NPASS Compound

Structure

NPC121290 OpenBabel07101718292D 40 44 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -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 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 20 2 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 29 1 0 0 0 0 13 27 1 0 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 26 1 0 0 0 0 21 38 1 6 0 0 0 22 12 1 6 0 0 0 22 23 1 0 0 0 0 22 40 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 1 0 0 0 24 25 1 0 0 0 0 24 34 1 6 0 0 0 25 28 1 0 0 0 0 25 35 1 1 0 0 0 26 14 1 6 0 0 0 26 37 1 0 0 0 0 27 36 2 0 0 0 0 27 38 1 0 0 0 0 28 39 1 6 0 0 0 28 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.16
Volume:	529.18
LogP:	1.839
LogD:	1.277
LogS:	-3.851
# Rotatable Bonds:	7
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	4.318
Fsp3:	0.321
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.646
MDCK Permeability:	1.170091036328813e-05
Pgp-inhibitor:	0.108
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.795
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	98.24639129638672%
Volume Distribution (VD):	0.526
Pgp-substrate:	2.88839054107666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.727
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	6.612
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.701
Carcinogencity:	0.358
Eye Corrosion:	0.003
Eye Irritation:	0.282
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC121290

Natural Product ID:	NPC121290
*Common Name:**	(-)-Epicatechin-5-O-Beta-D-Glucosyl-3-Benzoate
IUPAC Name:	[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-3-yl] benzoate
Synonyms:
Standard InCHIKey:	BZAMUAIUOGNDPV-FITCNNEASA-N
Standard InCHI:	InChI=1S/C28H28O12/c29-12-22-23(33)24(34)25(35)28(40-22)39-20-10-15(30)9-19-16(20)11-21(38-27(36)13-4-2-1-3-5-13)26(37-19)14-6-7-17(31)18(32)8-14/h1-10,21-26,28-35H,11-12H2/t21-,22-,23-,24+,25-,26-,28-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)cc3c2C[C@@H](OC(=O)c2ccccc2)[C@H](O3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473673
PubChem CID:	10392940
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	25.0	ug.mL-1	PMID[527444]

☑ 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 NPC121290 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	387
0.1-0.2	1596
0.2-0.3	3739
0.3-0.4	8637
0.4-0.5	9290
0.5-0.6	4277
0.6-0.7	5238
0.7-0.8	7074
0.8-0.85	1532
0.85-0.9	794
0.9-0.95	130
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC47140
0.9625	High Similarity	NPC67134
0.9427	High Similarity	NPC289346
0.9416	High Similarity	NPC474656
0.939	High Similarity	NPC476620
0.939	High Similarity	NPC476621
0.939	High Similarity	NPC476619
0.939	High Similarity	NPC476622
0.939	High Similarity	NPC476618
0.939	High Similarity	NPC476623
0.9329	High Similarity	NPC297574
0.9325	High Similarity	NPC472993
0.9321	High Similarity	NPC204937
0.9321	High Similarity	NPC149011
0.9317	High Similarity	NPC473818
0.9308	High Similarity	NPC285108
0.9308	High Similarity	NPC4013
0.9308	High Similarity	NPC33298
0.9308	High Similarity	NPC90905
0.9304	High Similarity	NPC24164
0.9299	High Similarity	NPC289322
0.9299	High Similarity	NPC68324
0.9299	High Similarity	NPC160512
0.9299	High Similarity	NPC114179
0.9299	High Similarity	NPC156818
0.9299	High Similarity	NPC38779
0.9277	High Similarity	NPC53680
0.9277	High Similarity	NPC469371
0.9277	High Similarity	NPC208797
0.9273	High Similarity	NPC472387
0.9268	High Similarity	NPC214621
0.9268	High Similarity	NPC34267
0.9268	High Similarity	NPC223426
0.9268	High Similarity	NPC81042
0.9259	High Similarity	NPC658
0.9259	High Similarity	NPC197708
0.925	High Similarity	NPC29830
0.9236	High Similarity	NPC250436
0.9236	High Similarity	NPC88803
0.9236	High Similarity	NPC291948
0.9236	High Similarity	NPC300845
0.9236	High Similarity	NPC104983
0.9212	High Similarity	NPC472992
0.9212	High Similarity	NPC67629
0.9212	High Similarity	NPC144097
0.9212	High Similarity	NPC61904
0.9212	High Similarity	NPC472991
0.9212	High Similarity	NPC79736
0.9207	High Similarity	NPC175230
0.9207	High Similarity	NPC88560
0.9207	High Similarity	NPC172033
0.9202	High Similarity	NPC231194
0.9202	High Similarity	NPC51326
0.9198	High Similarity	NPC45400
0.9187	High Similarity	NPC472876
0.9182	High Similarity	NPC53889
0.9182	High Similarity	NPC203020
0.9182	High Similarity	NPC239966
0.9157	High Similarity	NPC113836
0.9157	High Similarity	NPC139571
0.9157	High Similarity	NPC37668
0.9157	High Similarity	NPC217520
0.9157	High Similarity	NPC267549
0.9157	High Similarity	NPC253521
0.9157	High Similarity	NPC35167
0.9146	High Similarity	NPC5786
0.9146	High Similarity	NPC102851
0.9141	High Similarity	NPC198125
0.9141	High Similarity	NPC229687
0.9141	High Similarity	NPC95421
0.9141	High Similarity	NPC105283
0.9141	High Similarity	NPC43587
0.9136	High Similarity	NPC236934
0.9136	High Similarity	NPC8856
0.9136	High Similarity	NPC210073
0.9136	High Similarity	NPC115674
0.9136	High Similarity	NPC5778
0.913	High Similarity	NPC168822
0.9119	High Similarity	NPC289811
0.9119	High Similarity	NPC74319
0.9119	High Similarity	NPC287872
0.9119	High Similarity	NPC160780
0.9119	High Similarity	NPC87317
0.9114	High Similarity	NPC318432
0.9107	High Similarity	NPC156785
0.9107	High Similarity	NPC162394
0.9107	High Similarity	NPC470718
0.9107	High Similarity	NPC241781
0.9102	High Similarity	NPC80956
0.9102	High Similarity	NPC471030
0.9091	High Similarity	NPC166674
0.9091	High Similarity	NPC34436
0.9091	High Similarity	NPC263119
0.9091	High Similarity	NPC163165
0.9091	High Similarity	NPC46640
0.9091	High Similarity	NPC219600
0.9085	High Similarity	NPC78734
0.9085	High Similarity	NPC177731
0.9085	High Similarity	NPC181778
0.9085	High Similarity	NPC471416
0.9085	High Similarity	NPC218488
0.9085	High Similarity	NPC105095
0.9085	High Similarity	NPC34287
0.9085	High Similarity	NPC44328
0.9085	High Similarity	NPC150767
0.9085	High Similarity	NPC79056
0.908	High Similarity	NPC116745
0.908	High Similarity	NPC160156
0.908	High Similarity	NPC92565
0.908	High Similarity	NPC229729
0.9074	High Similarity	NPC165720
0.9068	High Similarity	NPC189142
0.9068	High Similarity	NPC127782
0.9068	High Similarity	NPC300537
0.9068	High Similarity	NPC148273
0.9068	High Similarity	NPC77660
0.9057	High Similarity	NPC133984
0.9057	High Similarity	NPC1913
0.9057	High Similarity	NPC472860
0.9053	High Similarity	NPC275977
0.9053	High Similarity	NPC223860
0.9053	High Similarity	NPC231254
0.9053	High Similarity	NPC249560
0.9053	High Similarity	NPC470717
0.9053	High Similarity	NPC460984
0.9053	High Similarity	NPC25946
0.9053	High Similarity	NPC470720
0.9053	High Similarity	NPC21359
0.9053	High Similarity	NPC470713
0.9048	High Similarity	NPC8940
0.9042	High Similarity	NPC293626
0.9042	High Similarity	NPC258044
0.9042	High Similarity	NPC217387
0.9042	High Similarity	NPC477895
0.9042	High Similarity	NPC196127
0.9042	High Similarity	NPC267680
0.9038	High Similarity	NPC93619
0.9036	High Similarity	NPC253685
0.903	High Similarity	NPC212038
0.903	High Similarity	NPC256760
0.903	High Similarity	NPC301683
0.903	High Similarity	NPC271848
0.903	High Similarity	NPC262580
0.903	High Similarity	NPC472386
0.903	High Similarity	NPC289396
0.903	High Similarity	NPC81332
0.9024	High Similarity	NPC471457
0.9024	High Similarity	NPC86008
0.9024	High Similarity	NPC52382
0.9024	High Similarity	NPC293629
0.9024	High Similarity	NPC209296
0.9024	High Similarity	NPC195257
0.9024	High Similarity	NPC170675
0.9024	High Similarity	NPC112755
0.9024	High Similarity	NPC270578
0.9012	High Similarity	NPC19709
0.9012	High Similarity	NPC127415
0.9012	High Similarity	NPC191306
0.9012	High Similarity	NPC270335
0.9012	High Similarity	NPC88043
0.9006	High Similarity	NPC472859
0.9006	High Similarity	NPC25389
0.9006	High Similarity	NPC477629
0.9006	High Similarity	NPC210961
0.9006	High Similarity	NPC311803
0.9006	High Similarity	NPC472994
0.9006	High Similarity	NPC270675
0.9006	High Similarity	NPC195685
0.9006	High Similarity	NPC477628
0.9	High Similarity	NPC33083
0.9	High Similarity	NPC473554
0.9	High Similarity	NPC470719
0.9	High Similarity	NPC295625
0.8994	High Similarity	NPC297503
0.8994	High Similarity	NPC36138
0.8994	High Similarity	NPC97119
0.8994	High Similarity	NPC135831
0.8994	High Similarity	NPC35924
0.8994	High Similarity	NPC199172
0.8982	High Similarity	NPC268533
0.8982	High Similarity	NPC89127
0.8982	High Similarity	NPC472723
0.8982	High Similarity	NPC296018
0.8982	High Similarity	NPC471669
0.8982	High Similarity	NPC154741
0.8981	High Similarity	NPC53587
0.8981	High Similarity	NPC169404
0.8981	High Similarity	NPC176186
0.8976	High Similarity	NPC239549
0.8976	High Similarity	NPC51774
0.8976	High Similarity	NPC473550
0.8976	High Similarity	NPC208668
0.8976	High Similarity	NPC236191
0.897	High Similarity	NPC95866
0.897	High Similarity	NPC244776
0.897	High Similarity	NPC155763
0.897	High Similarity	NPC67326
0.897	High Similarity	NPC156869
0.897	High Similarity	NPC183357
0.897	High Similarity	NPC29958

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 NPC121290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	892
0.2-0.3	1776
0.3-0.4	2624
0.4-0.5	1869
0.5-0.6	1006
0.6-0.7	466
0.7-0.8	141
0.8-0.85	19
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD4868	Clinical (unspecified phase)
0.9085	High Similarity	NPD7074	Phase 3
0.9024	High Similarity	NPD7054	Approved
0.897	High Similarity	NPD7472	Approved
0.8916	High Similarity	NPD6797	Phase 2
0.8916	High Similarity	NPD7993	Clinical (unspecified phase)
0.8862	High Similarity	NPD7251	Discontinued
0.8848	High Similarity	NPD3818	Discontinued
0.8841	High Similarity	NPD6168	Clinical (unspecified phase)
0.8841	High Similarity	NPD6167	Clinical (unspecified phase)
0.8841	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD4381	Clinical (unspecified phase)
0.881	High Similarity	NPD4338	Clinical (unspecified phase)
0.8698	High Similarity	NPD7808	Phase 3
0.8553	High Similarity	NPD1653	Approved
0.8529	High Similarity	NPD6559	Discontinued
0.8512	High Similarity	NPD7228	Approved
0.8462	Intermediate Similarity	NPD5844	Phase 1
0.8462	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8405	Intermediate Similarity	NPD8455	Phase 2
0.8324	Intermediate Similarity	NPD8312	Approved
0.8324	Intermediate Similarity	NPD8313	Approved
0.8269	Intermediate Similarity	NPD7266	Discontinued
0.8261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4380	Phase 2
0.8214	Intermediate Similarity	NPD7199	Phase 2
0.8204	Intermediate Similarity	NPD6234	Discontinued
0.8144	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD5402	Approved
0.8121	Intermediate Similarity	NPD37	Approved
0.8117	Intermediate Similarity	NPD1613	Approved
0.8117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD4967	Phase 2
0.8084	Intermediate Similarity	NPD4965	Approved
0.8075	Intermediate Similarity	NPD1511	Approved
0.8072	Intermediate Similarity	NPD2801	Approved
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8037	Intermediate Similarity	NPD5403	Approved
0.8012	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD7240	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7976	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD1512	Approved
0.7964	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD5401	Approved
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6959	Discontinued
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1549	Phase 2
0.787	Intermediate Similarity	NPD7768	Phase 2
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7819	Suspended
0.784	Intermediate Similarity	NPD6190	Approved
0.7836	Intermediate Similarity	NPD5494	Approved
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7473	Discontinued
0.7812	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7749	Intermediate Similarity	NPD8151	Discontinued
0.7744	Intermediate Similarity	NPD6799	Approved
0.7725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7688	Intermediate Similarity	NPD3748	Approved
0.7672	Intermediate Similarity	NPD7680	Approved
0.7647	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3787	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7616	Intermediate Similarity	NPD3749	Approved
0.761	Intermediate Similarity	NPD1933	Approved
0.759	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1510	Phase 2
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7574	Intermediate Similarity	NPD6599	Discontinued
0.7561	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6798	Discontinued
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.7531	Intermediate Similarity	NPD2796	Approved
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7585	Approved
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6782	Approved
0.7403	Intermediate Similarity	NPD1091	Approved
0.7394	Intermediate Similarity	NPD6674	Discontinued
0.7391	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD8127	Discontinued
0.7375	Intermediate Similarity	NPD6233	Phase 2
0.7371	Intermediate Similarity	NPD7583	Approved
0.7363	Intermediate Similarity	NPD7549	Discontinued
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD1240	Approved
0.7308	Intermediate Similarity	NPD7038	Approved
0.7308	Intermediate Similarity	NPD7039	Approved
0.7306	Intermediate Similarity	NPD7697	Approved
0.7306	Intermediate Similarity	NPD7698	Approved
0.7306	Intermediate Similarity	NPD7696	Phase 3
0.7301	Intermediate Similarity	NPD7097	Phase 1
0.7289	Intermediate Similarity	NPD1652	Phase 2
0.7284	Intermediate Similarity	NPD5124	Phase 1
0.7284	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD919	Approved
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7239	Intermediate Similarity	NPD1607	Approved
0.7235	Intermediate Similarity	NPD6273	Approved
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1203	Approved
0.7209	Intermediate Similarity	NPD3226	Approved
0.7207	Intermediate Similarity	NPD3926	Phase 2
0.7205	Intermediate Similarity	NPD3764	Approved
0.72	Intermediate Similarity	NPD4288	Approved
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7179	Intermediate Similarity	NPD8320	Phase 1
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD8319	Approved
0.7178	Intermediate Similarity	NPD6355	Discontinued
0.7176	Intermediate Similarity	NPD2533	Approved
0.7176	Intermediate Similarity	NPD2534	Approved
0.7176	Intermediate Similarity	NPD2532	Approved
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7119	Intermediate Similarity	NPD6971	Discontinued
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.7111	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7089	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD422	Phase 1
0.7066	Intermediate Similarity	NPD2346	Discontinued
0.7065	Intermediate Similarity	NPD5953	Discontinued
0.7059	Intermediate Similarity	NPD7440	Discontinued
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.705	Intermediate Similarity	NPD7801	Approved
0.7048	Intermediate Similarity	NPD2799	Discontinued
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7044	Intermediate Similarity	NPD3225	Approved
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.7021	Intermediate Similarity	NPD8434	Phase 2
0.7019	Intermediate Similarity	NPD9494	Approved
0.7019	Intermediate Similarity	NPD2861	Phase 2
0.7012	Intermediate Similarity	NPD4060	Phase 1
0.7011	Intermediate Similarity	NPD3455	Phase 2
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD3268	Approved
0.6994	Remote Similarity	NPD920	Approved
0.699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6842	Approved
0.6984	Remote Similarity	NPD6841	Approved
0.6984	Remote Similarity	NPD6843	Phase 3

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