NPASS Compound

Structure

NPC469456 OpenBabel07101718322D 35 39 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 -3.1904 -3.9701 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 -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 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 1.2319 -1.1783 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 0.0000 -0.0000 0.0000 C 0 0 1 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 0.5645 -1.4448 0.0000 C 0 0 3 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 -2.6457 -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 1.3349 -0.4671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 5.5694 -0.6524 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 -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 -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 23 1 0 0 0 0 2 32 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 13 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 25 1 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 12 33 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 6 0 0 0 15 27 2 0 0 0 0 16 11 1 6 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 24 1 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 31 2 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 1 0 0 0 24 25 1 6 0 0 0 25 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.2
Volume:	472.894
LogP:	0.841
LogD:	0.604
LogS:	-3.321
# Rotatable Bonds:	8
TPSA:	151.98
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	5.915
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.16
MDCK Permeability:	1.2887931916338857e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.775
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	25.16857147216797%
Volume Distribution (VD):	0.424
Pgp-substrate:	49.712162017822266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.108
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	4.53
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.089
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.042
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC469456

Natural Product ID:	NPC469456
*Common Name:**	Paeonidanin
IUPAC Name:	n.a.
Synonyms:	Paeonidanin
Standard InCHIKey:	SDCMIWDDPOQVAS-BWDMLNMCSA-N
Standard InCHI:	InChI=1S/C25H32O10/c1-23-9-15(27)14-8-25(23,35-22-20(30)19(29)18(28)16(11-26)34-22)24(14,17(10-23)32-2)12-33-21(31)13-6-4-3-5-7-13/h3-7,14,16-20,22,26,28-30H,8-12H2,1-2H3/t14-,16+,17?,18+,19-,20+,22-,23+,24+,25+/m0/s1
SMILES:	CC12CC(C3(C1(CC3C(=O)C2)OC4C(C(C(C(O4)CO)O)O)O)COC(=O)C5=CC=CC=C5)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079203
PubChem CID:	46882922
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
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	4

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	93.8	%	PMID[557442]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	92.2	%	PMID[557442]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	82.3	%	PMID[557442]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	70.5	%	PMID[557442]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[557442]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[557443]

☑ 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 NPC469456 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	324
0.1-0.2	1166
0.2-0.3	2498
0.3-0.4	4940
0.4-0.5	9727
0.5-0.6	13991
0.6-0.7	8300
0.7-0.8	1336
0.8-0.85	373
0.85-0.9	38
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC469417
0.9038	High Similarity	NPC477491
0.9007	High Similarity	NPC469477
0.9007	High Similarity	NPC133430
0.8933	High Similarity	NPC476173
0.8933	High Similarity	NPC469448
0.8896	High Similarity	NPC469399
0.8896	High Similarity	NPC476784
0.8868	High Similarity	NPC477488
0.8859	High Similarity	NPC469513
0.8758	High Similarity	NPC472658
0.8758	High Similarity	NPC472657
0.875	High Similarity	NPC469415
0.8733	High Similarity	NPC478263
0.8726	High Similarity	NPC55744
0.8701	High Similarity	NPC5115
0.8701	High Similarity	NPC469422
0.8701	High Similarity	NPC34066
0.8684	High Similarity	NPC303429
0.8684	High Similarity	NPC222102
0.8679	High Similarity	NPC475567
0.8679	High Similarity	NPC473557
0.8679	High Similarity	NPC473468
0.8667	High Similarity	NPC478264
0.8636	High Similarity	NPC471135
0.8625	High Similarity	NPC475198
0.8625	High Similarity	NPC475175
0.8625	High Similarity	NPC475531
0.8616	High Similarity	NPC477627
0.8611	High Similarity	NPC239358
0.8581	High Similarity	NPC469730
0.8581	High Similarity	NPC473632
0.8581	High Similarity	NPC469398
0.8581	High Similarity	NPC132599
0.8571	High Similarity	NPC469420
0.8562	High Similarity	NPC125033
0.8553	High Similarity	NPC205389
0.8552	High Similarity	NPC472248
0.8526	High Similarity	NPC70344
0.8526	High Similarity	NPC475548
0.8526	High Similarity	NPC290683
0.8526	High Similarity	NPC475638
0.8523	High Similarity	NPC242355
0.8523	High Similarity	NPC77493
0.8519	High Similarity	NPC469419
0.8514	High Similarity	NPC473301
0.85	High Similarity	NPC471493
0.8493	Intermediate Similarity	NPC311492
0.8493	Intermediate Similarity	NPC28836
0.8491	Intermediate Similarity	NPC165234
0.8491	Intermediate Similarity	NPC475536
0.8487	Intermediate Similarity	NPC170668
0.8483	Intermediate Similarity	NPC233860
0.8483	Intermediate Similarity	NPC233692
0.8481	Intermediate Similarity	NPC477623
0.8471	Intermediate Similarity	NPC318447
0.8471	Intermediate Similarity	NPC322048
0.8467	Intermediate Similarity	NPC475135
0.8462	Intermediate Similarity	NPC473611
0.8457	Intermediate Similarity	NPC40138
0.8456	Intermediate Similarity	NPC472547
0.8442	Intermediate Similarity	NPC25484
0.8442	Intermediate Similarity	NPC91730
0.8442	Intermediate Similarity	NPC232583
0.8438	Intermediate Similarity	NPC473797
0.8438	Intermediate Similarity	NPC475300
0.8438	Intermediate Similarity	NPC475464
0.8438	Intermediate Similarity	NPC473641
0.8438	Intermediate Similarity	NPC475505
0.8438	Intermediate Similarity	NPC475437
0.8435	Intermediate Similarity	NPC200154
0.8431	Intermediate Similarity	NPC327031
0.8421	Intermediate Similarity	NPC127857
0.8418	Intermediate Similarity	NPC319404
0.8411	Intermediate Similarity	NPC477894
0.8411	Intermediate Similarity	NPC45307
0.8411	Intermediate Similarity	NPC95449
0.8408	Intermediate Similarity	NPC323001
0.8408	Intermediate Similarity	NPC326235
0.84	Intermediate Similarity	NPC118080
0.84	Intermediate Similarity	NPC87448
0.84	Intermediate Similarity	NPC41481
0.84	Intermediate Similarity	NPC291599
0.84	Intermediate Similarity	NPC474303
0.84	Intermediate Similarity	NPC97947
0.84	Intermediate Similarity	NPC473497
0.84	Intermediate Similarity	NPC472576
0.84	Intermediate Similarity	NPC27377
0.84	Intermediate Similarity	NPC475413
0.8387	Intermediate Similarity	NPC471103
0.8387	Intermediate Similarity	NPC197037
0.8377	Intermediate Similarity	NPC60509
0.8377	Intermediate Similarity	NPC81698
0.8377	Intermediate Similarity	NPC250046
0.8375	Intermediate Similarity	NPC477188
0.8375	Intermediate Similarity	NPC43304
0.8375	Intermediate Similarity	NPC477190
0.8373	Intermediate Similarity	NPC195972
0.8366	Intermediate Similarity	NPC312393
0.8366	Intermediate Similarity	NPC473602
0.8366	Intermediate Similarity	NPC477737
0.8365	Intermediate Similarity	NPC326328
0.8365	Intermediate Similarity	NPC471138
0.8365	Intermediate Similarity	NPC309991
0.8365	Intermediate Similarity	NPC323356
0.8364	Intermediate Similarity	NPC469421
0.8345	Intermediate Similarity	NPC27712
0.8344	Intermediate Similarity	NPC102465
0.8344	Intermediate Similarity	NPC182869
0.8344	Intermediate Similarity	NPC471176
0.8344	Intermediate Similarity	NPC192658
0.8333	Intermediate Similarity	NPC275592
0.8333	Intermediate Similarity	NPC473440
0.8333	Intermediate Similarity	NPC90614
0.8333	Intermediate Similarity	NPC472548
0.8333	Intermediate Similarity	NPC477905
0.8333	Intermediate Similarity	NPC324769
0.8333	Intermediate Similarity	NPC475660
0.8333	Intermediate Similarity	NPC171207
0.8333	Intermediate Similarity	NPC97667
0.8333	Intermediate Similarity	NPC325732
0.8333	Intermediate Similarity	NPC100913
0.8323	Intermediate Similarity	NPC295408
0.8323	Intermediate Similarity	NPC329960
0.8323	Intermediate Similarity	NPC208676
0.8323	Intermediate Similarity	NPC165260
0.8323	Intermediate Similarity	NPC150893
0.8323	Intermediate Similarity	NPC7095
0.8323	Intermediate Similarity	NPC66193
0.8323	Intermediate Similarity	NPC161239
0.8323	Intermediate Similarity	NPC198455
0.8323	Intermediate Similarity	NPC130489
0.8322	Intermediate Similarity	NPC39549
0.8322	Intermediate Similarity	NPC27721
0.8312	Intermediate Similarity	NPC217918
0.8311	Intermediate Similarity	NPC475262
0.8311	Intermediate Similarity	NPC473399
0.8311	Intermediate Similarity	NPC290833
0.8311	Intermediate Similarity	NPC477896
0.8311	Intermediate Similarity	NPC473216
0.8311	Intermediate Similarity	NPC477893
0.8311	Intermediate Similarity	NPC265459
0.8301	Intermediate Similarity	NPC92867
0.8301	Intermediate Similarity	NPC311825
0.8293	Intermediate Similarity	NPC149002
0.8293	Intermediate Similarity	NPC88176
0.8293	Intermediate Similarity	NPC469458
0.8293	Intermediate Similarity	NPC469459
0.8293	Intermediate Similarity	NPC469396
0.8291	Intermediate Similarity	NPC154675
0.8289	Intermediate Similarity	NPC131966
0.8289	Intermediate Similarity	NPC191387
0.8289	Intermediate Similarity	NPC91703
0.8288	Intermediate Similarity	NPC72915
0.8282	Intermediate Similarity	NPC161151
0.828	Intermediate Similarity	NPC229545
0.828	Intermediate Similarity	NPC248265
0.828	Intermediate Similarity	NPC11588
0.828	Intermediate Similarity	NPC219419
0.828	Intermediate Similarity	NPC477098
0.828	Intermediate Similarity	NPC134685
0.828	Intermediate Similarity	NPC289021
0.828	Intermediate Similarity	NPC158546
0.828	Intermediate Similarity	NPC477100
0.8278	Intermediate Similarity	NPC16912
0.8272	Intermediate Similarity	NPC293568
0.8272	Intermediate Similarity	NPC471134
0.8272	Intermediate Similarity	NPC117943
0.8269	Intermediate Similarity	NPC96308
0.8269	Intermediate Similarity	NPC51602
0.8267	Intermediate Similarity	NPC9905
0.8267	Intermediate Similarity	NPC156393
0.8261	Intermediate Similarity	NPC478124
0.8258	Intermediate Similarity	NPC76103
0.8255	Intermediate Similarity	NPC472551
0.8255	Intermediate Similarity	NPC285221
0.8255	Intermediate Similarity	NPC194769
0.8255	Intermediate Similarity	NPC472545
0.8255	Intermediate Similarity	NPC202729
0.8247	Intermediate Similarity	NPC20255
0.8243	Intermediate Similarity	NPC153617
0.8243	Intermediate Similarity	NPC126516
0.8243	Intermediate Similarity	NPC472250
0.8243	Intermediate Similarity	NPC48929
0.8243	Intermediate Similarity	NPC322503
0.8243	Intermediate Similarity	NPC329913
0.8243	Intermediate Similarity	NPC470143
0.8239	Intermediate Similarity	NPC477735
0.8239	Intermediate Similarity	NPC181924
0.8235	Intermediate Similarity	NPC470152
0.8235	Intermediate Similarity	NPC38696
0.8235	Intermediate Similarity	NPC34943
0.8235	Intermediate Similarity	NPC475759
0.8235	Intermediate Similarity	NPC241951
0.8228	Intermediate Similarity	NPC472549
0.8228	Intermediate Similarity	NPC114357
0.8228	Intermediate Similarity	NPC155329
0.8228	Intermediate Similarity	NPC478235
0.8228	Intermediate Similarity	NPC259144
0.8228	Intermediate Similarity	NPC473670

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 NPC469456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	741
0.2-0.3	1631
0.3-0.4	3013
0.4-0.5	2248
0.5-0.6	964
0.6-0.7	250
0.7-0.8	28
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8466	Intermediate Similarity	NPD7799	Discontinued
0.8301	Intermediate Similarity	NPD7236	Approved
0.8153	Intermediate Similarity	NPD7239	Suspended
0.7765	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8368	Discontinued
0.7733	Intermediate Similarity	NPD7685	Pre-registration
0.7701	Intermediate Similarity	NPD8407	Phase 2
0.7697	Intermediate Similarity	NPD7058	Phase 2
0.7697	Intermediate Similarity	NPD7057	Phase 3
0.7616	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8361	Approved
0.7333	Intermediate Similarity	NPD8360	Approved
0.7333	Intermediate Similarity	NPD8435	Approved
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7195	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5125	Phase 3
0.7181	Intermediate Similarity	NPD5126	Approved
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD7507	Approved
0.7135	Intermediate Similarity	NPD6764	Approved
0.7135	Intermediate Similarity	NPD6765	Approved
0.7133	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7074	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7961	Discontinued
0.7048	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD7741	Discontinued
0.7035	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7013	Intermediate Similarity	NPD7319	Approved
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7007	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD7503	Approved
0.6978	Remote Similarity	NPD6784	Approved
0.6978	Remote Similarity	NPD6785	Approved
0.6954	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6559	Discontinued
0.6927	Remote Similarity	NPD8320	Phase 1
0.6927	Remote Similarity	NPD8319	Approved
0.6915	Remote Similarity	NPD8485	Approved
0.6914	Remote Similarity	NPD7199	Phase 2
0.691	Remote Similarity	NPD7228	Approved
0.691	Remote Similarity	NPD3818	Discontinued
0.6901	Remote Similarity	NPD37	Approved
0.6898	Remote Similarity	NPD6534	Approved
0.6898	Remote Similarity	NPD6535	Approved
0.6886	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7028	Phase 2
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD4965	Approved
0.6878	Remote Similarity	NPD7700	Phase 2
0.6878	Remote Similarity	NPD7699	Phase 2
0.6875	Remote Similarity	NPD7497	Discontinued
0.6875	Remote Similarity	NPD7435	Discontinued
0.6872	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5762	Approved
0.6871	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD6858	Approved
0.6871	Remote Similarity	NPD7094	Approved
0.6871	Remote Similarity	NPD5763	Approved
0.686	Remote Similarity	NPD7819	Suspended
0.686	Remote Similarity	NPD8455	Phase 2
0.686	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7305	Phase 1
0.6849	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7075	Discontinued
0.6835	Remote Similarity	NPD7008	Discontinued
0.6833	Remote Similarity	NPD7074	Phase 3
0.6806	Remote Similarity	NPD6685	Approved
0.68	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6234	Discontinued
0.6784	Remote Similarity	NPD4380	Phase 2
0.6778	Remote Similarity	NPD7054	Approved
0.6776	Remote Similarity	NPD8033	Approved
0.6768	Remote Similarity	NPD8462	Phase 1
0.6768	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6005	Phase 3
0.6768	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6002	Phase 3
0.6768	Remote Similarity	NPD6004	Phase 3
0.6759	Remote Similarity	NPD6686	Approved
0.6758	Remote Similarity	NPD7240	Approved
0.6755	Remote Similarity	NPD6213	Phase 3
0.6755	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6212	Phase 3
0.6752	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6085	Phase 2
0.675	Remote Similarity	NPD6663	Approved
0.6742	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7472	Approved
0.6733	Remote Similarity	NPD4198	Discontinued
0.6725	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6782	Approved
0.6719	Remote Similarity	NPD6777	Approved
0.6719	Remote Similarity	NPD6776	Approved
0.6719	Remote Similarity	NPD6780	Approved
0.6719	Remote Similarity	NPD6781	Approved
0.6719	Remote Similarity	NPD6779	Approved
0.6719	Remote Similarity	NPD6778	Approved
0.6712	Remote Similarity	NPD2182	Approved
0.6709	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD6190	Approved
0.6706	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7328	Approved
0.6689	Remote Similarity	NPD7327	Approved
0.6687	Remote Similarity	NPD3764	Approved
0.6686	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6599	Discontinued
0.6685	Remote Similarity	NPD5844	Phase 1
0.6684	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8166	Discontinued
0.6645	Remote Similarity	NPD7610	Discontinued
0.6645	Remote Similarity	NPD7516	Approved
0.6633	Remote Similarity	NPD7999	Approved
0.663	Remote Similarity	NPD7808	Phase 3
0.6628	Remote Similarity	NPD3226	Approved
0.6627	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6653	Approved
0.6624	Remote Similarity	NPD7736	Approved
0.6623	Remote Similarity	NPD6370	Approved
0.6622	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7696	Phase 3
0.6615	Remote Similarity	NPD7698	Approved
0.6615	Remote Similarity	NPD7697	Approved
0.6612	Remote Similarity	NPD6797	Phase 2
0.6609	Remote Similarity	NPD6801	Discontinued
0.6601	Remote Similarity	NPD7009	Phase 2
0.6601	Remote Similarity	NPD8377	Approved
0.6601	Remote Similarity	NPD8294	Approved
0.6599	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5765	Approved
0.6587	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7871	Phase 2
0.6582	Remote Similarity	NPD7870	Phase 2
0.6577	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6912	Phase 3
0.6577	Remote Similarity	NPD6882	Approved
0.6575	Remote Similarity	NPD6412	Phase 2
0.6566	Remote Similarity	NPD7701	Phase 2
0.6564	Remote Similarity	NPD6823	Phase 2
0.6558	Remote Similarity	NPD8379	Approved
0.6558	Remote Similarity	NPD8380	Approved
0.6558	Remote Similarity	NPD8335	Approved
0.6558	Remote Similarity	NPD8296	Approved
0.6558	Remote Similarity	NPD8378	Approved
0.6556	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8404	Phase 2
0.655	Remote Similarity	NPD7801	Approved
0.6538	Remote Similarity	NPD6287	Discontinued
0.6538	Remote Similarity	NPD7492	Approved
0.6535	Remote Similarity	NPD7930	Approved
0.6534	Remote Similarity	NPD5402	Approved
0.6533	Remote Similarity	NPD8151	Discontinued
0.6532	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6009	Approved
0.6509	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6100	Approved
0.6506	Remote Similarity	NPD6099	Approved
0.6503	Remote Similarity	NPD4140	Approved
0.65	Remote Similarity	NPD6232	Discontinued
0.6497	Remote Similarity	NPD6616	Approved
0.6494	Remote Similarity	NPD6054	Approved
0.6494	Remote Similarity	NPD6319	Approved
0.6491	Remote Similarity	NPD2532	Approved
0.6491	Remote Similarity	NPD2534	Approved
0.6491	Remote Similarity	NPD2533	Approved
0.649	Remote Similarity	NPD6010	Discontinued
0.6485	Remote Similarity	NPD7097	Phase 1
0.6483	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5494	Approved
0.6478	Remote Similarity	NPD3094	Phase 2
0.6477	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7783	Phase 2
0.6468	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD969	Suspended
0.6467	Remote Similarity	NPD8297	Approved
0.6467	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6355	Discontinued
0.6463	Remote Similarity	NPD230	Phase 1
0.6457	Remote Similarity	NPD7411	Suspended
0.6456	Remote Similarity	NPD8293	Discontinued

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