NPASS Compound

Structure

NPC142252 OpenBabel07101718292D 36 39 0 0 1 0 0 0 0 0999 V2000 3.3775 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9106 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9106 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -3.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0662 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2219 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0662 -0.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -3.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -0.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0662 -3.9000 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 35 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 22 2 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 11 27 2 0 0 0 0 13 17 1 0 0 0 0 13 26 2 0 0 0 0 14 18 2 0 0 0 0 14 26 1 0 0 0 0 15 22 1 0 0 0 0 15 23 2 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 25 1 0 0 0 0 20 32 1 1 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 12 1 6 0 0 0 25 36 1 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.15
Volume:	485.564
LogP:	3.623
LogD:	1.542
LogS:	-2.97
# Rotatable Bonds:	5
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	3.955
Fsp3:	0.269
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:	-6.421
MDCK Permeability:	5.953562776994659e-06
Pgp-inhibitor:	0.162
Pgp-substrate:	0.207
Human Intestinal Absorption (HIA):	0.15
20% Bioavailability (F20%):	0.755
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	93.0326919555664%
Volume Distribution (VD):	0.477
Pgp-substrate:	8.783134460449219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.528
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	9.795
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.96
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC142252

Natural Product ID:	NPC142252
*Common Name:**	Pilosanol N
IUPAC Name:	1-[3-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]methyl]-2,4-dihydroxy-6-methoxy-5-methylphenyl]ethanone
Synonyms:	Pilosanol N
Standard InCHIKey:	KPQVHJOZMIEZCA-NBGIEHNGSA-N
Standard InCHI:	InChI=1S/C26H26O10/c1-10-22(33)15(23(34)21(11(2)27)24(10)35-3)7-13-17(29)9-18(30)14-8-20(32)25(36-26(13)14)12-4-5-16(28)19(31)6-12/h4-6,9,20,25,28-34H,7-8H2,1-3H3/t20-,25+/m0/s1
SMILES:	Cc1c(c(Cc2c(cc(c3C[C@@H]([C@@H](c4ccc(c(c4)O)O)Oc23)O)O)O)c(c(C(=O)C)c1OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1949985
PubChem CID:	57333960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22281186]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588326]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18007	Agrimonia pilosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18007	Agrimonia pilosa	Species	Rosaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	60.0	%	PMID[448259]

☑ 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 NPC142252 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	417
0.1-0.2	1574
0.2-0.3	3730
0.3-0.4	9527
0.4-0.5	8883
0.5-0.6	3404
0.6-0.7	4709
0.7-0.8	5315
0.8-0.85	2773
0.85-0.9	1913
0.9-0.95	391
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC476247
0.974	High Similarity	NPC26326
0.974	High Similarity	NPC158188
0.9739	High Similarity	NPC117418
0.9739	High Similarity	NPC53545
0.9673	High Similarity	NPC472598
0.9673	High Similarity	NPC474055
0.9671	High Similarity	NPC321779
0.962	High Similarity	NPC475212
0.9613	High Similarity	NPC471499
0.9613	High Similarity	NPC165970
0.9613	High Similarity	NPC289771
0.9613	High Similarity	NPC305987
0.9613	High Similarity	NPC472634
0.9613	High Similarity	NPC474038
0.9613	High Similarity	NPC288131
0.9613	High Similarity	NPC472632
0.9613	High Similarity	NPC84324
0.9613	High Similarity	NPC66618
0.9613	High Similarity	NPC113163
0.961	High Similarity	NPC22192
0.961	High Similarity	NPC284127
0.961	High Similarity	NPC476410
0.961	High Similarity	NPC172202
0.9608	High Similarity	NPC195796
0.9608	High Similarity	NPC291878
0.9608	High Similarity	NPC278778
0.9608	High Similarity	NPC208152
0.9608	High Similarity	NPC78492
0.9608	High Similarity	NPC35038
0.9605	High Similarity	NPC213896
0.9605	High Similarity	NPC192083
0.956	High Similarity	NPC279209
0.956	High Similarity	NPC102277
0.9557	High Similarity	NPC260266
0.9554	High Similarity	NPC36
0.9554	High Similarity	NPC125039
0.9554	High Similarity	NPC471788
0.9554	High Similarity	NPC58223
0.9554	High Similarity	NPC36916
0.9554	High Similarity	NPC7154
0.9554	High Similarity	NPC72787
0.9554	High Similarity	NPC7688
0.9551	High Similarity	NPC474033
0.9551	High Similarity	NPC472635
0.9551	High Similarity	NPC474034
0.9548	High Similarity	NPC101731
0.9548	High Similarity	NPC119209
0.9548	High Similarity	NPC118256
0.9548	High Similarity	NPC287328
0.9548	High Similarity	NPC472630
0.9548	High Similarity	NPC475784
0.9548	High Similarity	NPC174953
0.9548	High Similarity	NPC470326
0.9548	High Similarity	NPC472631
0.9548	High Similarity	NPC282009
0.9548	High Similarity	NPC192686
0.9545	High Similarity	NPC27337
0.9545	High Similarity	NPC291508
0.9545	High Similarity	NPC471209
0.9545	High Similarity	NPC183851
0.9545	High Similarity	NPC63454
0.9542	High Similarity	NPC470327
0.9542	High Similarity	NPC45849
0.9542	High Similarity	NPC200761
0.9542	High Similarity	NPC477503
0.9539	High Similarity	NPC106976
0.9494	High Similarity	NPC471213
0.949	High Similarity	NPC472625
0.9487	High Similarity	NPC471211
0.9487	High Similarity	NPC471210
0.9487	High Similarity	NPC471212
0.9484	High Similarity	NPC473990
0.9481	High Similarity	NPC470328
0.9481	High Similarity	NPC209614
0.9481	High Similarity	NPC472626
0.9477	High Similarity	NPC74924
0.9477	High Similarity	NPC298692
0.9477	High Similarity	NPC18727
0.9434	High Similarity	NPC243877
0.9434	High Similarity	NPC14662
0.943	High Similarity	NPC477840
0.9427	High Similarity	NPC220912
0.9427	High Similarity	NPC477841
0.9427	High Similarity	NPC219927
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC472624
0.9423	High Similarity	NPC36217
0.9419	High Similarity	NPC473272
0.9419	High Similarity	NPC223787
0.9419	High Similarity	NPC284820
0.9416	High Similarity	NPC226025
0.9412	High Similarity	NPC244583
0.9412	High Similarity	NPC56232
0.9412	High Similarity	NPC236637
0.9412	High Similarity	NPC150123
0.9412	High Similarity	NPC302950
0.9412	High Similarity	NPC219582
0.9412	High Similarity	NPC161881
0.9412	High Similarity	NPC10807
0.9379	High Similarity	NPC257667
0.9379	High Similarity	NPC289396
0.9379	High Similarity	NPC212038
0.9379	High Similarity	NPC271848
0.9379	High Similarity	NPC186847
0.9379	High Similarity	NPC472454
0.9379	High Similarity	NPC81332
0.9379	High Similarity	NPC262580
0.9371	High Similarity	NPC13481
0.9371	High Similarity	NPC224851
0.9371	High Similarity	NPC320741
0.9371	High Similarity	NPC207575
0.9371	High Similarity	NPC171985
0.9367	High Similarity	NPC124038
0.9367	High Similarity	NPC476295
0.9367	High Similarity	NPC186686
0.9363	High Similarity	NPC228383
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC134783
0.9363	High Similarity	NPC198829
0.9359	High Similarity	NPC250214
0.9359	High Similarity	NPC95936
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC326037
0.9355	High Similarity	NPC471500
0.9355	High Similarity	NPC320825
0.9355	High Similarity	NPC13858
0.9355	High Similarity	NPC250922
0.9351	High Similarity	NPC244250
0.9351	High Similarity	NPC20907
0.9346	High Similarity	NPC477897
0.9346	High Similarity	NPC328740
0.9346	High Similarity	NPC209846
0.9346	High Similarity	NPC289774
0.9317	High Similarity	NPC150767
0.9317	High Similarity	NPC78734
0.9313	High Similarity	NPC295082
0.9313	High Similarity	NPC474024
0.9313	High Similarity	NPC477502
0.9308	High Similarity	NPC293319
0.9308	High Similarity	NPC62261
0.9304	High Similarity	NPC201800
0.9304	High Similarity	NPC474150
0.9304	High Similarity	NPC211107
0.9304	High Similarity	NPC474162
0.9304	High Similarity	NPC300537
0.9304	High Similarity	NPC127782
0.9299	High Similarity	NPC328102
0.9299	High Similarity	NPC470183
0.9295	High Similarity	NPC471479
0.9295	High Similarity	NPC52530
0.9295	High Similarity	NPC474208
0.9295	High Similarity	NPC48208
0.9295	High Similarity	NPC474836
0.9295	High Similarity	NPC52889
0.9295	High Similarity	NPC471515
0.9295	High Similarity	NPC156057
0.9295	High Similarity	NPC475267
0.9295	High Similarity	NPC78225
0.9295	High Similarity	NPC162869
0.929	High Similarity	NPC111341
0.929	High Similarity	NPC117992
0.929	High Similarity	NPC152951
0.929	High Similarity	NPC67396
0.929	High Similarity	NPC57674
0.929	High Similarity	NPC304745
0.929	High Similarity	NPC230149
0.929	High Similarity	NPC168247
0.9286	High Similarity	NPC240476
0.9286	High Similarity	NPC36835
0.9286	High Similarity	NPC323626
0.9286	High Similarity	NPC9743
0.9286	High Similarity	NPC260491
0.9286	High Similarity	NPC19721
0.9286	High Similarity	NPC246162
0.9286	High Similarity	NPC61506
0.9286	High Similarity	NPC471982
0.9286	High Similarity	NPC324233
0.9286	High Similarity	NPC475790
0.9286	High Similarity	NPC472912
0.9281	High Similarity	NPC3825
0.9281	High Similarity	NPC338131
0.9281	High Similarity	NPC88804
0.9276	High Similarity	NPC188679
0.9276	High Similarity	NPC294852
0.9276	High Similarity	NPC321011
0.9259	High Similarity	NPC4200
0.9259	High Similarity	NPC256760
0.9255	High Similarity	NPC107627
0.9255	High Similarity	NPC300307
0.9255	High Similarity	NPC188079
0.925	High Similarity	NPC119589
0.925	High Similarity	NPC5778
0.925	High Similarity	NPC236934
0.925	High Similarity	NPC43319
0.9245	High Similarity	NPC29830
0.9245	High Similarity	NPC19709
0.9241	High Similarity	NPC112418
0.9236	High Similarity	NPC123544
0.9236	High Similarity	NPC187792

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 NPC142252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	905
0.2-0.3	1726
0.3-0.4	2610
0.4-0.5	1834
0.5-0.6	1005
0.6-0.7	503
0.7-0.8	141
0.8-0.85	26
0.85-0.9	25
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9554	High Similarity	NPD6168	Clinical (unspecified phase)
0.9554	High Similarity	NPD6167	Clinical (unspecified phase)
0.9554	High Similarity	NPD6166	Phase 2
0.9412	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD4380	Phase 2
0.9108	High Similarity	NPD4868	Clinical (unspecified phase)
0.908	High Similarity	NPD7074	Phase 3
0.9018	High Similarity	NPD7054	Approved
0.8981	High Similarity	NPD2801	Approved
0.8963	High Similarity	NPD7472	Approved
0.8924	High Similarity	NPD8443	Clinical (unspecified phase)
0.8909	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD1511	Approved
0.8855	High Similarity	NPD7251	Discontinued
0.8841	High Similarity	NPD3818	Discontinued
0.8812	High Similarity	NPD7075	Discontinued
0.8812	High Similarity	NPD4381	Clinical (unspecified phase)
0.8774	High Similarity	NPD1512	Approved
0.8765	High Similarity	NPD6959	Discontinued
0.875	High Similarity	NPD3882	Suspended
0.8734	High Similarity	NPD7411	Suspended
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.871	High Similarity	NPD7410	Clinical (unspecified phase)
0.8704	High Similarity	NPD5494	Approved
0.869	High Similarity	NPD4338	Clinical (unspecified phase)
0.869	High Similarity	NPD7808	Phase 3
0.8688	High Similarity	NPD3817	Phase 2
0.8683	High Similarity	NPD7993	Clinical (unspecified phase)
0.8675	High Similarity	NPD5844	Phase 1
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8598	High Similarity	NPD6232	Discontinued
0.8562	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD1549	Phase 2
0.8554	High Similarity	NPD7473	Discontinued
0.8521	High Similarity	NPD6559	Discontinued
0.8509	High Similarity	NPD7819	Suspended
0.8383	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8232	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD7768	Phase 2
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8038	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3749	Approved
0.7914	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3027	Phase 3
0.7898	Intermediate Similarity	NPD8312	Approved
0.7898	Intermediate Similarity	NPD8313	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1247	Approved
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.787	Intermediate Similarity	NPD919	Approved
0.7857	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.784	Intermediate Similarity	NPD7390	Discontinued
0.7814	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7727	Intermediate Similarity	NPD4908	Phase 1
0.7716	Intermediate Similarity	NPD6190	Approved
0.7711	Intermediate Similarity	NPD3226	Approved
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD6651	Approved
0.7651	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4966	Approved
0.7644	Intermediate Similarity	NPD8151	Discontinued
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8455	Phase 2
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4360	Phase 2
0.7609	Intermediate Similarity	NPD4363	Phase 3
0.7605	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7562	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7584	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD447	Suspended
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7453	Intermediate Similarity	NPD3748	Approved
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7405	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7382	Intermediate Similarity	NPD7697	Approved
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD5124	Phase 1
0.7375	Intermediate Similarity	NPD1933	Approved
0.7375	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD6823	Phase 2
0.733	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD7229	Phase 3
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.7325	Intermediate Similarity	NPD9494	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7317	Intermediate Similarity	NPD2424	Discontinued
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7293	Intermediate Similarity	NPD7240	Approved
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5408	Approved
0.7195	Intermediate Similarity	NPD5404	Approved
0.7195	Intermediate Similarity	NPD5406	Approved
0.7195	Intermediate Similarity	NPD5405	Approved
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7585	Approved
0.7143	Intermediate Similarity	NPD3823	Discontinued
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7118	Intermediate Similarity	NPD6273	Approved
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7104	Intermediate Similarity	NPD7039	Approved
0.7104	Intermediate Similarity	NPD7038	Approved
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7095	Intermediate Similarity	NPD5242	Approved
0.7092	Intermediate Similarity	NPD7583	Approved
0.709	Intermediate Similarity	NPD6213	Phase 3
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data