NPASS Compound

Structure

NPC471746 OpenBabel07101718282D 37 39 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -2.5981 0.5000 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 -0.0000 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 -5.1962 -1.0000 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 3.5000 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 -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 -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 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 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 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 -0.8660 0.5000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -2.5981 3.5000 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 3.4641 -0.0000 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 -4.3301 0.5000 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 -1.7321 2.0000 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 16 2 0 0 0 0 8 19 1 0 0 0 0 9 17 2 0 0 0 0 9 20 1 0 0 0 0 10 17 1 0 0 0 0 10 21 2 0 0 0 0 11 26 2 0 0 0 0 11 32 1 0 0 0 0 12 27 2 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 30 2 0 0 0 0 15 36 1 0 0 0 0 17 32 1 0 0 0 0 18 19 2 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 22 2 0 0 0 0 20 35 1 0 0 0 0 21 22 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 23 25 1 0 0 0 0 23 31 2 0 0 0 0 24 16 1 1 0 0 0 24 25 1 0 0 0 0 24 37 1 0 0 0 0 25 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.11
Volume:	489.132
LogP:	1.461
LogD:	1.185
LogS:	-5.305
# Rotatable Bonds:	11
TPSA:	157.8
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	3.632
Fsp3:	0.28
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094
MDCK Permeability:	2.810625301208347e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.331
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.612

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.519
Plasma Protein Binding (PPB):	70.78986358642578%
Volume Distribution (VD):	0.546
Pgp-substrate:	33.42854309082031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.621
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	1.217
Half-life (T1/2):	0.442

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.004
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.891
Carcinogencity:	0.058
Eye Corrosion:	0.004
Eye Irritation:	0.178
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC471746

Natural Product ID:	NPC471746
*Common Name:**	Penta-Acetylcatechin
IUPAC Name:	[(2S,3S)-5,7-diacetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl] acetate
Synonyms:
Standard InCHIKey:	MNNMLZRGKMWAMG-LOSJGSFVSA-N
Standard InCHI:	InChI=1S/C25H22O12/c1-11(26)32-17-9-20(35-14(4)29)22-21(10-17)37-24(25(23(22)31)36-15(5)30)16-6-7-18(33-12(2)27)19(8-16)34-13(3)28/h6-10,24-25H,1-5H3/t24-,25+/m0/s1
SMILES:	CC(=O)Oc1cc2O[C@@H](c3ccc(c(c3)OC(=O)C)OC(=O)C)[C@@H](C(=O)c2c(c1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109444
PubChem CID:	26368956
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO33509	byrsonima coccolobifolia	Species	Malpighiaceae	Eukaryota	leaves and stems	cerrado at the Federal University of So Carlos (UFSCar), So Carlos, SP, Brazil	2011-Jul	PMID[24521209]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1662	Individual Protein	Arginase	Leishmania amazonensis	IC50	=	4800.0	nM	PMID[516700]

☑ 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 NPC471746 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	430
0.1-0.2	1694
0.2-0.3	4424
0.3-0.4	9905
0.4-0.5	8094
0.5-0.6	3645
0.6-0.7	5348
0.7-0.8	5932
0.8-0.85	2591
0.85-0.9	593
0.9-0.95	40
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9662	High Similarity	NPC474170
0.9662	High Similarity	NPC474388
0.9662	High Similarity	NPC472535
0.9595	High Similarity	NPC177839
0.9481	High Similarity	NPC471745
0.947	High Similarity	NPC122623
0.947	High Similarity	NPC276059
0.947	High Similarity	NPC34725
0.947	High Similarity	NPC241774
0.9416	High Similarity	NPC112418
0.9408	High Similarity	NPC257277
0.9396	High Similarity	NPC474648
0.9351	High Similarity	NPC477164
0.9351	High Similarity	NPC471744
0.9346	High Similarity	NPC108456
0.9329	High Similarity	NPC183236
0.9329	High Similarity	NPC476342
0.9324	High Similarity	NPC310259
0.9299	High Similarity	NPC475214
0.9276	High Similarity	NPC186507
0.9272	High Similarity	NPC474663
0.9272	High Similarity	NPC198615
0.9262	High Similarity	NPC299923
0.9221	High Similarity	NPC471515
0.9221	High Similarity	NPC471479
0.9205	High Similarity	NPC29056
0.9205	High Similarity	NPC259058
0.9205	High Similarity	NPC201547
0.9189	High Similarity	NPC293201
0.9182	High Similarity	NPC476180
0.9156	High Similarity	NPC474983
0.9156	High Similarity	NPC471500
0.9139	High Similarity	NPC238366
0.9139	High Similarity	NPC181250
0.9139	High Similarity	NPC69752
0.9133	High Similarity	NPC470511
0.9133	High Similarity	NPC117463
0.9128	High Similarity	NPC471590
0.9125	High Similarity	NPC475434
0.9122	High Similarity	NPC9966
0.9122	High Similarity	NPC70853
0.9108	High Similarity	NPC414831
0.9085	High Similarity	NPC475116
0.9085	High Similarity	NPC40033
0.9079	High Similarity	NPC338131
0.9073	High Similarity	NPC63256
0.9073	High Similarity	NPC10304
0.9073	High Similarity	NPC261548
0.906	High Similarity	NPC113089
0.9054	High Similarity	NPC29536
0.9045	High Similarity	NPC471499
0.9032	High Similarity	NPC155063
0.9032	High Similarity	NPC250922
0.9032	High Similarity	NPC303255
0.9032	High Similarity	NPC320825
0.9032	High Similarity	NPC13858
0.9032	High Similarity	NPC326037
0.9026	High Similarity	NPC18727
0.902	High Similarity	NPC236769
0.902	High Similarity	NPC76376
0.902	High Similarity	NPC473732
0.902	High Similarity	NPC295650
0.9013	High Similarity	NPC164299
0.9013	High Similarity	NPC477941
0.9007	High Similarity	NPC85233
0.9	High Similarity	NPC136278
0.9	High Similarity	NPC213482
0.8994	High Similarity	NPC280893
0.8994	High Similarity	NPC475369
0.8986	High Similarity	NPC474037
0.8981	High Similarity	NPC287328
0.8981	High Similarity	NPC470326
0.8981	High Similarity	NPC282009
0.8974	High Similarity	NPC67876
0.8974	High Similarity	NPC52530
0.8968	High Similarity	NPC222185
0.8968	High Similarity	NPC284353
0.8968	High Similarity	NPC37392
0.8968	High Similarity	NPC226025
0.8961	High Similarity	NPC302950
0.8961	High Similarity	NPC219582
0.8961	High Similarity	NPC134677
0.8961	High Similarity	NPC236637
0.8954	High Similarity	NPC166753
0.8954	High Similarity	NPC50728
0.8954	High Similarity	NPC219330
0.8951	High Similarity	NPC153755
0.8944	High Similarity	NPC477165
0.894	High Similarity	NPC106461
0.894	High Similarity	NPC110639
0.894	High Similarity	NPC215932
0.894	High Similarity	NPC40818
0.894	High Similarity	NPC283002
0.894	High Similarity	NPC231013
0.894	High Similarity	NPC302408
0.894	High Similarity	NPC14958
0.8926	High Similarity	NPC185607
0.8926	High Similarity	NPC28326
0.8924	High Similarity	NPC216092
0.8917	High Similarity	NPC257914
0.8917	High Similarity	NPC104459
0.8917	High Similarity	NPC22192
0.8917	High Similarity	NPC152904
0.8917	High Similarity	NPC238405
0.891	High Similarity	NPC195796
0.891	High Similarity	NPC35038
0.891	High Similarity	NPC278778
0.891	High Similarity	NPC178854
0.891	High Similarity	NPC291878
0.8903	High Similarity	NPC279930
0.8903	High Similarity	NPC236223
0.8903	High Similarity	NPC270620
0.8903	High Similarity	NPC162351
0.8903	High Similarity	NPC246204
0.8903	High Similarity	NPC475895
0.8903	High Similarity	NPC179126
0.8903	High Similarity	NPC473664
0.8903	High Similarity	NPC78326
0.8903	High Similarity	NPC58382
0.8902	High Similarity	NPC472384
0.8902	High Similarity	NPC472382
0.8902	High Similarity	NPC472380
0.8896	High Similarity	NPC4390
0.8889	High Similarity	NPC244776
0.8889	High Similarity	NPC116864
0.8889	High Similarity	NPC159103
0.8882	High Similarity	NPC205522
0.8875	High Similarity	NPC36916
0.8875	High Similarity	NPC36
0.8875	High Similarity	NPC7688
0.8875	High Similarity	NPC88243
0.8875	High Similarity	NPC72787
0.8875	High Similarity	NPC58223
0.8875	High Similarity	NPC125039
0.8875	High Similarity	NPC7154
0.8874	High Similarity	NPC165512
0.8868	High Similarity	NPC475144
0.8861	High Similarity	NPC263449
0.8861	High Similarity	NPC470183
0.8861	High Similarity	NPC243509
0.8854	High Similarity	NPC117478
0.8854	High Similarity	NPC27337
0.8854	High Similarity	NPC472598
0.8854	High Similarity	NPC473272
0.8854	High Similarity	NPC474208
0.8854	High Similarity	NPC258644
0.8854	High Similarity	NPC48208
0.8854	High Similarity	NPC474836
0.8854	High Similarity	NPC162869
0.8854	High Similarity	NPC474055
0.8854	High Similarity	NPC156057
0.8854	High Similarity	NPC284820
0.8854	High Similarity	NPC475267
0.8854	High Similarity	NPC291508
0.8846	High Similarity	NPC45849
0.8846	High Similarity	NPC200761
0.8846	High Similarity	NPC255807
0.8846	High Similarity	NPC470327
0.8846	High Similarity	NPC31018
0.8846	High Similarity	NPC477503
0.8846	High Similarity	NPC472909
0.8846	High Similarity	NPC32557
0.8846	High Similarity	NPC189960
0.8841	High Similarity	NPC264735
0.8839	High Similarity	NPC36835
0.8839	High Similarity	NPC61506
0.8839	High Similarity	NPC82325
0.8839	High Similarity	NPC9743
0.8839	High Similarity	NPC260491
0.8839	High Similarity	NPC472912
0.8839	High Similarity	NPC68882
0.8839	High Similarity	NPC279989
0.8839	High Similarity	NPC240476
0.8839	High Similarity	NPC123886
0.8839	High Similarity	NPC19721
0.8839	High Similarity	NPC246162
0.8834	High Similarity	NPC476370
0.8834	High Similarity	NPC190003
0.8834	High Similarity	NPC175107
0.8831	High Similarity	NPC189270
0.8831	High Similarity	NPC5840
0.8827	High Similarity	NPC270578
0.8827	High Similarity	NPC52382
0.8827	High Similarity	NPC203050
0.8827	High Similarity	NPC219904
0.8827	High Similarity	NPC223747
0.8827	High Similarity	NPC225434
0.8827	High Similarity	NPC120099
0.8827	High Similarity	NPC280493
0.8824	High Similarity	NPC195202
0.882	High Similarity	NPC155264
0.882	High Similarity	NPC471213
0.882	High Similarity	NPC193881
0.882	High Similarity	NPC67450
0.882	High Similarity	NPC210460
0.882	High Similarity	NPC477517
0.882	High Similarity	NPC113093
0.8816	High Similarity	NPC216314
0.8816	High Similarity	NPC195919
0.8816	High Similarity	NPC120924

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 NPC471746 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	964
0.2-0.3	1854
0.3-0.4	2558
0.4-0.5	1775
0.5-0.6	1005
0.6-0.7	443
0.7-0.8	138
0.8-0.85	32
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD3817	Phase 2
0.8961	High Similarity	NPD1934	Approved
0.8903	High Similarity	NPD7096	Clinical (unspecified phase)
0.8875	High Similarity	NPD6166	Phase 2
0.8875	High Similarity	NPD6167	Clinical (unspecified phase)
0.8875	High Similarity	NPD6168	Clinical (unspecified phase)
0.8854	High Similarity	NPD7075	Discontinued
0.8808	High Similarity	NPD6799	Approved
0.8797	High Similarity	NPD919	Approved
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD5494	Approved
0.8727	High Similarity	NPD4338	Clinical (unspecified phase)
0.8718	High Similarity	NPD6801	Discontinued
0.8671	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD7808	Phase 3
0.8606	High Similarity	NPD6797	Phase 2
0.8591	High Similarity	NPD2796	Approved
0.859	High Similarity	NPD6599	Discontinued
0.8554	High Similarity	NPD7251	Discontinued
0.8553	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD7074	Phase 3
0.8544	High Similarity	NPD2801	Approved
0.8544	High Similarity	NPD7819	Suspended
0.8491	Intermediate Similarity	NPD5402	Approved
0.8485	Intermediate Similarity	NPD7054	Approved
0.8452	Intermediate Similarity	NPD1512	Approved
0.8434	Intermediate Similarity	NPD7472	Approved
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.8397	Intermediate Similarity	NPD5403	Approved
0.8397	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD5401	Approved
0.8387	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD3926	Phase 2
0.8344	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD1511	Approved
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD4380	Phase 2
0.8235	Intermediate Similarity	NPD1549	Phase 2
0.8086	Intermediate Similarity	NPD1465	Phase 2
0.8079	Intermediate Similarity	NPD1933	Approved
0.805	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6832	Phase 2
0.7949	Intermediate Similarity	NPD1243	Approved
0.7925	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3748	Approved
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7911	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD447	Suspended
0.7843	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD1240	Approved
0.7771	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5353	Approved
0.7706	Intermediate Similarity	NPD5242	Approved
0.7677	Intermediate Similarity	NPD1607	Approved
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7673	Intermediate Similarity	NPD3750	Approved
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3887	Approved
0.7625	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD3226	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2533	Approved
0.7593	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7561	Intermediate Similarity	NPD1653	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.7548	Intermediate Similarity	NPD1613	Approved
0.7548	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6385	Approved
0.753	Intermediate Similarity	NPD6386	Approved
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3146	Approved
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7457	Intermediate Similarity	NPD2403	Approved
0.7446	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5953	Discontinued
0.7436	Intermediate Similarity	NPD943	Approved
0.7434	Intermediate Similarity	NPD3266	Approved
0.7434	Intermediate Similarity	NPD3267	Approved
0.7419	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD1019	Discontinued
0.7383	Intermediate Similarity	NPD17	Approved
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2353	Approved
0.7375	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD3027	Phase 3
0.7346	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.732	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7308	Intermediate Similarity	NPD3268	Approved
0.7284	Intermediate Similarity	NPD1652	Phase 2
0.7284	Intermediate Similarity	NPD2800	Approved
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD7228	Approved
0.7249	Intermediate Similarity	NPD5005	Approved
0.7249	Intermediate Similarity	NPD5006	Approved
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7222	Intermediate Similarity	NPD2897	Discontinued
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD2797	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7205	Intermediate Similarity	NPD6100	Approved
0.7205	Intermediate Similarity	NPD6099	Approved
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7195	Intermediate Similarity	NPD2354	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7178	Intermediate Similarity	NPD2654	Approved
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7151	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7128	Intermediate Similarity	NPD4420	Approved
0.7125	Intermediate Similarity	NPD6651	Approved
0.7124	Intermediate Similarity	NPD2981	Phase 2
0.7118	Intermediate Similarity	NPD5890	Approved
0.7118	Intermediate Similarity	NPD5889	Approved
0.7111	Intermediate Similarity	NPD7039	Approved
0.7111	Intermediate Similarity	NPD7038	Approved
0.7111	Intermediate Similarity	NPD7240	Approved
0.7107	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2438	Suspended
0.709	Intermediate Similarity	NPD8285	Discontinued
0.7089	Intermediate Similarity	NPD411	Approved
0.7079	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2163	Approved
0.7078	Intermediate Similarity	NPD2982	Phase 2
0.7078	Intermediate Similarity	NPD2983	Phase 2
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.707	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD4972	Discontinued
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD2344	Approved
0.7053	Intermediate Similarity	NPD6778	Approved
0.7053	Intermediate Similarity	NPD6781	Approved
0.7053	Intermediate Similarity	NPD6779	Approved
0.7053	Intermediate Similarity	NPD6780	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