NPASS Compound

Structure

NPC469438 OpenBabel07101718242D 37 42 0 0 1 0 0 0 0 0999 V2000 1.4362 -2.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2207 5.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0019 2.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5384 2.8266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5870 2.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9773 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7785 -1.2389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1381 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0262 2.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0992 3.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1235 3.7558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0018 0.5442 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5625 1.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5868 1.4734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0503 0.6565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4897 1.2489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4896 -0.2166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9295 -1.2794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6314 -1.8785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9295 0.3020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9773 -0.9773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6717 -3.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6357 4.5166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0990 2.2342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1476 2.3465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0746 0.7127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9289 0.3758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1139 1.2618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6842 4.6289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5140 1.3050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4653 -0.2727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9531 -1.0335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3220 -2.0295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5040 -0.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 6 24 1 0 0 0 0 7 33 1 0 0 0 0 8 21 1 0 0 0 0 8 23 1 0 0 0 0 9 22 1 0 0 0 0 9 25 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 34 1 0 0 0 0 14 22 1 1 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 1 0 0 0 17 19 1 0 0 0 0 17 29 1 6 0 0 0 18 30 2 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 19 35 1 1 0 0 0 20 22 1 1 0 0 0 20 36 1 0 0 0 0 20 37 1 0 0 0 0 21 24 1 1 0 0 0 21 36 1 0 0 0 0 22 24 1 6 0 0 0 23 31 1 6 0 0 0 23 37 1 0 0 0 0 24 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.17
Volume:	476.048
LogP:	0.723
LogD:	-0.148
LogS:	-3.525
# Rotatable Bonds:	8
TPSA:	193.83
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	6.301
Fsp3:	0.708
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.498
MDCK Permeability:	3.073003972531296e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.399
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	34.62029266357422%
Volume Distribution (VD):	0.361
Pgp-substrate:	43.03316879272461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.329
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	2.58
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.436
AMES Toxicity:	0.967
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.916
Carcinogencity:	0.957
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC469438

Natural Product ID:	NPC469438
*Common Name:**	Mudanpioside E
IUPAC Name:	n.a.
Synonyms:	Mudanpioside E
Standard InCHIKey:	OOVJYHFTGMUDDQ-PHWFTUJASA-N
Standard InCHI:	InChI=1S/C24H30O13/c1-21-8-23(31)14-6-24(21,22(14,9-25)20(36-21)37-23)35-19-17(29)16(28)15(27)13(34-19)7-33-18(30)10-3-4-11(26)12(5-10)32-2/h3-5,13-17,19-20,25-29,31H,6-9H2,1-2H3/t13-,14+,15-,16+,17-,19+,20-,21+,22+,23-,24-/m1/s1
SMILES:	CC12CC3(C4CC1(C4(C(O2)O3)CO)OC5C(C(C(C(O5)COC(=O)C6=CC(=C(C=C6)O)OC)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078748
PubChem CID:	46882884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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
IC50	2
Others	6

Activity Type	# Activity
Cell Line	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	86.2	%	PMID[486271]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	83.9	%	PMID[486271]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	80.9	%	PMID[486271]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	67.4	%	PMID[486271]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[486271]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[486272]
NPT610	Others	Molecular identity unknown		INH	=	1.12	mM	PMID[486273]
NPT610	Others	Molecular identity unknown		INH	=	0.89	mM	PMID[486273]

☑ 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 NPC469438 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	429
0.1-0.2	1607
0.2-0.3	3262
0.3-0.4	6418
0.4-0.5	9593
0.5-0.6	8721
0.6-0.7	8567
0.7-0.8	3908
0.8-0.85	114
0.85-0.9	61
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC188217
0.9578	High Similarity	NPC469397
0.9398	High Similarity	NPC148185
0.9387	High Similarity	NPC120012
0.929	High Similarity	NPC260300
0.929	High Similarity	NPC80360
0.9286	High Similarity	NPC469354
0.9264	High Similarity	NPC293568
0.9264	High Similarity	NPC117943
0.9235	High Similarity	NPC195114
0.9157	High Similarity	NPC469459
0.9157	High Similarity	NPC149002
0.9157	High Similarity	NPC469458
0.9157	High Similarity	NPC469396
0.9157	High Similarity	NPC88176
0.9152	High Similarity	NPC100420
0.9096	High Similarity	NPC265600
0.903	High Similarity	NPC477627
0.8963	High Similarity	NPC226759
0.8953	High Similarity	NPC469418
0.8941	High Similarity	NPC477617
0.8817	High Similarity	NPC469419
0.8779	High Similarity	NPC316539
0.8757	High Similarity	NPC180586
0.875	High Similarity	NPC41009
0.8735	High Similarity	NPC472860
0.8728	High Similarity	NPC193377
0.8698	High Similarity	NPC116759
0.8698	High Similarity	NPC14294
0.8686	High Similarity	NPC108191
0.8686	High Similarity	NPC93685
0.8683	High Similarity	NPC76211
0.8678	High Similarity	NPC475054
0.8678	High Similarity	NPC473713
0.8678	High Similarity	NPC196771
0.8675	High Similarity	NPC471405
0.8667	High Similarity	NPC194095
0.8667	High Similarity	NPC327032
0.8667	High Similarity	NPC191046
0.8652	High Similarity	NPC475360
0.8647	High Similarity	NPC475738
0.8639	High Similarity	NPC476011
0.8631	High Similarity	NPC203020
0.8631	High Similarity	NPC268718
0.8631	High Similarity	NPC150943
0.8631	High Similarity	NPC91634
0.8631	High Similarity	NPC239966
0.8623	High Similarity	NPC475663
0.8623	High Similarity	NPC4747
0.8623	High Similarity	NPC104275
0.8623	High Similarity	NPC286919
0.8619	High Similarity	NPC476358
0.8614	High Similarity	NPC10205
0.8605	High Similarity	NPC21956
0.8598	High Similarity	NPC469477
0.8598	High Similarity	NPC133430
0.858	High Similarity	NPC472859
0.858	High Similarity	NPC25389
0.858	High Similarity	NPC311803
0.8571	High Similarity	NPC289811
0.8571	High Similarity	NPC469384
0.8571	High Similarity	NPC160780
0.8563	High Similarity	NPC478055
0.8555	High Similarity	NPC472803
0.8555	High Similarity	NPC212748
0.8554	High Similarity	NPC62051
0.8547	High Similarity	NPC185498
0.8545	High Similarity	NPC36130
0.8545	High Similarity	NPC134905
0.8545	High Similarity	NPC267091
0.8537	High Similarity	NPC267469
0.8537	High Similarity	NPC116292
0.8537	High Similarity	NPC87630
0.8537	High Similarity	NPC179128
0.8531	High Similarity	NPC102367
0.8529	High Similarity	NPC76687
0.8528	High Similarity	NPC303429
0.8528	High Similarity	NPC222102
0.8521	High Similarity	NPC166277
0.8521	High Similarity	NPC474770
0.8521	High Similarity	NPC239818
0.8521	High Similarity	NPC119125
0.8521	High Similarity	NPC218471
0.8519	High Similarity	NPC473867
0.8514	High Similarity	NPC169645
0.8514	High Similarity	NPC84482
0.8512	High Similarity	NPC1913
0.8512	High Similarity	NPC133984
0.8506	High Similarity	NPC474075
0.8506	High Similarity	NPC312006
0.8506	High Similarity	NPC471921
0.8506	High Similarity	NPC471920
0.8506	High Similarity	NPC471922
0.8506	High Similarity	NPC20114
0.8506	High Similarity	NPC292712
0.8506	High Similarity	NPC129930
0.8506	High Similarity	NPC114550
0.8503	High Similarity	NPC38699
0.8503	High Similarity	NPC172920
0.8503	High Similarity	NPC156624
0.8497	Intermediate Similarity	NPC88557
0.8497	Intermediate Similarity	NPC266545
0.8497	Intermediate Similarity	NPC117911
0.8497	Intermediate Similarity	NPC202428
0.8494	Intermediate Similarity	NPC44730
0.8494	Intermediate Similarity	NPC245615
0.8494	Intermediate Similarity	NPC137813
0.8494	Intermediate Similarity	NPC157898
0.8494	Intermediate Similarity	NPC299706
0.8494	Intermediate Similarity	NPC61604
0.8494	Intermediate Similarity	NPC115466
0.8488	Intermediate Similarity	NPC301910
0.8488	Intermediate Similarity	NPC200726
0.8488	Intermediate Similarity	NPC130730
0.8485	Intermediate Similarity	NPC243891
0.8483	Intermediate Similarity	NPC473776
0.8483	Intermediate Similarity	NPC473205
0.8476	Intermediate Similarity	NPC478242
0.8476	Intermediate Similarity	NPC469415
0.8471	Intermediate Similarity	NPC100465
0.8471	Intermediate Similarity	NPC152424
0.8466	Intermediate Similarity	NPC79736
0.8466	Intermediate Similarity	NPC67629
0.8462	Intermediate Similarity	NPC287872
0.8462	Intermediate Similarity	NPC74319
0.8462	Intermediate Similarity	NPC68619
0.8462	Intermediate Similarity	NPC179914
0.8462	Intermediate Similarity	NPC475299
0.8457	Intermediate Similarity	NPC184624
0.8452	Intermediate Similarity	NPC237946
0.8452	Intermediate Similarity	NPC163635
0.8452	Intermediate Similarity	NPC32373
0.8452	Intermediate Similarity	NPC228357
0.8448	Intermediate Similarity	NPC475058
0.8448	Intermediate Similarity	NPC179240
0.8439	Intermediate Similarity	NPC298847
0.8439	Intermediate Similarity	NPC177362
0.8439	Intermediate Similarity	NPC79322
0.8439	Intermediate Similarity	NPC311912
0.8439	Intermediate Similarity	NPC116745
0.8434	Intermediate Similarity	NPC221249
0.8434	Intermediate Similarity	NPC289438
0.8434	Intermediate Similarity	NPC34066
0.8434	Intermediate Similarity	NPC124842
0.8434	Intermediate Similarity	NPC469422
0.843	Intermediate Similarity	NPC474301
0.8427	Intermediate Similarity	NPC170203
0.8427	Intermediate Similarity	NPC208797
0.8427	Intermediate Similarity	NPC53680
0.8424	Intermediate Similarity	NPC162569
0.8424	Intermediate Similarity	NPC205054
0.8424	Intermediate Similarity	NPC35160
0.8421	Intermediate Similarity	NPC22324
0.8421	Intermediate Similarity	NPC33298
0.8421	Intermediate Similarity	NPC285108
0.8421	Intermediate Similarity	NPC116838
0.8421	Intermediate Similarity	NPC22130
0.8418	Intermediate Similarity	NPC267549
0.8418	Intermediate Similarity	NPC35266
0.8412	Intermediate Similarity	NPC474936
0.8412	Intermediate Similarity	NPC24627
0.8402	Intermediate Similarity	NPC163527
0.8402	Intermediate Similarity	NPC115281
0.8402	Intermediate Similarity	NPC474990
0.8402	Intermediate Similarity	NPC181168
0.8402	Intermediate Similarity	NPC19947
0.8402	Intermediate Similarity	NPC207584
0.84	Intermediate Similarity	NPC469776
0.84	Intermediate Similarity	NPC469772
0.84	Intermediate Similarity	NPC295941
0.84	Intermediate Similarity	NPC469777
0.84	Intermediate Similarity	NPC135334
0.84	Intermediate Similarity	NPC235575
0.84	Intermediate Similarity	NPC469778
0.84	Intermediate Similarity	NPC471181
0.84	Intermediate Similarity	NPC469773
0.84	Intermediate Similarity	NPC469775
0.84	Intermediate Similarity	NPC178737
0.84	Intermediate Similarity	NPC469774
0.84	Intermediate Similarity	NPC100925
0.84	Intermediate Similarity	NPC32723
0.8393	Intermediate Similarity	NPC469399
0.8391	Intermediate Similarity	NPC476017
0.8389	Intermediate Similarity	NPC299855
0.8389	Intermediate Similarity	NPC96194
0.8383	Intermediate Similarity	NPC310661
0.8383	Intermediate Similarity	NPC105827
0.8383	Intermediate Similarity	NPC308555
0.8382	Intermediate Similarity	NPC174734
0.8382	Intermediate Similarity	NPC474042
0.8373	Intermediate Similarity	NPC140151
0.8373	Intermediate Similarity	NPC477700
0.8373	Intermediate Similarity	NPC32079
0.8372	Intermediate Similarity	NPC475865
0.8372	Intermediate Similarity	NPC109990
0.8372	Intermediate Similarity	NPC147596
0.8364	Intermediate Similarity	NPC476394
0.8364	Intermediate Similarity	NPC111785
0.8364	Intermediate Similarity	NPC98809
0.8363	Intermediate Similarity	NPC469889

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 NPC469438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	866
0.2-0.3	2034
0.3-0.4	2731
0.4-0.5	2013
0.5-0.6	828
0.6-0.7	239
0.7-0.8	72
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8686	High Similarity	NPD8055	Clinical (unspecified phase)
0.8571	High Similarity	NPD6234	Discontinued
0.8547	High Similarity	NPD7228	Approved
0.8452	Intermediate Similarity	NPD4967	Phase 2
0.8452	Intermediate Similarity	NPD4966	Approved
0.8452	Intermediate Similarity	NPD4965	Approved
0.8352	Intermediate Similarity	NPD7685	Pre-registration
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8274	Intermediate Similarity	NPD37	Approved
0.8101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7240	Approved
0.8034	Intermediate Similarity	NPD7074	Phase 3
0.8023	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7054	Approved
0.7978	Intermediate Similarity	NPD5844	Phase 1
0.7946	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7199	Phase 2
0.7933	Intermediate Similarity	NPD7472	Approved
0.7923	Intermediate Similarity	NPD8434	Phase 2
0.787	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6559	Discontinued
0.7838	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4628	Phase 3
0.7797	Intermediate Similarity	NPD6232	Discontinued
0.779	Intermediate Similarity	NPD6797	Phase 2
0.7784	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.7753	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7251	Discontinued
0.7746	Intermediate Similarity	NPD1934	Approved
0.7719	Intermediate Similarity	NPD1653	Approved
0.7705	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD1465	Phase 2
0.7701	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5494	Approved
0.7663	Intermediate Similarity	NPD8312	Approved
0.7663	Intermediate Similarity	NPD8313	Approved
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.764	Intermediate Similarity	NPD8127	Discontinued
0.7629	Intermediate Similarity	NPD7680	Approved
0.7614	Intermediate Similarity	NPD3882	Suspended
0.7611	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6166	Phase 2
0.76	Intermediate Similarity	NPD2801	Approved
0.7596	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7458	Discontinued
0.7538	Intermediate Similarity	NPD7435	Discontinued
0.7529	Intermediate Similarity	NPD7028	Phase 2
0.7529	Intermediate Similarity	NPD4380	Phase 2
0.7527	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7472	Intermediate Similarity	NPD7075	Discontinued
0.7458	Intermediate Similarity	NPD3817	Phase 2
0.7455	Intermediate Similarity	NPD230	Phase 1
0.7442	Intermediate Similarity	NPD2534	Approved
0.7442	Intermediate Similarity	NPD2533	Approved
0.7442	Intermediate Similarity	NPD2532	Approved
0.7401	Intermediate Similarity	NPD7819	Suspended
0.7341	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7874	Approved
0.731	Intermediate Similarity	NPD8166	Discontinued
0.731	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6273	Approved
0.7297	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD7697	Approved
0.7264	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7251	Intermediate Similarity	NPD6674	Discontinued
0.7249	Intermediate Similarity	NPD8407	Phase 2
0.7247	Intermediate Similarity	NPD6801	Discontinued
0.7243	Intermediate Similarity	NPD7799	Discontinued
0.7243	Intermediate Similarity	NPD3751	Discontinued
0.7236	Intermediate Similarity	NPD7871	Phase 2
0.7236	Intermediate Similarity	NPD7870	Phase 2
0.7232	Intermediate Similarity	NPD6599	Discontinued
0.7222	Intermediate Similarity	NPD6823	Phase 2
0.7216	Intermediate Similarity	NPD6535	Approved
0.7216	Intermediate Similarity	NPD6534	Approved
0.7214	Intermediate Similarity	NPD7701	Phase 2
0.7209	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4110	Phase 3
0.7207	Intermediate Similarity	NPD5761	Phase 2
0.7207	Intermediate Similarity	NPD5760	Phase 2
0.72	Intermediate Similarity	NPD7999	Approved
0.7195	Intermediate Similarity	NPD9494	Approved
0.7193	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7783	Phase 2
0.7192	Intermediate Similarity	NPD7801	Approved
0.7192	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7497	Discontinued
0.7184	Intermediate Similarity	NPD1511	Approved
0.7181	Intermediate Similarity	NPD8368	Discontinued
0.7176	Intermediate Similarity	NPD2935	Discontinued
0.7171	Intermediate Similarity	NPD7930	Approved
0.7169	Intermediate Similarity	NPD3764	Approved
0.7167	Intermediate Similarity	NPD5402	Approved
0.7151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8320	Phase 1
0.715	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD4665	Approved
0.7108	Intermediate Similarity	NPD3027	Phase 3
0.7107	Intermediate Similarity	NPD7700	Phase 2
0.7107	Intermediate Similarity	NPD7699	Phase 2
0.7102	Intermediate Similarity	NPD1512	Approved
0.7101	Intermediate Similarity	NPD8404	Phase 2
0.7095	Intermediate Similarity	NPD7411	Suspended
0.709	Intermediate Similarity	NPD6764	Approved
0.709	Intermediate Similarity	NPD6765	Approved
0.7088	Intermediate Similarity	NPD3749	Approved
0.7083	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3620	Phase 2
0.7079	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3226	Approved
0.7076	Intermediate Similarity	NPD6100	Approved
0.7076	Intermediate Similarity	NPD6099	Approved
0.7072	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5353	Approved
0.7065	Intermediate Similarity	NPD6959	Discontinued
0.7027	Intermediate Similarity	NPD5710	Approved
0.7027	Intermediate Similarity	NPD5711	Approved
0.702	Intermediate Similarity	NPD4420	Approved
0.7011	Intermediate Similarity	NPD3750	Approved
0.7011	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2493	Approved
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD2494	Approved
0.6994	Remote Similarity	NPD1549	Phase 2
0.6989	Remote Similarity	NPD6799	Approved
0.6989	Remote Similarity	NPD5242	Approved
0.6982	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1613	Approved
0.698	Remote Similarity	NPD4583	Approved
0.698	Remote Similarity	NPD4582	Approved
0.6967	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5005	Approved
0.6965	Remote Similarity	NPD5006	Approved
0.6959	Remote Similarity	NPD7097	Phase 1
0.6957	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD919	Approved
0.6952	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4111	Phase 1
0.6949	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6784	Approved
0.6943	Remote Similarity	NPD6785	Approved
0.6941	Remote Similarity	NPD1933	Approved
0.6941	Remote Similarity	NPD447	Suspended
0.6936	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2346	Discontinued
0.6933	Remote Similarity	NPD3705	Approved
0.6931	Remote Similarity	NPD4002	Approved
0.6931	Remote Similarity	NPD4004	Approved
0.6923	Remote Similarity	NPD8361	Approved
0.6923	Remote Similarity	NPD8360	Approved
0.6919	Remote Similarity	NPD1510	Phase 2
0.6915	Remote Similarity	NPD3450	Approved
0.6915	Remote Similarity	NPD3452	Approved
0.6907	Remote Similarity	NPD4663	Approved
0.6904	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6212	Phase 3
0.6904	Remote Similarity	NPD6213	Phase 3
0.6898	Remote Similarity	NPD3926	Phase 2
0.6887	Remote Similarity	NPD7907	Approved
0.6882	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD2438	Suspended
0.6878	Remote Similarity	NPD7585	Approved
0.6872	Remote Similarity	NPD5403	Approved
0.6857	Remote Similarity	NPD2800	Approved
0.6854	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7296	Approved
0.6852	Remote Similarity	NPD1357	Approved
0.6848	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7768	Phase 2
0.6845	Remote Similarity	NPD7229	Phase 3
0.6842	Remote Similarity	NPD6355	Discontinued
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD6003	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