NPASS Compound

Structure

NPC469419 OpenBabel07101719402D 44 49 0 0 1 0 0 0 0 0999 V2000 2.0396 0.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5791 3.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9837 3.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5726 3.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3817 2.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9706 2.9031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7696 -2.3378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0664 -2.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9512 -3.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2479 -3.6357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1270 0.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5759 -0.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9424 -1.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3752 2.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8272 -2.0034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1904 -3.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5329 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9805 -1.3419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3785 -2.2592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7831 -3.0626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7896 -2.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7733 1.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6457 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3915 -2.0313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5645 -1.4448 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3349 -0.4671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3719 -4.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4210 1.3286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3720 -2.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 -3.9800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1942 -3.7521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7668 1.0683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 -0.3711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4212 -2.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1778 0.3789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7033 -0.6855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9870 -1.2279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3981 -1.9174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2319 -1.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 39 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 31 1 0 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 14 40 1 0 0 0 0 15 30 1 0 0 0 0 15 41 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 33 2 0 0 0 0 21 14 1 6 0 0 0 21 22 1 0 0 0 0 21 42 1 0 0 0 0 22 23 1 0 0 0 0 22 34 1 1 0 0 0 23 24 1 0 0 0 0 23 35 1 6 0 0 0 24 27 1 0 0 0 0 24 36 1 1 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 38 2 0 0 0 0 26 41 1 0 0 0 0 27 42 1 0 0 0 0 27 43 1 6 0 0 0 28 30 1 6 0 0 0 28 39 1 0 0 0 0 28 44 1 0 0 0 0 29 31 1 1 0 0 0 29 44 1 0 0 0 0 30 31 1 1 0 0 0 31 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.2
Volume:	583.938
LogP:	2.061
LogD:	1.412
LogS:	-4.038
# Rotatable Bonds:	11
TPSA:	187.51
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	5.945
Fsp3:	0.516
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.056
MDCK Permeability:	3.40261758537963e-05
Pgp-inhibitor:	0.13
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.26
20% Bioavailability (F20%):	0.619
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	95.44824981689453%
Volume Distribution (VD):	0.523
Pgp-substrate:	10.135141372680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	6.934
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.848
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.576
Carcinogencity:	0.55
Eye Corrosion:	0.003
Eye Irritation:	0.287
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC469419

Natural Product ID:	NPC469419
*Common Name:**	Paeonidanin C
IUPAC Name:	n.a.
Synonyms:	paeonidanin C
Standard InCHIKey:	PBDROKLULCIDPL-WNKDLFHOSA-N
Standard InCHI:	InChI=1S/C31H34O13/c1-29-13-20(33)19-12-31(29,30(19,28(39-2)44-29)15-41-26(38)17-8-10-18(32)11-9-17)43-27-24(36)23(35)22(34)21(42-27)14-40-25(37)16-6-4-3-5-7-16/h3-11,19,21-24,27-28,32,34-36H,12-15H2,1-2H3/t19-,21-,22-,23+,24-,27+,28+,29+,30+,31-/m1/s1
SMILES:	CC12CC(=O)C3CC1(C3(C(O2)OC)COC(=O)C4=CC=C(C=C4)O)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078414
PubChem CID:	46883513
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	106.5	%	PMID[570111]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	111.0	%	PMID[570111]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	94.3	%	PMID[570111]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	80.3	%	PMID[570111]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[570111]

☑ 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 NPC469419 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	370
0.1-0.2	1335
0.2-0.3	2685
0.3-0.4	5038
0.4-0.5	9529
0.5-0.6	9531
0.6-0.7	8802
0.7-0.8	4985
0.8-0.85	379
0.85-0.9	38
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC477627
0.9512	High Similarity	NPC469418
0.95	High Similarity	NPC88176
0.95	High Similarity	NPC469458
0.95	High Similarity	NPC469396
0.95	High Similarity	NPC149002
0.9379	High Similarity	NPC469459
0.9359	High Similarity	NPC469417
0.9268	High Similarity	NPC148185
0.9268	High Similarity	NPC477617
0.9177	High Similarity	NPC469399
0.9162	High Similarity	NPC260300
0.913	High Similarity	NPC293568
0.913	High Similarity	NPC117943
0.9048	High Similarity	NPC80360
0.8994	High Similarity	NPC195114
0.8981	High Similarity	NPC116292
0.8981	High Similarity	NPC267469
0.8981	High Similarity	NPC179128
0.8981	High Similarity	NPC87630
0.8974	High Similarity	NPC469448
0.8963	High Similarity	NPC265600
0.8941	High Similarity	NPC188217
0.8924	High Similarity	NPC133430
0.8924	High Similarity	NPC469477
0.8861	High Similarity	NPC35160
0.8861	High Similarity	NPC162569
0.8848	High Similarity	NPC469420
0.8827	High Similarity	NPC206641
0.8827	High Similarity	NPC208651
0.8817	High Similarity	NPC469438
0.879	High Similarity	NPC470330
0.8788	High Similarity	NPC120012
0.8782	High Similarity	NPC469513
0.8765	High Similarity	NPC283480
0.8765	High Similarity	NPC469397
0.8765	High Similarity	NPC148323
0.875	High Similarity	NPC5115
0.875	High Similarity	NPC34066
0.8727	High Similarity	NPC187934
0.8727	High Similarity	NPC97637
0.8726	High Similarity	NPC208293
0.872	High Similarity	NPC130489
0.872	High Similarity	NPC208676
0.8704	High Similarity	NPC3449
0.8704	High Similarity	NPC472807
0.8704	High Similarity	NPC82190
0.8704	High Similarity	NPC174599
0.8704	High Similarity	NPC192219
0.8698	High Similarity	NPC13989
0.8659	High Similarity	NPC314795
0.8659	High Similarity	NPC53139
0.8654	High Similarity	NPC478250
0.8647	High Similarity	NPC195972
0.8642	High Similarity	NPC209393
0.8642	High Similarity	NPC205172
0.8639	High Similarity	NPC469421
0.8634	High Similarity	NPC469422
0.8625	High Similarity	NPC477905
0.8625	High Similarity	NPC472548
0.8623	High Similarity	NPC102465
0.8623	High Similarity	NPC478020
0.8623	High Similarity	NPC478022
0.8608	High Similarity	NPC320734
0.858	High Similarity	NPC476017
0.858	High Similarity	NPC257847
0.8563	High Similarity	NPC161151
0.8563	High Similarity	NPC100420
0.8554	High Similarity	NPC471493
0.8538	High Similarity	NPC316539
0.8529	High Similarity	NPC475058
0.8519	High Similarity	NPC469456
0.8519	High Similarity	NPC472549
0.8509	High Similarity	NPC327962
0.8494	Intermediate Similarity	NPC329960
0.8494	Intermediate Similarity	NPC295408
0.8494	Intermediate Similarity	NPC150893
0.8488	Intermediate Similarity	NPC469354
0.8485	Intermediate Similarity	NPC226759
0.8485	Intermediate Similarity	NPC4747
0.8485	Intermediate Similarity	NPC104275
0.848	Intermediate Similarity	NPC294501
0.848	Intermediate Similarity	NPC183441
0.8466	Intermediate Similarity	NPC96194
0.8466	Intermediate Similarity	NPC106895
0.8466	Intermediate Similarity	NPC299855
0.8462	Intermediate Similarity	NPC296558
0.8462	Intermediate Similarity	NPC477471
0.8462	Intermediate Similarity	NPC477469
0.8462	Intermediate Similarity	NPC477473
0.8462	Intermediate Similarity	NPC77493
0.8462	Intermediate Similarity	NPC477466
0.8457	Intermediate Similarity	NPC474620
0.8452	Intermediate Similarity	NPC109990
0.8452	Intermediate Similarity	NPC471861
0.8447	Intermediate Similarity	NPC469415
0.8447	Intermediate Similarity	NPC471103
0.8443	Intermediate Similarity	NPC471134
0.8439	Intermediate Similarity	NPC475613
0.8439	Intermediate Similarity	NPC475233
0.8438	Intermediate Similarity	NPC81698
0.8438	Intermediate Similarity	NPC250046
0.8438	Intermediate Similarity	NPC60509
0.8436	Intermediate Similarity	NPC475299
0.843	Intermediate Similarity	NPC471871
0.843	Intermediate Similarity	NPC199357
0.8424	Intermediate Similarity	NPC477623
0.8421	Intermediate Similarity	NPC472803
0.8421	Intermediate Similarity	NPC478021
0.8418	Intermediate Similarity	NPC189704
0.8418	Intermediate Similarity	NPC204644
0.8405	Intermediate Similarity	NPC282239
0.8405	Intermediate Similarity	NPC469398
0.8405	Intermediate Similarity	NPC473670
0.8405	Intermediate Similarity	NPC21410
0.8402	Intermediate Similarity	NPC475738
0.8402	Intermediate Similarity	NPC470735
0.8402	Intermediate Similarity	NPC329647
0.8402	Intermediate Similarity	NPC478026
0.8402	Intermediate Similarity	NPC178281
0.84	Intermediate Similarity	NPC477860
0.84	Intermediate Similarity	NPC102367
0.84	Intermediate Similarity	NPC475161
0.8395	Intermediate Similarity	NPC478219
0.8393	Intermediate Similarity	NPC471850
0.8393	Intermediate Similarity	NPC145847
0.8385	Intermediate Similarity	NPC222102
0.8385	Intermediate Similarity	NPC165260
0.8385	Intermediate Similarity	NPC7095
0.8385	Intermediate Similarity	NPC198455
0.8385	Intermediate Similarity	NPC161239
0.8385	Intermediate Similarity	NPC303429
0.8383	Intermediate Similarity	NPC66193
0.8382	Intermediate Similarity	NPC68381
0.8375	Intermediate Similarity	NPC473867
0.8373	Intermediate Similarity	NPC257309
0.8373	Intermediate Similarity	NPC187205
0.8371	Intermediate Similarity	NPC476067
0.8371	Intermediate Similarity	NPC475121
0.8365	Intermediate Similarity	NPC127857
0.8364	Intermediate Similarity	NPC172920
0.8364	Intermediate Similarity	NPC203757
0.8364	Intermediate Similarity	NPC156624
0.8363	Intermediate Similarity	NPC471870
0.8363	Intermediate Similarity	NPC222455
0.8354	Intermediate Similarity	NPC217091
0.8354	Intermediate Similarity	NPC87403
0.8344	Intermediate Similarity	NPC304876
0.8344	Intermediate Similarity	NPC1173
0.8344	Intermediate Similarity	NPC472005
0.8344	Intermediate Similarity	NPC249471
0.8344	Intermediate Similarity	NPC473414
0.8344	Intermediate Similarity	NPC289021
0.8344	Intermediate Similarity	NPC158333
0.8344	Intermediate Similarity	NPC158546
0.8344	Intermediate Similarity	NPC472022
0.8344	Intermediate Similarity	NPC242262
0.8344	Intermediate Similarity	NPC472030
0.8344	Intermediate Similarity	NPC237549
0.8344	Intermediate Similarity	NPC265395
0.8344	Intermediate Similarity	NPC257213
0.8344	Intermediate Similarity	NPC256142
0.8343	Intermediate Similarity	NPC254588
0.8333	Intermediate Similarity	NPC471858
0.8333	Intermediate Similarity	NPC475054
0.8333	Intermediate Similarity	NPC101043
0.8333	Intermediate Similarity	NPC306799
0.8333	Intermediate Similarity	NPC197037
0.8333	Intermediate Similarity	NPC51602
0.8333	Intermediate Similarity	NPC176246
0.8333	Intermediate Similarity	NPC88841
0.8333	Intermediate Similarity	NPC288602
0.8333	Intermediate Similarity	NPC161955
0.8333	Intermediate Similarity	NPC470153
0.8324	Intermediate Similarity	NPC98776
0.8324	Intermediate Similarity	NPC472054
0.8314	Intermediate Similarity	NPC298778
0.8313	Intermediate Similarity	NPC478223
0.8313	Intermediate Similarity	NPC10945
0.8313	Intermediate Similarity	NPC477737
0.8303	Intermediate Similarity	NPC474621
0.8303	Intermediate Similarity	NPC477735
0.8303	Intermediate Similarity	NPC474622
0.8303	Intermediate Similarity	NPC472393
0.8302	Intermediate Similarity	NPC241951
0.8302	Intermediate Similarity	NPC475759
0.8302	Intermediate Similarity	NPC470152
0.8294	Intermediate Similarity	NPC99216
0.8294	Intermediate Similarity	NPC180586
0.8294	Intermediate Similarity	NPC294722
0.8294	Intermediate Similarity	NPC475979
0.8293	Intermediate Similarity	NPC132599
0.8293	Intermediate Similarity	NPC228204
0.8293	Intermediate Similarity	NPC26033
0.8293	Intermediate Similarity	NPC114410
0.8293	Intermediate Similarity	NPC221249
0.8293	Intermediate Similarity	NPC469730
0.8293	Intermediate Similarity	NPC473632
0.8293	Intermediate Similarity	NPC112523
0.8284	Intermediate Similarity	NPC278329

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 NPC469419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	766
0.2-0.3	1666
0.3-0.4	2644
0.4-0.5	2285
0.5-0.6	1065
0.6-0.7	305
0.7-0.8	102
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8312	Approved
0.8125	Intermediate Similarity	NPD8313	Approved
0.809	Intermediate Similarity	NPD8434	Phase 2
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD7228	Approved
0.7989	Intermediate Similarity	NPD3818	Discontinued
0.7989	Intermediate Similarity	NPD7799	Discontinued
0.7989	Intermediate Similarity	NPD8150	Discontinued
0.7952	Intermediate Similarity	NPD7458	Discontinued
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD7074	Phase 3
0.7841	Intermediate Similarity	NPD7054	Approved
0.7841	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8320	Phase 1
0.7831	Intermediate Similarity	NPD8319	Approved
0.7826	Intermediate Similarity	NPD7266	Discontinued
0.7811	Intermediate Similarity	NPD37	Approved
0.7802	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4380	Phase 2
0.7797	Intermediate Similarity	NPD7472	Approved
0.7791	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD7435	Discontinued
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4965	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7075	Discontinued
0.773	Intermediate Similarity	NPD6534	Approved
0.773	Intermediate Similarity	NPD6535	Approved
0.7727	Intermediate Similarity	NPD7473	Discontinued
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7701	Intermediate Similarity	NPD7700	Phase 2
0.7701	Intermediate Similarity	NPD7699	Phase 2
0.768	Intermediate Similarity	NPD8407	Phase 2
0.7674	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.7658	Intermediate Similarity	NPD3764	Approved
0.7654	Intermediate Similarity	NPD6797	Phase 2
0.7636	Intermediate Similarity	NPD6190	Approved
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7611	Intermediate Similarity	NPD7240	Approved
0.7611	Intermediate Similarity	NPD8368	Discontinued
0.7609	Intermediate Similarity	NPD8360	Approved
0.7609	Intermediate Similarity	NPD8361	Approved
0.7577	Intermediate Similarity	NPD8151	Discontinued
0.7576	Intermediate Similarity	NPD8166	Discontinued
0.7558	Intermediate Similarity	NPD7819	Suspended
0.7558	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8455	Phase 2
0.7557	Intermediate Similarity	NPD6232	Discontinued
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5844	Phase 1
0.7542	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8435	Approved
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6213	Phase 3
0.7487	Intermediate Similarity	NPD6212	Phase 3
0.7485	Intermediate Similarity	NPD7236	Approved
0.7484	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6166	Phase 2
0.7472	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7457	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7443	Intermediate Similarity	NPD5494	Approved
0.7442	Intermediate Similarity	NPD7411	Suspended
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7429	Intermediate Similarity	NPD3749	Approved
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7801	Approved
0.7405	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8127	Discontinued
0.7401	Intermediate Similarity	NPD7199	Phase 2
0.7399	Intermediate Similarity	NPD1934	Approved
0.7399	Intermediate Similarity	NPD6801	Discontinued
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD6599	Discontinued
0.7368	Intermediate Similarity	NPD7239	Suspended
0.7363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5761	Phase 2
0.7356	Intermediate Similarity	NPD5760	Phase 2
0.7353	Intermediate Similarity	NPD6273	Approved
0.7346	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3226	Approved
0.7305	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6959	Discontinued
0.7294	Intermediate Similarity	NPD2533	Approved
0.7294	Intermediate Similarity	NPD2534	Approved
0.7294	Intermediate Similarity	NPD2532	Approved
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7228	Intermediate Similarity	NPD8404	Phase 2
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3817	Phase 2
0.7216	Intermediate Similarity	NPD5402	Approved
0.7214	Intermediate Similarity	NPD7930	Approved
0.7202	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD230	Phase 1
0.7193	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8485	Approved
0.7175	Intermediate Similarity	NPD7768	Phase 2
0.7171	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7003	Approved
0.7159	Intermediate Similarity	NPD2801	Approved
0.7159	Intermediate Similarity	NPD1465	Phase 2
0.7157	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7135	Intermediate Similarity	NPD6799	Approved
0.7126	Intermediate Similarity	NPD5405	Approved
0.7126	Intermediate Similarity	NPD5404	Approved
0.7126	Intermediate Similarity	NPD2935	Discontinued
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5406	Approved
0.7126	Intermediate Similarity	NPD5408	Approved
0.711	Intermediate Similarity	NPD5403	Approved
0.7108	Intermediate Similarity	NPD7097	Phase 1
0.7101	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7028	Phase 2
0.7083	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6663	Approved
0.7071	Intermediate Similarity	NPD7999	Approved
0.7066	Intermediate Similarity	NPD1510	Phase 2
0.7066	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3750	Approved
0.7056	Intermediate Similarity	NPD7497	Discontinued
0.7051	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5736	Approved
0.7035	Intermediate Similarity	NPD7390	Discontinued
0.7035	Intermediate Similarity	NPD7584	Approved
0.7019	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6674	Discontinued
0.6994	Remote Similarity	NPD5401	Approved
0.6983	Remote Similarity	NPD7057	Phase 3
0.6983	Remote Similarity	NPD7058	Phase 2
0.6964	Remote Similarity	NPD7033	Discontinued
0.6952	Remote Similarity	NPD6765	Approved
0.6952	Remote Similarity	NPD6764	Approved
0.6946	Remote Similarity	NPD1607	Approved
0.6936	Remote Similarity	NPD1511	Approved
0.6931	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD943	Approved
0.6928	Remote Similarity	NPD1240	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6923	Remote Similarity	NPD2796	Approved
0.6919	Remote Similarity	NPD8059	Phase 3
0.6919	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7585	Approved
0.6901	Remote Similarity	NPD2800	Approved
0.6897	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6355	Discontinued
0.6885	Remote Similarity	NPD5710	Approved
0.6885	Remote Similarity	NPD5711	Approved
0.6882	Remote Similarity	NPD2344	Approved
0.6875	Remote Similarity	NPD1201	Approved
0.6875	Remote Similarity	NPD1653	Approved
0.6871	Remote Similarity	NPD2798	Approved
0.6866	Remote Similarity	NPD7583	Approved
0.6857	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD5125	Phase 3
0.6855	Remote Similarity	NPD5126	Approved
0.6837	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD920	Approved
0.6807	Remote Similarity	NPD2313	Discontinued
0.6806	Remote Similarity	NPD6785	Approved
0.6806	Remote Similarity	NPD6784	Approved
0.6805	Remote Similarity	NPD4978	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