NPASS Compound

Structure

CID266931 OpenBabel06191716072D 26 28 0 0 0 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0660 -1.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7570 -2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 6.4187 -0.6422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3969 -0.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -2.3364 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -3.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7059 0.5168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 15 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 3 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.14
Volume:	362.233
LogP:	2.69
LogD:	2.958
LogS:	-3.581
# Rotatable Bonds:	7
TPSA:	94.58
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	2.299
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.303
MDCK Permeability:	7.65647564548999e-06
Pgp-inhibitor:	0.026
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	96.98847198486328%
Volume Distribution (VD):	0.747
Pgp-substrate:	1.7999699115753174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	9.469
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.372
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.32
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.943
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.572

Download Data

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

Natural Product: NPC266931

Natural Product ID:	NPC266931
*Common Name:**	N-Feruloyl Serotonin
IUPAC Name:	(E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Synonyms:	N-Feruloyl Serotonin; N-Feruloylserotonin
Standard InCHIKey:	WGHKJYWENWLOMY-XVNBXDOJSA-N
Standard InCHI:	InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+
SMILES:	COc1cc(/C=C/C(=NCCc2c[nH]c3c2cc(O)cc3)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564482
PubChem CID:	5969616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives [CHEMONTID:0001637] Serotonins [CHEMONTID:0004271] N-acylserotonins

*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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11352	Centaurea cyanus	Species	Asteraceae	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
EC50	1
IC50	7
Ki	1
Others	7

Activity Type	# Activity
Cell Line	6
Individual Protein	8
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Activity	=	100.0	%	PMID[529566]
NPT319	Cell Line	B16	Mus musculus	IC50	=	23000.0	nM	PMID[529566]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Activity	=	29.0	%	PMID[529566]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	IC50	=	216000.0	nM	PMID[529566]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	8000.0	nM	PMID[529567]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	2.7	%	PMID[529568]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	18.8	%	PMID[529568]
NPT526	Individual Protein	Alpha-glucosidase MAL62	Saccharomyces cerevisiae	Ki	=	129800.0	nM	PMID[529569]
NPT526	Individual Protein	Alpha-glucosidase MAL62	Saccharomyces cerevisiae	IC50	=	99800.0	nM	PMID[529569]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	123140.0	nM	PMID[529571]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14740.0	nM	PMID[529571]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	52.17	%	PMID[529571]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	25.1	%	PMID[529571]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	48.0	%	PMID[529566]
NPT1	Others	Radical scavenging activity		EC50	=	22800.0	nM	PMID[529567]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	81000.0	nM	PMID[529570]

☑ 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 NPC266931 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	482
0.1-0.2	3743
0.2-0.3	13522
0.3-0.4	5071
0.4-0.5	12741
0.5-0.6	4317
0.6-0.7	2159
0.7-0.8	579
0.8-0.85	63
0.85-0.9	17
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9433	High Similarity	NPC316981
0.9048	High Similarity	NPC307963
0.8995	High Similarity	NPC99666
0.8969	High Similarity	NPC135887
0.8969	High Similarity	NPC199277
0.8889	High Similarity	NPC76748
0.8854	High Similarity	NPC251090
0.8842	High Similarity	NPC92111
0.8836	High Similarity	NPC296527
0.8726	High Similarity	NPC295228
0.8677	High Similarity	NPC314002
0.8647	High Similarity	NPC280272
0.8632	High Similarity	NPC171171
0.8624	High Similarity	NPC204717
0.8608	High Similarity	NPC326634
0.8571	High Similarity	NPC220765
0.8565	High Similarity	NPC217554
0.8532	High Similarity	NPC284141
0.852	High Similarity	NPC77555
0.8485	Intermediate Similarity	NPC176538
0.848	Intermediate Similarity	NPC202605
0.848	Intermediate Similarity	NPC112206
0.8473	Intermediate Similarity	NPC11464
0.8472	Intermediate Similarity	NPC11408
0.845	Intermediate Similarity	NPC223427
0.841	Intermediate Similarity	NPC133140
0.841	Intermediate Similarity	NPC195268
0.836	Intermediate Similarity	NPC184964
0.8341	Intermediate Similarity	NPC208284
0.8333	Intermediate Similarity	NPC156704
0.8325	Intermediate Similarity	NPC213530
0.8325	Intermediate Similarity	NPC193267
0.8317	Intermediate Similarity	NPC285558
0.83	Intermediate Similarity	NPC234197
0.8299	Intermediate Similarity	NPC46580
0.8284	Intermediate Similarity	NPC476465
0.8281	Intermediate Similarity	NPC176127
0.8278	Intermediate Similarity	NPC204446
0.825	Intermediate Similarity	NPC4071
0.825	Intermediate Similarity	NPC476578
0.825	Intermediate Similarity	NPC476582
0.8235	Intermediate Similarity	NPC193777
0.8227	Intermediate Similarity	NPC475070
0.8182	Intermediate Similarity	NPC170114
0.8174	Intermediate Similarity	NPC473183
0.8168	Intermediate Similarity	NPC232727
0.815	Intermediate Similarity	NPC70956
0.815	Intermediate Similarity	NPC243834
0.8146	Intermediate Similarity	NPC313189
0.8137	Intermediate Similarity	NPC16452
0.8137	Intermediate Similarity	NPC476581
0.8137	Intermediate Similarity	NPC36229
0.8134	Intermediate Similarity	NPC470549
0.8122	Intermediate Similarity	NPC118121
0.8119	Intermediate Similarity	NPC477019
0.8116	Intermediate Similarity	NPC5145
0.81	Intermediate Similarity	NPC13880
0.8088	Intermediate Similarity	NPC475774
0.8082	Intermediate Similarity	NPC473184
0.8071	Intermediate Similarity	NPC32771
0.8058	Intermediate Similarity	NPC88008
0.805	Intermediate Similarity	NPC131017
0.804	Intermediate Similarity	NPC324149
0.8038	Intermediate Similarity	NPC53069
0.8038	Intermediate Similarity	NPC202768
0.8038	Intermediate Similarity	NPC296482
0.8037	Intermediate Similarity	NPC122463
0.803	Intermediate Similarity	NPC315491
0.803	Intermediate Similarity	NPC45459
0.8029	Intermediate Similarity	NPC167860
0.8029	Intermediate Similarity	NPC123976
0.8028	Intermediate Similarity	NPC174049
0.8019	Intermediate Similarity	NPC473822
0.799	Intermediate Similarity	NPC31930
0.7972	Intermediate Similarity	NPC110151
0.7971	Intermediate Similarity	NPC135549
0.7969	Intermediate Similarity	NPC312872
0.7959	Intermediate Similarity	NPC84478
0.7952	Intermediate Similarity	NPC48353
0.7943	Intermediate Similarity	NPC188420
0.7941	Intermediate Similarity	NPC213308
0.7941	Intermediate Similarity	NPC329793
0.7938	Intermediate Similarity	NPC88363
0.7934	Intermediate Similarity	NPC173080
0.7925	Intermediate Similarity	NPC470799
0.7925	Intermediate Similarity	NPC8022
0.7915	Intermediate Similarity	NPC469592
0.7915	Intermediate Similarity	NPC471080
0.7915	Intermediate Similarity	NPC271215
0.7915	Intermediate Similarity	NPC149471
0.7915	Intermediate Similarity	NPC477610
0.7913	Intermediate Similarity	NPC245816
0.7913	Intermediate Similarity	NPC162484
0.7913	Intermediate Similarity	NPC476138
0.7907	Intermediate Similarity	NPC60621
0.7907	Intermediate Similarity	NPC310118
0.7887	Intermediate Similarity	NPC96890
0.7873	Intermediate Similarity	NPC473182
0.7867	Intermediate Similarity	NPC171409
0.7867	Intermediate Similarity	NPC251160
0.7867	Intermediate Similarity	NPC96405
0.7864	Intermediate Similarity	NPC475085
0.7864	Intermediate Similarity	NPC291535
0.7864	Intermediate Similarity	NPC475112
0.7857	Intermediate Similarity	NPC290689
0.7854	Intermediate Similarity	NPC19872
0.7854	Intermediate Similarity	NPC315957
0.785	Intermediate Similarity	NPC469594
0.7848	Intermediate Similarity	NPC15801
0.7838	Intermediate Similarity	NPC277351
0.783	Intermediate Similarity	NPC162530
0.783	Intermediate Similarity	NPC478074
0.7814	Intermediate Similarity	NPC74360
0.7808	Intermediate Similarity	NPC473185
0.7805	Intermediate Similarity	NPC128823
0.7804	Intermediate Similarity	NPC476041
0.7804	Intermediate Similarity	NPC304926
0.78	Intermediate Similarity	NPC128751
0.78	Intermediate Similarity	NPC246700
0.7794	Intermediate Similarity	NPC153042
0.7793	Intermediate Similarity	NPC235076
0.7789	Intermediate Similarity	NPC204385
0.7788	Intermediate Similarity	NPC118832
0.7788	Intermediate Similarity	NPC165349
0.7788	Intermediate Similarity	NPC329708
0.7788	Intermediate Similarity	NPC264166
0.7788	Intermediate Similarity	NPC274291
0.7788	Intermediate Similarity	NPC47059
0.7788	Intermediate Similarity	NPC470500
0.7783	Intermediate Similarity	NPC201508
0.7783	Intermediate Similarity	NPC26679
0.7778	Intermediate Similarity	NPC276657
0.7778	Intermediate Similarity	NPC132642
0.7773	Intermediate Similarity	NPC471304
0.7767	Intermediate Similarity	NPC100079
0.7767	Intermediate Similarity	NPC23614
0.7767	Intermediate Similarity	NPC477609
0.7767	Intermediate Similarity	NPC249040
0.7767	Intermediate Similarity	NPC329747
0.7767	Intermediate Similarity	NPC121772
0.7766	Intermediate Similarity	NPC206201
0.7763	Intermediate Similarity	NPC214980
0.7762	Intermediate Similarity	NPC475910
0.7761	Intermediate Similarity	NPC469497
0.7761	Intermediate Similarity	NPC106833
0.7755	Intermediate Similarity	NPC72980
0.7745	Intermediate Similarity	NPC222018
0.7745	Intermediate Similarity	NPC242209
0.7742	Intermediate Similarity	NPC473317
0.7734	Intermediate Similarity	NPC106937
0.7725	Intermediate Similarity	NPC185782
0.7718	Intermediate Similarity	NPC476167
0.7717	Intermediate Similarity	NPC125597
0.7713	Intermediate Similarity	NPC255800
0.7713	Intermediate Similarity	NPC96584
0.77	Intermediate Similarity	NPC94157
0.7692	Intermediate Similarity	NPC252251
0.7684	Intermediate Similarity	NPC131718
0.7682	Intermediate Similarity	NPC24370
0.7682	Intermediate Similarity	NPC319232
0.7678	Intermediate Similarity	NPC171787
0.7678	Intermediate Similarity	NPC82548
0.7674	Intermediate Similarity	NPC288349
0.767	Intermediate Similarity	NPC192315
0.767	Intermediate Similarity	NPC72211
0.7667	Intermediate Similarity	NPC476106
0.7664	Intermediate Similarity	NPC236668
0.7653	Intermediate Similarity	NPC246518
0.765	Intermediate Similarity	NPC46451
0.765	Intermediate Similarity	NPC473179
0.765	Intermediate Similarity	NPC94943
0.7644	Intermediate Similarity	NPC272549
0.7642	Intermediate Similarity	NPC201697
0.7642	Intermediate Similarity	NPC476116
0.7634	Intermediate Similarity	NPC323752
0.7628	Intermediate Similarity	NPC146976
0.7624	Intermediate Similarity	NPC242928
0.7623	Intermediate Similarity	NPC477531
0.7619	Intermediate Similarity	NPC210256
0.7617	Intermediate Similarity	NPC219087
0.7604	Intermediate Similarity	NPC102423
0.7604	Intermediate Similarity	NPC264285
0.7604	Intermediate Similarity	NPC311276
0.76	Intermediate Similarity	NPC190007
0.7594	Intermediate Similarity	NPC477111
0.7594	Intermediate Similarity	NPC18348
0.7591	Intermediate Similarity	NPC130570
0.7589	Intermediate Similarity	NPC469554
0.7583	Intermediate Similarity	NPC472111
0.7581	Intermediate Similarity	NPC476287
0.758	Intermediate Similarity	NPC477532
0.7578	Intermediate Similarity	NPC209174
0.7577	Intermediate Similarity	NPC63751
0.7573	Intermediate Similarity	NPC70259
0.7565	Intermediate Similarity	NPC78609
0.7562	Intermediate Similarity	NPC163421
0.7562	Intermediate Similarity	NPC188387
0.7559	Intermediate Similarity	NPC469589
0.7551	Intermediate Similarity	NPC474409
0.7551	Intermediate Similarity	NPC313791

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 NPC266931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	706
0.2-0.3	859
0.3-0.4	1356
0.4-0.5	2467
0.5-0.6	2346
0.6-0.7	956
0.7-0.8	185
0.8-0.85	18
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9289	High Similarity	NPD5612	Discontinued
0.9048	High Similarity	NPD1038	Approved
0.8848	High Similarity	NPD1304	Clinical (unspecified phase)
0.8653	High Similarity	NPD5575	Clinical (unspecified phase)
0.865	High Similarity	NPD5658	Approved
0.8426	Intermediate Similarity	NPD7948	Phase 1
0.841	Intermediate Similarity	NPD3923	Approved
0.841	Intermediate Similarity	NPD3924	Approved
0.841	Intermediate Similarity	NPD3921	Approved
0.841	Intermediate Similarity	NPD3922	Approved
0.8342	Intermediate Similarity	NPD3825	Phase 3
0.8284	Intermediate Similarity	NPD2187	Approved
0.8284	Intermediate Similarity	NPD2189	Approved
0.8252	Intermediate Similarity	NPD5066	Phase 2
0.8252	Intermediate Similarity	NPD5067	Phase 2
0.8221	Intermediate Similarity	NPD5903	Approved
0.8221	Intermediate Similarity	NPD5902	Approved
0.8203	Intermediate Similarity	NPD7558	Phase 2
0.8203	Intermediate Similarity	NPD6494	Phase 2
0.8199	Intermediate Similarity	NPD6242	Discontinued
0.8173	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1392	Approved
0.8141	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3003	Approved
0.8069	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD7222	Phase 2
0.8058	Intermediate Similarity	NPD7452	Approved
0.8058	Intermediate Similarity	NPD7453	Approved
0.8038	Intermediate Similarity	NPD3815	Phase 1
0.8038	Intermediate Similarity	NPD3816	Phase 1
0.803	Intermediate Similarity	NPD484	Approved
0.801	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4795	Phase 2
0.796	Intermediate Similarity	NPD4418	Discontinued
0.7925	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1954	Phase 1
0.7854	Intermediate Similarity	NPD1740	Approved
0.7854	Intermediate Similarity	NPD1739	Approved
0.7854	Intermediate Similarity	NPD5559	Phase 2
0.785	Intermediate Similarity	NPD3354	Phase 2
0.7846	Intermediate Similarity	NPD3920	Phase 2
0.7839	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8512	Phase 3
0.7805	Intermediate Similarity	NPD1768	Approved
0.7804	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4454	Phase 2
0.7793	Intermediate Similarity	NPD4080	Discontinued
0.7788	Intermediate Similarity	NPD4038	Approved
0.7788	Intermediate Similarity	NPD4033	Approved
0.7788	Intermediate Similarity	NPD4035	Approved
0.7788	Intermediate Similarity	NPD4034	Approved
0.7788	Intermediate Similarity	NPD4122	Approved
0.7788	Intermediate Similarity	NPD31	Approved
0.7788	Intermediate Similarity	NPD32	Approved
0.7788	Intermediate Similarity	NPD4037	Approved
0.7788	Intermediate Similarity	NPD4036	Approved
0.7788	Intermediate Similarity	NPD4039	Approved
0.7772	Intermediate Similarity	NPD4083	Discontinued
0.7767	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6964	Approved
0.7758	Intermediate Similarity	NPD6963	Approved
0.7748	Intermediate Similarity	NPD4885	Approved
0.7736	Intermediate Similarity	NPD4502	Phase 2
0.7736	Intermediate Similarity	NPD4131	Phase 3
0.7734	Intermediate Similarity	NPD802	Phase 2
0.7709	Intermediate Similarity	NPD4876	Phase 3
0.7709	Intermediate Similarity	NPD4875	Phase 3
0.7706	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5065	Approved
0.7668	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD3763	Approved
0.7644	Intermediate Similarity	NPD4511	Phase 1
0.7642	Intermediate Similarity	NPD6230	Discontinued
0.7617	Intermediate Similarity	NPD8091	Phase 3
0.7615	Intermediate Similarity	NPD5930	Phase 3
0.7602	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6569	Phase 2
0.7555	Intermediate Similarity	NPD6517	Phase 3
0.7536	Intermediate Similarity	NPD3397	Phase 2
0.7536	Intermediate Similarity	NPD2952	Discontinued
0.7534	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7859	Phase 2
0.7511	Intermediate Similarity	NPD6243	Phase 3
0.7511	Intermediate Similarity	NPD6244	Phase 3
0.7489	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD949	Phase 1
0.7475	Intermediate Similarity	NPD4889	Approved
0.7467	Intermediate Similarity	NPD5905	Phase 1
0.7455	Intermediate Similarity	NPD7555	Discontinued
0.745	Intermediate Similarity	NPD6595	Phase 3
0.7449	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6985	Discontinued
0.7429	Intermediate Similarity	NPD6219	Discontinued
0.7422	Intermediate Similarity	NPD7567	Approved
0.7418	Intermediate Similarity	NPD8403	Phase 1
0.7418	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4203	Approved
0.7413	Intermediate Similarity	NPD4204	Approved
0.7411	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7194	Discontinued
0.7407	Intermediate Similarity	NPD7470	Discontinued
0.7399	Intermediate Similarity	NPD7719	Discontinued
0.7391	Intermediate Similarity	NPD4551	Phase 2
0.7389	Intermediate Similarity	NPD4995	Approved
0.7389	Intermediate Similarity	NPD4996	Approved
0.7381	Intermediate Similarity	NPD3814	Phase 1
0.7373	Intermediate Similarity	NPD7069	Discontinued
0.7366	Intermediate Similarity	NPD4021	Phase 2
0.7366	Intermediate Similarity	NPD7603	Discontinued
0.736	Intermediate Similarity	NPD1325	Approved
0.736	Intermediate Similarity	NPD1326	Approved
0.7358	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4072	Approved
0.735	Intermediate Similarity	NPD4071	Approved
0.7345	Intermediate Similarity	NPD4925	Approved
0.734	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3402	Phase 1
0.7325	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5164	Discontinued
0.7315	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8442	Discontinued
0.7306	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4548	Discontinued
0.7299	Intermediate Similarity	NPD2176	Approved
0.7299	Intermediate Similarity	NPD2175	Phase 3
0.7299	Intermediate Similarity	NPD2177	Approved
0.7295	Intermediate Similarity	NPD5641	Discontinued
0.7294	Intermediate Similarity	NPD3330	Phase 1
0.7285	Intermediate Similarity	NPD5632	Approved
0.7277	Intermediate Similarity	NPD6975	Discontinued
0.7277	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3396	Approved
0.7273	Intermediate Similarity	NPD3395	Approved
0.7269	Intermediate Similarity	NPD5022	Discontinued
0.7269	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6530	Approved
0.7261	Intermediate Similarity	NPD6531	Approved
0.726	Intermediate Similarity	NPD5944	Phase 1
0.726	Intermediate Similarity	NPD5945	Phase 1
0.7256	Intermediate Similarity	NPD5530	Phase 1
0.7253	Intermediate Similarity	NPD6473	Phase 1
0.7249	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD8431	Approved
0.7232	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4343	Phase 1
0.7225	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6290	Phase 2
0.7222	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8395	Approved
0.7217	Intermediate Similarity	NPD8396	Approved
0.7217	Intermediate Similarity	NPD5999	Phase 2
0.7212	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5913	Phase 3
0.7207	Intermediate Similarity	NPD4429	Discontinued
0.7198	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3931	Approved
0.7196	Intermediate Similarity	NPD3928	Approved
0.7195	Intermediate Similarity	NPD7112	Discontinued
0.7193	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4350	Approved
0.7191	Intermediate Similarity	NPD4349	Approved
0.719	Intermediate Similarity	NPD6590	Discontinued
0.7189	Intermediate Similarity	NPD5529	Phase 1
0.7189	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4375	Approved
0.7182	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4845	Discontinued
0.7179	Intermediate Similarity	NPD5833	Phase 1
0.7173	Intermediate Similarity	NPD4558	Phase 2
0.7169	Intermediate Similarity	NPD5936	Approved
0.7169	Intermediate Similarity	NPD5939	Approved
0.7169	Intermediate Similarity	NPD6220	Phase 3
0.7167	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3386	Phase 2
0.7156	Intermediate Similarity	NPD1856	Discontinued
0.715	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4897	Phase 2
0.7149	Intermediate Similarity	NPD7067	Approved
0.7149	Intermediate Similarity	NPD7068	Approved
0.7143	Intermediate Similarity	NPD6856	Discontinued
0.7136	Intermediate Similarity	NPD5097	Phase 2
0.7136	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2781	Approved
0.713	Intermediate Similarity	NPD5901	Discontinued
0.7123	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2092	Phase 2
0.7122	Intermediate Similarity	NPD2095	Phase 2
0.7122	Intermediate Similarity	NPD2094	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