NPASS Compound

Structure

NPC469459 OpenBabel07101718322D 43 49 0 0 1 0 0 0 0 0999 V2000 1.4408 -2.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7346 -3.0701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7558 -3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2728 -2.2506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3152 -2.1379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8322 -1.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3476 -5.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2984 -4.5834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1599 -6.5394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1108 -5.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9804 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9933 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 -1.2428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1385 -2.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8534 -1.3184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4168 -5.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0415 -6.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0145 0.5459 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 3.5738 1.4218 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5950 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0568 0.6586 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4128 -0.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6045 -4.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4975 -0.2172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9325 -1.2834 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6334 -1.8845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9325 0.3030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9804 -0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8538 -6.6594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1120 2.2413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1544 2.3540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0780 0.7149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9509 0.3770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2771 -4.8924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1175 1.2658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4339 -0.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6738 -3.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4763 -0.2736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9593 -1.0368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3230 -2.0360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 11 30 1 0 0 0 0 12 38 1 0 0 0 0 13 27 1 0 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 14 39 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 31 1 0 0 0 0 18 12 1 1 0 0 0 18 20 1 0 0 0 0 18 40 1 0 0 0 0 19 28 1 1 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 25 1 0 0 0 0 22 34 1 6 0 0 0 23 35 2 0 0 0 0 23 38 1 0 0 0 0 24 36 2 0 0 0 0 24 39 1 0 0 0 0 25 40 1 0 0 0 0 25 41 1 6 0 0 0 26 28 1 0 0 0 0 26 42 1 0 0 0 0 26 43 1 0 0 0 0 27 30 1 1 0 0 0 27 42 1 0 0 0 0 28 30 1 6 0 0 0 29 37 1 6 0 0 0 29 43 1 0 0 0 0 30 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.18
Volume:	560.722
LogP:	2.225
LogD:	1.548
LogS:	-3.648
# Rotatable Bonds:	10
TPSA:	190.67
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	9
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	6.164
Fsp3:	0.533
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:	-6.305
MDCK Permeability:	2.073093673971016e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.909
Human Intestinal Absorption (HIA):	0.6
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	90.8501205444336%
Volume Distribution (VD):	0.489
Pgp-substrate:	6.89522123336792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	7.351
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.507
AMES Toxicity:	0.813
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.904
Carcinogencity:	0.784
Eye Corrosion:	0.003
Eye Irritation:	0.411
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC469459

Natural Product ID:	NPC469459
*Common Name:**	VIWQCBZFJFSCLC-YRXJMFGJSA-N
IUPAC Name:	n.a.
Synonyms:	Alpha-Benzoyloxypaeoniflorin
Standard InCHIKey:	VIWQCBZFJFSCLC-YRXJMFGJSA-N
Standard InCHI:	InChI=1S/C30H32O13/c1-27-13-29(37)19-11-30(27,28(19,26(42-27)43-29)14-39-24(36)16-7-9-17(31)10-8-16)41-25-22(34)21(33)20(32)18(40-25)12-38-23(35)15-5-3-2-4-6-15/h2-10,18-22,25-26,31-34,37H,11-14H2,1H3/t18-,19+,20-,21+,22-,25-,26?,27+,28+,29-,30-/m1/s1
SMILES:	CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=C(C=C5)O)OC6C(C(C(C(O6)COC(=O)C7=CC=CC=C7)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079225
PubChem CID:	46883189
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]
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]
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]
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

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[511085]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[511085]

☑ 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 NPC469459 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	395
0.1-0.2	1438
0.2-0.3	2879
0.3-0.4	5786
0.4-0.5	9582
0.5-0.6	10099
0.6-0.7	9378
0.7-0.8	2878
0.8-0.85	220
0.85-0.9	16
0.9-0.95	13
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC149002
0.9873	High Similarity	NPC469458
0.9873	High Similarity	NPC88176
0.9873	High Similarity	NPC469396
0.975	High Similarity	NPC477617
0.9744	High Similarity	NPC293568
0.9744	High Similarity	NPC117943
0.9627	High Similarity	NPC148185
0.956	High Similarity	NPC265600
0.9512	High Similarity	NPC80360
0.9455	High Similarity	NPC195114
0.9398	High Similarity	NPC188217
0.9394	High Similarity	NPC260300
0.9379	High Similarity	NPC469419
0.9375	High Similarity	NPC120012
0.9333	High Similarity	NPC469397
0.925	High Similarity	NPC477627
0.9231	High Similarity	NPC469422
0.9157	High Similarity	NPC469438
0.9108	High Similarity	NPC34066
0.9048	High Similarity	NPC469418
0.9038	High Similarity	NPC469415
0.9	High Similarity	NPC477623
0.8987	High Similarity	NPC469398
0.8981	High Similarity	NPC267469
0.8981	High Similarity	NPC87630
0.8981	High Similarity	NPC179128
0.8981	High Similarity	NPC116292
0.8974	High Similarity	NPC303429
0.8974	High Similarity	NPC222102
0.8938	High Similarity	NPC469399
0.8861	High Similarity	NPC35160
0.8861	High Similarity	NPC162569
0.8854	High Similarity	NPC469448
0.8805	High Similarity	NPC133430
0.8805	High Similarity	NPC469477
0.8758	High Similarity	NPC469417
0.875	High Similarity	NPC5115
0.8726	High Similarity	NPC208293
0.8671	High Similarity	NPC470330
0.8654	High Similarity	NPC478250
0.8639	High Similarity	NPC469421
0.8623	High Similarity	NPC469420
0.8608	High Similarity	NPC320734
0.8596	High Similarity	NPC469354
0.8535	High Similarity	NPC204644
0.8485	Intermediate Similarity	NPC4747
0.8485	Intermediate Similarity	NPC104275
0.8466	Intermediate Similarity	NPC257847
0.8452	Intermediate Similarity	NPC161151
0.8452	Intermediate Similarity	NPC109990
0.8452	Intermediate Similarity	NPC471861
0.8452	Intermediate Similarity	NPC100420
0.8443	Intermediate Similarity	NPC69868
0.8439	Intermediate Similarity	NPC475613
0.8418	Intermediate Similarity	NPC475759
0.8418	Intermediate Similarity	NPC470152
0.8418	Intermediate Similarity	NPC241951
0.84	Intermediate Similarity	NPC102367
0.8395	Intermediate Similarity	NPC327962
0.8393	Intermediate Similarity	NPC145847
0.8373	Intermediate Similarity	NPC226759
0.8373	Intermediate Similarity	NPC187205
0.8373	Intermediate Similarity	NPC257309
0.8372	Intermediate Similarity	NPC13989
0.8365	Intermediate Similarity	NPC476973
0.8365	Intermediate Similarity	NPC29704
0.8365	Intermediate Similarity	NPC472575
0.8365	Intermediate Similarity	NPC472572
0.8365	Intermediate Similarity	NPC171525
0.8365	Intermediate Similarity	NPC471104
0.8365	Intermediate Similarity	NPC184817
0.8365	Intermediate Similarity	NPC470159
0.8365	Intermediate Similarity	NPC70403
0.8365	Intermediate Similarity	NPC472568
0.8365	Intermediate Similarity	NPC200471
0.8365	Intermediate Similarity	NPC177940
0.8365	Intermediate Similarity	NPC174982
0.8365	Intermediate Similarity	NPC470157
0.8365	Intermediate Similarity	NPC473088
0.8365	Intermediate Similarity	NPC472571
0.8365	Intermediate Similarity	NPC96903
0.8365	Intermediate Similarity	NPC158663
0.8365	Intermediate Similarity	NPC469349
0.8364	Intermediate Similarity	NPC172920
0.8364	Intermediate Similarity	NPC472807
0.8364	Intermediate Similarity	NPC156624
0.8354	Intermediate Similarity	NPC163087
0.8344	Intermediate Similarity	NPC291599
0.8344	Intermediate Similarity	NPC289021
0.8344	Intermediate Similarity	NPC27377
0.8344	Intermediate Similarity	NPC118080
0.8344	Intermediate Similarity	NPC158546
0.8344	Intermediate Similarity	NPC87448
0.8344	Intermediate Similarity	NPC97947
0.8344	Intermediate Similarity	NPC41481
0.8344	Intermediate Similarity	NPC472576
0.8333	Intermediate Similarity	NPC11062
0.8333	Intermediate Similarity	NPC471493
0.8333	Intermediate Similarity	NPC161955
0.8324	Intermediate Similarity	NPC316539
0.8323	Intermediate Similarity	NPC314795
0.8323	Intermediate Similarity	NPC53139
0.8314	Intermediate Similarity	NPC475058
0.8313	Intermediate Similarity	NPC148323
0.8313	Intermediate Similarity	NPC469513
0.8313	Intermediate Similarity	NPC283480
0.8302	Intermediate Similarity	NPC125106
0.8302	Intermediate Similarity	NPC57628
0.8302	Intermediate Similarity	NPC163719
0.8302	Intermediate Similarity	NPC70716
0.8302	Intermediate Similarity	NPC472570
0.8302	Intermediate Similarity	NPC476974
0.8302	Intermediate Similarity	NPC25768
0.8302	Intermediate Similarity	NPC188865
0.8302	Intermediate Similarity	NPC475122
0.8302	Intermediate Similarity	NPC472573
0.8302	Intermediate Similarity	NPC11685
0.8302	Intermediate Similarity	NPC95810
0.8302	Intermediate Similarity	NPC95265
0.8302	Intermediate Similarity	NPC472569
0.8294	Intermediate Similarity	NPC102465
0.8293	Intermediate Similarity	NPC132599
0.8293	Intermediate Similarity	NPC469730
0.8293	Intermediate Similarity	NPC473632
0.8293	Intermediate Similarity	NPC469456
0.8293	Intermediate Similarity	NPC478235
0.8284	Intermediate Similarity	NPC97637
0.8284	Intermediate Similarity	NPC477491
0.8284	Intermediate Similarity	NPC187934
0.8282	Intermediate Similarity	NPC477905
0.8282	Intermediate Similarity	NPC472548
0.8282	Intermediate Similarity	NPC182350
0.8282	Intermediate Similarity	NPC35097
0.8282	Intermediate Similarity	NPC247219
0.828	Intermediate Similarity	NPC100913
0.828	Intermediate Similarity	NPC97667
0.828	Intermediate Similarity	NPC171207
0.828	Intermediate Similarity	NPC275592
0.828	Intermediate Similarity	NPC90614
0.8274	Intermediate Similarity	NPC130489
0.8274	Intermediate Similarity	NPC269668
0.8274	Intermediate Similarity	NPC208676
0.8272	Intermediate Similarity	NPC477483
0.8272	Intermediate Similarity	NPC325032
0.8269	Intermediate Similarity	NPC471345
0.8263	Intermediate Similarity	NPC208651
0.8263	Intermediate Similarity	NPC206641
0.8261	Intermediate Similarity	NPC473867
0.8256	Intermediate Similarity	NPC21956
0.8256	Intermediate Similarity	NPC476017
0.8253	Intermediate Similarity	NPC203757
0.8253	Intermediate Similarity	NPC82190
0.8253	Intermediate Similarity	NPC174599
0.8253	Intermediate Similarity	NPC192219
0.825	Intermediate Similarity	NPC472556
0.8246	Intermediate Similarity	NPC477469
0.8246	Intermediate Similarity	NPC477466
0.8246	Intermediate Similarity	NPC477471
0.8246	Intermediate Similarity	NPC477473
0.8242	Intermediate Similarity	NPC229354
0.8239	Intermediate Similarity	NPC91703
0.8239	Intermediate Similarity	NPC108191
0.8239	Intermediate Similarity	NPC93685
0.8235	Intermediate Similarity	NPC97574
0.8235	Intermediate Similarity	NPC93172
0.8232	Intermediate Similarity	NPC474620
0.8232	Intermediate Similarity	NPC140151
0.8232	Intermediate Similarity	NPC472658
0.8232	Intermediate Similarity	NPC472657
0.8228	Intermediate Similarity	NPC16912
0.8225	Intermediate Similarity	NPC471134
0.8221	Intermediate Similarity	NPC470153
0.8218	Intermediate Similarity	NPC195972
0.821	Intermediate Similarity	NPC270590
0.821	Intermediate Similarity	NPC476975
0.821	Intermediate Similarity	NPC92293
0.821	Intermediate Similarity	NPC471101
0.821	Intermediate Similarity	NPC266265
0.821	Intermediate Similarity	NPC301556
0.8199	Intermediate Similarity	NPC474935
0.8198	Intermediate Similarity	NPC185498
0.8198	Intermediate Similarity	NPC82602
0.8193	Intermediate Similarity	NPC209393
0.8193	Intermediate Similarity	NPC322048
0.8193	Intermediate Similarity	NPC205172
0.8193	Intermediate Similarity	NPC318447
0.8187	Intermediate Similarity	NPC329647
0.8187	Intermediate Similarity	NPC478020
0.8187	Intermediate Similarity	NPC478022
0.8187	Intermediate Similarity	NPC470735
0.8187	Intermediate Similarity	NPC38696
0.8187	Intermediate Similarity	NPC476358
0.8187	Intermediate Similarity	NPC475979
0.8187	Intermediate Similarity	NPC99216
0.8182	Intermediate Similarity	NPC473611
0.8182	Intermediate Similarity	NPC472549
0.8182	Intermediate Similarity	NPC221249
0.8176	Intermediate Similarity	NPC475567
0.8176	Intermediate Similarity	NPC473557

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 NPC469459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	797
0.2-0.3	1790
0.3-0.4	2847
0.4-0.5	2177
0.5-0.6	928
0.6-0.7	227
0.7-0.8	53
0.8-0.85	0
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)
0.8198	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD7266	Discontinued
0.7912	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7685	Pre-registration
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.7889	Intermediate Similarity	NPD8434	Phase 2
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4966	Approved
0.7882	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7240	Approved
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.7791	Intermediate Similarity	NPD4628	Phase 3
0.774	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7054	Approved
0.7738	Intermediate Similarity	NPD7458	Discontinued
0.7722	Intermediate Similarity	NPD8312	Approved
0.7722	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7706	Intermediate Similarity	NPD37	Approved
0.7697	Intermediate Similarity	NPD7472	Approved
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7684	Intermediate Similarity	NPD7799	Discontinued
0.764	Intermediate Similarity	NPD5844	Phase 1
0.7636	Intermediate Similarity	NPD6190	Approved
0.7611	Intermediate Similarity	NPD7251	Discontinued
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7588	Intermediate Similarity	NPD4380	Phase 2
0.7572	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7808	Phase 3
0.7569	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8455	Phase 2
0.7556	Intermediate Similarity	NPD6797	Phase 2
0.7552	Intermediate Similarity	NPD8320	Phase 1
0.7552	Intermediate Similarity	NPD8319	Approved
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8407	Phase 2
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7438	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8368	Discontinued
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8166	Discontinued
0.7356	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7819	Suspended
0.7345	Intermediate Similarity	NPD5494	Approved
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7326	Intermediate Similarity	NPD8360	Approved
0.7326	Intermediate Similarity	NPD8361	Approved
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7680	Approved
0.732	Intermediate Similarity	NPD7698	Approved
0.7318	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7303	Intermediate Similarity	NPD8127	Discontinued
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD7236	Approved
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6232	Discontinued
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7257	Intermediate Similarity	NPD1465	Phase 2
0.7257	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6273	Approved
0.7236	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7783	Phase 2
0.7234	Intermediate Similarity	NPD8435	Approved
0.7231	Intermediate Similarity	NPD7497	Discontinued
0.7216	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6801	Discontinued
0.72	Intermediate Similarity	NPD1934	Approved
0.7195	Intermediate Similarity	NPD230	Phase 1
0.7194	Intermediate Similarity	NPD7871	Phase 2
0.7194	Intermediate Similarity	NPD7870	Phase 2
0.7184	Intermediate Similarity	NPD6599	Discontinued
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7168	Intermediate Similarity	NPD7239	Suspended
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7999	Approved
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7129	Intermediate Similarity	NPD7930	Approved
0.7128	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6212	Phase 3
0.712	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6213	Phase 3
0.7111	Intermediate Similarity	NPD6959	Discontinued
0.7104	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2532	Approved
0.7093	Intermediate Similarity	NPD2533	Approved
0.7093	Intermediate Similarity	NPD2534	Approved
0.7086	Intermediate Similarity	NPD7028	Phase 2
0.7077	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6663	Approved
0.7069	Intermediate Similarity	NPD1653	Approved
0.7062	Intermediate Similarity	NPD5760	Phase 2
0.7062	Intermediate Similarity	NPD5761	Phase 2
0.7059	Intermediate Similarity	NPD8404	Phase 2
0.7059	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3750	Approved
0.7051	Intermediate Similarity	NPD9545	Approved
0.7039	Intermediate Similarity	NPD3749	Approved
0.703	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2935	Discontinued
0.7022	Intermediate Similarity	NPD5402	Approved
0.7022	Intermediate Similarity	NPD3817	Phase 2
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7585	Approved
0.6995	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3882	Suspended
0.6983	Remote Similarity	NPD7768	Phase 2
0.6978	Remote Similarity	NPD3787	Discontinued
0.6966	Remote Similarity	NPD2801	Approved
0.6952	Remote Similarity	NPD6765	Approved
0.6952	Remote Similarity	NPD6764	Approved
0.695	Remote Similarity	NPD7583	Approved
0.6941	Remote Similarity	NPD1549	Phase 2
0.6941	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6799	Approved
0.6933	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8485	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6914	Remote Similarity	NPD5403	Approved
0.6905	Remote Similarity	NPD7097	Phase 1
0.6901	Remote Similarity	NPD6674	Discontinued
0.69	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7584	Approved
0.6864	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5125	Phase 3
0.6855	Remote Similarity	NPD5126	Approved
0.6836	Remote Similarity	NPD3226	Approved
0.6824	Remote Similarity	NPD5404	Approved
0.6824	Remote Similarity	NPD5406	Approved
0.6824	Remote Similarity	NPD5408	Approved
0.6824	Remote Similarity	NPD5405	Approved
0.6807	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6785	Approved
0.6806	Remote Similarity	NPD6784	Approved
0.6805	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5401	Approved
0.68	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7057	Phase 3
0.6796	Remote Similarity	NPD7058	Phase 2
0.6765	Remote Similarity	NPD3748	Approved
0.6765	Remote Similarity	NPD7033	Discontinued
0.6763	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1607	Approved
0.6743	Remote Similarity	NPD7390	Discontinued
0.6743	Remote Similarity	NPD1511	Approved
0.6726	Remote Similarity	NPD1240	Approved
0.6725	Remote Similarity	NPD2796	Approved
0.6725	Remote Similarity	NPD2438	Suspended
0.6721	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5710	Approved
0.6703	Remote Similarity	NPD5711	Approved
0.6703	Remote Similarity	NPD7229	Phase 3
0.6699	Remote Similarity	NPD8462	Phase 1
0.6686	Remote Similarity	NPD6002	Phase 3
0.6686	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2346	Discontinued
0.6686	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6005	Phase 3
0.6686	Remote Similarity	NPD6004	Phase 3
0.6682	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8059	Phase 3
0.6667	Remote Similarity	NPD1509	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