity	NPD5772	Approved
0.7195	Intermediate Similarity	NPD2801	Approved
0.7195	Intermediate Similarity	NPD5773	Approved
0.7192	Intermediate Similarity	NPD2981	Phase 2
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7171	Intermediate Similarity	NPD4140	Approved
0.716	Intermediate Similarity	NPD2969	Approved
0.716	Intermediate Similarity	NPD2970	Approved
0.716	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4663	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7134	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7028	Phase 2
0.7114	Intermediate Similarity	NPD6584	Phase 3
0.7107	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7103	Intermediate Similarity	NPD5846	Approved
0.7101	Intermediate Similarity	NPD3051	Approved
0.7101	Intermediate Similarity	NPD6071	Discontinued
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7095	Intermediate Similarity	NPD6696	Suspended
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7086	Intermediate Similarity	NPD4578	Approved
0.7086	Intermediate Similarity	NPD4577	Approved
0.7083	Intermediate Similarity	NPD5494	Approved
0.7081	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7526	Approved
0.7078	Intermediate Similarity	NPD6353	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7051	Intermediate Similarity	NPD2161	Phase 2
0.7048	Intermediate Similarity	NPD2563	Approved
0.7048	Intermediate Similarity	NPD2560	Approved
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7047	Intermediate Similarity	NPD3094	Phase 2
0.7044	Intermediate Similarity	NPD2677	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.703	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3382	Approved
0.703	Intermediate Similarity	NPD3384	Approved
0.703	Intermediate Similarity	NPD3383	Approved
0.7029	Intermediate Similarity	NPD290	Approved
0.7027	Intermediate Similarity	NPD3685	Discontinued
0.7027	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4162	Approved
0.7022	Intermediate Similarity	NPD6843	Phase 3
0.7022	Intermediate Similarity	NPD6842	Approved
0.7022	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6841	Approved
0.702	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4123	Phase 3
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4210	Discontinued
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6993	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1465	Phase 2
0.6988	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4535	Phase 3
0.6981	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5604	Discontinued
0.6964	Remote Similarity	NPD7075	Discontinued
0.6962	Remote Similarity	NPD2424	Discontinued
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD2235	Phase 2
0.6959	Remote Similarity	NPD2231	Phase 2
0.6957	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD968	Approved
0.6948	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6937	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3751	Discontinued
0.6932	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data