NPASS Compound

Structure

CID326860 OpenBabel06191716192D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 10 1 0 0 0 0 2 6 1 0 0 0 0 2 11 2 0 0 0 0 3 6 1 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 7 24 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	776.69
Volume:	379.693
LogP:	5.234
LogD:	2.412
LogS:	-2.618
# Rotatable Bonds:	5
TPSA:	92.78
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	3.366
Fsp3:	0.133
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:	-4.799
MDCK Permeability:	1.8098387954523787e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.3073501586914%
Volume Distribution (VD):	0.431
Pgp-substrate:	3.166424036026001%

ADMET: Metabolism

CYP1A2-inhibitor:	0.383
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	1.532
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.879
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC326860

Natural Product ID:	NPC326860
*Common Name:**	Thyroxine
IUPAC Name:	2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
Synonyms:
Standard InCHIKey:	XUIIKFGFIJCVMT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)
SMILES:	OC(=O)C(Cc1cc(I)c(c(c1)I)Oc1cc(I)c(c(c1)I)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL42115
PubChem CID:	853 25201456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine 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
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24211545]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	Urine	n.a.	n.a.	PMID[6330305]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[932730]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	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	11
Potency	17

Activity Type	# Activity
Individual Protein	17
NON-MOLECULAR	4
Organism	2
Others	5
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	10000.0	nM	PMID[492311]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[492311]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	25118.9	nM	PMID[492311]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[492311]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[492311]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[492311]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[492311]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[492311]
NPT5122	Individual Protein	Thyroxine-binding globulin	Homo sapiens	RBA	=	100.0	%	PMID[492314]
NPT5122	Individual Protein	Thyroxine-binding globulin	Homo sapiens	log(%)	=	2.0	n.a.	PMID[492314]
NPT1250	Individual Protein	Macrophage migration inhibitory factor	Homo sapiens	IC50	=	15800.0	nM	PMID[492315]
NPT77	Individual Protein	Transthyretin	Homo sapiens	Concentration	=	0.000000016	M	PMID[492310]
NPT77	Individual Protein	Transthyretin	Homo sapiens	Binding affinity	=	63.0	n.a.	PMID[492310]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	15848.9	nM	PMID[492311]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	12589.3	nM	PMID[492311]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	10000.0	nM	PMID[492311]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	23694.5	nM	PMID[492312]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	5.3	nM	PMID[492312]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	10583.9	nM	PMID[492312]
NPT2	Others	Unspecified		log(activity)	=	2.0	n.a.	PMID[492313]
NPT2	Others	Unspecified		RBA	=	13.85	%	PMID[492314]
NPT2	Others	Unspecified		log(%)	=	1.141	n.a.	PMID[492314]
NPT2	Others	Unspecified		RBA	=	12.5	%	PMID[492314]
NPT2	Others	Unspecified		log(%)	=	1.097	n.a.	PMID[492314]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	18.1	%	PMID[492314]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	log(%)	=	1.258	n.a.	PMID[492314]

☑ 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 NPC326860 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	245
0.1-0.2	1686
0.2-0.3	6628
0.3-0.4	11946
0.4-0.5	5019
0.5-0.6	13174
0.6-0.7	3907
0.7-0.8	75
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197239
0.9847	High Similarity	NPC317741
0.9847	High Similarity	NPC328137
0.9847	High Similarity	NPC282087
0.9847	High Similarity	NPC259800
0.9847	High Similarity	NPC318028
0.9847	High Similarity	NPC241086
0.9847	High Similarity	NPC318984
0.855	High Similarity	NPC318357
0.8472	Intermediate Similarity	NPC17760
0.8462	Intermediate Similarity	NPC317784
0.8462	Intermediate Similarity	NPC142638
0.8397	Intermediate Similarity	NPC239697
0.8168	Intermediate Similarity	NPC281686
0.8168	Intermediate Similarity	NPC188867
0.8168	Intermediate Similarity	NPC106551
0.8014	Intermediate Similarity	NPC470392
0.7945	Intermediate Similarity	NPC66518
0.7929	Intermediate Similarity	NPC325651
0.7842	Intermediate Similarity	NPC124776
0.782	Intermediate Similarity	NPC51345
0.781	Intermediate Similarity	NPC27581
0.7737	Intermediate Similarity	NPC56634
0.7737	Intermediate Similarity	NPC326079
0.7606	Intermediate Similarity	NPC16031
0.7606	Intermediate Similarity	NPC161593
0.7606	Intermediate Similarity	NPC145888
0.7591	Intermediate Similarity	NPC319950
0.7591	Intermediate Similarity	NPC264976
0.7569	Intermediate Similarity	NPC45191
0.7569	Intermediate Similarity	NPC326966
0.7564	Intermediate Similarity	NPC56635
0.7554	Intermediate Similarity	NPC142577
0.7517	Intermediate Similarity	NPC88667
0.7407	Intermediate Similarity	NPC26524
0.7329	Intermediate Similarity	NPC48909
0.7293	Intermediate Similarity	NPC97811
0.7292	Intermediate Similarity	NPC476353
0.7279	Intermediate Similarity	NPC244866
0.7273	Intermediate Similarity	NPC89630
0.726	Intermediate Similarity	NPC241354
0.7241	Intermediate Similarity	NPC296712
0.7239	Intermediate Similarity	NPC259554
0.7239	Intermediate Similarity	NPC234639
0.723	Intermediate Similarity	NPC307289
0.7226	Intermediate Similarity	NPC132771
0.7181	Intermediate Similarity	NPC470441
0.7174	Intermediate Similarity	NPC296526
0.7172	Intermediate Similarity	NPC321561
0.7143	Intermediate Similarity	NPC311091
0.7143	Intermediate Similarity	NPC471033
0.7133	Intermediate Similarity	NPC6913
0.7124	Intermediate Similarity	NPC204546
0.7122	Intermediate Similarity	NPC19290
0.7122	Intermediate Similarity	NPC128249
0.7117	Intermediate Similarity	NPC158900
0.7105	Intermediate Similarity	NPC40321
0.7075	Intermediate Similarity	NPC2596
0.7075	Intermediate Similarity	NPC478147
0.7073	Intermediate Similarity	NPC314725
0.7073	Intermediate Similarity	NPC313375
0.7068	Intermediate Similarity	NPC42383
0.7042	Intermediate Similarity	NPC474874
0.7042	Intermediate Similarity	NPC263835
0.7039	Intermediate Similarity	NPC223616
0.7034	Intermediate Similarity	NPC474237
0.7029	Intermediate Similarity	NPC109241
0.7019	Intermediate Similarity	NPC212699
0.7019	Intermediate Similarity	NPC207675
0.7015	Intermediate Similarity	NPC1065
0.7007	Intermediate Similarity	NPC266932
0.7007	Intermediate Similarity	NPC233238
0.7	Intermediate Similarity	NPC243404
0.6994	Remote Similarity	NPC235194
0.6986	Remote Similarity	NPC3221
0.6986	Remote Similarity	NPC88403
0.6985	Remote Similarity	NPC79543
0.6972	Remote Similarity	NPC43275
0.6966	Remote Similarity	NPC13020
0.6966	Remote Similarity	NPC140359
0.6959	Remote Similarity	NPC226661
0.6957	Remote Similarity	NPC17693
0.6947	Remote Similarity	NPC245561
0.6947	Remote Similarity	NPC125732
0.6944	Remote Similarity	NPC474862
0.6944	Remote Similarity	NPC194416
0.6944	Remote Similarity	NPC177291
0.6939	Remote Similarity	NPC475236
0.6939	Remote Similarity	NPC474476
0.6933	Remote Similarity	NPC141549
0.6928	Remote Similarity	NPC48202
0.6906	Remote Similarity	NPC309808
0.6903	Remote Similarity	NPC79372
0.6903	Remote Similarity	NPC13696
0.6901	Remote Similarity	NPC205502
0.6901	Remote Similarity	NPC293424
0.6897	Remote Similarity	NPC302211
0.6897	Remote Similarity	NPC69403
0.6897	Remote Similarity	NPC291189
0.6894	Remote Similarity	NPC52472
0.6892	Remote Similarity	NPC22783
0.6892	Remote Similarity	NPC142087
0.6892	Remote Similarity	NPC95034
0.6884	Remote Similarity	NPC21890
0.6879	Remote Similarity	NPC163398
0.6871	Remote Similarity	NPC168259
0.6871	Remote Similarity	NPC319320
0.6871	Remote Similarity	NPC320242
0.6871	Remote Similarity	NPC287757
0.6871	Remote Similarity	NPC4164
0.6871	Remote Similarity	NPC280767
0.6867	Remote Similarity	NPC326599
0.6867	Remote Similarity	NPC278787
0.6867	Remote Similarity	NPC257390
0.6867	Remote Similarity	NPC329595
0.6867	Remote Similarity	NPC475102
0.6867	Remote Similarity	NPC7569
0.6867	Remote Similarity	NPC2989
0.6861	Remote Similarity	NPC290566
0.6861	Remote Similarity	NPC145638
0.6859	Remote Similarity	NPC183642
0.6859	Remote Similarity	NPC310370
0.6857	Remote Similarity	NPC235250
0.6855	Remote Similarity	NPC324081
0.6849	Remote Similarity	NPC328267
0.6849	Remote Similarity	NPC473942
0.6846	Remote Similarity	NPC201419
0.6842	Remote Similarity	NPC307425
0.6839	Remote Similarity	NPC91953
0.6839	Remote Similarity	NPC470709
0.6838	Remote Similarity	NPC186469
0.6835	Remote Similarity	NPC313414
0.6835	Remote Similarity	NPC9373
0.6828	Remote Similarity	NPC187868
0.6824	Remote Similarity	NPC218323
0.6821	Remote Similarity	NPC258073
0.6815	Remote Similarity	NPC473855
0.6815	Remote Similarity	NPC13495
0.6812	Remote Similarity	NPC183700
0.6809	Remote Similarity	NPC301321
0.6806	Remote Similarity	NPC14177
0.6803	Remote Similarity	NPC221798
0.6803	Remote Similarity	NPC62101
0.6803	Remote Similarity	NPC193805
0.6803	Remote Similarity	NPC95733
0.6803	Remote Similarity	NPC229113
0.6803	Remote Similarity	NPC111088
0.68	Remote Similarity	NPC473019
0.68	Remote Similarity	NPC238309
0.6797	Remote Similarity	NPC5310
0.6797	Remote Similarity	NPC68779
0.6797	Remote Similarity	NPC300776
0.6797	Remote Similarity	NPC6570
0.6797	Remote Similarity	NPC4982
0.6797	Remote Similarity	NPC176814
0.6794	Remote Similarity	NPC122493
0.6794	Remote Similarity	NPC293628
0.6794	Remote Similarity	NPC10781
0.6791	Remote Similarity	NPC298224
0.6788	Remote Similarity	NPC31274
0.6788	Remote Similarity	NPC206341
0.6781	Remote Similarity	NPC311219
0.6776	Remote Similarity	NPC169766
0.6776	Remote Similarity	NPC113006
0.6774	Remote Similarity	NPC197921
0.677	Remote Similarity	NPC139839
0.6767	Remote Similarity	NPC107101
0.6765	Remote Similarity	NPC188677
0.6765	Remote Similarity	NPC113457
0.6765	Remote Similarity	NPC70843
0.6761	Remote Similarity	NPC470860
0.6761	Remote Similarity	NPC33717
0.6757	Remote Similarity	NPC257589
0.6757	Remote Similarity	NPC53305
0.6757	Remote Similarity	NPC29477
0.6755	Remote Similarity	NPC275538
0.6755	Remote Similarity	NPC109778
0.6753	Remote Similarity	NPC476018
0.6753	Remote Similarity	NPC475011
0.6753	Remote Similarity	NPC475029
0.6753	Remote Similarity	NPC248872
0.6753	Remote Similarity	NPC113295
0.6752	Remote Similarity	NPC326065
0.6752	Remote Similarity	NPC170812
0.6741	Remote Similarity	NPC38209
0.6741	Remote Similarity	NPC8931
0.6741	Remote Similarity	NPC261573
0.6741	Remote Similarity	NPC120693
0.6741	Remote Similarity	NPC283546
0.6736	Remote Similarity	NPC283760
0.6736	Remote Similarity	NPC61779
0.6735	Remote Similarity	NPC14141
0.6735	Remote Similarity	NPC248786
0.6735	Remote Similarity	NPC93730
0.6735	Remote Similarity	NPC211218
0.6733	Remote Similarity	NPC2401
0.6732	Remote Similarity	NPC287533
0.6731	Remote Similarity	NPC189724
0.6731	Remote Similarity	NPC469360
0.6731	Remote Similarity	NPC212850

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 NPC326860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	726
0.2-0.3	1294
0.3-0.4	2220
0.4-0.5	2394
0.5-0.6	1674
0.6-0.7	603
0.7-0.8	51
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1522	Approved
1.0	High Similarity	NPD1523	Approved
0.9847	High Similarity	NPD1537	Approved
0.9847	High Similarity	NPD1538	Phase 1
0.9847	High Similarity	NPD1519	Approved
0.9846	High Similarity	NPD1521	Approved
0.9846	High Similarity	NPD1520	Approved
0.9695	High Similarity	NPD1536	Approved
0.8626	High Similarity	NPD1535	Discovery
0.8561	High Similarity	NPD1481	Phase 2
0.8433	Intermediate Similarity	NPD196	Phase 1
0.8321	Intermediate Similarity	NPD2614	Approved
0.8168	Intermediate Similarity	NPD9568	Approved
0.8138	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1894	Discontinued
0.7703	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD256	Approved
0.7687	Intermediate Similarity	NPD255	Approved
0.7632	Intermediate Similarity	NPD3536	Discontinued
0.7606	Intermediate Similarity	NPD9569	Approved
0.7568	Intermediate Similarity	NPD2240	Approved
0.7568	Intermediate Similarity	NPD2239	Approved
0.7534	Intermediate Similarity	NPD555	Phase 2
0.7517	Intermediate Similarity	NPD259	Phase 1
0.7516	Intermediate Similarity	NPD5356	Approved
0.7516	Intermediate Similarity	NPD5355	Approved
0.75	Intermediate Similarity	NPD9536	Phase 1
0.75	Intermediate Similarity	NPD5163	Phase 2
0.75	Intermediate Similarity	NPD9537	Phase 1
0.7483	Intermediate Similarity	NPD3054	Approved
0.7483	Intermediate Similarity	NPD3052	Approved
0.7436	Intermediate Similarity	NPD3455	Phase 2
0.7329	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5745	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.726	Intermediate Similarity	NPD3136	Phase 2
0.726	Intermediate Similarity	NPD9718	Approved
0.7254	Intermediate Similarity	NPD2231	Phase 2
0.7254	Intermediate Similarity	NPD2235	Phase 2
0.7234	Intermediate Similarity	NPD3847	Discontinued
0.7219	Intermediate Similarity	NPD9570	Approved
0.7197	Intermediate Similarity	NPD7131	Phase 3
0.7188	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD257	Approved
0.7172	Intermediate Similarity	NPD258	Approved
0.7152	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7608	Discontinued
0.7152	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5746	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7125	Intermediate Similarity	NPD6677	Suspended
0.7125	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2030	Discontinued
0.7121	Intermediate Similarity	NPD9610	Approved
0.7121	Intermediate Similarity	NPD9608	Approved
0.7114	Intermediate Similarity	NPD825	Approved
0.7114	Intermediate Similarity	NPD826	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD7450	Phase 2
0.7103	Intermediate Similarity	NPD1203	Approved
0.7086	Intermediate Similarity	NPD5688	Approved
0.7086	Intermediate Similarity	NPD5689	Approved
0.7075	Intermediate Similarity	NPD596	Approved
0.7075	Intermediate Similarity	NPD600	Approved
0.7073	Intermediate Similarity	NPD5709	Phase 3
0.707	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6502	Phase 2
0.7055	Intermediate Similarity	NPD558	Phase 2
0.7044	Intermediate Similarity	NPD3686	Approved
0.7044	Intermediate Similarity	NPD3687	Approved
0.7037	Intermediate Similarity	NPD7972	Discontinued
0.703	Intermediate Similarity	NPD4666	Phase 3
0.7025	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6390	Discontinued
0.702	Intermediate Similarity	NPD2653	Approved
0.7018	Intermediate Similarity	NPD7039	Approved
0.7018	Intermediate Similarity	NPD7038	Approved
0.7014	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD3769	Discontinued
0.6986	Remote Similarity	NPD2797	Approved
0.698	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6798	Discontinued
0.698	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6315	Phase 2
0.6966	Remote Similarity	NPD6582	Phase 2
0.6966	Remote Similarity	NPD6583	Phase 3
0.6957	Remote Similarity	NPD5535	Approved
0.6954	Remote Similarity	NPD4618	Approved
0.6954	Remote Similarity	NPD4622	Approved
0.6943	Remote Similarity	NPD6667	Approved
0.6943	Remote Similarity	NPD6666	Approved
0.6933	Remote Similarity	NPD4062	Phase 3
0.6923	Remote Similarity	NPD3400	Discontinued
0.6918	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2203	Discontinued
0.6883	Remote Similarity	NPD6032	Approved
0.6883	Remote Similarity	NPD2935	Discontinued
0.6882	Remote Similarity	NPD3909	Discontinued
0.6875	Remote Similarity	NPD7427	Discontinued
0.6871	Remote Similarity	NPD1817	Approved
0.6871	Remote Similarity	NPD1818	Approved
0.6871	Remote Similarity	NPD1820	Approved
0.6871	Remote Similarity	NPD8019	Approved
0.6871	Remote Similarity	NPD1819	Approved
0.6867	Remote Similarity	NPD3268	Approved
0.6861	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2460	Phase 3
0.6859	Remote Similarity	NPD2459	Approved
0.6859	Remote Similarity	NPD2458	Approved
0.6849	Remote Similarity	NPD2428	Approved
0.6849	Remote Similarity	NPD2429	Approved
0.6849	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD274	Approved
0.6842	Remote Similarity	NPD275	Approved
0.6839	Remote Similarity	NPD7978	Discontinued
0.6839	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6746	Phase 2
0.6824	Remote Similarity	NPD6584	Phase 3
0.6806	Remote Similarity	NPD17	Approved
0.6806	Remote Similarity	NPD2556	Approved
0.6806	Remote Similarity	NPD2554	Approved
0.6803	Remote Similarity	NPD3225	Approved
0.6803	Remote Similarity	NPD1283	Approved
0.6802	Remote Similarity	NPD5557	Phase 1
0.68	Remote Similarity	NPD6179	Discontinued
0.6794	Remote Similarity	NPD9566	Approved
0.6792	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1241	Discontinued
0.6783	Remote Similarity	NPD1759	Phase 1
0.6781	Remote Similarity	NPD2562	Approved
0.6781	Remote Similarity	NPD9717	Approved
0.6781	Remote Similarity	NPD2561	Approved
0.677	Remote Similarity	NPD7523	Phase 3
0.6768	Remote Similarity	NPD7495	Discontinued
0.6768	Remote Similarity	NPD4433	Discontinued
0.6763	Remote Similarity	NPD6297	Approved
0.6755	Remote Similarity	NPD2313	Discontinued
0.6752	Remote Similarity	NPD4162	Approved
0.6752	Remote Similarity	NPD3060	Approved
0.675	Remote Similarity	NPD2874	Phase 2
0.6738	Remote Similarity	NPD9614	Approved
0.6738	Remote Similarity	NPD593	Approved
0.6738	Remote Similarity	NPD595	Approved
0.6738	Remote Similarity	NPD9618	Approved
0.6736	Remote Similarity	NPD6382	Discontinued
0.6736	Remote Similarity	NPD3049	Approved
0.6731	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3366	Approved
0.6713	Remote Similarity	NPD317	Approved
0.6713	Remote Similarity	NPD1758	Phase 1
0.6713	Remote Similarity	NPD318	Approved
0.6712	Remote Similarity	NPD422	Phase 1
0.6711	Remote Similarity	NPD839	Approved
0.6711	Remote Similarity	NPD840	Approved
0.6711	Remote Similarity	NPD3691	Phase 2
0.6711	Remote Similarity	NPD3690	Phase 2
0.6711	Remote Similarity	NPD7451	Discontinued
0.6711	Remote Similarity	NPD7477	Discontinued
0.6711	Remote Similarity	NPD1423	Approved
0.671	Remote Similarity	NPD2799	Discontinued
0.6709	Remote Similarity	NPD4110	Phase 3
0.6709	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3750	Approved
0.6708	Remote Similarity	NPD2186	Approved
0.6708	Remote Similarity	NPD2676	Approved
0.6708	Remote Similarity	NPD2675	Approved
0.6707	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD955	Approved
0.6707	Remote Similarity	NPD8031	Discontinued
0.6707	Remote Similarity	NPD6386	Approved
0.6707	Remote Similarity	NPD6385	Approved
0.6705	Remote Similarity	NPD6851	Approved
0.6705	Remote Similarity	NPD6853	Approved
0.669	Remote Similarity	NPD2667	Approved
0.669	Remote Similarity	NPD2668	Approved
0.6689	Remote Similarity	NPD3166	Approved
0.6689	Remote Similarity	NPD3167	Approved
0.6689	Remote Similarity	NPD3164	Approved
0.6689	Remote Similarity	NPD3179	Approved
0.6689	Remote Similarity	NPD3165	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD3180	Approved
0.6688	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7485	Phase 3
0.6686	Remote Similarity	NPD6620	Discovery
0.6686	Remote Similarity	NPD7484	Phase 3
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD454	Approved
0.6667	Remote Similarity	NPD592	Approved
0.6667	Remote Similarity	NPD594	Approved
0.6647	Remote Similarity	NPD5095	Phase 3

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