NPASS Compound

Structure

NPC469421 OpenBabel07101719132D 67 77 0 0 1 0 0 0 0 0999 V2000 0.2362 -1.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5362 -1.9030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1869 3.7065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1359 -7.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2288 3.8834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5128 2.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 -7.2393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4803 -6.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5966 3.1421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8805 2.0470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3843 -6.3112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7767 -5.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1237 -1.0980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0021 -2.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8777 -4.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9749 -1.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0306 -3.9176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3002 0.9182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2735 -3.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9224 2.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7287 -5.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3262 -0.5192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9839 -3.6858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9391 -1.0361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1417 -2.9726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2012 -4.2660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3004 -0.1312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3074 -3.8781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2646 0.0084 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1964 -2.9102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8676 -0.7569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2902 1.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0251 -4.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9791 -2.3301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5064 -1.6618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4076 -0.5500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0122 -4.0723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4551 -1.3005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1982 -2.6179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9743 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1774 -3.1121 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5724 -3.8465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9743 -0.9743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0379 -2.1479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9887 -5.0416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2944 -0.4101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3122 -5.2339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5246 -4.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6259 0.9132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3026 -2.5224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8319 -0.6173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 0.5644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3696 -3.9416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5457 -3.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3719 -0.4104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6679 1.6595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9771 -4.4550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8729 -2.7179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5421 -1.8013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8681 -1.3621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1094 -2.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1480 -1.2002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1853 -3.5801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8744 -4.5262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 41 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 13 45 1 0 0 0 0 14 24 1 0 0 0 0 14 40 1 0 0 0 0 15 27 1 0 0 0 0 15 46 1 0 0 0 0 16 47 1 0 0 0 0 17 58 1 0 0 0 0 18 41 1 0 0 0 0 18 44 1 0 0 0 0 19 42 1 0 0 0 0 19 59 1 0 0 0 0 20 43 1 0 0 0 0 20 60 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 23 24 1 0 0 0 0 23 42 1 1 0 0 0 24 48 2 0 0 0 0 25 16 1 1 0 0 0 25 28 1 0 0 0 0 25 61 1 0 0 0 0 26 17 1 1 0 0 0 26 29 1 0 0 0 0 26 62 1 0 0 0 0 27 43 1 1 0 0 0 27 44 1 0 0 0 0 28 30 1 0 0 0 0 28 49 1 6 0 0 0 29 31 1 0 0 0 0 29 50 1 6 0 0 0 30 32 1 0 0 0 0 30 51 1 1 0 0 0 31 33 1 0 0 0 0 31 52 1 1 0 0 0 32 36 1 0 0 0 0 32 53 1 6 0 0 0 33 37 1 0 0 0 0 33 54 1 6 0 0 0 34 55 2 0 0 0 0 34 59 1 0 0 0 0 35 56 2 0 0 0 0 35 60 1 0 0 0 0 36 61 1 0 0 0 0 36 63 1 1 0 0 0 37 62 1 0 0 0 0 37 64 1 1 0 0 0 38 42 1 6 0 0 0 38 58 1 0 0 0 0 38 65 1 0 0 0 0 39 43 1 1 0 0 0 39 66 1 0 0 0 0 39 67 1 0 0 0 0 40 45 1 1 0 0 0 40 65 1 0 0 0 0 41 46 1 1 0 0 0 41 66 1 0 0 0 0 42 45 1 1 0 0 0 43 46 1 6 0 0 0 44 57 1 6 0 0 0 44 67 1 0 0 0 0 45 63 1 6 0 0 0 46 64 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	942.32
Volume:	870.917
LogP:	1.415
LogD:	0.572
LogS:	-3.703
# Rotatable Bonds:	16
TPSA:	305.35
# H-Bond Aceptor:	21
# H-Bond Donor:	8
# Rings:	14
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	7.987
Fsp3:	0.674
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:	-6.795
MDCK Permeability:	7.100372749846429e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.903
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	45.20929718017578%
Volume Distribution (VD):	0.395
Pgp-substrate:	12.490682601928711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.182
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.503
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	1.241
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.972
Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.87
Carcinogencity:	0.917
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC469421

Natural Product ID:	NPC469421
*Common Name:**	Paeonidanin E
IUPAC Name:	n.a.
Synonyms:	Paeonidanin E
Standard InCHIKey:	FPEQOYMLKLIEMS-IYNAHQBOSA-N
Standard InCHI:	InChI=1S/C46H54O21/c1-40-14-24(48)23-13-45(40,63-36-32(53)30(51)28(49)25(16-47)61-36)42(23,19-59-34(55)21-9-5-3-6-10-21)38(65-40)58-17-26-29(50)31(52)33(54)37(62-26)64-46-15-27-43(46,20-60-35(56)22-11-7-4-8-12-22)39-66-41(46,2)18-44(27,57)67-39/h3-12,23,25-33,36-39,47,49-54,57H,13-20H2,1-2H3/t23-,25-,26-,27+,28-,29-,30+,31+,32-,33-,36+,37+,38+,39-,40+,41+,42+,43+,44-,45-,46-/m1/s1
SMILES:	CC12CC(=O)C3CC1(C3(C(O2)OCC4C(C(C(C(O4)OC56CC7C5(C8OC6(CC7(O8)O)C)COC(=O)C9=CC=CC=C9)O)O)O)COC(=O)C1=CC=CC=C1)OC1C(C(C(C(O1)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078416
PubChem CID:	46883515
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	4

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	101.9	%	PMID[522330]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	101.8	%	PMID[522330]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	88.8	%	PMID[522330]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	69.2	%	PMID[522330]
NPT848	Cell Line	N9	Homo sapiens	IC50	=	64700.0	nM	PMID[522330]

☑ 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 NPC469421 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	432
0.1-0.2	1544
0.2-0.3	3153
0.3-0.4	7163
0.4-0.5	11561
0.5-0.6	12660
0.6-0.7	5299
0.7-0.8	772
0.8-0.85	76
0.85-0.9	30
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC469420
0.9245	High Similarity	NPC469399
0.9187	High Similarity	NPC477623
0.9182	High Similarity	NPC469417
0.9057	High Similarity	NPC34066
0.9057	High Similarity	NPC469422
0.8994	High Similarity	NPC133430
0.8994	High Similarity	NPC469477
0.8976	High Similarity	NPC477469
0.8976	High Similarity	NPC477471
0.8976	High Similarity	NPC477473
0.8976	High Similarity	NPC477466
0.8938	High Similarity	NPC5115
0.8938	High Similarity	NPC469398
0.8931	High Similarity	NPC477905
0.8916	High Similarity	NPC102465
0.8902	High Similarity	NPC150893
0.8902	High Similarity	NPC295408
0.8902	High Similarity	NPC329960
0.8876	High Similarity	NPC477617
0.8868	High Similarity	NPC469415
0.8812	High Similarity	NPC472548
0.8805	High Similarity	NPC469448
0.8805	High Similarity	NPC222102
0.8805	High Similarity	NPC303429
0.8795	High Similarity	NPC477491
0.8765	High Similarity	NPC106895
0.875	High Similarity	NPC477488
0.8712	High Similarity	NPC477735
0.8704	High Similarity	NPC472549
0.8704	High Similarity	NPC228204
0.8704	High Similarity	NPC282239
0.8704	High Similarity	NPC26033
0.8675	High Similarity	NPC66193
0.8659	High Similarity	NPC477736
0.8659	High Similarity	NPC471102
0.8642	High Similarity	NPC472005
0.8642	High Similarity	NPC304876
0.8642	High Similarity	NPC472022
0.8642	High Similarity	NPC472030
0.8642	High Similarity	NPC473414
0.8642	High Similarity	NPC257213
0.8642	High Similarity	NPC242262
0.8642	High Similarity	NPC158333
0.8642	High Similarity	NPC249471
0.8642	High Similarity	NPC265395
0.8642	High Similarity	NPC237549
0.8642	High Similarity	NPC1173
0.8642	High Similarity	NPC256142
0.8639	High Similarity	NPC469396
0.8639	High Similarity	NPC149002
0.8639	High Similarity	NPC469459
0.8639	High Similarity	NPC469458
0.8639	High Similarity	NPC88176
0.8639	High Similarity	NPC469419
0.8623	High Similarity	NPC471134
0.8623	High Similarity	NPC471493
0.8616	High Similarity	NPC469513
0.8598	High Similarity	NPC472393
0.8589	High Similarity	NPC112523
0.8589	High Similarity	NPC114410
0.8571	High Similarity	NPC61891
0.8571	High Similarity	NPC475567
0.8571	High Similarity	NPC473468
0.8571	High Similarity	NPC473557
0.8571	High Similarity	NPC7095
0.8553	High Similarity	NPC472572
0.8553	High Similarity	NPC200471
0.8553	High Similarity	NPC476973
0.8553	High Similarity	NPC184817
0.8553	High Similarity	NPC174982
0.8553	High Similarity	NPC158663
0.8553	High Similarity	NPC177940
0.8553	High Similarity	NPC29704
0.8553	High Similarity	NPC171525
0.8553	High Similarity	NPC470159
0.8553	High Similarity	NPC473088
0.8553	High Similarity	NPC471104
0.8553	High Similarity	NPC469349
0.8553	High Similarity	NPC472571
0.8553	High Similarity	NPC472575
0.8553	High Similarity	NPC472568
0.8553	High Similarity	NPC470157
0.8553	High Similarity	NPC70403
0.8553	High Similarity	NPC96903
0.8537	High Similarity	NPC217091
0.8528	High Similarity	NPC77719
0.8521	High Similarity	NPC475175
0.8521	High Similarity	NPC475531
0.8521	High Similarity	NPC475198
0.8519	High Similarity	NPC471103
0.8519	High Similarity	NPC470153
0.8519	High Similarity	NPC51602
0.8509	High Similarity	NPC92293
0.8509	High Similarity	NPC301556
0.8509	High Similarity	NPC250046
0.8509	High Similarity	NPC266265
0.8509	High Similarity	NPC60509
0.8509	High Similarity	NPC81698
0.8509	High Similarity	NPC270590
0.8509	High Similarity	NPC471101
0.8491	Intermediate Similarity	NPC475122
0.8491	Intermediate Similarity	NPC11685
0.8491	Intermediate Similarity	NPC163719
0.8491	Intermediate Similarity	NPC472569
0.8491	Intermediate Similarity	NPC70716
0.8491	Intermediate Similarity	NPC475759
0.8491	Intermediate Similarity	NPC470152
0.8491	Intermediate Similarity	NPC25768
0.8491	Intermediate Similarity	NPC95265
0.8491	Intermediate Similarity	NPC241951
0.8491	Intermediate Similarity	NPC472570
0.8491	Intermediate Similarity	NPC188865
0.8491	Intermediate Similarity	NPC476974
0.8491	Intermediate Similarity	NPC95810
0.8491	Intermediate Similarity	NPC57628
0.8491	Intermediate Similarity	NPC125106
0.8491	Intermediate Similarity	NPC472573
0.8485	Intermediate Similarity	NPC469771
0.8471	Intermediate Similarity	NPC40138
0.8457	Intermediate Similarity	NPC112216
0.8457	Intermediate Similarity	NPC198455
0.8457	Intermediate Similarity	NPC473214
0.8457	Intermediate Similarity	NPC161239
0.8457	Intermediate Similarity	NPC254558
0.8457	Intermediate Similarity	NPC470245
0.8457	Intermediate Similarity	NPC165260
0.8452	Intermediate Similarity	NPC478073
0.8447	Intermediate Similarity	NPC281717
0.8439	Intermediate Similarity	NPC148185
0.8434	Intermediate Similarity	NPC477467
0.8434	Intermediate Similarity	NPC476784
0.8428	Intermediate Similarity	NPC163087
0.8415	Intermediate Similarity	NPC472658
0.8415	Intermediate Similarity	NPC69425
0.8415	Intermediate Similarity	NPC472657
0.8409	Intermediate Similarity	NPC195114
0.8402	Intermediate Similarity	NPC117943
0.8402	Intermediate Similarity	NPC293568
0.8402	Intermediate Similarity	NPC477627
0.8395	Intermediate Similarity	NPC476975
0.8395	Intermediate Similarity	NPC473215
0.8393	Intermediate Similarity	NPC275477
0.8393	Intermediate Similarity	NPC43304
0.8393	Intermediate Similarity	NPC477188
0.8393	Intermediate Similarity	NPC477190
0.8373	Intermediate Similarity	NPC477474
0.8373	Intermediate Similarity	NPC477472
0.8373	Intermediate Similarity	NPC477470
0.8364	Intermediate Similarity	NPC21410
0.8364	Intermediate Similarity	NPC469456
0.8364	Intermediate Similarity	NPC473670
0.8352	Intermediate Similarity	NPC469418
0.8352	Intermediate Similarity	NPC260300
0.8352	Intermediate Similarity	NPC80360
0.8344	Intermediate Similarity	NPC91730
0.8333	Intermediate Similarity	NPC476077
0.8323	Intermediate Similarity	NPC472556
0.8323	Intermediate Similarity	NPC127857
0.8304	Intermediate Similarity	NPC120012
0.8302	Intermediate Similarity	NPC77493
0.8302	Intermediate Similarity	NPC118080
0.8302	Intermediate Similarity	NPC27377
0.8302	Intermediate Similarity	NPC97947
0.8302	Intermediate Similarity	NPC291599
0.8302	Intermediate Similarity	NPC87448
0.8302	Intermediate Similarity	NPC41481
0.8302	Intermediate Similarity	NPC16912
0.8302	Intermediate Similarity	NPC472576
0.8293	Intermediate Similarity	NPC197037
0.8293	Intermediate Similarity	NPC329657
0.8272	Intermediate Similarity	NPC474935
0.8272	Intermediate Similarity	NPC477737
0.8263	Intermediate Similarity	NPC318447
0.8263	Intermediate Similarity	NPC322048
0.8258	Intermediate Similarity	NPC188217
0.8256	Intermediate Similarity	NPC265600
0.8253	Intermediate Similarity	NPC132599
0.8253	Intermediate Similarity	NPC469730
0.8253	Intermediate Similarity	NPC473632
0.8253	Intermediate Similarity	NPC473611
0.8239	Intermediate Similarity	NPC476094
0.8239	Intermediate Similarity	NPC4341
0.8239	Intermediate Similarity	NPC275592
0.8239	Intermediate Similarity	NPC473112
0.8239	Intermediate Similarity	NPC200592
0.8239	Intermediate Similarity	NPC147880
0.8239	Intermediate Similarity	NPC90614
0.8239	Intermediate Similarity	NPC97667
0.8239	Intermediate Similarity	NPC473613
0.8239	Intermediate Similarity	NPC473109
0.8239	Intermediate Similarity	NPC473085
0.8239	Intermediate Similarity	NPC43241
0.8239	Intermediate Similarity	NPC473758
0.8239	Intermediate Similarity	NPC473081
0.8239	Intermediate Similarity	NPC171207
0.8239	Intermediate Similarity	NPC211137
0.8239	Intermediate Similarity	NPC100913
0.8239	Intermediate Similarity	NPC184747
0.8239	Intermediate Similarity	NPC473060

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 NPC469421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	846
0.2-0.3	2121
0.3-0.4	3360
0.4-0.5	1805
0.5-0.6	523
0.6-0.7	123
0.7-0.8	9
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
0.8057	Intermediate Similarity	NPD7799	Discontinued
0.7944	Intermediate Similarity	NPD8407	Phase 2
0.7877	Intermediate Similarity	NPD8368	Discontinued
0.7709	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8361	Approved
0.7676	Intermediate Similarity	NPD8435	Approved
0.7676	Intermediate Similarity	NPD8360	Approved
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7596	Intermediate Similarity	NPD8312	Approved
0.7596	Intermediate Similarity	NPD8313	Approved
0.7592	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8485	Approved
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.738	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD7236	Approved
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7317	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7240	Approved
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD7239	Suspended
0.724	Intermediate Similarity	NPD6535	Approved
0.724	Intermediate Similarity	NPD6534	Approved
0.7239	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7435	Discontinued
0.7135	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7696	Phase 3
0.7121	Intermediate Similarity	NPD7697	Approved
0.7121	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8151	Discontinued
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD7074	Phase 3
0.7097	Intermediate Similarity	NPD7472	Approved
0.7079	Intermediate Similarity	NPD7874	Approved
0.7079	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7808	Phase 3
0.7065	Intermediate Similarity	NPD7701	Phase 2
0.7056	Intermediate Similarity	NPD6778	Approved
0.7056	Intermediate Similarity	NPD4965	Approved
0.7056	Intermediate Similarity	NPD6779	Approved
0.7056	Intermediate Similarity	NPD6781	Approved
0.7056	Intermediate Similarity	NPD6780	Approved
0.7056	Intermediate Similarity	NPD6782	Approved
0.7056	Intermediate Similarity	NPD4967	Phase 2
0.7056	Intermediate Similarity	NPD4966	Approved
0.7056	Intermediate Similarity	NPD6776	Approved
0.7056	Intermediate Similarity	NPD6777	Approved
0.7043	Intermediate Similarity	NPD7054	Approved
0.7021	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD7251	Discontinued
0.7017	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8462	Phase 1
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7870	Phase 2
0.6989	Remote Similarity	NPD3818	Discontinued
0.6978	Remote Similarity	NPD6234	Discontinued
0.6971	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6797	Phase 2
0.6961	Remote Similarity	NPD7801	Approved
0.6931	Remote Similarity	NPD6559	Discontinued
0.6923	Remote Similarity	NPD6213	Phase 3
0.6923	Remote Similarity	NPD6212	Phase 3
0.6923	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6823	Phase 2
0.6895	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD37	Approved
0.6878	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8404	Phase 2
0.6868	Remote Similarity	NPD7057	Phase 3
0.6868	Remote Similarity	NPD7058	Phase 2
0.6866	Remote Similarity	NPD7680	Approved
0.6865	Remote Similarity	NPD3787	Discontinued
0.6851	Remote Similarity	NPD7819	Suspended
0.6848	Remote Similarity	NPD5494	Approved
0.6809	Remote Similarity	NPD3751	Discontinued
0.6796	Remote Similarity	NPD7783	Phase 2
0.6796	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4380	Phase 2
0.6772	Remote Similarity	NPD5844	Phase 1
0.6763	Remote Similarity	NPD7266	Discontinued
0.6758	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7473	Discontinued
0.6745	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4628	Phase 3
0.6743	Remote Similarity	NPD8166	Discontinued
0.6739	Remote Similarity	NPD7075	Discontinued
0.6728	Remote Similarity	NPD5126	Approved
0.6728	Remote Similarity	NPD5125	Phase 3
0.672	Remote Similarity	NPD8127	Discontinued
0.672	Remote Similarity	NPD7199	Phase 2
0.6716	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6190	Approved
0.6704	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6166	Phase 2
0.6702	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7497	Discontinued
0.6687	Remote Similarity	NPD8328	Phase 3
0.6685	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD5760	Phase 2
0.6647	Remote Similarity	NPD7961	Discontinued
0.6631	Remote Similarity	NPD6959	Discontinued
0.663	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7008	Discontinued
0.6614	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6232	Discontinued
0.6593	Remote Similarity	NPD6599	Discontinued
0.6587	Remote Similarity	NPD7319	Approved
0.6564	Remote Similarity	NPD8513	Phase 3
0.6564	Remote Similarity	NPD8517	Approved
0.6564	Remote Similarity	NPD8515	Approved
0.6564	Remote Similarity	NPD8516	Approved
0.6561	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7411	Suspended
0.6556	Remote Similarity	NPD6273	Approved
0.6548	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5402	Approved
0.6538	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6801	Discontinued
0.6514	Remote Similarity	NPD8059	Phase 3
0.6514	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3764	Approved
0.6486	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7999	Approved
0.6471	Remote Similarity	NPD3749	Approved
0.6462	Remote Similarity	NPD7930	Approved
0.6452	Remote Similarity	NPD3817	Phase 2
0.6448	Remote Similarity	NPD3226	Approved
0.6432	Remote Similarity	NPD1934	Approved
0.6417	Remote Similarity	NPD7768	Phase 2
0.641	Remote Similarity	NPD6765	Approved
0.641	Remote Similarity	NPD6764	Approved
0.6409	Remote Similarity	NPD2532	Approved
0.6409	Remote Similarity	NPD2534	Approved
0.6409	Remote Similarity	NPD2533	Approved
0.6407	Remote Similarity	NPD7507	Approved
0.6402	Remote Similarity	NPD7741	Discontinued
0.64	Remote Similarity	NPD7097	Phase 1
0.6384	Remote Similarity	NPD2346	Discontinued
0.6376	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7003	Approved
0.6358	Remote Similarity	NPD2629	Approved
0.6354	Remote Similarity	NPD6799	Approved
0.6339	Remote Similarity	NPD5403	Approved
0.6331	Remote Similarity	NPD7736	Approved
0.633	Remote Similarity	NPD3882	Suspended
0.6325	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7028	Phase 2
0.6319	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4198	Discontinued
0.6319	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5401	Approved
0.6313	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1465	Phase 2
0.631	Remote Similarity	NPD2801	Approved
0.6287	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6784	Approved
0.6281	Remote Similarity	NPD6785	Approved
0.627	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD8296	Approved
0.6265	Remote Similarity	NPD8033	Approved
0.6265	Remote Similarity	NPD8380	Approved
0.6265	Remote Similarity	NPD8335	Approved
0.6265	Remote Similarity	NPD8379	Approved
0.6265	Remote Similarity	NPD8378	Approved
0.6264	Remote Similarity	NPD7390	Discontinued
0.6262	Remote Similarity	NPD8285	Discontinued
0.6258	Remote Similarity	NPD5951	Approved
0.6242	Remote Similarity	NPD7516	Approved
0.6236	Remote Similarity	NPD5406	Approved
0.6236	Remote Similarity	NPD5405	Approved
0.6236	Remote Similarity	NPD5404	Approved
0.6236	Remote Similarity	NPD5408	Approved
0.6231	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6674	Discontinued
0.6209	Remote Similarity	NPD7584	Approved
0.6205	Remote Similarity	NPD8377	Approved
0.6205	Remote Similarity	NPD8294	Approved
0.6193	Remote Similarity	NPD230	Phase 1
0.6188	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7327	Approved
0.6182	Remote Similarity	NPD7328	Approved
0.618	Remote Similarity	NPD2799	Discontinued
0.6167	Remote Similarity	NPD1549	Phase 2
0.6154	Remote Similarity	NPD7274	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