NPASS Compound

Structure

NPC474656 OpenBabel07101718222D 29 32 0 0 1 0 0 0 0 0999 V2000 4.3301 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 4.3301 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 3.4641 3.0000 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 -2.5981 1.5000 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 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 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 1.0000 0.0000 C 0 0 2 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 1.7321 -3.0000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 0.8660 2.5000 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 12 2 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 19 2 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 13 1 6 0 0 0 21 28 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.11
Volume:	390.009
LogP:	3.659
LogD:	2.973
LogS:	-3.948
# Rotatable Bonds:	4
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	3.237
Fsp3:	0.136
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.888
MDCK Permeability:	7.1515260060550645e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	98.99864959716797%
Volume Distribution (VD):	0.559
Pgp-substrate:	1.343031883239746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.62
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.35
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	13.387
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.928
Carcinogencity:	0.408
Eye Corrosion:	0.003
Eye Irritation:	0.925
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC474656

Natural Product ID:	NPC474656
*Common Name:**	(-)-Epicatechin-3-Benzoate
IUPAC Name:	[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] benzoate
Synonyms:
Standard InCHIKey:	KYOUXLCBBPBCLD-NHCUHLMSSA-N
Standard InCHI:	InChI=1S/C22H18O7/c23-14-9-17(25)15-11-20(29-22(27)12-4-2-1-3-5-12)21(28-19(15)10-14)13-6-7-16(24)18(26)8-13/h1-10,20-21,23-26H,11H2/t20-,21-/m1/s1
SMILES:	C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478577
PubChem CID:	10453226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*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	=	17.0	ug.mL-1	PMID[447924]

☑ 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 NPC474656 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	374
0.1-0.2	1598
0.2-0.3	3975
0.3-0.4	9338
0.4-0.5	8768
0.5-0.6	3244
0.6-0.7	4965
0.7-0.8	6871
0.8-0.85	2901
0.85-0.9	611
0.9-0.95	30
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC38779
0.9732	High Similarity	NPC68324
0.9732	High Similarity	NPC114179
0.9732	High Similarity	NPC160512
0.9732	High Similarity	NPC289322
0.9732	High Similarity	NPC156818
0.9664	High Similarity	NPC88803
0.9664	High Similarity	NPC104983
0.9664	High Similarity	NPC291948
0.9664	High Similarity	NPC250436
0.9664	High Similarity	NPC300845
0.9603	High Similarity	NPC53889
0.9603	High Similarity	NPC24164
0.9536	High Similarity	NPC87317
0.9533	High Similarity	NPC318432
0.9416	High Similarity	NPC121290
0.9384	High Similarity	NPC40222
0.9384	High Similarity	NPC268515
0.9236	High Similarity	NPC473818
0.9231	High Similarity	NPC142614
0.9226	High Similarity	NPC476371
0.9226	High Similarity	NPC476372
0.9119	High Similarity	NPC476365
0.9108	High Similarity	NPC471788
0.9103	High Similarity	NPC476247
0.9097	High Similarity	NPC289346
0.9097	High Similarity	NPC476373
0.9079	High Similarity	NPC199773
0.9062	High Similarity	NPC81332
0.9062	High Similarity	NPC262580
0.9062	High Similarity	NPC289396
0.9062	High Similarity	NPC271848
0.9062	High Similarity	NPC47140
0.9062	High Similarity	NPC67134
0.9062	High Similarity	NPC212038
0.9057	High Similarity	NPC476279
0.9038	High Similarity	NPC142252
0.9038	High Similarity	NPC158188
0.9038	High Similarity	NPC112418
0.9026	High Similarity	NPC165483
0.902	High Similarity	NPC18727
0.9013	High Similarity	NPC75695
0.9007	High Similarity	NPC1612
0.9007	High Similarity	NPC183959
0.9006	High Similarity	NPC98583
0.9	High Similarity	NPC204937
0.9	High Similarity	NPC149011
0.9	High Similarity	NPC180768
0.8981	High Similarity	NPC477841
0.8981	High Similarity	NPC219927
0.8981	High Similarity	NPC473445
0.8981	High Similarity	NPC33298
0.8981	High Similarity	NPC42797
0.8981	High Similarity	NPC471745
0.8981	High Similarity	NPC4013
0.8981	High Similarity	NPC90905
0.8981	High Similarity	NPC285108
0.8974	High Similarity	NPC471744
0.8974	High Similarity	NPC24627
0.8968	High Similarity	NPC108456
0.8968	High Similarity	NPC291508
0.8954	High Similarity	NPC236637
0.8954	High Similarity	NPC219582
0.8954	High Similarity	NPC302950
0.8944	High Similarity	NPC100251
0.8944	High Similarity	NPC65333
0.894	High Similarity	NPC321011
0.894	High Similarity	NPC294852
0.894	High Similarity	NPC107636
0.894	High Similarity	NPC476394
0.894	High Similarity	NPC98809
0.894	High Similarity	NPC188679
0.8933	High Similarity	NPC476347
0.8931	High Similarity	NPC207575
0.8931	High Similarity	NPC13481
0.8924	High Similarity	NPC291977
0.8917	High Similarity	NPC113163
0.8917	High Similarity	NPC84324
0.8917	High Similarity	NPC66618
0.8917	High Similarity	NPC288131
0.8917	High Similarity	NPC165970
0.8917	High Similarity	NPC216916
0.8917	High Similarity	NPC305987
0.891	High Similarity	NPC24339
0.891	High Similarity	NPC98083
0.891	High Similarity	NPC94220
0.891	High Similarity	NPC7543
0.891	High Similarity	NPC166456
0.891	High Similarity	NPC53545
0.891	High Similarity	NPC117418
0.891	High Similarity	NPC172202
0.891	High Similarity	NPC476410
0.891	High Similarity	NPC284127
0.8903	High Similarity	NPC227062
0.8903	High Similarity	NPC195796
0.8903	High Similarity	NPC471500
0.8903	High Similarity	NPC208152
0.8903	High Similarity	NPC35038
0.8903	High Similarity	NPC278778
0.8903	High Similarity	NPC78492
0.8903	High Similarity	NPC291878
0.8896	High Similarity	NPC67629
0.8896	High Similarity	NPC298802
0.8896	High Similarity	NPC469888
0.8896	High Similarity	NPC213896
0.8896	High Similarity	NPC256346
0.8896	High Similarity	NPC141212
0.8896	High Similarity	NPC246328
0.8896	High Similarity	NPC79736
0.8896	High Similarity	NPC192083
0.8896	High Similarity	NPC27532
0.8896	High Similarity	NPC325028
0.8889	High Similarity	NPC120774
0.8889	High Similarity	NPC172033
0.8889	High Similarity	NPC175230
0.8889	High Similarity	NPC264875
0.8889	High Similarity	NPC88560
0.8889	High Similarity	NPC472993
0.8889	High Similarity	NPC476434
0.8889	High Similarity	NPC163598
0.8882	High Similarity	NPC105512
0.8882	High Similarity	NPC221091
0.8882	High Similarity	NPC473091
0.8882	High Similarity	NPC259576
0.8875	High Similarity	NPC14662
0.8875	High Similarity	NPC243877
0.8875	High Similarity	NPC260266
0.8874	High Similarity	NPC142528
0.8874	High Similarity	NPC95864
0.8874	High Similarity	NPC187398
0.8874	High Similarity	NPC476348
0.8874	High Similarity	NPC139839
0.8868	High Similarity	NPC58223
0.8868	High Similarity	NPC125039
0.8868	High Similarity	NPC477840
0.8868	High Similarity	NPC7154
0.8868	High Similarity	NPC36916
0.8868	High Similarity	NPC36
0.8868	High Similarity	NPC7688
0.8868	High Similarity	NPC72787
0.8867	High Similarity	NPC262282
0.8861	High Similarity	NPC474034
0.8861	High Similarity	NPC474033
0.8861	High Similarity	NPC249070
0.8854	High Similarity	NPC118256
0.8854	High Similarity	NPC239966
0.8854	High Similarity	NPC119209
0.8854	High Similarity	NPC292415
0.8854	High Similarity	NPC192686
0.8854	High Similarity	NPC203020
0.8854	High Similarity	NPC301089
0.8854	High Similarity	NPC101731
0.8846	High Similarity	NPC474208
0.8846	High Similarity	NPC35598
0.8846	High Similarity	NPC183851
0.8846	High Similarity	NPC63454
0.8846	High Similarity	NPC129684
0.8846	High Similarity	NPC222689
0.8846	High Similarity	NPC299520
0.8846	High Similarity	NPC474836
0.8846	High Similarity	NPC474055
0.8846	High Similarity	NPC162869
0.8846	High Similarity	NPC52530
0.8846	High Similarity	NPC471515
0.8846	High Similarity	NPC475267
0.8846	High Similarity	NPC156057
0.8846	High Similarity	NPC210084
0.8846	High Similarity	NPC27337
0.8846	High Similarity	NPC472598
0.8846	High Similarity	NPC48208
0.8846	High Similarity	NPC99597
0.8846	High Similarity	NPC471479
0.8846	High Similarity	NPC67876
0.8846	High Similarity	NPC471209
0.8841	High Similarity	NPC476622
0.8841	High Similarity	NPC476620
0.8841	High Similarity	NPC267549
0.8841	High Similarity	NPC476623
0.8841	High Similarity	NPC476621
0.8841	High Similarity	NPC476619
0.8841	High Similarity	NPC476618
0.8839	High Similarity	NPC203757
0.8839	High Similarity	NPC470327
0.8839	High Similarity	NPC67396
0.8839	High Similarity	NPC222185
0.8839	High Similarity	NPC286052
0.8839	High Similarity	NPC321779
0.8839	High Similarity	NPC477503
0.8839	High Similarity	NPC45849
0.8839	High Similarity	NPC200761
0.8834	High Similarity	NPC81042
0.8834	High Similarity	NPC223426
0.8834	High Similarity	NPC214621
0.8834	High Similarity	NPC34267
0.8831	High Similarity	NPC106976
0.8831	High Similarity	NPC36835
0.8831	High Similarity	NPC61506
0.8831	High Similarity	NPC9743
0.8831	High Similarity	NPC477231
0.8831	High Similarity	NPC472912

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 NPC474656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	893
0.2-0.3	1702
0.3-0.4	2519
0.4-0.5	1843
0.5-0.6	1074
0.6-0.7	563
0.7-0.8	148
0.8-0.85	42
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD4868	Clinical (unspecified phase)
0.8954	High Similarity	NPD1934	Approved
0.8944	High Similarity	NPD7993	Clinical (unspecified phase)
0.8896	High Similarity	NPD2393	Clinical (unspecified phase)
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD5844	Phase 1
0.8654	High Similarity	NPD1465	Phase 2
0.8553	High Similarity	NPD1511	Approved
0.8537	High Similarity	NPD7074	Phase 3
0.8535	High Similarity	NPD2801	Approved
0.8528	High Similarity	NPD3818	Discontinued
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1613	Approved
0.8493	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7075	Discontinued
0.8481	Intermediate Similarity	NPD3817	Phase 2
0.8477	Intermediate Similarity	NPD3750	Approved
0.8476	Intermediate Similarity	NPD7054	Approved
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD1512	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8424	Intermediate Similarity	NPD7472	Approved
0.8418	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6797	Phase 2
0.8365	Intermediate Similarity	NPD5402	Approved
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8323	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD5403	Approved
0.8217	Intermediate Similarity	NPD1653	Approved
0.8214	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD6799	Approved
0.8188	Intermediate Similarity	NPD230	Phase 1
0.8187	Intermediate Similarity	NPD7819	Suspended
0.817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.816	Intermediate Similarity	NPD5494	Approved
0.8153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD3748	Approved
0.8141	Intermediate Similarity	NPD5401	Approved
0.8137	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8125	Intermediate Similarity	NPD6801	Discontinued
0.8117	Intermediate Similarity	NPD4628	Phase 3
0.8098	Intermediate Similarity	NPD6234	Discontinued
0.8092	Intermediate Similarity	NPD1551	Phase 2
0.8072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6190	Approved
0.805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3027	Phase 3
0.8037	Intermediate Similarity	NPD3749	Approved
0.8026	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD6798	Discontinued
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7228	Approved
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD2796	Approved
0.7973	Intermediate Similarity	NPD4908	Phase 1
0.7962	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD37	Approved
0.7885	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4967	Phase 2
0.7866	Intermediate Similarity	NPD4965	Approved
0.7866	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD8455	Phase 2
0.7829	Intermediate Similarity	NPD447	Suspended
0.7816	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6233	Phase 2
0.7806	Intermediate Similarity	NPD7266	Discontinued
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1240	Approved
0.7763	Intermediate Similarity	NPD943	Approved
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1933	Approved
0.7688	Intermediate Similarity	NPD7685	Pre-registration
0.7665	Intermediate Similarity	NPD919	Approved
0.7662	Intermediate Similarity	NPD1607	Approved
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD1203	Approved
0.7644	Intermediate Similarity	NPD7549	Discontinued
0.7632	Intermediate Similarity	NPD3764	Approved
0.7622	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7597	Intermediate Similarity	NPD6355	Discontinued
0.7595	Intermediate Similarity	NPD1652	Phase 2
0.759	Intermediate Similarity	NPD4288	Approved
0.7586	Intermediate Similarity	NPD7039	Approved
0.7586	Intermediate Similarity	NPD7038	Approved
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD8127	Discontinued
0.7568	Intermediate Similarity	NPD9269	Phase 2
0.7564	Intermediate Similarity	NPD4308	Phase 3
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2797	Approved
0.7531	Intermediate Similarity	NPD6273	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6971	Discontinued
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD5242	Approved
0.7485	Intermediate Similarity	NPD5353	Approved
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7467	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7453	Intermediate Similarity	NPD7440	Discontinued
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD8166	Discontinued
0.7438	Intermediate Similarity	NPD7003	Approved
0.7434	Intermediate Similarity	NPD2861	Phase 2
0.7434	Intermediate Similarity	NPD9494	Approved
0.7432	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD5408	Approved
0.7405	Intermediate Similarity	NPD5404	Approved
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7405	Intermediate Similarity	NPD5406	Approved
0.7403	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD3455	Phase 2
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD7095	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.733	Intermediate Similarity	NPD5953	Discontinued
0.7329	Intermediate Similarity	NPD4110	Phase 3
0.7329	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD4307	Phase 2
0.7305	Intermediate Similarity	NPD6386	Approved
0.7305	Intermediate Similarity	NPD6385	Approved
0.7297	Intermediate Similarity	NPD9268	Approved
0.729	Intermediate Similarity	NPD1296	Phase 2
0.7278	Intermediate Similarity	NPD7097	Phase 1
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD1243	Approved
0.7257	Intermediate Similarity	NPD7177	Discontinued
0.7256	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4062	Phase 3
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9545	Approved
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7219	Intermediate Similarity	NPD1481	Phase 2
0.7209	Intermediate Similarity	NPD6746	Phase 2
0.7196	Intermediate Similarity	NPD7680	Approved
0.7195	Intermediate Similarity	NPD7213	Phase 3
0.7195	Intermediate Similarity	NPD7212	Phase 2
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD411	Approved
0.7171	Intermediate Similarity	NPD4749	Approved
0.7167	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7152	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD7784	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