NPASS Compound

Structure

NPC469418 OpenBabel07101718192D 46 51 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 -4.3489 -0.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5305 -1.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 -0.3711 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 -2.6457 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7537 0.8404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5563 -0.8803 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 -2.8272 -2.0034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1583 0.0370 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 8.7472 0.7265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5498 -0.9943 0.0000 C 0 0 0 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 9.1453 -0.1909 0.0000 C 0 0 0 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 -2.0664 -2.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1648 0.1510 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 9.3426 1.5299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9479 -1.9117 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 10.1388 -0.3048 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 -2.2479 -3.6357 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 0.4212 -2.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5694 -0.6524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1240 -2.3178 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 41 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 14 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 18 2 0 0 0 0 10 16 1 0 0 0 0 10 31 1 0 0 0 0 11 19 1 0 0 0 0 11 29 1 0 0 0 0 12 42 1 0 0 0 0 13 30 1 0 0 0 0 13 43 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 1 0 0 0 17 21 2 0 0 0 0 17 32 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 0 0 0 0 19 34 2 0 0 0 0 20 12 1 6 0 0 0 20 22 1 0 0 0 0 20 44 1 0 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 36 1 1 0 0 0 23 24 1 0 0 0 0 23 37 1 6 0 0 0 24 27 1 0 0 0 0 24 38 1 1 0 0 0 25 39 2 0 0 0 0 25 43 1 0 0 0 0 26 40 2 0 0 0 0 26 42 1 0 0 0 0 27 44 1 0 0 0 0 27 45 1 6 0 0 0 28 30 1 6 0 0 0 28 41 1 0 0 0 0 28 46 1 0 0 0 0 29 31 1 1 0 0 0 29 46 1 0 0 0 0 30 31 1 1 0 0 0 31 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.19
Volume:	601.519
LogP:	1.569
LogD:	0.703
LogS:	-3.291
# Rotatable Bonds:	11
TPSA:	227.97
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	6.141
Fsp3:	0.516
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.634
MDCK Permeability:	2.336732177354861e-05
Pgp-inhibitor:	0.188
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.612
20% Bioavailability (F20%):	0.808
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	95.80415344238281%
Volume Distribution (VD):	0.308
Pgp-substrate:	10.281448364257812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.572
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	6.385
Half-life (T1/2):	0.929

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.881
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.925
Carcinogencity:	0.202
Eye Corrosion:	0.003
Eye Irritation:	0.559
Respiratory Toxicity:	0.641

Download Data

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

Natural Product: NPC469418

Natural Product ID:	NPC469418
*Common Name:**	Paeonidanin B
IUPAC Name:	n.a.
Synonyms:	6'-O-Galloylpaeonidanin
Standard InCHIKey:	MCPINUIKOMHPEA-XYRACALWSA-N
Standard InCHI:	InChI=1S/C31H34O15/c1-29-11-19(34)16-10-31(29,30(16,28(41-2)46-29)13-43-25(39)14-6-4-3-5-7-14)45-27-24(38)23(37)22(36)20(44-27)12-42-26(40)15-8-17(32)21(35)18(33)9-15/h3-9,16,20,22-24,27-28,32-33,35-38H,10-13H2,1-2H3/t16-,20-,22-,23+,24-,27+,28+,29+,30+,31-/m1/s1
SMILES:	CC12CC(=O)C3CC1(C3(C(O2)OC)COC(=O)C4=CC=CC=C4)OC5C(C(C(C(O5)COC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078413
PubChem CID:	46883512
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	=	63.0	%	PMID[464394]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	64.1	%	PMID[464394]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	52.2	%	PMID[464394]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	43.5	%	PMID[464394]
NPT848	Cell Line	N9	Homo sapiens	IC50	=	13900.0	nM	PMID[464394]

☑ 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 NPC469418 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	402
0.1-0.2	1515
0.2-0.3	2881
0.3-0.4	6021
0.4-0.5	9837
0.5-0.6	8144
0.6-0.7	7289
0.7-0.8	6097
0.8-0.85	474
0.85-0.9	31
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC260300
0.9524	High Similarity	NPC80360
0.9512	High Similarity	NPC469419
0.9467	High Similarity	NPC195114
0.9268	High Similarity	NPC477627
0.9162	High Similarity	NPC469396
0.9162	High Similarity	NPC469458
0.9162	High Similarity	NPC149002
0.9162	High Similarity	NPC88176
0.9075	High Similarity	NPC188217
0.9053	High Similarity	NPC476017
0.9048	High Similarity	NPC469459
0.9	High Similarity	NPC475058
0.897	High Similarity	NPC4747
0.897	High Similarity	NPC104275
0.8953	High Similarity	NPC469438
0.8953	High Similarity	NPC469354
0.8947	High Similarity	NPC477617
0.8947	High Similarity	NPC148185
0.8902	High Similarity	NPC469417
0.8902	High Similarity	NPC469397
0.8876	High Similarity	NPC475738
0.8857	High Similarity	NPC102367
0.8848	High Similarity	NPC156624
0.8848	High Similarity	NPC172920
0.8848	High Similarity	NPC469399
0.8848	High Similarity	NPC203757
0.881	High Similarity	NPC293568
0.881	High Similarity	NPC117943
0.878	High Similarity	NPC221249
0.8757	High Similarity	NPC14030
0.8757	High Similarity	NPC291957
0.872	High Similarity	NPC140151
0.8706	High Similarity	NPC470898
0.8698	High Similarity	NPC266365
0.8671	High Similarity	NPC212748
0.8659	High Similarity	NPC105591
0.8655	High Similarity	NPC265600
0.8644	High Similarity	NPC469371
0.8644	High Similarity	NPC170203
0.8636	High Similarity	NPC267549
0.8631	High Similarity	NPC49173
0.8629	High Similarity	NPC171706
0.8621	High Similarity	NPC235575
0.8621	High Similarity	NPC261254
0.8614	High Similarity	NPC3746
0.8614	High Similarity	NPC16024
0.8614	High Similarity	NPC205037
0.8614	High Similarity	NPC44260
0.8614	High Similarity	NPC61152
0.8606	High Similarity	NPC133430
0.8606	High Similarity	NPC469477
0.8598	High Similarity	NPC92117
0.8598	High Similarity	NPC75945
0.8596	High Similarity	NPC199172
0.8596	High Similarity	NPC100420
0.8596	High Similarity	NPC35924
0.8588	High Similarity	NPC212290
0.858	High Similarity	NPC67629
0.858	High Similarity	NPC79736
0.858	High Similarity	NPC475233
0.8571	High Similarity	NPC316539
0.8571	High Similarity	NPC172033
0.8571	High Similarity	NPC88560
0.8571	High Similarity	NPC175230
0.8564	High Similarity	NPC230670
0.8564	High Similarity	NPC71385
0.8563	High Similarity	NPC204937
0.8563	High Similarity	NPC470272
0.8563	High Similarity	NPC149011
0.8555	High Similarity	NPC470271
0.8555	High Similarity	NPC116745
0.8555	High Similarity	NPC311389
0.8547	High Similarity	NPC471788
0.8547	High Similarity	NPC478022
0.8547	High Similarity	NPC478020
0.8545	High Similarity	NPC116292
0.8545	High Similarity	NPC87630
0.8545	High Similarity	NPC179128
0.8545	High Similarity	NPC267469
0.8539	High Similarity	NPC53680
0.8539	High Similarity	NPC477860
0.8539	High Similarity	NPC475161
0.8539	High Similarity	NPC208797
0.8537	High Similarity	NPC120621
0.8537	High Similarity	NPC469448
0.8537	High Similarity	NPC248257
0.8525	High Similarity	NPC476358
0.8523	High Similarity	NPC68381
0.8521	High Similarity	NPC206641
0.8521	High Similarity	NPC472860
0.8521	High Similarity	NPC257309
0.8521	High Similarity	NPC226759
0.8521	High Similarity	NPC135222
0.8521	High Similarity	NPC474010
0.8521	High Similarity	NPC208651
0.8516	High Similarity	NPC112708
0.8516	High Similarity	NPC264302
0.8514	High Similarity	NPC47140
0.8514	High Similarity	NPC67134
0.8514	High Similarity	NPC469506
0.8506	High Similarity	NPC229687
0.8506	High Similarity	NPC222455
0.8497	Intermediate Similarity	NPC175793
0.8492	Intermediate Similarity	NPC473205
0.8492	Intermediate Similarity	NPC473883
0.8492	Intermediate Similarity	NPC473776
0.8488	Intermediate Similarity	NPC14294
0.8488	Intermediate Similarity	NPC120012
0.8488	Intermediate Similarity	NPC116759
0.8488	Intermediate Similarity	NPC109990
0.8483	Intermediate Similarity	NPC244903
0.8483	Intermediate Similarity	NPC198902
0.8475	Intermediate Similarity	NPC473713
0.8475	Intermediate Similarity	NPC154741
0.8475	Intermediate Similarity	NPC257714
0.8475	Intermediate Similarity	NPC296018
0.847	Intermediate Similarity	NPC475299
0.847	Intermediate Similarity	NPC473711
0.8466	Intermediate Similarity	NPC98776
0.8466	Intermediate Similarity	NPC472993
0.8466	Intermediate Similarity	NPC472054
0.8466	Intermediate Similarity	NPC471871
0.8466	Intermediate Similarity	NPC477881
0.8462	Intermediate Similarity	NPC283480
0.8462	Intermediate Similarity	NPC148323
0.8457	Intermediate Similarity	NPC298778
0.8457	Intermediate Similarity	NPC472803
0.8453	Intermediate Similarity	NPC475360
0.8453	Intermediate Similarity	NPC65489
0.8448	Intermediate Similarity	NPC229729
0.8448	Intermediate Similarity	NPC261411
0.8448	Intermediate Similarity	NPC43918
0.8448	Intermediate Similarity	NPC45400
0.8448	Intermediate Similarity	NPC190204
0.8448	Intermediate Similarity	NPC185498
0.8448	Intermediate Similarity	NPC107009
0.8444	Intermediate Similarity	NPC231254
0.8443	Intermediate Similarity	NPC227485
0.8443	Intermediate Similarity	NPC5115
0.8443	Intermediate Similarity	NPC34066
0.8439	Intermediate Similarity	NPC165720
0.8439	Intermediate Similarity	NPC469420
0.8434	Intermediate Similarity	NPC35160
0.8434	Intermediate Similarity	NPC162569
0.843	Intermediate Similarity	NPC33298
0.843	Intermediate Similarity	NPC187934
0.843	Intermediate Similarity	NPC300537
0.843	Intermediate Similarity	NPC41009
0.843	Intermediate Similarity	NPC97637
0.843	Intermediate Similarity	NPC285108
0.843	Intermediate Similarity	NPC148273
0.843	Intermediate Similarity	NPC127782
0.843	Intermediate Similarity	NPC145847
0.843	Intermediate Similarity	NPC76687
0.8427	Intermediate Similarity	NPC477882
0.8427	Intermediate Similarity	NPC472387
0.8427	Intermediate Similarity	NPC476622
0.8427	Intermediate Similarity	NPC477880
0.8427	Intermediate Similarity	NPC476620
0.8427	Intermediate Similarity	NPC476619
0.8427	Intermediate Similarity	NPC35167
0.8427	Intermediate Similarity	NPC476618
0.8427	Intermediate Similarity	NPC476773
0.8427	Intermediate Similarity	NPC241196
0.8427	Intermediate Similarity	NPC476623
0.8427	Intermediate Similarity	NPC476621
0.8421	Intermediate Similarity	NPC203020
0.8421	Intermediate Similarity	NPC472055
0.8421	Intermediate Similarity	NPC239966
0.8421	Intermediate Similarity	NPC289346
0.8418	Intermediate Similarity	NPC108202
0.8418	Intermediate Similarity	NPC169645
0.8418	Intermediate Similarity	NPC474345
0.8418	Intermediate Similarity	NPC294149
0.8418	Intermediate Similarity	NPC84482
0.8418	Intermediate Similarity	NPC472607
0.8418	Intermediate Similarity	NPC146803
0.8415	Intermediate Similarity	NPC473867
0.8412	Intermediate Similarity	NPC172419
0.8412	Intermediate Similarity	NPC187205
0.8412	Intermediate Similarity	NPC238419
0.8409	Intermediate Similarity	NPC211594
0.8409	Intermediate Similarity	NPC175107
0.8409	Intermediate Similarity	NPC271385
0.8409	Intermediate Similarity	NPC254540
0.8409	Intermediate Similarity	NPC205076
0.8409	Intermediate Similarity	NPC13989
0.8409	Intermediate Similarity	NPC48773
0.8409	Intermediate Similarity	NPC76128
0.8409	Intermediate Similarity	NPC294501
0.8409	Intermediate Similarity	NPC190003
0.8409	Intermediate Similarity	NPC472386
0.8409	Intermediate Similarity	NPC471181
0.8409	Intermediate Similarity	NPC307518
0.8409	Intermediate Similarity	NPC245452
0.8409	Intermediate Similarity	NPC111536
0.8409	Intermediate Similarity	NPC30432
0.8409	Intermediate Similarity	NPC172807
0.8409	Intermediate Similarity	NPC5029

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 NPC469418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	830
0.2-0.3	1803
0.3-0.4	2757
0.4-0.5	2130
0.5-0.6	932
0.6-0.7	253
0.7-0.8	102
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD3818	Discontinued
0.8448	Intermediate Similarity	NPD7228	Approved
0.838	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD7074	Phase 3
0.8295	Intermediate Similarity	NPD7054	Approved
0.8256	Intermediate Similarity	NPD6234	Discontinued
0.8249	Intermediate Similarity	NPD7472	Approved
0.8212	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD37	Approved
0.8156	Intermediate Similarity	NPD7251	Discontinued
0.8152	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD4967	Phase 2
0.814	Intermediate Similarity	NPD4965	Approved
0.814	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD4966	Approved
0.8101	Intermediate Similarity	NPD6797	Phase 2
0.8092	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD6559	Discontinued
0.8056	Intermediate Similarity	NPD7685	Pre-registration
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.7956	Intermediate Similarity	NPD7240	Approved
0.7921	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6166	Phase 2
0.7921	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6232	Discontinued
0.7889	Intermediate Similarity	NPD5844	Phase 1
0.7889	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7266	Discontinued
0.7869	Intermediate Similarity	NPD8313	Approved
0.7869	Intermediate Similarity	NPD8312	Approved
0.7861	Intermediate Similarity	NPD1934	Approved
0.7849	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4380	Phase 2
0.7838	Intermediate Similarity	NPD8150	Discontinued
0.7838	Intermediate Similarity	NPD8434	Phase 2
0.7802	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6190	Approved
0.7797	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7784	Intermediate Similarity	NPD8320	Phase 1
0.7784	Intermediate Similarity	NPD8319	Approved
0.7753	Intermediate Similarity	NPD7199	Phase 2
0.7732	Intermediate Similarity	NPD7435	Discontinued
0.7727	Intermediate Similarity	NPD3882	Suspended
0.7716	Intermediate Similarity	NPD8151	Discontinued
0.7714	Intermediate Similarity	NPD7819	Suspended
0.7684	Intermediate Similarity	NPD6534	Approved
0.7684	Intermediate Similarity	NPD6535	Approved
0.7683	Intermediate Similarity	NPD230	Phase 1
0.7656	Intermediate Similarity	NPD7699	Phase 2
0.7656	Intermediate Similarity	NPD7700	Phase 2
0.7637	Intermediate Similarity	NPD7799	Discontinued
0.7633	Intermediate Similarity	NPD8166	Discontinued
0.7617	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD1465	Phase 2
0.7614	Intermediate Similarity	NPD2801	Approved
0.7614	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7458	Discontinued
0.7577	Intermediate Similarity	NPD6778	Approved
0.7577	Intermediate Similarity	NPD6779	Approved
0.7577	Intermediate Similarity	NPD6781	Approved
0.7577	Intermediate Similarity	NPD6782	Approved
0.7577	Intermediate Similarity	NPD6777	Approved
0.7577	Intermediate Similarity	NPD6780	Approved
0.7577	Intermediate Similarity	NPD6776	Approved
0.7571	Intermediate Similarity	NPD3817	Phase 2
0.7571	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7680	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.7486	Intermediate Similarity	NPD3749	Approved
0.7462	Intermediate Similarity	NPD7697	Approved
0.7462	Intermediate Similarity	NPD7698	Approved
0.7462	Intermediate Similarity	NPD7696	Phase 3
0.7459	Intermediate Similarity	NPD6959	Discontinued
0.7458	Intermediate Similarity	NPD6801	Discontinued
0.7457	Intermediate Similarity	NPD2533	Approved
0.7457	Intermediate Similarity	NPD2534	Approved
0.7457	Intermediate Similarity	NPD2532	Approved
0.7447	Intermediate Similarity	NPD8407	Phase 2
0.7446	Intermediate Similarity	NPD3751	Discontinued
0.7443	Intermediate Similarity	NPD6599	Discontinued
0.7427	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD7870	Phase 2
0.7424	Intermediate Similarity	NPD7871	Phase 2
0.7411	Intermediate Similarity	NPD6823	Phase 2
0.741	Intermediate Similarity	NPD943	Approved
0.74	Intermediate Similarity	NPD7701	Phase 2
0.7399	Intermediate Similarity	NPD1511	Approved
0.7382	Intermediate Similarity	NPD8361	Approved
0.7382	Intermediate Similarity	NPD8360	Approved
0.738	Intermediate Similarity	NPD8368	Discontinued
0.7376	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7801	Approved
0.7376	Intermediate Similarity	NPD7783	Phase 2
0.7374	Intermediate Similarity	NPD5402	Approved
0.7363	Intermediate Similarity	NPD8127	Discontinued
0.7358	Intermediate Similarity	NPD6212	Phase 3
0.7358	Intermediate Similarity	NPD6213	Phase 3
0.7358	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1653	Approved
0.7322	Intermediate Similarity	NPD3787	Discontinued
0.7314	Intermediate Similarity	NPD1512	Approved
0.7312	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8435	Approved
0.7289	Intermediate Similarity	NPD3764	Approved
0.7257	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7768	Phase 2
0.7235	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.7209	Intermediate Similarity	NPD1549	Phase 2
0.7209	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6799	Approved
0.72	Intermediate Similarity	NPD7390	Discontinued
0.7175	Intermediate Similarity	NPD5403	Approved
0.7159	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1510	Phase 2
0.7129	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD5760	Phase 2
0.7127	Intermediate Similarity	NPD5761	Phase 2
0.7126	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6273	Approved
0.7101	Intermediate Similarity	NPD7930	Approved
0.7098	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3226	Approved
0.7094	Intermediate Similarity	NPD7584	Approved
0.7093	Intermediate Similarity	NPD6100	Approved
0.7093	Intermediate Similarity	NPD6099	Approved
0.7065	Intermediate Similarity	NPD919	Approved
0.7062	Intermediate Similarity	NPD5401	Approved
0.7056	Intermediate Similarity	NPD7028	Phase 2
0.7043	Intermediate Similarity	NPD5710	Approved
0.7043	Intermediate Similarity	NPD5711	Approved
0.7039	Intermediate Similarity	NPD7239	Suspended
0.7033	Intermediate Similarity	NPD8404	Phase 2
0.7018	Intermediate Similarity	NPD1607	Approved
0.7012	Intermediate Similarity	NPD9269	Phase 2
0.7005	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2796	Approved
0.6994	Remote Similarity	NPD5404	Approved
0.6994	Remote Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD2935	Discontinued
0.6994	Remote Similarity	NPD5408	Approved
0.6994	Remote Similarity	NPD5405	Approved
0.6985	Remote Similarity	NPD8485	Approved
0.6976	Remote Similarity	NPD7585	Approved
0.6971	Remote Similarity	NPD2800	Approved
0.6971	Remote Similarity	NPD6674	Discontinued
0.6971	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4665	Approved
0.6952	Remote Similarity	NPD7229	Phase 3
0.6927	Remote Similarity	NPD7583	Approved
0.6923	Remote Similarity	NPD3027	Phase 3
0.6902	Remote Similarity	NPD5353	Approved
0.6901	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1613	Approved
0.69	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8059	Phase 3
0.6898	Remote Similarity	NPD1247	Approved
0.6889	Remote Similarity	NPD920	Approved
0.6881	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7999	Approved
0.6863	Remote Similarity	NPD7497	Discontinued
0.6857	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD6663	Approved
0.6839	Remote Similarity	NPD3748	Approved
0.6836	Remote Similarity	NPD7003	Approved
0.6825	Remote Similarity	NPD5242	Approved
0.6822	Remote Similarity	NPD7907	Approved
0.6821	Remote Similarity	NPD6651	Approved
0.6814	Remote Similarity	NPD5006	Approved
0.6814	Remote Similarity	NPD5005	Approved
0.6808	Remote Similarity	NPD4111	Phase 1
0.6805	Remote Similarity	NPD5736	Approved
0.68	Remote Similarity	NPD1551	Phase 2
0.6791	Remote Similarity	NPD5537	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