NPASS Compound

Structure

CID47398 OpenBabel06191715382D 23 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -1.0000 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 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 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 -3.4641 0.0000 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 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 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 -3.4641 -1.0000 0.0000 C 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -4.3301 -1.5000 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 22 1 0 0 0 0 2 7 2 0 0 0 0 2 11 1 0 0 0 0 3 7 1 0 0 0 0 3 12 2 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 6 0 0 0 14 23 1 0 0 0 0 15 7 1 6 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.09
Volume:	305.336
LogP:	1.164
LogD:	1.35
LogS:	-2.673
# Rotatable Bonds:	2
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	3.526
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.241
MDCK Permeability:	4.346996774984291e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.057
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.866
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	92.10637664794922%
Volume Distribution (VD):	0.587
Pgp-substrate:	8.064188003540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.555
CYP1A2-substrate:	0.597
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	13.403
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.32
Rat Oral Acute Toxicity:	0.451
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.942
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.898
Respiratory Toxicity:	0.291

Download Data

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

Natural Product: NPC47398

Natural Product ID:	NPC47398
*Common Name:**	Ouratea-Catechin
IUPAC Name:	(2R,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:	4'-O-Methylepigallocatechin; Ouratea-Catechin
Standard InCHIKey:	ITDYPNOEEHONAH-UKRRQHHQSA-N
Standard InCHI:	InChI=1S/C16H16O7/c1-22-16-11(19)2-7(3-12(16)20)15-13(21)6-9-10(18)4-8(17)5-14(9)23-15/h2-5,13,15,17-21H,6H2,1H3/t13-,15-/m1/s1
SMILES:	COc1c(cc(cc1O)[C@@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485460
PubChem CID:	176920
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 [CHEMONTID:0001594] Epigallocatechins

*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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[21080642]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	bark	Santa Maria, Rio Grande do Sul, Brazil	2007-OCT	PMID[21080642]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO21327	Ramalina stenospora	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23614	Ovophis okinavensis	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14242	Maytenus laevis	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	2
Others	7

Activity Type	# Activity
Cell Line	6
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	3300.0	nM	PMID[448911]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	23.0	%	PMID[448911]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	662.9	pg/ml	PMID[448912]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[448912]
NPT283	Individual Protein	MAP kinase p38 alpha	Homo sapiens	IC50	=	39160.0	nM	PMID[448913]

☑ 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 NPC47398 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	420
0.1-0.2	1631
0.2-0.3	4966
0.3-0.4	12454
0.4-0.5	5405
0.5-0.6	4074
0.6-0.7	5803
0.7-0.8	5874
0.8-0.85	1078
0.85-0.9	635
0.9-0.95	299
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234333
1.0	High Similarity	NPC260898
0.9922	High Similarity	NPC306441
0.9922	High Similarity	NPC16435
0.9845	High Similarity	NPC112246
0.9845	High Similarity	NPC470356
0.9845	High Similarity	NPC121812
0.9845	High Similarity	NPC94750
0.9845	High Similarity	NPC112939
0.9845	High Similarity	NPC61946
0.9845	High Similarity	NPC474206
0.9769	High Similarity	NPC230734
0.9769	High Similarity	NPC227503
0.9769	High Similarity	NPC470802
0.9769	High Similarity	NPC269091
0.9769	High Similarity	NPC474639
0.9769	High Similarity	NPC302701
0.9766	High Similarity	NPC127624
0.9695	High Similarity	NPC102904
0.9695	High Similarity	NPC103976
0.9695	High Similarity	NPC474282
0.9695	High Similarity	NPC326797
0.9695	High Similarity	NPC211549
0.9695	High Similarity	NPC107551
0.9695	High Similarity	NPC176051
0.9692	High Similarity	NPC151224
0.9692	High Similarity	NPC164787
0.969	High Similarity	NPC263064
0.969	High Similarity	NPC11060
0.969	High Similarity	NPC475840
0.9688	High Similarity	NPC220825
0.9688	High Similarity	NPC268342
0.9688	High Similarity	NPC268266
0.9688	High Similarity	NPC42760
0.9624	High Similarity	NPC471389
0.9618	High Similarity	NPC265433
0.9618	High Similarity	NPC472336
0.9618	High Similarity	NPC472334
0.9618	High Similarity	NPC162659
0.9618	High Similarity	NPC270456
0.9618	High Similarity	NPC248727
0.9615	High Similarity	NPC170694
0.9615	High Similarity	NPC317380
0.9612	High Similarity	NPC261619
0.9612	High Similarity	NPC253105
0.9612	High Similarity	NPC78770
0.9612	High Similarity	NPC86655
0.9612	High Similarity	NPC202762
0.9612	High Similarity	NPC185604
0.9612	High Similarity	NPC61477
0.9612	High Similarity	NPC15658
0.9612	High Similarity	NPC201587
0.9612	High Similarity	NPC219876
0.9612	High Similarity	NPC126029
0.9549	High Similarity	NPC184797
0.9549	High Similarity	NPC309124
0.9545	High Similarity	NPC276490
0.9542	High Similarity	NPC472337
0.9542	High Similarity	NPC473413
0.9538	High Similarity	NPC229442
0.9538	High Similarity	NPC168059
0.9535	High Similarity	NPC472597
0.9535	High Similarity	NPC309787
0.9478	High Similarity	NPC247291
0.9474	High Similarity	NPC319647
0.9474	High Similarity	NPC245207
0.9474	High Similarity	NPC127218
0.9474	High Similarity	NPC70682
0.9474	High Similarity	NPC473739
0.9474	High Similarity	NPC25966
0.9474	High Similarity	NPC232164
0.9474	High Similarity	NPC260741
0.9474	High Similarity	NPC236306
0.9474	High Similarity	NPC471388
0.947	High Similarity	NPC234952
0.9466	High Similarity	NPC478085
0.9462	High Similarity	NPC35932
0.9462	High Similarity	NPC7903
0.9462	High Similarity	NPC470752
0.9462	High Similarity	NPC184447
0.9462	High Similarity	NPC160991
0.9462	High Similarity	NPC16208
0.9457	High Similarity	NPC472338
0.9407	High Similarity	NPC107161
0.9403	High Similarity	NPC22317
0.9403	High Similarity	NPC259519
0.9394	High Similarity	NPC195022
0.938	High Similarity	NPC86030
0.938	High Similarity	NPC5851
0.938	High Similarity	NPC190629
0.938	High Similarity	NPC285339
0.938	High Similarity	NPC212015
0.938	High Similarity	NPC218856
0.938	High Similarity	NPC273295
0.938	High Similarity	NPC222004
0.938	High Similarity	NPC476968
0.938	High Similarity	NPC202582
0.938	High Similarity	NPC170844
0.938	High Similarity	NPC210623
0.938	High Similarity	NPC3439
0.938	High Similarity	NPC226788
0.938	High Similarity	NPC470258
0.9375	High Similarity	NPC5447
0.9375	High Similarity	NPC250432
0.9343	High Similarity	NPC475096
0.9343	High Similarity	NPC277867
0.9343	High Similarity	NPC161700
0.9338	High Similarity	NPC81638
0.9338	High Similarity	NPC85264
0.9338	High Similarity	NPC47633
0.9338	High Similarity	NPC102044
0.9333	High Similarity	NPC178054
0.9333	High Similarity	NPC35216
0.9333	High Similarity	NPC263261
0.9333	High Similarity	NPC311530
0.9333	High Similarity	NPC87725
0.9328	High Similarity	NPC22517
0.9328	High Similarity	NPC32630
0.9323	High Similarity	NPC173660
0.9318	High Similarity	NPC310854
0.9318	High Similarity	NPC106215
0.9308	High Similarity	NPC214860
0.9308	High Similarity	NPC469614
0.9308	High Similarity	NPC469612
0.9308	High Similarity	NPC91291
0.9302	High Similarity	NPC470213
0.9302	High Similarity	NPC252307
0.9302	High Similarity	NPC206615
0.9302	High Similarity	NPC245826
0.9302	High Similarity	NPC474178
0.9302	High Similarity	NPC186843
0.9302	High Similarity	NPC98631
0.9302	High Similarity	NPC226331
0.9302	High Similarity	NPC72529
0.9302	High Similarity	NPC46274
0.9302	High Similarity	NPC31707
0.9275	High Similarity	NPC125755
0.9275	High Similarity	NPC99515
0.9275	High Similarity	NPC190714
0.927	High Similarity	NPC171932
0.927	High Similarity	NPC280092
0.927	High Similarity	NPC63879
0.927	High Similarity	NPC50250
0.927	High Similarity	NPC12641
0.927	High Similarity	NPC28440
0.927	High Similarity	NPC45257
0.927	High Similarity	NPC93323
0.927	High Similarity	NPC473108
0.9265	High Similarity	NPC475891
0.9265	High Similarity	NPC204347
0.9265	High Similarity	NPC475084
0.9265	High Similarity	NPC189115
0.9265	High Similarity	NPC59841
0.9265	High Similarity	NPC2613
0.9259	High Similarity	NPC266197
0.9259	High Similarity	NPC160283
0.9259	High Similarity	NPC254759
0.9259	High Similarity	NPC291101
0.9259	High Similarity	NPC27495
0.9254	High Similarity	NPC474390
0.9248	High Similarity	NPC134968
0.9248	High Similarity	NPC256262
0.9237	High Similarity	NPC469613
0.9237	High Similarity	NPC470095
0.9237	High Similarity	NPC469625
0.9237	High Similarity	NPC474017
0.9237	High Similarity	NPC470096
0.9237	High Similarity	NPC30043
0.9237	High Similarity	NPC103799
0.9231	High Similarity	NPC45824
0.9231	High Similarity	NPC469951
0.9231	High Similarity	NPC469963
0.9225	High Similarity	NPC242032
0.9225	High Similarity	NPC236791
0.9225	High Similarity	NPC293054
0.9225	High Similarity	NPC324112
0.9225	High Similarity	NPC111247
0.9225	High Similarity	NPC147821
0.9225	High Similarity	NPC169474
0.9225	High Similarity	NPC183181
0.9225	High Similarity	NPC319625
0.9225	High Similarity	NPC292056
0.9225	High Similarity	NPC74817
0.9225	High Similarity	NPC82679
0.9225	High Similarity	NPC163332
0.9225	High Similarity	NPC124452
0.9225	High Similarity	NPC474119
0.9225	High Similarity	NPC246620
0.9225	High Similarity	NPC118787
0.9225	High Similarity	NPC282000
0.9225	High Similarity	NPC210355
0.9225	High Similarity	NPC41706
0.9225	High Similarity	NPC159968
0.9209	High Similarity	NPC227902
0.9209	High Similarity	NPC474397
0.9209	High Similarity	NPC101376
0.9197	High Similarity	NPC37793
0.9197	High Similarity	NPC477616
0.9191	High Similarity	NPC265075
0.9191	High Similarity	NPC83375

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 NPC47398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	895
0.2-0.3	2044
0.3-0.4	2669
0.4-0.5	1520
0.5-0.6	836
0.6-0.7	641
0.7-0.8	159
0.8-0.85	14
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9612	High Similarity	NPD1612	Clinical (unspecified phase)
0.9612	High Similarity	NPD1613	Approved
0.938	High Similarity	NPD3027	Phase 3
0.9375	High Similarity	NPD1530	Clinical (unspecified phase)
0.9302	High Similarity	NPD1529	Clinical (unspecified phase)
0.8582	High Similarity	NPD4908	Phase 1
0.8571	High Similarity	NPD1934	Approved
0.8473	Intermediate Similarity	NPD1610	Phase 2
0.8456	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD1548	Phase 1
0.8299	Intermediate Similarity	NPD1653	Approved
0.8278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8235	Intermediate Similarity	NPD2861	Phase 2
0.8209	Intermediate Similarity	NPD4749	Approved
0.8188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2801	Approved
0.8116	Intermediate Similarity	NPD4625	Phase 3
0.8102	Intermediate Similarity	NPD3018	Phase 2
0.805	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7987	Intermediate Similarity	NPD7054	Approved
0.7941	Intermediate Similarity	NPD2983	Phase 2
0.7941	Intermediate Similarity	NPD2982	Phase 2
0.7937	Intermediate Similarity	NPD7472	Approved
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7926	Intermediate Similarity	NPD1091	Approved
0.7925	Intermediate Similarity	NPD3818	Discontinued
0.7922	Intermediate Similarity	NPD3882	Suspended
0.7907	Intermediate Similarity	NPD228	Approved
0.7905	Intermediate Similarity	NPD1511	Approved
0.7868	Intermediate Similarity	NPD2981	Phase 2
0.7843	Intermediate Similarity	NPD37	Approved
0.7817	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3620	Phase 2
0.7812	Intermediate Similarity	NPD7228	Approved
0.7806	Intermediate Similarity	NPD4967	Phase 2
0.7806	Intermediate Similarity	NPD4965	Approved
0.7806	Intermediate Similarity	NPD4966	Approved
0.78	Intermediate Similarity	NPD1512	Approved
0.7786	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD4536	Approved
0.7778	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4538	Approved
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD1652	Phase 2
0.7742	Intermediate Similarity	NPD3817	Phase 2
0.774	Intermediate Similarity	NPD7266	Discontinued
0.773	Intermediate Similarity	NPD7251	Discontinued
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD1558	Phase 1
0.7683	Intermediate Similarity	NPD7808	Phase 3
0.7683	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1465	Phase 2
0.7676	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2684	Approved
0.7669	Intermediate Similarity	NPD6671	Approved
0.7667	Intermediate Similarity	NPD7213	Phase 3
0.7667	Intermediate Similarity	NPD7212	Phase 2
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5124	Phase 1
0.7635	Intermediate Similarity	NPD5177	Phase 3
0.7628	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD8651	Approved
0.7619	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7447	Phase 1
0.7603	Intermediate Similarity	NPD5588	Approved
0.7603	Intermediate Similarity	NPD5960	Phase 3
0.7597	Intermediate Similarity	NPD4678	Approved
0.7597	Intermediate Similarity	NPD290	Approved
0.7597	Intermediate Similarity	NPD4675	Approved
0.7576	Intermediate Similarity	NPD7843	Approved
0.7568	Intermediate Similarity	NPD1549	Phase 2
0.7551	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD5494	Approved
0.7537	Intermediate Similarity	NPD7157	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7536	Intermediate Similarity	NPD422	Phase 1
0.7533	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7075	Discontinued
0.7532	Intermediate Similarity	NPD4005	Discontinued
0.7516	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3540	Phase 1
0.7483	Intermediate Similarity	NPD5058	Phase 3
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.7452	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3539	Phase 1
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7417	Intermediate Similarity	NPD2677	Approved
0.741	Intermediate Similarity	NPD6559	Discontinued
0.74	Intermediate Similarity	NPD3060	Approved
0.7394	Intermediate Similarity	NPD6584	Phase 3
0.7391	Intermediate Similarity	NPD5846	Approved
0.7391	Intermediate Similarity	NPD6516	Phase 2
0.7381	Intermediate Similarity	NPD8053	Approved
0.7381	Intermediate Similarity	NPD8054	Approved
0.7365	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7549	Discontinued
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3892	Phase 2
0.7346	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2424	Discontinued
0.7325	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1774	Approved
0.7319	Intermediate Similarity	NPD1357	Approved
0.7315	Intermediate Similarity	NPD2796	Approved
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7240	Approved
0.7303	Intermediate Similarity	NPD6190	Approved
0.7296	Intermediate Similarity	NPD5402	Approved
0.7296	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4236	Phase 3
0.7285	Intermediate Similarity	NPD4162	Approved
0.7285	Intermediate Similarity	NPD4237	Approved
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7279	Intermediate Similarity	NPD5735	Approved
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4123	Phase 3
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD5762	Approved
0.726	Intermediate Similarity	NPD6233	Phase 2
0.7256	Intermediate Similarity	NPD27	Approved
0.7256	Intermediate Similarity	NPD2489	Approved
0.7252	Intermediate Similarity	NPD968	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD1510	Phase 2
0.7241	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD3787	Discontinued
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7237	Intermediate Similarity	NPD6331	Phase 2
0.7237	Intermediate Similarity	NPD4535	Phase 3
0.7237	Intermediate Similarity	NPD3750	Approved
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD2238	Phase 2
0.7209	Intermediate Similarity	NPD291	Approved
0.7209	Intermediate Similarity	NPD940	Approved
0.7209	Intermediate Similarity	NPD846	Approved
0.7208	Intermediate Similarity	NPD4357	Discontinued
0.7208	Intermediate Similarity	NPD6799	Approved
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2970	Approved
0.7195	Intermediate Similarity	NPD2969	Approved
0.7193	Intermediate Similarity	NPD4663	Approved
0.719	Intermediate Similarity	NPD2219	Phase 1
0.7188	Intermediate Similarity	NPD2560	Approved
0.7188	Intermediate Similarity	NPD2563	Approved
0.7183	Intermediate Similarity	NPD6583	Phase 3
0.7183	Intermediate Similarity	NPD6582	Phase 2
0.7179	Intermediate Similarity	NPD5403	Approved
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.7172	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7151	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7134	Intermediate Similarity	NPD3051	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7134	Intermediate Similarity	NPD3687	Approved
0.7134	Intermediate Similarity	NPD6071	Discontinued
0.7133	Intermediate Similarity	NPD6696	Suspended
0.7132	Intermediate Similarity	NPD1242	Phase 1
0.7125	Intermediate Similarity	NPD2977	Approved
0.7125	Intermediate Similarity	NPD5773	Approved
0.7125	Intermediate Similarity	NPD5772	Approved
0.7125	Intermediate Similarity	NPD2978	Approved
0.7125	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8455	Phase 2
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7466	Approved
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7118	Intermediate Similarity	NPD7311	Approved
0.7118	Intermediate Similarity	NPD7313	Approved
0.7118	Intermediate Similarity	NPD4577	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