NPASS Compound

Structure

NPC110063 OpenBabel07101719252D 43 46 0 0 1 0 0 0 0 0999 V2000 -7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4006 5.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3142 5.5861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5916 5.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4187 4.5916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6961 4.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7142 3.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9052 2.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6097 4.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0097 1.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 1 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 -2.7026 -0.5055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9233 1.0202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -1.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2007 0.8392 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 -3.5686 -0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 18 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 39 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 16 40 1 0 0 0 0 17 30 1 0 0 0 0 17 41 1 0 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 38 1 0 0 0 0 22 15 1 6 0 0 0 22 24 1 0 0 0 0 22 42 1 0 0 0 0 23 33 2 0 0 0 0 23 40 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 1 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 25 35 1 1 0 0 0 26 43 1 6 0 0 0 27 29 1 0 0 0 0 27 30 1 6 0 0 0 27 36 1 0 0 0 0 28 39 1 6 0 0 0 28 42 1 0 0 0 0 29 41 1 0 0 0 0 29 43 1 1 0 0 0 30 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.22
Volume:	583.755
LogP:	1.224
LogD:	1.005
LogS:	-3.624
# Rotatable Bonds:	13
TPSA:	193.83
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.659
Fsp3:	0.433
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:	-5.803
MDCK Permeability:	7.40760833650711e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.806
20% Bioavailability (F20%):	0.711
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	92.34600067138672%
Volume Distribution (VD):	0.374
Pgp-substrate:	4.442257881164551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.173
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	1.112
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.62
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.856
Carcinogencity:	0.25
Eye Corrosion:	0.003
Eye Irritation:	0.05
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC110063

Natural Product ID:	NPC110063
*Common Name:**	Visartiside F
IUPAC Name:	[(3S,4R,5S)-5-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoxy]-6-(hydroxymethyl)oxan-4-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:	Visartiside F
Standard InCHIKey:	BBTWTPYIAYLACY-NADHDMBGSA-N
Standard InCHI:	InChI=1S/C30H36O13/c1-38-21-11-9-19(14-20(21)32)8-5-13-39-28-25(35)26(24(34)22(15-31)42-28)43-29-27(36)30(37,17-41-29)16-40-23(33)12-10-18-6-3-2-4-7-18/h2-12,14,22,24-29,31-32,34-37H,13,15-17H2,1H3/b8-5+,12-10+/t22-,24-,25-,26+,27+,28-,29+,30-/m1/s1
SMILES:	COc1ccc(/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O[C@H]2[C@@H]([C@@](COC(=O)/C=C/c3ccccc3)(CO2)O)O)O)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077015
PubChem CID:	46184807
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
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121165]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16561	Viscum articulatum	Species	Viscaceae	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
ED50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	27800.0	nM	PMID[515061]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	85.2	%	PMID[515061]
NPT1	Others	Radical scavenging activity		ED50	>	100.0	uM	PMID[515061]

☑ 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 NPC110063 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	303
0.1-0.2	1382
0.2-0.3	3390
0.3-0.4	8670
0.4-0.5	9857
0.5-0.6	6169
0.6-0.7	8593
0.7-0.8	3610
0.8-0.85	504
0.85-0.9	157
0.9-0.95	44
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC216819
0.9783	High Similarity	NPC287615
0.9783	High Similarity	NPC83743
0.9783	High Similarity	NPC262182
0.9632	High Similarity	NPC226005
0.9577	High Similarity	NPC470934
0.9577	High Similarity	NPC188393
0.9574	High Similarity	NPC192763
0.9574	High Similarity	NPC300262
0.9574	High Similarity	NPC80732
0.9574	High Similarity	NPC215095
0.9574	High Similarity	NPC261122
0.9574	High Similarity	NPC210611
0.9574	High Similarity	NPC28651
0.9574	High Similarity	NPC201148
0.9574	High Similarity	NPC3460
0.9574	High Similarity	NPC199311
0.9565	High Similarity	NPC157816
0.9565	High Similarity	NPC140502
0.9507	High Similarity	NPC90896
0.9507	High Similarity	NPC283839
0.95	High Similarity	NPC100998
0.95	High Similarity	NPC34587
0.95	High Similarity	NPC252292
0.95	High Similarity	NPC476382
0.95	High Similarity	NPC34927
0.9496	High Similarity	NPC478239
0.9485	High Similarity	NPC157554
0.9433	High Similarity	NPC476865
0.9429	High Similarity	NPC297342
0.9375	High Similarity	NPC143480
0.9375	High Similarity	NPC7145
0.9375	High Similarity	NPC85192
0.9375	High Similarity	NPC125823
0.9366	High Similarity	NPC232992
0.9362	High Similarity	NPC476864
0.9362	High Similarity	NPC476866
0.9362	High Similarity	NPC476869
0.9362	High Similarity	NPC476868
0.9353	High Similarity	NPC186406
0.9348	High Similarity	NPC321184
0.9348	High Similarity	NPC171134
0.9348	High Similarity	NPC100389
0.9348	High Similarity	NPC321638
0.9348	High Similarity	NPC328273
0.931	High Similarity	NPC472611
0.931	High Similarity	NPC478268
0.931	High Similarity	NPC472612
0.931	High Similarity	NPC289967
0.9296	High Similarity	NPC199928
0.9291	High Similarity	NPC232228
0.9291	High Similarity	NPC476867
0.9281	High Similarity	NPC202700
0.9265	High Similarity	NPC254398
0.9236	High Similarity	NPC259347
0.9236	High Similarity	NPC106138
0.9236	High Similarity	NPC471062
0.9236	High Similarity	NPC94871
0.9236	High Similarity	NPC476398
0.9236	High Similarity	NPC306890
0.9236	High Similarity	NPC478242
0.9236	High Similarity	NPC476386
0.9236	High Similarity	NPC473427
0.9236	High Similarity	NPC470933
0.9203	High Similarity	NPC37468
0.9203	High Similarity	NPC186418
0.9197	High Similarity	NPC471883
0.9191	High Similarity	NPC252833
0.9191	High Similarity	NPC473924
0.9172	High Similarity	NPC257970
0.9172	High Similarity	NPC470927
0.9167	High Similarity	NPC478237
0.9155	High Similarity	NPC292443
0.9155	High Similarity	NPC196063
0.9155	High Similarity	NPC141455
0.9155	High Similarity	NPC300894
0.9155	High Similarity	NPC296954
0.913	High Similarity	NPC476870
0.9128	High Similarity	NPC226759
0.9124	High Similarity	NPC6836
0.9118	High Similarity	NPC219677
0.911	High Similarity	NPC269914
0.911	High Similarity	NPC478249
0.9085	High Similarity	NPC105005
0.9085	High Similarity	NPC40305
0.9085	High Similarity	NPC46092
0.9078	High Similarity	NPC476385
0.9078	High Similarity	NPC472711
0.9078	High Similarity	NPC134405
0.9071	High Similarity	NPC68092
0.9071	High Similarity	NPC64141
0.9071	High Similarity	NPC81515
0.9071	High Similarity	NPC197316
0.9071	High Similarity	NPC476383
0.9071	High Similarity	NPC472350
0.9071	High Similarity	NPC89105
0.9065	High Similarity	NPC52277
0.9065	High Similarity	NPC199459
0.9065	High Similarity	NPC177035
0.906	High Similarity	NPC11411
0.9058	High Similarity	NPC886
0.9058	High Similarity	NPC135127
0.9058	High Similarity	NPC34293
0.9058	High Similarity	NPC470881
0.9058	High Similarity	NPC287597
0.9051	High Similarity	NPC473285
0.9041	High Similarity	NPC476871
0.9028	High Similarity	NPC229505
0.9021	High Similarity	NPC129417
0.9021	High Similarity	NPC470235
0.9021	High Similarity	NPC84181
0.9021	High Similarity	NPC283995
0.9014	High Similarity	NPC265648
0.9014	High Similarity	NPC222433
0.9	High Similarity	NPC260425
0.9	High Similarity	NPC138738
0.9	High Similarity	NPC195196
0.9	High Similarity	NPC126206
0.9	High Similarity	NPC470413
0.9	High Similarity	NPC78363
0.8971	High Similarity	NPC477294
0.8971	High Similarity	NPC477293
0.8971	High Similarity	NPC229784
0.8971	High Similarity	NPC307110
0.8958	High Similarity	NPC18979
0.8951	High Similarity	NPC477898
0.8951	High Similarity	NPC470950
0.8951	High Similarity	NPC185307
0.8944	High Similarity	NPC476377
0.8944	High Similarity	NPC47471
0.894	High Similarity	NPC478269
0.8936	High Similarity	NPC205195
0.8933	High Similarity	NPC478266
0.8933	High Similarity	NPC228357
0.8929	High Similarity	NPC471665
0.8929	High Similarity	NPC471664
0.8921	High Similarity	NPC35731
0.8919	High Similarity	NPC203664
0.8912	High Similarity	NPC147224
0.8904	High Similarity	NPC308178
0.8897	High Similarity	NPC232880
0.8897	High Similarity	NPC112861
0.8897	High Similarity	NPC225307
0.8882	High Similarity	NPC478265
0.8881	High Similarity	NPC67467
0.8881	High Similarity	NPC476356
0.8873	High Similarity	NPC475530
0.8873	High Similarity	NPC473799
0.8867	High Similarity	NPC38699
0.8865	High Similarity	NPC476376
0.8865	High Similarity	NPC304152
0.8859	High Similarity	NPC89693
0.8859	High Similarity	NPC478241
0.8859	High Similarity	NPC61604
0.8859	High Similarity	NPC299706
0.8859	High Similarity	NPC229548
0.8859	High Similarity	NPC245615
0.8859	High Similarity	NPC115466
0.8859	High Similarity	NPC44730
0.8857	High Similarity	NPC55040
0.8849	High Similarity	NPC25821
0.8844	High Similarity	NPC111785
0.8841	High Similarity	NPC478255
0.8841	High Similarity	NPC248307
0.8841	High Similarity	NPC65942
0.8828	High Similarity	NPC38041
0.8828	High Similarity	NPC279298
0.8828	High Similarity	NPC22150
0.8824	High Similarity	NPC476873
0.8824	High Similarity	NPC149873
0.8824	High Similarity	NPC478267
0.8824	High Similarity	NPC7191
0.8819	High Similarity	NPC247032
0.8819	High Similarity	NPC269141
0.8819	High Similarity	NPC264632
0.8819	High Similarity	NPC96795
0.8819	High Similarity	NPC76406
0.8819	High Similarity	NPC476381
0.8819	High Similarity	NPC476375
0.8819	High Similarity	NPC112
0.8819	High Similarity	NPC476380
0.8819	High Similarity	NPC476378
0.8819	High Similarity	NPC175214
0.8819	High Similarity	NPC205864
0.8819	High Similarity	NPC119537
0.8819	High Similarity	NPC476384
0.8819	High Similarity	NPC476397
0.8819	High Similarity	NPC298257
0.8808	High Similarity	NPC163635
0.8808	High Similarity	NPC478248
0.8803	High Similarity	NPC212770
0.8803	High Similarity	NPC98777
0.8803	High Similarity	NPC220942
0.88	High Similarity	NPC191046
0.88	High Similarity	NPC327032
0.88	High Similarity	NPC194095
0.8794	High Similarity	NPC471988
0.8794	High Similarity	NPC470572
0.8786	High Similarity	NPC187194
0.8776	High Similarity	NPC93924

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 NPC110063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	780
0.2-0.3	1717
0.3-0.4	2884
0.4-0.5	1952
0.5-0.6	1098
0.6-0.7	427
0.7-0.8	58
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9071	High Similarity	NPD7266	Discontinued
0.8591	High Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD7685	Pre-registration
0.8086	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6234	Discontinued
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7947	Intermediate Similarity	NPD6190	Approved
0.7927	Intermediate Similarity	NPD7054	Approved
0.7917	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1357	Approved
0.7898	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7879	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4966	Approved
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3705	Approved
0.7692	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7251	Discontinued
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7606	Intermediate Similarity	NPD1091	Approved
0.7582	Intermediate Similarity	NPD6674	Discontinued
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7574	Intermediate Similarity	NPD7240	Approved
0.7561	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD5536	Phase 2
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1934	Approved
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7415	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2977	Approved
0.7407	Intermediate Similarity	NPD8455	Phase 2
0.7407	Intermediate Similarity	NPD2978	Approved
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD228	Approved
0.7317	Intermediate Similarity	NPD3882	Suspended
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.7255	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD8127	Discontinued
0.7238	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7095	Approved
0.7195	Intermediate Similarity	NPD2801	Approved
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5844	Phase 1
0.7192	Intermediate Similarity	NPD2981	Phase 2
0.7191	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8313	Approved
0.7184	Intermediate Similarity	NPD8312	Approved
0.7181	Intermediate Similarity	NPD9494	Approved
0.7181	Intermediate Similarity	NPD2861	Phase 2
0.7174	Intermediate Similarity	NPD7680	Approved
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4357	Discontinued
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7124	Intermediate Similarity	NPD1933	Approved
0.7124	Intermediate Similarity	NPD4340	Discontinued
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD5283	Phase 1
0.7091	Intermediate Similarity	NPD1465	Phase 2
0.708	Intermediate Similarity	NPD3134	Approved
0.7078	Intermediate Similarity	NPD2492	Phase 1
0.7078	Intermediate Similarity	NPD6653	Approved
0.7067	Intermediate Similarity	NPD3018	Phase 2
0.7025	Intermediate Similarity	NPD4237	Approved
0.7025	Intermediate Similarity	NPD4236	Phase 3
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6232	Discontinued
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7033	Discontinued
0.6987	Remote Similarity	NPD5588	Approved
0.6986	Remote Similarity	NPD5126	Approved
0.6986	Remote Similarity	NPD5125	Phase 3
0.6981	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8166	Discontinued
0.6977	Remote Similarity	NPD7473	Discontinued
0.6975	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6386	Approved
0.697	Remote Similarity	NPD6385	Approved
0.6964	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1511	Approved
0.695	Remote Similarity	NPD969	Suspended
0.6948	Remote Similarity	NPD1558	Phase 1
0.6946	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD2935	Discontinued
0.6939	Remote Similarity	NPD3496	Discontinued
0.6936	Remote Similarity	NPD3751	Discontinued
0.6932	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3
0.6927	Remote Similarity	NPD6842	Approved
0.6923	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4536	Approved
0.6923	Remote Similarity	NPD4538	Approved
0.6918	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3060	Approved
0.6908	Remote Similarity	NPD4908	Phase 1
0.6903	Remote Similarity	NPD447	Suspended
0.6901	Remote Similarity	NPD7843	Approved
0.6899	Remote Similarity	NPD1375	Discontinued
0.6892	Remote Similarity	NPD422	Phase 1
0.6886	Remote Similarity	NPD7819	Suspended
0.6882	Remote Similarity	NPD5494	Approved
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD7039	Approved
0.6875	Remote Similarity	NPD7038	Approved
0.6871	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD2424	Discontinued
0.6848	Remote Similarity	NPD3455	Phase 2
0.6848	Remote Similarity	NPD7458	Discontinued
0.6845	Remote Similarity	NPD5353	Approved
0.6839	Remote Similarity	NPD4140	Approved
0.6829	Remote Similarity	NPD5403	Approved
0.6826	Remote Similarity	NPD6801	Discontinued
0.6818	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3021	Approved
0.6809	Remote Similarity	NPD3022	Approved
0.6809	Remote Similarity	NPD7435	Discontinued
0.6802	Remote Similarity	NPD3787	Discontinued
0.6792	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5773	Approved
0.6786	Remote Similarity	NPD5772	Approved
0.6783	Remote Similarity	NPD5535	Approved
0.6779	Remote Similarity	NPD1610	Phase 2
0.6778	Remote Similarity	NPD8434	Phase 2
0.6774	Remote Similarity	NPD4062	Phase 3
0.6772	Remote Similarity	NPD4108	Discontinued
0.6772	Remote Similarity	NPD5960	Phase 3
0.677	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5604	Discontinued
0.6759	Remote Similarity	NPD6671	Approved
0.6757	Remote Similarity	NPD4626	Approved
0.6755	Remote Similarity	NPD3225	Approved
0.6748	Remote Similarity	NPD5297	Approved
0.6748	Remote Similarity	NPD6799	Approved
0.6746	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2684	Approved
0.6737	Remote Similarity	NPD7999	Approved
0.6735	Remote Similarity	NPD9545	Approved
0.6735	Remote Similarity	NPD1548	Phase 1
0.671	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5177	Phase 3
0.6707	Remote Similarity	NPD3536	Discontinued
0.6707	Remote Similarity	NPD4123	Phase 3
0.6707	Remote Similarity	NPD5401	Approved
0.6689	Remote Similarity	NPD5585	Approved
0.6689	Remote Similarity	NPD5691	Approved
0.6688	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD291	Approved
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6777	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