NPASS Compound

Structure

NPC473924 OpenBabel07101718242D 33 35 0 0 1 0 0 0 0 0999 V2000 -7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 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 -7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 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 2 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 -10.4968 -0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4968 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 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 -0.9706 -1.4945 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 -2.7026 -2.4945 0.0000 O 0 0 0 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 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 30 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 20 1 0 0 0 0 8 31 1 0 0 0 0 10 11 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 6 1 1 0 0 0 12 14 1 0 0 0 0 12 32 1 0 0 0 0 13 24 2 0 0 0 0 13 33 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 6 0 0 0 15 16 1 0 0 0 0 15 26 1 1 0 0 0 16 18 1 0 0 0 0 16 27 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 17 28 1 0 0 0 0 18 32 1 0 0 0 0 18 33 1 1 0 0 0 19 30 1 1 0 0 0 19 31 1 0 0 0 0 20 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.14
Volume:	429.897
LogP:	-0.405
LogD:	-0.401
LogS:	-1.442
# Rotatable Bonds:	8
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.112
Synthetic Accessibility Score:	4.557
Fsp3:	0.55
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.55
MDCK Permeability:	2.811239392030984e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.799
20% Bioavailability (F20%):	0.791
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	69.20137023925781%
Volume Distribution (VD):	0.368
Pgp-substrate:	38.35683059692383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	1.164
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.62
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.927
Carcinogencity:	0.276
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC473924

Natural Product ID:	NPC473924
*Common Name:**	1-O-Caffeoyl-Beta-D-Apiofuranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	[(2R,3S,4R,5R,6S)-6-[[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	LULOGYYPGZOKQW-IRXYIGQESA-N
Standard InCHI:	InChI=1S/C20H26O13/c21-7-20(29)8-31-19(17(20)28)30-6-12-14(25)15(26)16(27)18(32-12)33-13(24)4-2-9-1-3-10(22)11(23)5-9/h1-5,12,14-19,21-23,25-29H,6-8H2/b4-2+/t12-,14-,15+,16-,17+,18+,19-,20-/m0/s1
SMILES:	OC[C@]1(O)CO[C@@H]([C@H]1O)OC[C@@H]1O[C@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455347
PubChem CID:	44558989
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid 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
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	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
IC50	1
Others	1

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.	Activity	=	3.86	n.a.	PMID[507679]
NPT1	Others	Radical scavenging activity		IC50	=	19800.0	nM	PMID[507679]

☑ 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 NPC473924 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	287
0.1-0.2	1277
0.2-0.3	3268
0.3-0.4	8265
0.4-0.5	10153
0.5-0.6	8088
0.6-0.7	8681
0.7-0.8	2201
0.8-0.85	317
0.85-0.9	123
0.9-0.95	28
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC254398
0.992	High Similarity	NPC219677
0.976	High Similarity	NPC477294
0.976	High Similarity	NPC229784
0.976	High Similarity	NPC477293
0.9688	High Similarity	NPC471883
0.968	High Similarity	NPC232880
0.96	High Similarity	NPC476873
0.9542	High Similarity	NPC321184
0.9542	High Similarity	NPC171134
0.9542	High Similarity	NPC321638
0.9542	High Similarity	NPC328273
0.9538	High Similarity	NPC470572
0.9531	High Similarity	NPC473285
0.9394	High Similarity	NPC220942
0.9394	High Similarity	NPC226005
0.9385	High Similarity	NPC287597
0.9385	High Similarity	NPC886
0.9385	High Similarity	NPC34293
0.9313	High Similarity	NPC476870
0.9259	High Similarity	NPC40305
0.9259	High Similarity	NPC105005
0.9242	High Similarity	NPC157554
0.92	High Similarity	NPC52097
0.9191	High Similarity	NPC196063
0.9191	High Similarity	NPC110063
0.9191	High Similarity	NPC296954
0.9191	High Similarity	NPC300894
0.9191	High Similarity	NPC141455
0.9173	High Similarity	NPC78363
0.9173	High Similarity	NPC260425
0.9173	High Similarity	NPC476376
0.9141	High Similarity	NPC156692
0.9141	High Similarity	NPC471882
0.9141	High Similarity	NPC471881
0.9141	High Similarity	NPC35288
0.9141	High Similarity	NPC45224
0.9141	High Similarity	NPC173150
0.9134	High Similarity	NPC83218
0.9134	High Similarity	NPC90318
0.9134	High Similarity	NPC126991
0.912	High Similarity	NPC11724
0.9104	High Similarity	NPC472350
0.9104	High Similarity	NPC100389
0.9104	High Similarity	NPC81515
0.9104	High Similarity	NPC89105
0.9104	High Similarity	NPC205195
0.9104	High Similarity	NPC476383
0.9104	High Similarity	NPC197316
0.9104	High Similarity	NPC64141
0.9104	High Similarity	NPC68092
0.9098	High Similarity	NPC186418
0.907	High Similarity	NPC225307
0.9062	High Similarity	NPC471157
0.9062	High Similarity	NPC252114
0.9058	High Similarity	NPC473867
0.9058	High Similarity	NPC229505
0.9051	High Similarity	NPC297342
0.904	High Similarity	NPC476872
0.9037	High Similarity	NPC202700
0.9008	High Similarity	NPC478255
0.8992	High Similarity	NPC106677
0.8986	High Similarity	NPC262182
0.8986	High Similarity	NPC287615
0.8986	High Similarity	NPC216819
0.8986	High Similarity	NPC83743
0.8971	High Similarity	NPC134405
0.8971	High Similarity	NPC186406
0.8971	High Similarity	NPC476385
0.8971	High Similarity	NPC476377
0.8971	High Similarity	NPC47471
0.8955	High Similarity	NPC37468
0.8939	High Similarity	NPC252833
0.8915	High Similarity	NPC61181
0.8905	High Similarity	NPC222433
0.8905	High Similarity	NPC140502
0.8905	High Similarity	NPC265648
0.8905	High Similarity	NPC157816
0.8897	High Similarity	NPC475530
0.8897	High Similarity	NPC473799
0.8872	High Similarity	NPC6836
0.8864	High Similarity	NPC281798
0.8857	High Similarity	NPC18789
0.8846	High Similarity	NPC103533
0.8846	High Similarity	NPC288416
0.8841	High Similarity	NPC175214
0.8841	High Similarity	NPC476378
0.8841	High Similarity	NPC205864
0.8841	High Similarity	NPC476380
0.8841	High Similarity	NPC119537
0.8841	High Similarity	NPC476397
0.8841	High Similarity	NPC269141
0.8841	High Similarity	NPC478239
0.8841	High Similarity	NPC298257
0.8841	High Similarity	NPC247032
0.8841	High Similarity	NPC476384
0.8841	High Similarity	NPC476381
0.8841	High Similarity	NPC264632
0.8841	High Similarity	NPC476375
0.8841	High Similarity	NPC76406
0.8841	High Similarity	NPC96795
0.8841	High Similarity	NPC112
0.8828	High Similarity	NPC224208
0.8828	High Similarity	NPC474275
0.8819	High Similarity	NPC266045
0.8815	High Similarity	NPC471872
0.8815	High Similarity	NPC154485
0.8806	High Similarity	NPC470881
0.8803	High Similarity	NPC188393
0.8803	High Similarity	NPC470934
0.8794	High Similarity	NPC28651
0.8794	High Similarity	NPC210611
0.8794	High Similarity	NPC261122
0.8794	High Similarity	NPC80732
0.8794	High Similarity	NPC201148
0.8794	High Similarity	NPC215095
0.8794	High Similarity	NPC199311
0.8794	High Similarity	NPC192763
0.8794	High Similarity	NPC3460
0.8794	High Similarity	NPC300262
0.8777	High Similarity	NPC476867
0.8777	High Similarity	NPC292443
0.8777	High Similarity	NPC64195
0.8777	High Similarity	NPC232228
0.8768	High Similarity	NPC296643
0.8732	High Similarity	NPC283839
0.8732	High Similarity	NPC90896
0.8731	High Similarity	NPC28637
0.8722	High Similarity	NPC254819
0.8714	High Similarity	NPC34587
0.8714	High Similarity	NPC476866
0.8714	High Similarity	NPC476868
0.8714	High Similarity	NPC476864
0.8714	High Similarity	NPC100998
0.8714	High Similarity	NPC34927
0.8714	High Similarity	NPC476382
0.8714	High Similarity	NPC476869
0.8714	High Similarity	NPC252292
0.8712	High Similarity	NPC307110
0.8712	High Similarity	NPC253595
0.8652	High Similarity	NPC199928
0.8652	High Similarity	NPC476865
0.8613	High Similarity	NPC195196
0.8611	High Similarity	NPC7145
0.8611	High Similarity	NPC143480
0.8611	High Similarity	NPC85192
0.8611	High Similarity	NPC125823
0.8611	High Similarity	NPC478249
0.8611	High Similarity	NPC269914
0.8603	High Similarity	NPC55040
0.8603	High Similarity	NPC123988
0.8601	High Similarity	NPC478242
0.8593	High Similarity	NPC25821
0.8592	High Similarity	NPC232992
0.8582	High Similarity	NPC235294
0.8582	High Similarity	NPC138777
0.8582	High Similarity	NPC246869
0.8582	High Similarity	NPC65942
0.8582	High Similarity	NPC46137
0.8582	High Similarity	NPC225384
0.8582	High Similarity	NPC248307
0.8561	High Similarity	NPC264900
0.8561	High Similarity	NPC79715
0.8561	High Similarity	NPC108659
0.8561	High Similarity	NPC231607
0.8552	High Similarity	NPC289967
0.8552	High Similarity	NPC472611
0.8552	High Similarity	NPC472612
0.8552	High Similarity	NPC478268
0.8542	High Similarity	NPC69367
0.8531	High Similarity	NPC478237
0.8529	High Similarity	NPC474895
0.8529	High Similarity	NPC135127
0.8527	High Similarity	NPC147654
0.8519	High Similarity	NPC254275
0.8496	Intermediate Similarity	NPC148982
0.8493	Intermediate Similarity	NPC229548
0.8493	Intermediate Similarity	NPC478241
0.8493	Intermediate Similarity	NPC89693
0.8492	Intermediate Similarity	NPC281277
0.8485	Intermediate Similarity	NPC475695
0.8485	Intermediate Similarity	NPC94179
0.848	Intermediate Similarity	NPC217472
0.848	Intermediate Similarity	NPC313193
0.8478	Intermediate Similarity	NPC100558
0.8478	Intermediate Similarity	NPC310252
0.8478	Intermediate Similarity	NPC84789
0.8478	Intermediate Similarity	NPC302583
0.8472	Intermediate Similarity	NPC94871
0.8472	Intermediate Similarity	NPC476398
0.8472	Intermediate Similarity	NPC75945
0.8472	Intermediate Similarity	NPC259347
0.8472	Intermediate Similarity	NPC306890
0.8472	Intermediate Similarity	NPC470933
0.8472	Intermediate Similarity	NPC471062
0.8472	Intermediate Similarity	NPC473427
0.8472	Intermediate Similarity	NPC476386
0.8472	Intermediate Similarity	NPC106138
0.8467	Intermediate Similarity	NPC185778
0.8462	Intermediate Similarity	NPC41844

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 NPC473924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	742
0.2-0.3	1719
0.3-0.4	3033
0.4-0.5	1953
0.5-0.6	1134
0.6-0.7	318
0.7-0.8	22
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
0.9104	High Similarity	NPD7266	Discontinued
0.8345	Intermediate Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD6190	Approved
0.7654	Intermediate Similarity	NPD7685	Pre-registration
0.7612	Intermediate Similarity	NPD1357	Approved
0.7574	Intermediate Similarity	NPD1091	Approved
0.7552	Intermediate Similarity	NPD230	Phase 1
0.7518	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD3818	Discontinued
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3705	Approved
0.7407	Intermediate Similarity	NPD7228	Approved
0.7405	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD969	Suspended
0.7361	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1613	Approved
0.7308	Intermediate Similarity	NPD37	Approved
0.7289	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7054	Approved
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7212	Intermediate Similarity	NPD7472	Approved
0.7169	Intermediate Similarity	NPD6797	Phase 2
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1358	Approved
0.7097	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8166	Discontinued
0.7029	Intermediate Similarity	NPD9545	Approved
0.7021	Intermediate Similarity	NPD9269	Phase 2
0.7015	Intermediate Similarity	NPD228	Approved
0.7014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7199	Phase 2
0.6992	Remote Similarity	NPD3021	Approved
0.6992	Remote Similarity	NPD3022	Approved
0.6986	Remote Similarity	NPD3764	Approved
0.6982	Remote Similarity	NPD7808	Phase 3
0.698	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6674	Discontinued
0.6957	Remote Similarity	NPD5536	Phase 2
0.6948	Remote Similarity	NPD5058	Phase 3
0.6937	Remote Similarity	NPD2977	Approved
0.6937	Remote Similarity	NPD2978	Approved
0.6937	Remote Similarity	NPD8455	Phase 2
0.6929	Remote Similarity	NPD5125	Phase 3
0.6929	Remote Similarity	NPD5126	Approved
0.6928	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD7240	Approved
0.6913	Remote Similarity	NPD2492	Phase 1
0.6899	Remote Similarity	NPD3455	Phase 2
0.6897	Remote Similarity	NPD9494	Approved
0.6894	Remote Similarity	NPD3134	Approved
0.6892	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1934	Approved
0.6864	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1652	Phase 2
0.6852	Remote Similarity	NPD3882	Suspended
0.6842	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD9384	Approved
0.6807	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6653	Approved
0.6781	Remote Similarity	NPD2861	Phase 2
0.6779	Remote Similarity	NPD4060	Phase 1
0.6776	Remote Similarity	NPD9570	Approved
0.6766	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6166	Phase 2
0.6761	Remote Similarity	NPD3496	Discontinued
0.6755	Remote Similarity	NPD7097	Phase 1
0.675	Remote Similarity	NPD4380	Phase 2
0.6744	Remote Similarity	NPD8312	Approved
0.6744	Remote Similarity	NPD8313	Approved
0.6738	Remote Similarity	NPD9268	Approved
0.6736	Remote Similarity	NPD2983	Phase 2
0.6736	Remote Similarity	NPD2982	Phase 2
0.6733	Remote Similarity	NPD4340	Discontinued
0.6733	Remote Similarity	NPD5124	Phase 1
0.6733	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3686	Approved
0.673	Remote Similarity	NPD3687	Approved
0.6713	Remote Similarity	NPD422	Phase 1
0.6691	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4357	Discontinued
0.6688	Remote Similarity	NPD2424	Discontinued
0.6687	Remote Similarity	NPD3817	Phase 2
0.6687	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD2981	Phase 2
0.6667	Remote Similarity	NPD3062	Approved
0.6667	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD3061	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5844	Phase 1
0.6645	Remote Similarity	NPD4237	Approved
0.6645	Remote Similarity	NPD4236	Phase 3
0.6644	Remote Similarity	NPD3094	Phase 2
0.6641	Remote Similarity	NPD1242	Phase 1
0.663	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2801	Approved
0.6626	Remote Similarity	NPD1465	Phase 2
0.6623	Remote Similarity	NPD5763	Approved
0.6623	Remote Similarity	NPD447	Suspended
0.6623	Remote Similarity	NPD1375	Discontinued
0.6623	Remote Similarity	NPD5762	Approved
0.6621	Remote Similarity	NPD9622	Approved
0.6606	Remote Similarity	NPD7075	Discontinued
0.6604	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4110	Phase 3
0.6603	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5588	Approved
0.66	Remote Similarity	NPD6233	Phase 2
0.6594	Remote Similarity	NPD7843	Approved
0.6591	Remote Similarity	NPD6842	Approved
0.6591	Remote Similarity	NPD6841	Approved
0.6591	Remote Similarity	NPD6843	Phase 3
0.6588	Remote Similarity	NPD3751	Discontinued
0.6585	Remote Similarity	NPD5402	Approved
0.6582	Remote Similarity	NPD1511	Approved
0.6579	Remote Similarity	NPD5314	Approved
0.6577	Remote Similarity	NPD7095	Approved
0.6576	Remote Similarity	NPD7680	Approved
0.6573	Remote Similarity	NPD4626	Approved
0.6571	Remote Similarity	NPD7157	Approved
0.6558	Remote Similarity	NPD2935	Discontinued
0.6556	Remote Similarity	NPD943	Approved
0.6554	Remote Similarity	NPD3018	Phase 2
0.6554	Remote Similarity	NPD5736	Approved
0.6547	Remote Similarity	NPD5283	Phase 1
0.6544	Remote Similarity	NPD2684	Approved
0.6543	Remote Similarity	NPD7028	Phase 2
0.6541	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6355	Discontinued
0.6513	Remote Similarity	NPD555	Phase 2
0.6513	Remote Similarity	NPD1933	Approved
0.6508	Remote Similarity	NPD689	Discontinued
0.6503	Remote Similarity	NPD5691	Approved
0.65	Remote Similarity	NPD1512	Approved
0.6497	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7033	Discontinued
0.6486	Remote Similarity	NPD9619	Approved
0.6486	Remote Similarity	NPD9620	Approved
0.6486	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9621	Approved
0.6485	Remote Similarity	NPD5353	Approved
0.6483	Remote Similarity	NPD3092	Approved
0.6478	Remote Similarity	NPD5297	Approved
0.6471	Remote Similarity	NPD823	Approved
0.6471	Remote Similarity	NPD817	Approved
0.6471	Remote Similarity	NPD290	Approved
0.6471	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5403	Approved
0.6458	Remote Similarity	NPD1778	Approved
0.6454	Remote Similarity	NPD6671	Approved
0.645	Remote Similarity	NPD3787	Discontinued
0.645	Remote Similarity	NPD6232	Discontinued
0.6447	Remote Similarity	NPD4140	Approved
0.6447	Remote Similarity	NPD1558	Phase 1
0.6438	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3060	Approved
0.6429	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4538	Approved
0.6429	Remote Similarity	NPD4536	Approved
0.6424	Remote Similarity	NPD5772	Approved
0.6424	Remote Similarity	NPD597	Approved
0.6424	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6798	Discontinued
0.6424	Remote Similarity	NPD598	Approved
0.6424	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD601	Approved
0.6424	Remote Similarity	NPD5773	Approved
0.641	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6005	Phase 3
0.641	Remote Similarity	NPD6002	Phase 3
0.641	Remote Similarity	NPD6004	Phase 3
0.6408	Remote Similarity	NPD9493	Approved
0.6407	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6385	Approved
0.6402	Remote Similarity	NPD6386	Approved
0.64	Remote Similarity	NPD4908	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