NPASS Compound

Structure

NPC471745 OpenBabel07101718282D 31 33 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 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 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 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 -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 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 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 22 2 0 0 0 0 9 28 1 0 0 0 0 10 23 2 0 0 0 0 10 29 1 0 0 0 0 11 24 2 0 0 0 0 11 30 1 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 12 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 0 0 0 0 21 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.09
Volume:	407.64
LogP:	1.349
LogD:	1.185
LogS:	-4.617
# Rotatable Bonds:	7
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	3.542
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	3.8232628867262974e-05
Pgp-inhibitor:	0.884
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	74.25196075439453%
Volume Distribution (VD):	0.477
Pgp-substrate:	39.827877044677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.587
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	1.216
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.51
Skin Sensitization:	0.23
Carcinogencity:	0.183
Eye Corrosion:	0.004
Eye Irritation:	0.638
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC471745

Natural Product ID:	NPC471745
*Common Name:**	3,5,7-Triacetylcatechin
IUPAC Name:	[(2S,3S)-5,7-diacetyloxy-2-(3,4-dihydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl] acetate
Synonyms:
Standard InCHIKey:	DJVADJFNDQYSQR-LEWJYISDSA-N
Standard InCHI:	InChI=1S/C21H18O10/c1-9(22)28-13-7-16(29-10(2)23)18-17(8-13)31-20(21(19(18)27)30-11(3)24)12-4-5-14(25)15(26)6-12/h4-8,20-21,25-26H,1-3H3/t20-,21+/m0/s1
SMILES:	CC(=O)Oc1cc2O[C@@H](c3ccc(c(c3)O)O)[C@@H](C(=O)c2c(c1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109443
PubChem CID:	76317499
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
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1662	Individual Protein	Arginase	Leishmania amazonensis	Ki	=	900.0	nM	PMID[476611]
NPT1662	Individual Protein	Arginase	Leishmania amazonensis	IC50	=	900.0	nM	PMID[476611]

☑ 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 NPC471745 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	377
0.1-0.2	1529
0.2-0.3	4081
0.3-0.4	8869
0.4-0.5	9067
0.5-0.6	3740
0.6-0.7	4695
0.7-0.8	5490
0.8-0.85	3088
0.85-0.9	1499
0.9-0.95	255
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC112418
0.9869	High Similarity	NPC471744
0.9673	High Similarity	NPC471500
0.961	High Similarity	NPC471479
0.961	High Similarity	NPC471515
0.9484	High Similarity	NPC108456
0.9481	High Similarity	NPC471746
0.9427	High Similarity	NPC471499
0.9423	High Similarity	NPC22192
0.9419	High Similarity	NPC250922
0.9419	High Similarity	NPC326037
0.9419	High Similarity	NPC320825
0.9419	High Similarity	NPC13858
0.9416	High Similarity	NPC18727
0.9379	High Similarity	NPC116864
0.9379	High Similarity	NPC244776
0.9371	High Similarity	NPC88243
0.9363	High Similarity	NPC287328
0.9363	High Similarity	NPC470183
0.9363	High Similarity	NPC282009
0.9363	High Similarity	NPC470326
0.9359	High Similarity	NPC52530
0.9359	High Similarity	NPC67876
0.9351	High Similarity	NPC61506
0.9351	High Similarity	NPC240476
0.9351	High Similarity	NPC246162
0.9351	High Similarity	NPC9743
0.9351	High Similarity	NPC36835
0.9351	High Similarity	NPC302950
0.9351	High Similarity	NPC219582
0.9351	High Similarity	NPC19721
0.9351	High Similarity	NPC260491
0.9351	High Similarity	NPC236637
0.9321	High Similarity	NPC175107
0.9321	High Similarity	NPC190003
0.9321	High Similarity	NPC153755
0.9317	High Similarity	NPC52382
0.9317	High Similarity	NPC270578
0.9304	High Similarity	NPC289771
0.9295	High Similarity	NPC195796
0.9295	High Similarity	NPC291878
0.9295	High Similarity	NPC35038
0.9295	High Similarity	NPC278778
0.929	High Similarity	NPC256346
0.929	High Similarity	NPC192083
0.929	High Similarity	NPC246328
0.929	High Similarity	NPC141212
0.929	High Similarity	NPC27532
0.929	High Similarity	NPC78326
0.929	High Similarity	NPC236223
0.929	High Similarity	NPC162351
0.929	High Similarity	NPC325028
0.929	High Similarity	NPC58382
0.929	High Similarity	NPC270620
0.929	High Similarity	NPC179126
0.929	High Similarity	NPC213896
0.9286	High Similarity	NPC295650
0.9281	High Similarity	NPC477941
0.9264	High Similarity	NPC4390
0.9259	High Similarity	NPC155763
0.9259	High Similarity	NPC235260
0.9259	High Similarity	NPC20505
0.9255	High Similarity	NPC223424
0.9255	High Similarity	NPC173637
0.9255	High Similarity	NPC127546
0.9255	High Similarity	NPC52550
0.9255	High Similarity	NPC160156
0.9255	High Similarity	NPC92565
0.9255	High Similarity	NPC317489
0.9255	High Similarity	NPC84362
0.925	High Similarity	NPC58223
0.925	High Similarity	NPC36916
0.925	High Similarity	NPC36
0.925	High Similarity	NPC72787
0.925	High Similarity	NPC7688
0.925	High Similarity	NPC7154
0.925	High Similarity	NPC125039
0.9245	High Similarity	NPC300537
0.9245	High Similarity	NPC127782
0.9241	High Similarity	NPC263449
0.9236	High Similarity	NPC474836
0.9236	High Similarity	NPC472598
0.9236	High Similarity	NPC27337
0.9236	High Similarity	NPC48208
0.9236	High Similarity	NPC475267
0.9236	High Similarity	NPC474208
0.9236	High Similarity	NPC156057
0.9236	High Similarity	NPC162869
0.9236	High Similarity	NPC474055
0.9236	High Similarity	NPC291508
0.9231	High Similarity	NPC45849
0.9231	High Similarity	NPC200761
0.9231	High Similarity	NPC133392
0.9231	High Similarity	NPC477503
0.9231	High Similarity	NPC470327
0.9231	High Similarity	NPC321779
0.9231	High Similarity	NPC67396
0.9226	High Similarity	NPC106976
0.9226	High Similarity	NPC472912
0.9226	High Similarity	NPC279989
0.9226	High Similarity	NPC82325
0.9226	High Similarity	NPC123886
0.9221	High Similarity	NPC286342
0.9221	High Similarity	NPC188871
0.9221	High Similarity	NPC149127
0.9221	High Similarity	NPC338131
0.9216	High Similarity	NPC188679
0.9216	High Similarity	NPC321011
0.9216	High Similarity	NPC294852
0.9202	High Similarity	NPC476370
0.9198	High Similarity	NPC203050
0.9198	High Similarity	NPC138927
0.9198	High Similarity	NPC280493
0.9198	High Similarity	NPC225434
0.9198	High Similarity	NPC120099
0.9198	High Similarity	NPC219904
0.9198	High Similarity	NPC223747
0.9193	High Similarity	NPC276222
0.9193	High Similarity	NPC274618
0.9193	High Similarity	NPC56077
0.9193	High Similarity	NPC179950
0.9193	High Similarity	NPC281131
0.9193	High Similarity	NPC328940
0.9193	High Similarity	NPC471213
0.9193	High Similarity	NPC145038
0.9193	High Similarity	NPC207575
0.9193	High Similarity	NPC477517
0.9193	High Similarity	NPC253662
0.9193	High Similarity	NPC308404
0.9193	High Similarity	NPC113968
0.9193	High Similarity	NPC135599
0.9193	High Similarity	NPC118284
0.9193	High Similarity	NPC88789
0.9193	High Similarity	NPC277174
0.9193	High Similarity	NPC73855
0.9193	High Similarity	NPC13481
0.9187	High Similarity	NPC472625
0.9182	High Similarity	NPC142252
0.9182	High Similarity	NPC472634
0.9182	High Similarity	NPC26326
0.9182	High Similarity	NPC308992
0.9182	High Similarity	NPC158188
0.9182	High Similarity	NPC173137
0.9177	High Similarity	NPC9609
0.9177	High Similarity	NPC130894
0.9177	High Similarity	NPC152166
0.9177	High Similarity	NPC300943
0.9177	High Similarity	NPC53545
0.9177	High Similarity	NPC18772
0.9177	High Similarity	NPC176300
0.9177	High Similarity	NPC253634
0.9177	High Similarity	NPC105242
0.9177	High Similarity	NPC115798
0.9177	High Similarity	NPC152904
0.9177	High Similarity	NPC22472
0.9177	High Similarity	NPC55738
0.9177	High Similarity	NPC143828
0.9177	High Similarity	NPC19687
0.9177	High Similarity	NPC7846
0.9177	High Similarity	NPC4481
0.9177	High Similarity	NPC204854
0.9177	High Similarity	NPC261004
0.9177	High Similarity	NPC25495
0.9177	High Similarity	NPC191459
0.9177	High Similarity	NPC288669
0.9177	High Similarity	NPC18607
0.9177	High Similarity	NPC117418
0.9172	High Similarity	NPC470328
0.9172	High Similarity	NPC100916
0.9172	High Similarity	NPC201837
0.9172	High Similarity	NPC235165
0.9172	High Similarity	NPC24640
0.9172	High Similarity	NPC474638
0.9172	High Similarity	NPC209614
0.9172	High Similarity	NPC255106
0.9172	High Similarity	NPC55619
0.9172	High Similarity	NPC200388
0.9172	High Similarity	NPC265511
0.9172	High Similarity	NPC472626
0.9172	High Similarity	NPC227062
0.9167	High Similarity	NPC298692
0.9167	High Similarity	NPC74924
0.9161	High Similarity	NPC50403
0.9161	High Similarity	NPC54394
0.9161	High Similarity	NPC133953
0.9161	High Similarity	NPC236769
0.9161	High Similarity	NPC28274
0.9161	High Similarity	NPC125062
0.9161	High Similarity	NPC260895
0.9161	High Similarity	NPC252933
0.9161	High Similarity	NPC474388
0.9161	High Similarity	NPC472535
0.9161	High Similarity	NPC200740
0.9161	High Similarity	NPC76376
0.9161	High Similarity	NPC474170
0.9156	High Similarity	NPC1612
0.9156	High Similarity	NPC183959
0.9156	High Similarity	NPC270465
0.9156	High Similarity	NPC87125
0.9152	High Similarity	NPC473862

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 NPC471745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	920
0.2-0.3	1830
0.3-0.4	2545
0.4-0.5	1808
0.5-0.6	1038
0.6-0.7	482
0.7-0.8	141
0.8-0.85	36
0.85-0.9	16
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD3817	Phase 2
0.9351	High Similarity	NPD1934	Approved
0.929	High Similarity	NPD2393	Clinical (unspecified phase)
0.925	High Similarity	NPD6168	Clinical (unspecified phase)
0.925	High Similarity	NPD6167	Clinical (unspecified phase)
0.925	High Similarity	NPD6166	Phase 2
0.9236	High Similarity	NPD7075	Discontinued
0.9091	High Similarity	NPD4338	Clinical (unspecified phase)
0.9085	High Similarity	NPD6797	Phase 2
0.9051	High Similarity	NPD4868	Clinical (unspecified phase)
0.9051	High Similarity	NPD3882	Suspended
0.9045	High Similarity	NPD7096	Clinical (unspecified phase)
0.903	High Similarity	NPD7251	Discontinued
0.8961	High Similarity	NPD1512	Approved
0.8924	High Similarity	NPD2801	Approved
0.8909	High Similarity	NPD7074	Phase 3
0.8862	High Similarity	NPD7808	Phase 3
0.8861	High Similarity	NPD6801	Discontinued
0.8848	High Similarity	NPD7054	Approved
0.8831	High Similarity	NPD1511	Approved
0.8831	High Similarity	NPD6799	Approved
0.8795	High Similarity	NPD7472	Approved
0.8788	High Similarity	NPD3818	Discontinued
0.8743	High Similarity	NPD7993	Clinical (unspecified phase)
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8642	High Similarity	NPD4381	Clinical (unspecified phase)
0.8634	High Similarity	NPD5402	Approved
0.8623	High Similarity	NPD7804	Clinical (unspecified phase)
0.8616	High Similarity	NPD6599	Discontinued
0.8616	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8544	High Similarity	NPD5403	Approved
0.8506	High Similarity	NPD1549	Phase 2
0.8457	Intermediate Similarity	NPD1465	Phase 2
0.8447	Intermediate Similarity	NPD7411	Suspended
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8418	Intermediate Similarity	NPD5401	Approved
0.8402	Intermediate Similarity	NPD5844	Phase 1
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8364	Intermediate Similarity	NPD919	Approved
0.8313	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2796	Approved
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8118	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6190	Approved
0.8075	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1613	Approved
0.8052	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD230	Phase 1
0.7976	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7949	Intermediate Similarity	NPD1607	Approved
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1247	Approved
0.7937	Intermediate Similarity	NPD4628	Phase 3
0.7937	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD943	Approved
0.7927	Intermediate Similarity	NPD1653	Approved
0.7922	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7768	Phase 2
0.7911	Intermediate Similarity	NPD1551	Phase 2
0.7911	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD447	Suspended
0.7875	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD2532	Approved
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6234	Discontinued
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7806	Intermediate Similarity	NPD6798	Discontinued
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7772	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD920	Approved
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.7684	Intermediate Similarity	NPD5953	Discontinued
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6832	Phase 2
0.7658	Intermediate Similarity	NPD1933	Approved
0.7658	Intermediate Similarity	NPD6355	Discontinued
0.7654	Intermediate Similarity	NPD1243	Approved
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3748	Approved
0.7624	Intermediate Similarity	NPD8434	Phase 2
0.7622	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7228	Approved
0.7607	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.7597	Intermediate Similarity	NPD1203	Approved
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7556	Intermediate Similarity	NPD8312	Approved
0.7556	Intermediate Similarity	NPD8313	Approved
0.7547	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2800	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4060	Phase 1
0.7469	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1652	Phase 2
0.7423	Intermediate Similarity	NPD7266	Discontinued
0.7403	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD6651	Approved
0.7386	Intermediate Similarity	NPD5711	Approved
0.7386	Intermediate Similarity	NPD5710	Approved
0.7372	Intermediate Similarity	NPD2797	Approved
0.7368	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7349	Intermediate Similarity	NPD2354	Approved
0.7349	Intermediate Similarity	NPD3887	Approved
0.7345	Intermediate Similarity	NPD5242	Approved
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7341	Intermediate Similarity	NPD5353	Approved
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2344	Approved
0.7312	Intermediate Similarity	NPD4062	Phase 3
0.7308	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4308	Phase 3
0.7296	Intermediate Similarity	NPD7095	Approved
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD9269	Phase 2
0.729	Intermediate Similarity	NPD1608	Approved
0.7283	Intermediate Similarity	NPD8455	Phase 2
0.7278	Intermediate Similarity	NPD9494	Approved
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD411	Approved
0.725	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7231	Intermediate Similarity	NPD7584	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7207	Intermediate Similarity	NPD2403	Approved
0.7197	Intermediate Similarity	NPD3225	Approved
0.7196	Intermediate Similarity	NPD4360	Phase 2
0.7196	Intermediate Similarity	NPD4363	Phase 3
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD5049	Phase 3
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.7165	Intermediate Similarity	NPD7696	Phase 3
0.7165	Intermediate Similarity	NPD7698	Approved
0.7165	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7240	Approved
0.7158	Intermediate Similarity	NPD7038	Approved
0.7158	Intermediate Similarity	NPD7039	Approved
0.7152	Intermediate Similarity	NPD3266	Approved
0.7152	Intermediate Similarity	NPD3267	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD2309	Approved
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD7871	Phase 2
0.7128	Intermediate Similarity	NPD8319	Approved
0.7128	Intermediate Similarity	NPD7870	Phase 2
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7119	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3146	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