NPASS Compound

Structure

NPC471744 OpenBabel07101718282D 25 27 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 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 -3.4641 -0.0000 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 1.7321 -0.0000 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 -2.5981 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 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 -2.5981 -3.5000 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 -2.5981 2.5000 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 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 18 2 0 0 0 0 7 24 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.07
Volume:	326.149
LogP:	1.694
LogD:	1.654
LogS:	-4.124
# Rotatable Bonds:	3
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	3.453
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.524
MDCK Permeability:	9.296662028646097e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	92.18791961669922%
Volume Distribution (VD):	0.554
Pgp-substrate:	8.3346586227417%

ADMET: Metabolism

CYP1A2-inhibitor:	0.539
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.62
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	9.073
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.191
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.867
Carcinogencity:	0.165
Eye Corrosion:	0.006
Eye Irritation:	0.912
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC471744

Natural Product ID:	NPC471744
*Common Name:**	3-Acetyl Catechin
IUPAC Name:	[(2S,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-3-yl] acetate
Synonyms:
Standard InCHIKey:	NPWRSXJQDKRXOR-DLBZAZTESA-N
Standard InCHI:	InChI=1S/C17H14O8/c1-7(18)24-17-15(23)14-12(22)5-9(19)6-13(14)25-16(17)8-2-3-10(20)11(21)4-8/h2-6,16-17,19-22H,1H3/t16-,17+/m0/s1
SMILES:	CC(=O)OC1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109442
PubChem CID:	76313957
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	=	3700.0	nM	PMID[480201]

☑ 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 NPC471744 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	1612
0.2-0.3	4195
0.3-0.4	9065
0.4-0.5	8726
0.5-0.6	3688
0.6-0.7	4727
0.7-0.8	5386
0.8-0.85	3031
0.85-0.9	1583
0.9-0.95	300
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC112418
0.9869	High Similarity	NPC471745
0.9671	High Similarity	NPC471500
0.9608	High Similarity	NPC471479
0.9608	High Similarity	NPC471515
0.9542	High Similarity	NPC320825
0.9542	High Similarity	NPC250922
0.9542	High Similarity	NPC326037
0.9542	High Similarity	NPC13858
0.9481	High Similarity	NPC52530
0.9474	High Similarity	NPC260491
0.9474	High Similarity	NPC240476
0.9474	High Similarity	NPC9743
0.9474	High Similarity	NPC61506
0.9474	High Similarity	NPC219582
0.9474	High Similarity	NPC302950
0.9474	High Similarity	NPC36835
0.9474	High Similarity	NPC236637
0.9474	High Similarity	NPC246162
0.9474	High Similarity	NPC19721
0.9423	High Similarity	NPC471499
0.9419	High Similarity	NPC22192
0.9412	High Similarity	NPC325028
0.9412	High Similarity	NPC27532
0.9412	High Similarity	NPC246328
0.9412	High Similarity	NPC256346
0.9412	High Similarity	NPC18727
0.9412	High Similarity	NPC141212
0.9404	High Similarity	NPC477941
0.9375	High Similarity	NPC116864
0.9375	High Similarity	NPC244776
0.9367	High Similarity	NPC88243
0.9359	High Similarity	NPC470326
0.9359	High Similarity	NPC287328
0.9359	High Similarity	NPC470183
0.9359	High Similarity	NPC263449
0.9359	High Similarity	NPC282009
0.9355	High Similarity	NPC108456
0.9355	High Similarity	NPC67876
0.9351	High Similarity	NPC471746
0.9346	High Similarity	NPC279989
0.9346	High Similarity	NPC123886
0.9346	High Similarity	NPC82325
0.9342	High Similarity	NPC188871
0.9342	High Similarity	NPC149127
0.9342	High Similarity	NPC286342
0.9338	High Similarity	NPC321011
0.9338	High Similarity	NPC294852
0.9338	High Similarity	NPC188679
0.9317	High Similarity	NPC190003
0.9317	High Similarity	NPC153755
0.9317	High Similarity	NPC175107
0.9313	High Similarity	NPC270578
0.9313	High Similarity	NPC52382
0.9299	High Similarity	NPC173137
0.9299	High Similarity	NPC289771
0.9299	High Similarity	NPC308992
0.9295	High Similarity	NPC55738
0.929	High Similarity	NPC278778
0.929	High Similarity	NPC235165
0.929	High Similarity	NPC474638
0.929	High Similarity	NPC291878
0.929	High Similarity	NPC227062
0.929	High Similarity	NPC35038
0.929	High Similarity	NPC255106
0.929	High Similarity	NPC195796
0.929	High Similarity	NPC201837
0.9286	High Similarity	NPC162351
0.9286	High Similarity	NPC236223
0.9286	High Similarity	NPC270620
0.9286	High Similarity	NPC58382
0.9286	High Similarity	NPC213896
0.9286	High Similarity	NPC179126
0.9286	High Similarity	NPC78326
0.9286	High Similarity	NPC192083
0.9281	High Similarity	NPC50403
0.9281	High Similarity	NPC295650
0.9281	High Similarity	NPC260895
0.9281	High Similarity	NPC133953
0.9281	High Similarity	NPC200740
0.9281	High Similarity	NPC28274
0.9281	High Similarity	NPC125062
0.9281	High Similarity	NPC54394
0.9281	High Similarity	NPC252933
0.9276	High Similarity	NPC270465
0.9276	High Similarity	NPC1612
0.9276	High Similarity	NPC183959
0.9276	High Similarity	NPC87125
0.9259	High Similarity	NPC4390
0.9255	High Similarity	NPC155763
0.9255	High Similarity	NPC235260
0.9255	High Similarity	NPC20505
0.925	High Similarity	NPC52550
0.925	High Similarity	NPC317489
0.925	High Similarity	NPC127546
0.925	High Similarity	NPC92565
0.925	High Similarity	NPC223424
0.925	High Similarity	NPC84362
0.925	High Similarity	NPC160156
0.925	High Similarity	NPC173637
0.9245	High Similarity	NPC72787
0.9245	High Similarity	NPC7154
0.9245	High Similarity	NPC36916
0.9245	High Similarity	NPC36
0.9245	High Similarity	NPC125039
0.9245	High Similarity	NPC58223
0.9245	High Similarity	NPC7688
0.9241	High Similarity	NPC127782
0.9241	High Similarity	NPC300537
0.9236	High Similarity	NPC130955
0.9231	High Similarity	NPC472598
0.9231	High Similarity	NPC210084
0.9231	High Similarity	NPC475267
0.9231	High Similarity	NPC474836
0.9231	High Similarity	NPC163524
0.9231	High Similarity	NPC27337
0.9231	High Similarity	NPC48208
0.9231	High Similarity	NPC474208
0.9231	High Similarity	NPC291508
0.9231	High Similarity	NPC305663
0.9231	High Similarity	NPC156057
0.9231	High Similarity	NPC162869
0.9231	High Similarity	NPC474055
0.9231	High Similarity	NPC176665
0.9231	High Similarity	NPC287979
0.9231	High Similarity	NPC99597
0.9226	High Similarity	NPC470327
0.9226	High Similarity	NPC321779
0.9226	High Similarity	NPC477503
0.9226	High Similarity	NPC67396
0.9226	High Similarity	NPC45849
0.9226	High Similarity	NPC200761
0.9226	High Similarity	NPC214138
0.9226	High Similarity	NPC133392
0.9221	High Similarity	NPC106976
0.9221	High Similarity	NPC472912
0.9221	High Similarity	NPC260979
0.9221	High Similarity	NPC55205
0.9216	High Similarity	NPC338131
0.9211	High Similarity	NPC218569
0.9211	High Similarity	NPC3036
0.9198	High Similarity	NPC476370
0.9193	High Similarity	NPC203050
0.9193	High Similarity	NPC138927
0.9193	High Similarity	NPC120099
0.9193	High Similarity	NPC223747
0.9193	High Similarity	NPC219904
0.9193	High Similarity	NPC225434
0.9187	High Similarity	NPC207575
0.9187	High Similarity	NPC253662
0.9187	High Similarity	NPC308404
0.9187	High Similarity	NPC113968
0.9187	High Similarity	NPC179950
0.9187	High Similarity	NPC274618
0.9187	High Similarity	NPC88789
0.9187	High Similarity	NPC277174
0.9187	High Similarity	NPC145038
0.9187	High Similarity	NPC276222
0.9187	High Similarity	NPC73855
0.9187	High Similarity	NPC13481
0.9187	High Similarity	NPC56077
0.9187	High Similarity	NPC281131
0.9187	High Similarity	NPC328940
0.9187	High Similarity	NPC135599
0.9187	High Similarity	NPC471213
0.9187	High Similarity	NPC118284
0.9187	High Similarity	NPC477517
0.9182	High Similarity	NPC472625
0.9177	High Similarity	NPC142252
0.9177	High Similarity	NPC26326
0.9177	High Similarity	NPC472634
0.9177	High Similarity	NPC158188
0.9172	High Similarity	NPC22472
0.9172	High Similarity	NPC130894
0.9172	High Similarity	NPC152166
0.9172	High Similarity	NPC300943
0.9172	High Similarity	NPC9609
0.9172	High Similarity	NPC53545
0.9172	High Similarity	NPC18772
0.9172	High Similarity	NPC176300
0.9172	High Similarity	NPC253634
0.9172	High Similarity	NPC105242
0.9172	High Similarity	NPC115798
0.9172	High Similarity	NPC152904
0.9172	High Similarity	NPC143828
0.9172	High Similarity	NPC191459
0.9172	High Similarity	NPC19687
0.9172	High Similarity	NPC7846
0.9172	High Similarity	NPC117418
0.9172	High Similarity	NPC261004
0.9172	High Similarity	NPC4481
0.9172	High Similarity	NPC204854
0.9172	High Similarity	NPC25495
0.9172	High Similarity	NPC288669
0.9172	High Similarity	NPC18607
0.9167	High Similarity	NPC209614
0.9167	High Similarity	NPC200388
0.9167	High Similarity	NPC100916
0.9167	High Similarity	NPC247017
0.9167	High Similarity	NPC55619

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 NPC471744 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	920
0.2-0.3	1838
0.3-0.4	2541
0.4-0.5	1789
0.5-0.6	1040
0.6-0.7	478
0.7-0.8	134
0.8-0.85	40
0.85-0.9	17
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD1934	Approved
0.9351	High Similarity	NPD3817	Phase 2
0.9286	High Similarity	NPD2393	Clinical (unspecified phase)
0.9245	High Similarity	NPD6166	Phase 2
0.9245	High Similarity	NPD6168	Clinical (unspecified phase)
0.9245	High Similarity	NPD6167	Clinical (unspecified phase)
0.9231	High Similarity	NPD7075	Discontinued
0.9085	High Similarity	NPD4338	Clinical (unspecified phase)
0.908	High Similarity	NPD6797	Phase 2
0.9079	High Similarity	NPD1512	Approved
0.9045	High Similarity	NPD3882	Suspended
0.9045	High Similarity	NPD4868	Clinical (unspecified phase)
0.9038	High Similarity	NPD7096	Clinical (unspecified phase)
0.9024	High Similarity	NPD7251	Discontinued
0.8947	High Similarity	NPD1511	Approved
0.8917	High Similarity	NPD2801	Approved
0.8902	High Similarity	NPD7074	Phase 3
0.8855	High Similarity	NPD7808	Phase 3
0.8854	High Similarity	NPD6801	Discontinued
0.8841	High Similarity	NPD7054	Approved
0.8824	High Similarity	NPD6799	Approved
0.8788	High Similarity	NPD7472	Approved
0.878	High Similarity	NPD3818	Discontinued
0.8735	High Similarity	NPD7993	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8625	High Similarity	NPD5402	Approved
0.8618	High Similarity	NPD1549	Phase 2
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8608	High Similarity	NPD4380	Phase 2
0.8608	High Similarity	NPD6599	Discontinued
0.8562	High Similarity	NPD7819	Suspended
0.8535	High Similarity	NPD5403	Approved
0.8526	High Similarity	NPD5401	Approved
0.8447	Intermediate Similarity	NPD1465	Phase 2
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD919	Approved
0.8303	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2796	Approved
0.8246	Intermediate Similarity	NPD6559	Discontinued
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD1613	Approved
0.8144	Intermediate Similarity	NPD6959	Discontinued
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD230	Phase 1
0.8101	Intermediate Similarity	NPD6190	Approved
0.8063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1607	Approved
0.8047	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD943	Approved
0.8038	Intermediate Similarity	NPD3750	Approved
0.8036	Intermediate Similarity	NPD1247	Approved
0.8013	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.7964	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3926	Phase 2
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4628	Phase 3
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3751	Discontinued
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7871	Intermediate Similarity	NPD447	Suspended
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7824	Intermediate Similarity	NPD7199	Phase 2
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7805	Intermediate Similarity	NPD1653	Approved
0.7792	Intermediate Similarity	NPD6798	Discontinued
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD3226	Approved
0.7756	Intermediate Similarity	NPD1933	Approved
0.7744	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3748	Approved
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5953	Discontinued
0.7669	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6355	Discontinued
0.764	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD2800	Approved
0.7628	Intermediate Similarity	NPD6233	Phase 2
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD37	Approved
0.7611	Intermediate Similarity	NPD8434	Phase 2
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7228	Approved
0.7588	Intermediate Similarity	NPD4965	Approved
0.7588	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD4967	Phase 2
0.7582	Intermediate Similarity	NPD1203	Approved
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7542	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7486	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7453	Intermediate Similarity	NPD6099	Approved
0.7453	Intermediate Similarity	NPD6100	Approved
0.7447	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2354	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD1608	Approved
0.7386	Intermediate Similarity	NPD9269	Phase 2
0.7386	Intermediate Similarity	NPD9717	Approved
0.7375	Intermediate Similarity	NPD6651	Approved
0.7372	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7354	Intermediate Similarity	NPD6779	Approved
0.7354	Intermediate Similarity	NPD6778	Approved
0.7354	Intermediate Similarity	NPD6782	Approved
0.7354	Intermediate Similarity	NPD6776	Approved
0.7354	Intermediate Similarity	NPD6781	Approved
0.7354	Intermediate Similarity	NPD6777	Approved
0.7354	Intermediate Similarity	NPD6780	Approved
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD3887	Approved
0.733	Intermediate Similarity	NPD5242	Approved
0.7326	Intermediate Similarity	NPD5353	Approved
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD422	Phase 1
0.732	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD8151	Discontinued
0.7317	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD4062	Phase 3
0.7293	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4308	Phase 3
0.7284	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7244	Intermediate Similarity	NPD2797	Approved
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD411	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2309	Approved
0.7226	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7584	Approved
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2353	Approved
0.7191	Intermediate Similarity	NPD2403	Approved
0.719	Intermediate Similarity	NPD17	Approved
0.7181	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD3225	Approved
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7171	Intermediate Similarity	NPD9545	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7151	Intermediate Similarity	NPD6385	Approved
0.7151	Intermediate Similarity	NPD6386	Approved
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7124	Intermediate Similarity	NPD9268	Approved
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7113	Intermediate Similarity	NPD7870	Phase 2
0.7113	Intermediate Similarity	NPD8320	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data