NPASS Compound

Structure

NPC469397 OpenBabel07101718242D 44 50 0 0 1 0 0 0 0 0999 V2000 -2.4417 -1.4413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4652 -7.2464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1127 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5419 -2.1607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -3.1120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9927 -1.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5851 -2.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8144 -3.7704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6342 -4.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8819 -5.1904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1184 -3.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3549 -2.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2433 0.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9376 0.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9382 -4.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0143 -1.4174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5779 -5.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7017 -5.7288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4787 -2.5960 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 1.4223 -3.5752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5462 -4.0160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2737 -3.4776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4651 -0.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2173 -2.4984 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2839 0.9328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8852 -0.6337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9808 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3031 0.9328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9808 -0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3977 -5.8264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2422 -4.1136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4898 -4.9952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1499 -3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8943 0.2772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2663 1.1179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6453 -6.7080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1747 -2.6936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4867 -0.6740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6589 -2.0576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0372 -1.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0368 0.3232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4904 1.5093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 38 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 17 2 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 11 31 1 0 0 0 0 12 16 1 0 0 0 0 12 39 1 0 0 0 0 13 39 1 0 0 0 0 14 28 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 15 40 1 0 0 0 0 17 25 1 0 0 0 0 18 19 2 0 0 0 0 18 32 1 0 0 0 0 19 38 1 0 0 0 0 20 13 1 6 0 0 0 20 22 1 0 0 0 0 20 41 1 0 0 0 0 21 29 1 1 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 36 2 0 0 0 0 25 40 1 0 0 0 0 26 41 1 0 0 0 0 26 42 1 6 0 0 0 27 29 1 1 0 0 0 27 43 1 0 0 0 0 27 44 1 0 0 0 0 28 31 1 1 0 0 0 28 43 1 0 0 0 0 29 31 1 6 0 0 0 30 37 1 6 0 0 0 30 44 1 0 0 0 0 31 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.22
Volume:	580.343
LogP:	-0.141
LogD:	-0.287
LogS:	-3.273
# Rotatable Bonds:	10
TPSA:	243.52
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	9
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	6.66
Fsp3:	0.759
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.801
MDCK Permeability:	5.6017772294580936e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.566
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	28.184764862060547%
Volume Distribution (VD):	0.462
Pgp-substrate:	35.47650146484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	0.792
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.924
Carcinogencity:	0.656
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC469397

Natural Product ID:	NPC469397
*Common Name:**	TUUZZRKOUMSRMU-ZHNAOBHOSA-N
IUPAC Name:	n.a.
Synonyms:	6'-O-Vanillylpaeoniflorin
Standard InCHIKey:	TUUZZRKOUMSRMU-ZHNAOBHOSA-N
Standard InCHI:	InChI=1S/C31H36O13/c1-28-14-30(37)21-11-31(28,29(21,27(43-28)44-30)15-40-25(36)17-6-4-3-5-7-17)42-26-24(35)23(34)22(33)20(41-26)13-39-12-16-8-9-18(32)19(10-16)38-2/h3-10,20-24,26-27,32-35,37H,11-15H2,1-2H3/t20-,21+,22-,23+,24-,26+,27-,28+,29+,30-,31-/m1/s1
SMILES:	COc1cc(COC[C@H]2O[C@@H](O[C@]34C[C@H]5[C@@]4(COC(=O)c4ccccc4)[C@@H]4O[C@@]3(C)C[C@]5(O4)O)[C@@H]([C@H]([C@@H]2O)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077644
PubChem CID:	46882881
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	1
Others	6

Activity Type	# Activity
Cell Line	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	107.1	%	PMID[456647]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	106.3	%	PMID[456647]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	99.8	%	PMID[456647]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	90.1	%	PMID[456647]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[456647]
NPT610	Others	Molecular identity unknown		INH	=	2.78	mM	PMID[456648]
NPT610	Others	Molecular identity unknown		INH	=	2.02	mM	PMID[456648]

☑ 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 NPC469397 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	421
0.1-0.2	1569
0.2-0.3	3165
0.3-0.4	6506
0.4-0.5	9758
0.5-0.6	8623
0.6-0.7	8821
0.7-0.8	3642
0.8-0.85	133
0.85-0.9	42
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9819	High Similarity	NPC188217
0.9578	High Similarity	NPC469438
0.9458	High Similarity	NPC148185
0.9349	High Similarity	NPC80360
0.9333	High Similarity	NPC469459
0.9294	High Similarity	NPC195114
0.9235	High Similarity	NPC260300
0.9217	High Similarity	NPC149002
0.9217	High Similarity	NPC469396
0.9217	High Similarity	NPC469458
0.9217	High Similarity	NPC88176
0.9212	High Similarity	NPC120012
0.9112	High Similarity	NPC477617
0.9091	High Similarity	NPC117943
0.9091	High Similarity	NPC293568
0.9006	High Similarity	NPC469354
0.8929	High Similarity	NPC265600
0.8902	High Similarity	NPC469418
0.8869	High Similarity	NPC100420
0.8834	High Similarity	NPC469422
0.8824	High Similarity	NPC185498
0.8795	High Similarity	NPC226759
0.8786	High Similarity	NPC193377
0.8765	High Similarity	NPC469419
0.8757	High Similarity	NPC116759
0.8757	High Similarity	NPC14294
0.8728	High Similarity	NPC316539
0.8721	High Similarity	NPC179240
0.872	High Similarity	NPC34066
0.8671	High Similarity	NPC32723
0.8671	High Similarity	NPC469776
0.8671	High Similarity	NPC135334
0.8671	High Similarity	NPC469774
0.8671	High Similarity	NPC295941
0.8671	High Similarity	NPC469778
0.8671	High Similarity	NPC469777
0.8671	High Similarity	NPC469773
0.8671	High Similarity	NPC469775
0.8671	High Similarity	NPC469772
0.8671	High Similarity	NPC100925
0.8663	High Similarity	NPC21956
0.865	High Similarity	NPC469415
0.8639	High Similarity	NPC477627
0.8639	High Similarity	NPC152424
0.8639	High Similarity	NPC100465
0.8636	High Similarity	NPC108191
0.8636	High Similarity	NPC93685
0.8623	High Similarity	NPC477623
0.8606	High Similarity	NPC469398
0.8589	High Similarity	NPC222102
0.8589	High Similarity	NPC303429
0.8588	High Similarity	NPC246024
0.858	High Similarity	NPC35266
0.858	High Similarity	NPC268718
0.858	High Similarity	NPC150943
0.858	High Similarity	NPC91634
0.8571	High Similarity	NPC476358
0.8563	High Similarity	NPC38699
0.8563	High Similarity	NPC474075
0.8563	High Similarity	NPC471921
0.8563	High Similarity	NPC312006
0.8563	High Similarity	NPC20114
0.8563	High Similarity	NPC471920
0.8563	High Similarity	NPC114550
0.8563	High Similarity	NPC471922
0.8563	High Similarity	NPC292712
0.8563	High Similarity	NPC129930
0.8555	High Similarity	NPC88557
0.8554	High Similarity	NPC245615
0.8554	High Similarity	NPC299706
0.8554	High Similarity	NPC61604
0.8554	High Similarity	NPC115466
0.8547	High Similarity	NPC306475
0.8531	High Similarity	NPC275690
0.8531	High Similarity	NPC161609
0.8523	High Similarity	NPC475054
0.8514	High Similarity	NPC475197
0.8514	High Similarity	NPC473467
0.8512	High Similarity	NPC11411
0.8512	High Similarity	NPC228357
0.8512	High Similarity	NPC163635
0.8512	High Similarity	NPC478055
0.8497	Intermediate Similarity	NPC286809
0.8497	Intermediate Similarity	NPC298847
0.8497	Intermediate Similarity	NPC79322
0.8497	Intermediate Similarity	NPC311912
0.8494	Intermediate Similarity	NPC478268
0.8492	Intermediate Similarity	NPC167045
0.8492	Intermediate Similarity	NPC114120
0.8488	Intermediate Similarity	NPC475738
0.8488	Intermediate Similarity	NPC222531
0.8485	Intermediate Similarity	NPC188393
0.8485	Intermediate Similarity	NPC470934
0.8476	Intermediate Similarity	NPC469448
0.8475	Intermediate Similarity	NPC241196
0.8466	Intermediate Similarity	NPC84482
0.8466	Intermediate Similarity	NPC169645
0.8462	Intermediate Similarity	NPC472860
0.8457	Intermediate Similarity	NPC261254
0.8448	Intermediate Similarity	NPC117911
0.8448	Intermediate Similarity	NPC202428
0.8448	Intermediate Similarity	NPC266545
0.8439	Intermediate Similarity	NPC83049
0.8439	Intermediate Similarity	NPC320471
0.8439	Intermediate Similarity	NPC118162
0.8436	Intermediate Similarity	NPC473205
0.8436	Intermediate Similarity	NPC473776
0.843	Intermediate Similarity	NPC25889
0.843	Intermediate Similarity	NPC109990
0.843	Intermediate Similarity	NPC121290
0.8424	Intermediate Similarity	NPC111785
0.8424	Intermediate Similarity	NPC478242
0.8421	Intermediate Similarity	NPC115624
0.8418	Intermediate Similarity	NPC196771
0.8418	Intermediate Similarity	NPC79736
0.8418	Intermediate Similarity	NPC67629
0.8418	Intermediate Similarity	NPC473713
0.8415	Intermediate Similarity	NPC475299
0.8412	Intermediate Similarity	NPC478269
0.8412	Intermediate Similarity	NPC469384
0.8409	Intermediate Similarity	NPC184624
0.8405	Intermediate Similarity	NPC476382
0.8405	Intermediate Similarity	NPC34927
0.8405	Intermediate Similarity	NPC252292
0.8405	Intermediate Similarity	NPC100998
0.8405	Intermediate Similarity	NPC34587
0.8402	Intermediate Similarity	NPC471405
0.8402	Intermediate Similarity	NPC32373
0.8402	Intermediate Similarity	NPC237946
0.84	Intermediate Similarity	NPC52598
0.84	Intermediate Similarity	NPC472803
0.8398	Intermediate Similarity	NPC313063
0.8398	Intermediate Similarity	NPC475360
0.8398	Intermediate Similarity	NPC286301
0.8393	Intermediate Similarity	NPC194095
0.8393	Intermediate Similarity	NPC327032
0.8393	Intermediate Similarity	NPC191046
0.8391	Intermediate Similarity	NPC177362
0.8383	Intermediate Similarity	NPC267091
0.8382	Intermediate Similarity	NPC180586
0.8382	Intermediate Similarity	NPC474301
0.838	Intermediate Similarity	NPC53680
0.838	Intermediate Similarity	NPC208797
0.8373	Intermediate Similarity	NPC158635
0.8373	Intermediate Similarity	NPC229882
0.8373	Intermediate Similarity	NPC116292
0.8373	Intermediate Similarity	NPC267469
0.8373	Intermediate Similarity	NPC179128
0.8373	Intermediate Similarity	NPC87630
0.8372	Intermediate Similarity	NPC22130
0.8372	Intermediate Similarity	NPC22324
0.8372	Intermediate Similarity	NPC148273
0.8372	Intermediate Similarity	NPC145847
0.8372	Intermediate Similarity	NPC41009
0.8372	Intermediate Similarity	NPC116838
0.8371	Intermediate Similarity	NPC267549
0.8363	Intermediate Similarity	NPC24627
0.8363	Intermediate Similarity	NPC239966
0.8363	Intermediate Similarity	NPC203020
0.8353	Intermediate Similarity	NPC475663
0.8353	Intermediate Similarity	NPC471878
0.8353	Intermediate Similarity	NPC163527
0.8353	Intermediate Similarity	NPC19947
0.8353	Intermediate Similarity	NPC133984
0.8353	Intermediate Similarity	NPC104275
0.8353	Intermediate Similarity	NPC4747
0.8353	Intermediate Similarity	NPC187205
0.8353	Intermediate Similarity	NPC181168
0.8353	Intermediate Similarity	NPC207584
0.8353	Intermediate Similarity	NPC115281
0.8353	Intermediate Similarity	NPC286919
0.8352	Intermediate Similarity	NPC235575
0.8344	Intermediate Similarity	NPC110063
0.8344	Intermediate Similarity	NPC84181
0.8343	Intermediate Similarity	NPC299855
0.8343	Intermediate Similarity	NPC469399
0.8343	Intermediate Similarity	NPC131532
0.8343	Intermediate Similarity	NPC10205
0.8343	Intermediate Similarity	NPC96194
0.8333	Intermediate Similarity	NPC174734
0.8333	Intermediate Similarity	NPC474042
0.8333	Intermediate Similarity	NPC157898
0.8333	Intermediate Similarity	NPC200726
0.8333	Intermediate Similarity	NPC473883
0.8324	Intermediate Similarity	NPC147596
0.8323	Intermediate Similarity	NPC32079
0.8323	Intermediate Similarity	NPC477700
0.8323	Intermediate Similarity	NPC243891
0.8314	Intermediate Similarity	NPC311803
0.8314	Intermediate Similarity	NPC472859
0.8314	Intermediate Similarity	NPC216916
0.8314	Intermediate Similarity	NPC25389
0.8314	Intermediate Similarity	NPC149873
0.8314	Intermediate Similarity	NPC288149
0.8314	Intermediate Similarity	NPC7191
0.8314	Intermediate Similarity	NPC478267
0.8305	Intermediate Similarity	NPC166674
0.8305	Intermediate Similarity	NPC34436
0.8305	Intermediate Similarity	NPC46640
0.8305	Intermediate Similarity	NPC163165

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 NPC469397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	845
0.2-0.3	1885
0.3-0.4	2758
0.4-0.5	2073
0.5-0.6	905
0.6-0.7	269
0.7-0.8	57
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
0.8824	High Similarity	NPD7228	Approved
0.8636	High Similarity	NPD8055	Clinical (unspecified phase)
0.8521	High Similarity	NPD6234	Discontinued
0.8402	Intermediate Similarity	NPD4967	Phase 2
0.8402	Intermediate Similarity	NPD4966	Approved
0.8402	Intermediate Similarity	NPD4965	Approved
0.8305	Intermediate Similarity	NPD7685	Pre-registration
0.8305	Intermediate Similarity	NPD7240	Approved
0.8225	Intermediate Similarity	NPD37	Approved
0.8192	Intermediate Similarity	NPD7074	Phase 3
0.8136	Intermediate Similarity	NPD7054	Approved
0.809	Intermediate Similarity	NPD7472	Approved
0.8079	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD7266	Discontinued
0.7956	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD5844	Phase 1
0.7912	Intermediate Similarity	NPD8312	Approved
0.7912	Intermediate Similarity	NPD8313	Approved
0.7903	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD7251	Discontinued
0.7892	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7680	Approved
0.7857	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7808	Phase 3
0.7845	Intermediate Similarity	NPD6797	Phase 2
0.7797	Intermediate Similarity	NPD8127	Discontinued
0.7797	Intermediate Similarity	NPD7199	Phase 2
0.7784	Intermediate Similarity	NPD8434	Phase 2
0.7727	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4628	Phase 3
0.7674	Intermediate Similarity	NPD1653	Approved
0.7667	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6166	Phase 2
0.7657	Intermediate Similarity	NPD1465	Phase 2
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.764	Intermediate Similarity	NPD5494	Approved
0.7637	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7458	Discontinued
0.7624	Intermediate Similarity	NPD7473	Discontinued
0.7611	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1934	Approved
0.7586	Intermediate Similarity	NPD7028	Phase 2
0.7581	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6232	Discontinued
0.7554	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD4380	Phase 2
0.7471	Intermediate Similarity	NPD8166	Discontinued
0.7457	Intermediate Similarity	NPD6273	Approved
0.7446	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7075	Discontinued
0.7412	Intermediate Similarity	NPD6674	Discontinued
0.7374	Intermediate Similarity	NPD3882	Suspended
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2801	Approved
0.736	Intermediate Similarity	NPD6823	Phase 2
0.736	Intermediate Similarity	NPD7819	Suspended
0.7347	Intermediate Similarity	NPD6781	Approved
0.7347	Intermediate Similarity	NPD6779	Approved
0.7347	Intermediate Similarity	NPD6782	Approved
0.7347	Intermediate Similarity	NPD6777	Approved
0.7347	Intermediate Similarity	NPD6780	Approved
0.7347	Intermediate Similarity	NPD6778	Approved
0.7347	Intermediate Similarity	NPD6776	Approved
0.7323	Intermediate Similarity	NPD7696	Phase 3
0.7323	Intermediate Similarity	NPD7698	Approved
0.7323	Intermediate Similarity	NPD7697	Approved
0.7318	Intermediate Similarity	NPD3817	Phase 2
0.7313	Intermediate Similarity	NPD8151	Discontinued
0.7299	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7874	Approved
0.7277	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7701	Phase 2
0.7263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7783	Phase 2
0.7235	Intermediate Similarity	NPD2935	Discontinued
0.7232	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD5402	Approved
0.7204	Intermediate Similarity	NPD7799	Discontinued
0.72	Intermediate Similarity	NPD7870	Phase 2
0.72	Intermediate Similarity	NPD8320	Phase 1
0.72	Intermediate Similarity	NPD7871	Phase 2
0.72	Intermediate Similarity	NPD8319	Approved
0.719	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7168	Intermediate Similarity	NPD3750	Approved
0.7168	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4110	Phase 3
0.7168	Intermediate Similarity	NPD7003	Approved
0.7164	Intermediate Similarity	NPD7999	Approved
0.7157	Intermediate Similarity	NPD7699	Phase 2
0.7157	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7497	Discontinued
0.7136	Intermediate Similarity	NPD7930	Approved
0.7127	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3764	Approved
0.712	Intermediate Similarity	NPD6959	Discontinued
0.7112	Intermediate Similarity	NPD3751	Discontinued
0.7111	Intermediate Similarity	NPD6801	Discontinued
0.7102	Intermediate Similarity	NPD2533	Approved
0.7102	Intermediate Similarity	NPD2532	Approved
0.7102	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD6599	Discontinued
0.7092	Intermediate Similarity	NPD6534	Approved
0.7092	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD7768	Phase 2
0.7066	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD1511	Approved
0.7041	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1613	Approved
0.7041	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3620	Phase 2
0.7031	Intermediate Similarity	NPD8407	Phase 2
0.7022	Intermediate Similarity	NPD5403	Approved
0.7019	Intermediate Similarity	NPD7047	Phase 3
0.7018	Intermediate Similarity	NPD7097	Phase 1
0.7011	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6989	Remote Similarity	NPD3787	Discontinued
0.6986	Remote Similarity	NPD8404	Phase 2
0.6985	Remote Similarity	NPD4420	Approved
0.6978	Remote Similarity	NPD5760	Phase 2
0.6978	Remote Similarity	NPD5761	Phase 2
0.6966	Remote Similarity	NPD1512	Approved
0.6963	Remote Similarity	NPD8368	Discontinued
0.6959	Remote Similarity	NPD4663	Approved
0.6957	Remote Similarity	NPD3749	Approved
0.6954	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3226	Approved
0.6936	Remote Similarity	NPD2438	Suspended
0.6936	Remote Similarity	NPD6099	Approved
0.6936	Remote Similarity	NPD6100	Approved
0.6934	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5005	Approved
0.6931	Remote Similarity	NPD5006	Approved
0.6927	Remote Similarity	NPD7585	Approved
0.6919	Remote Similarity	NPD4665	Approved
0.6915	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5401	Approved
0.691	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6997	Phase 2
0.6897	Remote Similarity	NPD2346	Discontinued
0.689	Remote Similarity	NPD3705	Approved
0.6888	Remote Similarity	NPD8361	Approved
0.6888	Remote Similarity	NPD8360	Approved
0.6882	Remote Similarity	NPD6663	Approved
0.6879	Remote Similarity	NPD3748	Approved
0.6878	Remote Similarity	NPD7583	Approved
0.6875	Remote Similarity	NPD6765	Approved
0.6875	Remote Similarity	NPD6764	Approved
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7039	Approved
0.6875	Remote Similarity	NPD7038	Approved
0.6868	Remote Similarity	NPD6386	Approved
0.6868	Remote Similarity	NPD6873	Phase 2
0.6868	Remote Similarity	NPD6385	Approved
0.6864	Remote Similarity	NPD7095	Approved
0.6857	Remote Similarity	NPD1549	Phase 2
0.6854	Remote Similarity	NPD6799	Approved
0.6848	Remote Similarity	NPD5353	Approved
0.6845	Remote Similarity	NPD9494	Approved
0.6842	Remote Similarity	NPD4060	Phase 1
0.6837	Remote Similarity	NPD7906	Approved
0.6828	Remote Similarity	NPD919	Approved
0.6818	Remote Similarity	NPD7296	Approved
0.6816	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1357	Approved
0.6805	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8435	Approved
0.6802	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD5763	Approved
0.68	Remote Similarity	NPD6005	Phase 3
0.68	Remote Similarity	NPD6004	Phase 3
0.68	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5762	Approved
0.68	Remote Similarity	NPD6002	Phase 3
0.68	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2493	Approved
0.6798	Remote Similarity	NPD7236	Approved
0.6798	Remote Similarity	NPD2494	Approved
0.6796	Remote Similarity	NPD7584	Approved
0.6794	Remote Similarity	NPD7827	Phase 1
0.6784	Remote Similarity	NPD6233	Phase 2

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