NPASS Compound

Structure

CID44063 OpenBabel06191715372D 29 32 0 0 1 0 0 0 0 0999 V2000 2.7718 1.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8424 0.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5287 -3.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6860 -2.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0548 -1.9437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8410 -1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2127 -1.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8412 -0.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2132 -3.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6851 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9236 1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0492 2.5244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3711 -2.9171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0550 -2.9166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6857 -1.9447 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8430 -1.4585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5278 -0.4857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0006 0.9719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5281 -1.4580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3708 -1.9442 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8427 -0.4862 0.0000 C 0 0 2 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 2.2507 3.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9284 -3.4203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4008 0.0186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7232 1.6218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1251 2.2235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 29 1 0 0 0 0 13 24 2 0 0 0 0 13 29 1 0 0 0 0 14 21 1 0 0 0 0 15 25 2 0 0 0 0 16 5 1 1 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 6 0 0 0 19 23 1 0 0 0 0 19 27 2 0 0 0 0 20 21 1 6 0 0 0 21 2 1 6 0 0 0 22 23 1 1 0 0 0 23 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.2
Volume:	411.697
LogP:	2.487
LogD:	2.249
LogS:	-4.104
# Rotatable Bonds:	4
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	4.579
Fsp3:	0.696
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:	-4.81
MDCK Permeability:	2.8242455300642177e-05
Pgp-inhibitor:	0.365
Pgp-substrate:	0.386
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	53.015037536621094%
Volume Distribution (VD):	0.406
Pgp-substrate:	39.57550048828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	5.788
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.361
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.725
Carcinogencity:	0.892
Eye Corrosion:	0.152
Eye Irritation:	0.112
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC44063

Natural Product ID:	NPC44063
*Common Name:**	Prednisolone Acetate
IUPAC Name:	[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
Synonyms:	Econopred; Flo-Pred; Meticortelone; Omnipred; Pred Forte; Pred Fte; Pred Mild; Prednisolone acetate; Sterane; Ultracortenol
Standard InCHIKey:	LRJOMUJRLNCICJ-JZYPGELDSA-N
Standard InCHI:	InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
SMILES:	CC(=O)OCC(=O)[C@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@H](C[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1152
PubChem CID:	5834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins and derivatives

*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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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
AC50	3
Others	19
Potency	28

Activity Type	# Activity
Cell Line	1
Individual Protein	13
Organism	13
Others	20
SINGLE PROTEIN	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	25.1	nM	PMID[463338]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	51.7	nM	PMID[463339]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	446.7	nM	PMID[463339]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[463339]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[463339]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	41.1	nM	PMID[463339]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	149.6	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	1068.2	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	237.1	nM	PubChem BioAssay data set
NPT897	Others	Monoclonal antibody (mAb)		IC50 ratio	=	12000.0	n.a.	PMID[463333]
NPT605	Organism	Homo sapiens	Homo sapiens	Potency	=	1.0	n.a.	PMID[463334]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Potency	=	3.0	n.a.	PMID[463334]
NPT35	Others	n.a.		logS0	=	-4.37	n.a.	PMID[463336]
NPT27	Others	Unspecified		log Ks	=	3.76	n.a.	PMID[463337]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	46.5	nM	PMID[463338]
NPT2	Others	Unspecified		Potency	n.a.	115.8	nM	PMID[463338]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[463339]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	20786.5	nM	PMID[463338]
NPT2	Others	Unspecified		Potency	n.a.	326.4	nM	PMID[463338]
NPT2	Others	Unspecified		Potency	n.a.	25929.0	nM	PMID[463339]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[463339]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	106.69	%	PMID[463340]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	63.69	%	PMID[463340]
NPT2	Others	Unspecified		AC50	n.a.	7079.5	nM	PMID[463341]
NPT2	Others	Unspecified		Ac50	n.a.	44.67	uM	PMID[463341]
NPT2	Others	Unspecified		Ac50	n.a.	7.079	uM	PMID[463341]
NPT2	Others	Unspecified		Ac50	n.a.	28.18	uM	PMID[463341]
NPT2	Others	Unspecified		AC50	n.a.	44668.4	nM	PMID[463341]
NPT2	Others	Unspecified		AC50	n.a.	28183.8	nM	PMID[463341]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	59.99	%	PMID[463342]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	38.15	%	PMID[463343]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.63	%	PMID[463344]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	0.73	%	PMID[463345]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-1.37	%	PMID[463345]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	1.81	%	PMID[463345]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	12.95	%	PMID[463345]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	16.93	%	PMID[463345]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	25.62	%	PMID[463345]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	11.59	%	PMID[463345]
NPT2	Others	Unspecified		Potency	n.a.	11883.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2389.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	237.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	169.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	473	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	149.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	150.9	nM	PubChem BioAssay data set

☑ 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 NPC44063 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	201
0.1-0.2	1230
0.2-0.3	4753
0.3-0.4	9248
0.4-0.5	11664
0.5-0.6	6184
0.6-0.7	6007
0.7-0.8	3003
0.8-0.85	334
0.85-0.9	63
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC2766
0.9388	High Similarity	NPC144956
0.9184	High Similarity	NPC18509
0.902	High Similarity	NPC235889
0.8962	High Similarity	NPC71348
0.8932	High Similarity	NPC181265
0.8889	High Similarity	NPC270958
0.8868	High Similarity	NPC43775
0.8835	High Similarity	NPC137657
0.8824	High Similarity	NPC22388
0.8807	High Similarity	NPC471854
0.8785	High Similarity	NPC475524
0.8785	High Similarity	NPC100267
0.8774	High Similarity	NPC197428
0.8727	High Similarity	NPC118638
0.8727	High Similarity	NPC311554
0.8727	High Similarity	NPC257457
0.8713	High Similarity	NPC114274
0.8704	High Similarity	NPC202889
0.8704	High Similarity	NPC194100
0.8692	High Similarity	NPC118860
0.8692	High Similarity	NPC214797
0.8692	High Similarity	NPC231589
0.8679	High Similarity	NPC241927
0.8679	High Similarity	NPC258543
0.8673	High Similarity	NPC185936
0.8673	High Similarity	NPC168027
0.8667	High Similarity	NPC475294
0.8654	High Similarity	NPC29705
0.8641	High Similarity	NPC271266
0.8641	High Similarity	NPC308351
0.8611	High Similarity	NPC170487
0.8598	High Similarity	NPC235077
0.8586	High Similarity	NPC109414
0.8585	High Similarity	NPC94529
0.8571	High Similarity	NPC196528
0.8558	High Similarity	NPC311612
0.8545	High Similarity	NPC148458
0.8544	High Similarity	NPC476223
0.8544	High Similarity	NPC81530
0.8544	High Similarity	NPC476240
0.8544	High Similarity	NPC224720
0.8529	High Similarity	NPC477854
0.8515	High Similarity	NPC96859
0.8515	High Similarity	NPC305483
0.8515	High Similarity	NPC477853
0.8515	High Similarity	NPC328162
0.8505	High Similarity	NPC214644
0.8505	High Similarity	NPC304495
0.8505	High Similarity	NPC41405
0.8491	Intermediate Similarity	NPC185
0.8491	Intermediate Similarity	NPC220974
0.8469	Intermediate Similarity	NPC326627
0.8469	Intermediate Similarity	NPC310010
0.8468	Intermediate Similarity	NPC239273
0.8462	Intermediate Similarity	NPC136289
0.8462	Intermediate Similarity	NPC119601
0.8462	Intermediate Similarity	NPC473928
0.8462	Intermediate Similarity	NPC308726
0.8462	Intermediate Similarity	NPC87351
0.8447	Intermediate Similarity	NPC476274
0.8447	Intermediate Similarity	NPC472972
0.844	Intermediate Similarity	NPC221144
0.844	Intermediate Similarity	NPC147180
0.844	Intermediate Similarity	NPC264634
0.844	Intermediate Similarity	NPC280782
0.8431	Intermediate Similarity	NPC108078
0.8421	Intermediate Similarity	NPC313528
0.8416	Intermediate Similarity	NPC317586
0.8416	Intermediate Similarity	NPC477438
0.8416	Intermediate Similarity	NPC477437
0.8416	Intermediate Similarity	NPC469599
0.8416	Intermediate Similarity	NPC470016
0.8411	Intermediate Similarity	NPC472825
0.84	Intermediate Similarity	NPC470376
0.84	Intermediate Similarity	NPC477435
0.84	Intermediate Similarity	NPC470375
0.84	Intermediate Similarity	NPC477436
0.8396	Intermediate Similarity	NPC265127
0.8396	Intermediate Similarity	NPC278628
0.8396	Intermediate Similarity	NPC470267
0.8396	Intermediate Similarity	NPC231530
0.8381	Intermediate Similarity	NPC140723
0.8367	Intermediate Similarity	NPC328539
0.8365	Intermediate Similarity	NPC163372
0.8365	Intermediate Similarity	NPC477051
0.8365	Intermediate Similarity	NPC477052
0.8365	Intermediate Similarity	NPC477053
0.8365	Intermediate Similarity	NPC302537
0.8364	Intermediate Similarity	NPC962
0.8364	Intermediate Similarity	NPC52634
0.8364	Intermediate Similarity	NPC250109
0.835	Intermediate Similarity	NPC222011
0.8349	Intermediate Similarity	NPC207689
0.8333	Intermediate Similarity	NPC49371
0.8333	Intermediate Similarity	NPC192428
0.8319	Intermediate Similarity	NPC61520
0.8317	Intermediate Similarity	NPC166906
0.8317	Intermediate Similarity	NPC477439
0.8317	Intermediate Similarity	NPC111015
0.83	Intermediate Similarity	NPC154101
0.8286	Intermediate Similarity	NPC477054
0.8283	Intermediate Similarity	NPC305039
0.8283	Intermediate Similarity	NPC475921
0.8283	Intermediate Similarity	NPC474704
0.8276	Intermediate Similarity	NPC473255
0.8273	Intermediate Similarity	NPC152117
0.8273	Intermediate Similarity	NPC234042
0.8269	Intermediate Similarity	NPC474720
0.8269	Intermediate Similarity	NPC83709
0.8269	Intermediate Similarity	NPC15390
0.8261	Intermediate Similarity	NPC222688
0.8257	Intermediate Similarity	NPC5284
0.8252	Intermediate Similarity	NPC473456
0.8252	Intermediate Similarity	NPC226986
0.8252	Intermediate Similarity	NPC107243
0.8252	Intermediate Similarity	NPC57416
0.8252	Intermediate Similarity	NPC43747
0.8252	Intermediate Similarity	NPC69385
0.8246	Intermediate Similarity	NPC109973
0.8241	Intermediate Similarity	NPC469844
0.8241	Intermediate Similarity	NPC470269
0.8241	Intermediate Similarity	NPC177064
0.8235	Intermediate Similarity	NPC184848
0.8235	Intermediate Similarity	NPC69548
0.823	Intermediate Similarity	NPC329736
0.8224	Intermediate Similarity	NPC60681
0.8224	Intermediate Similarity	NPC475571
0.8224	Intermediate Similarity	NPC257353
0.8218	Intermediate Similarity	NPC294263
0.8218	Intermediate Similarity	NPC79117
0.8218	Intermediate Similarity	NPC233118
0.8214	Intermediate Similarity	NPC266728
0.8214	Intermediate Similarity	NPC298278
0.8214	Intermediate Similarity	NPC49492
0.8208	Intermediate Similarity	NPC179208
0.8208	Intermediate Similarity	NPC159442
0.8208	Intermediate Similarity	NPC191892
0.8208	Intermediate Similarity	NPC70967
0.8208	Intermediate Similarity	NPC111323
0.8208	Intermediate Similarity	NPC112009
0.8208	Intermediate Similarity	NPC33973
0.8208	Intermediate Similarity	NPC264048
0.8208	Intermediate Similarity	NPC470839
0.8208	Intermediate Similarity	NPC236390
0.82	Intermediate Similarity	NPC471896
0.8198	Intermediate Similarity	NPC255017
0.8198	Intermediate Similarity	NPC472926
0.819	Intermediate Similarity	NPC474327
0.819	Intermediate Similarity	NPC473979
0.8174	Intermediate Similarity	NPC470921
0.8173	Intermediate Similarity	NPC197386
0.8173	Intermediate Similarity	NPC176845
0.8173	Intermediate Similarity	NPC477813
0.8165	Intermediate Similarity	NPC475941
0.8165	Intermediate Similarity	NPC474901
0.8163	Intermediate Similarity	NPC327115
0.8158	Intermediate Similarity	NPC472933
0.8155	Intermediate Similarity	NPC471039
0.8155	Intermediate Similarity	NPC95565
0.8155	Intermediate Similarity	NPC173272
0.8155	Intermediate Similarity	NPC249954
0.8155	Intermediate Similarity	NPC471153
0.8155	Intermediate Similarity	NPC13949
0.8148	Intermediate Similarity	NPC3316
0.8148	Intermediate Similarity	NPC472925
0.8148	Intermediate Similarity	NPC144854
0.8148	Intermediate Similarity	NPC83744
0.8142	Intermediate Similarity	NPC470959
0.8142	Intermediate Similarity	NPC243065
0.8142	Intermediate Similarity	NPC476965
0.8137	Intermediate Similarity	NPC196485
0.8137	Intermediate Similarity	NPC169751
0.8137	Intermediate Similarity	NPC272635
0.8137	Intermediate Similarity	NPC245972
0.8137	Intermediate Similarity	NPC471040
0.8136	Intermediate Similarity	NPC470882
0.8136	Intermediate Similarity	NPC473265
0.8136	Intermediate Similarity	NPC473253
0.8131	Intermediate Similarity	NPC255309
0.8131	Intermediate Similarity	NPC470251
0.8131	Intermediate Similarity	NPC472228
0.8131	Intermediate Similarity	NPC472227
0.8131	Intermediate Similarity	NPC135854
0.8131	Intermediate Similarity	NPC96268
0.8131	Intermediate Similarity	NPC75531
0.8131	Intermediate Similarity	NPC2436
0.8131	Intermediate Similarity	NPC216245
0.8131	Intermediate Similarity	NPC471293
0.8131	Intermediate Similarity	NPC149124
0.8125	Intermediate Similarity	NPC473798
0.8125	Intermediate Similarity	NPC470953
0.8119	Intermediate Similarity	NPC218301
0.8119	Intermediate Similarity	NPC23434
0.8119	Intermediate Similarity	NPC272746
0.8113	Intermediate Similarity	NPC195290
0.8113	Intermediate Similarity	NPC477915
0.8113	Intermediate Similarity	NPC473424
0.8113	Intermediate Similarity	NPC473163
0.8113	Intermediate Similarity	NPC185530

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 NPC44063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1458
0.2-0.3	3911
0.3-0.4	2356
0.4-0.5	738
0.5-0.6	185
0.6-0.7	142
0.7-0.8	67
0.8-0.85	46
0.85-0.9	30
0.9-0.95	23
0.95-1	25

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5697	Approved
0.9899	High Similarity	NPD6899	Approved
0.9899	High Similarity	NPD6881	Approved
0.98	High Similarity	NPD6014	Approved
0.98	High Similarity	NPD6013	Approved
0.98	High Similarity	NPD6012	Approved
0.9703	High Similarity	NPD7102	Approved
0.9703	High Similarity	NPD7290	Approved
0.9703	High Similarity	NPD6883	Approved
0.97	High Similarity	NPD6011	Approved
0.9697	High Similarity	NPD6675	Approved
0.9697	High Similarity	NPD7128	Approved
0.9697	High Similarity	NPD5739	Approved
0.9697	High Similarity	NPD6402	Approved
0.9608	High Similarity	NPD8130	Phase 1
0.9608	High Similarity	NPD6650	Approved
0.9608	High Similarity	NPD6869	Approved
0.9608	High Similarity	NPD6649	Approved
0.9608	High Similarity	NPD6617	Approved
0.9608	High Similarity	NPD6847	Approved
0.96	High Similarity	NPD5701	Approved
0.9515	High Similarity	NPD8297	Approved
0.9515	High Similarity	NPD6882	Approved
0.9505	High Similarity	NPD7320	Approved
0.9412	High Similarity	NPD6372	Approved
0.9412	High Similarity	NPD6373	Approved
0.9388	High Similarity	NPD5286	Approved
0.9388	High Similarity	NPD4696	Approved
0.9388	High Similarity	NPD5285	Approved
0.92	High Similarity	NPD5226	Approved
0.92	High Similarity	NPD5211	Phase 2
0.92	High Similarity	NPD5224	Approved
0.92	High Similarity	NPD4633	Approved
0.92	High Similarity	NPD5225	Approved
0.9184	High Similarity	NPD4755	Approved
0.9109	High Similarity	NPD5175	Approved
0.9109	High Similarity	NPD5174	Approved
0.91	High Similarity	NPD5223	Approved
0.9065	High Similarity	NPD6274	Approved
0.9048	High Similarity	NPD6401	Clinical (unspecified phase)
0.902	High Similarity	NPD5141	Approved
0.9	High Similarity	NPD4700	Approved
0.8991	High Similarity	NPD7101	Approved
0.8991	High Similarity	NPD7100	Approved
0.899	High Similarity	NPD6084	Phase 2
0.899	High Similarity	NPD6083	Phase 2
0.8981	High Similarity	NPD6317	Approved
0.8909	High Similarity	NPD6319	Approved
0.8899	High Similarity	NPD6335	Approved
0.8899	High Similarity	NPD6313	Approved
0.8899	High Similarity	NPD6314	Approved
0.8879	High Similarity	NPD4632	Approved
0.8807	High Similarity	NPD6009	Approved
0.8788	High Similarity	NPD5695	Phase 3
0.8762	High Similarity	NPD4730	Approved
0.8762	High Similarity	NPD4729	Approved
0.8713	High Similarity	NPD5696	Approved
0.87	High Similarity	NPD5222	Approved
0.87	High Similarity	NPD5221	Approved
0.87	High Similarity	NPD5220	Clinical (unspecified phase)
0.8661	High Similarity	NPD5983	Phase 2
0.8614	High Similarity	NPD5173	Approved
0.8598	High Similarity	NPD5251	Approved
0.8598	High Similarity	NPD4634	Approved
0.8598	High Similarity	NPD5248	Approved
0.8598	High Similarity	NPD5247	Approved
0.8598	High Similarity	NPD5249	Phase 3
0.8598	High Similarity	NPD5250	Approved
0.8596	High Similarity	NPD7492	Approved
0.8585	High Similarity	NPD5128	Approved
0.8571	High Similarity	NPD4767	Approved
0.8571	High Similarity	NPD6054	Approved
0.8571	High Similarity	NPD4768	Approved
0.8558	High Similarity	NPD4754	Approved
0.8522	High Similarity	NPD6616	Approved
0.8519	High Similarity	NPD5217	Approved
0.8519	High Similarity	NPD5216	Approved
0.8519	High Similarity	NPD5215	Approved
0.8509	High Similarity	NPD7604	Phase 2
0.8496	Intermediate Similarity	NPD6016	Approved
0.8496	Intermediate Similarity	NPD6908	Approved
0.8496	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD6015	Approved
0.8496	Intermediate Similarity	NPD6909	Approved
0.8485	Intermediate Similarity	NPD6079	Approved
0.8469	Intermediate Similarity	NPD4753	Phase 2
0.8448	Intermediate Similarity	NPD7078	Approved
0.8426	Intermediate Similarity	NPD5169	Approved
0.8426	Intermediate Similarity	NPD5135	Approved
0.8426	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6370	Approved
0.8421	Intermediate Similarity	NPD5988	Approved
0.8416	Intermediate Similarity	NPD5210	Approved
0.8416	Intermediate Similarity	NPD4629	Approved
0.84	Intermediate Similarity	NPD4202	Approved
0.8378	Intermediate Similarity	NPD6868	Approved
0.8376	Intermediate Similarity	NPD7736	Approved
0.8362	Intermediate Similarity	NPD6336	Discontinued
0.8349	Intermediate Similarity	NPD5127	Approved
0.8333	Intermediate Similarity	NPD4697	Phase 3
0.8283	Intermediate Similarity	NPD6080	Approved
0.8283	Intermediate Similarity	NPD6904	Approved
0.8283	Intermediate Similarity	NPD6673	Approved
0.8283	Intermediate Similarity	NPD5328	Approved
0.8246	Intermediate Similarity	NPD6059	Approved
0.8224	Intermediate Similarity	NPD6008	Approved
0.8182	Intermediate Similarity	NPD6672	Approved
0.8182	Intermediate Similarity	NPD5737	Approved
0.8136	Intermediate Similarity	NPD8293	Discontinued
0.8125	Intermediate Similarity	NPD5167	Approved
0.8119	Intermediate Similarity	NPD5694	Approved
0.8119	Intermediate Similarity	NPD5693	Phase 1
0.8039	Intermediate Similarity	NPD6399	Phase 3
0.802	Intermediate Similarity	NPD5692	Phase 3
0.798	Intermediate Similarity	NPD6098	Approved
0.798	Intermediate Similarity	NPD7521	Approved
0.798	Intermediate Similarity	NPD5690	Phase 2
0.798	Intermediate Similarity	NPD7146	Approved
0.798	Intermediate Similarity	NPD7334	Approved
0.798	Intermediate Similarity	NPD5330	Approved
0.798	Intermediate Similarity	NPD6684	Approved
0.798	Intermediate Similarity	NPD6409	Approved
0.798	Intermediate Similarity	NPD3618	Phase 1
0.7959	Intermediate Similarity	NPD4197	Approved
0.7959	Intermediate Similarity	NPD3666	Approved
0.7959	Intermediate Similarity	NPD3665	Phase 1
0.7959	Intermediate Similarity	NPD3133	Approved
0.7941	Intermediate Similarity	NPD6050	Approved
0.7941	Intermediate Similarity	NPD5281	Approved
0.7941	Intermediate Similarity	NPD5284	Approved
0.7909	Intermediate Similarity	NPD5168	Approved
0.79	Intermediate Similarity	NPD3573	Approved
0.7885	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5329	Approved
0.7826	Intermediate Similarity	NPD7115	Discovery
0.7822	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD6903	Approved
0.7788	Intermediate Similarity	NPD7748	Approved
0.7767	Intermediate Similarity	NPD7515	Phase 2
0.7755	Intermediate Similarity	NPD4221	Approved
0.7755	Intermediate Similarity	NPD4223	Phase 3
0.7736	Intermediate Similarity	NPD7902	Approved
0.7664	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD5208	Approved
0.7624	Intermediate Similarity	NPD5279	Phase 3
0.7624	Intermediate Similarity	NPD4694	Approved
0.7624	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5280	Approved
0.7623	Intermediate Similarity	NPD6033	Approved
0.7619	Intermediate Similarity	NPD6001	Approved
0.76	Intermediate Similarity	NPD4786	Approved
0.7593	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD7640	Approved
0.7576	Intermediate Similarity	NPD3667	Approved
0.7547	Intermediate Similarity	NPD5654	Approved
0.75	Intermediate Similarity	NPD6334	Approved
0.75	Intermediate Similarity	NPD5207	Approved
0.75	Intermediate Similarity	NPD6614	Approved
0.75	Intermediate Similarity	NPD6333	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7459	Intermediate Similarity	NPD7507	Approved
0.7453	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7900	Approved
0.7451	Intermediate Similarity	NPD4689	Approved
0.7451	Intermediate Similarity	NPD4688	Approved
0.7451	Intermediate Similarity	NPD5205	Approved
0.7451	Intermediate Similarity	NPD4690	Approved
0.7451	Intermediate Similarity	NPD4138	Approved
0.7451	Intermediate Similarity	NPD4693	Phase 3
0.7449	Intermediate Similarity	NPD4195	Approved
0.7429	Intermediate Similarity	NPD8035	Phase 2
0.7429	Intermediate Similarity	NPD8034	Phase 2
0.7407	Intermediate Similarity	NPD5959	Approved
0.74	Intermediate Similarity	NPD6435	Approved
0.7353	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6053	Discontinued
0.7327	Intermediate Similarity	NPD4788	Approved
0.7297	Intermediate Similarity	NPD5091	Approved
0.7295	Intermediate Similarity	NPD8328	Phase 3
0.728	Intermediate Similarity	NPD7319	Approved
0.7264	Intermediate Similarity	NPD6411	Approved
0.725	Intermediate Similarity	NPD4522	Approved
0.7222	Intermediate Similarity	NPD5956	Approved
0.7206	Intermediate Similarity	NPD7236	Approved
0.72	Intermediate Similarity	NPD7525	Registered
0.72	Intermediate Similarity	NPD5368	Approved
0.72	Intermediate Similarity	NPD4695	Discontinued
0.7172	Intermediate Similarity	NPD3617	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3668	Phase 3
0.7075	Intermediate Similarity	NPD6101	Approved
0.7075	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5133	Approved
0.7027	Intermediate Similarity	NPD4225	Approved
0.7019	Intermediate Similarity	NPD1694	Approved
0.6992	Remote Similarity	NPD7503	Approved
0.6991	Remote Similarity	NPD7632	Discontinued
0.697	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7239	Suspended

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