NPASS Compound

Structure

CID47653 OpenBabel06191715382D 26 26 0 0 1 0 0 0 0 0999 V2000 12.5662 -7.6050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9730 -6.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3852 -5.8825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3906 -5.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8029 -5.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8083 -5.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2206 -4.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2260 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6382 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6437 -3.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0559 -3.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0614 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4736 -2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4791 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8913 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4901 -2.6736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 16 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.26
Volume:	399.257
LogP:	6.977
LogD:	4.438
LogS:	-3.511
# Rotatable Bonds:	16
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	2.652
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.958
MDCK Permeability:	2.526546631997917e-05
Pgp-inhibitor:	0.627
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	99.9429931640625%
Volume Distribution (VD):	2.419
Pgp-substrate:	1.384075403213501%

ADMET: Metabolism

CYP1A2-inhibitor:	0.394
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.567
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.4
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	4.275
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.417
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.768
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.134
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC47653

Natural Product ID:	NPC47653
*Common Name:**	(R)-5-Ethyl-3-Hexadecanoyl-4-Methyl-5H-Furan-2-Oneo
IUPAC Name:	(2R)-4-hexadecanoyl-3-hydroxy-2-(hydroxymethyl)-2H-furan-5-one
Synonyms:	RK-682
Standard InCHIKey:	KZTSLHQKWLYYAC-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C21H36O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(23)19-20(24)18(16-22)26-21(19)25/h18,22,24H,2-16H2,1H3/t18-/m1/s1
SMILES:	CCCCCCCCCCCCCCCC(=O)C1=C(O)[C@H](OC1=O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426373
PubChem CID:	54678922
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO31296	Rhododendron brachycarpum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/BF02856638]
NPO30392	Morus	Genus	Sulidae	Eukaryota	root bark	n.a.	n.a.	PMID[16356713]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16580200]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO15696	Polytrichastrum alpinum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053716]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288807]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO30392	Morus	Genus	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21319773]
NPO30392	Morus	Genus	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22297755]
NPO31296	Rhododendron brachycarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940448]
NPO40840	Eremophila spp.	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26960032]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29878768]
NPO40121	Eremophila oppositifolia subsp. Angustifolia	Strain	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32255628]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15696	Polytrichastrum alpinum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	Species	Fabaceae	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	34
Others	1

Activity Type	# Activity
Cell Line	4
Individual Protein	29
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	IC50	=	11600.0	nM	PMID[573499]
NPT3011	Individual Protein	Dual specificity phosphatase Cdc25B	Mus musculus	IC50	=	2200.0	nM	PMID[573499]
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	IC50	=	11700.0	nM	PMID[573500]
NPT3011	Individual Protein	Dual specificity phosphatase Cdc25B	Mus musculus	IC50	=	5100.0	nM	PMID[573500]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573501]
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	IC50	=	10200.0	nM	PMID[573501]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4.5	nM	PMID[573502]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573503]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573504]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	45000.0	nM	PMID[573505]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573506]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573507]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4100.0	nM	PMID[573508]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4700.0	nM	PMID[573509]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573510]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4700.0	nM	PMID[573511]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573512]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[573512]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[573512]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4400.0	nM	PMID[573513]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4000.0	nM	PMID[573514]
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	IC50	=	5100.0	nM	PMID[573515]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5620.0	nM	PMID[573515]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	99.1	%	PMID[573515]
NPT3012	Individual Protein	Heparanase	Homo sapiens	IC50	=	17000.0	nM	PMID[573516]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4600.0	nM	PMID[573517]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4490.0	nM	PMID[573518]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4500.0	nM	PMID[573519]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4400.0	nM	PMID[573520]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	4400.0	nM	PMID[573521]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	7300.0	nM	PMID[573522]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[573499]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[573500]

☑ 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 NPC47653 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	227
0.1-0.2	1967
0.2-0.3	6057
0.3-0.4	14912
0.4-0.5	12007
0.5-0.6	5423
0.6-0.7	1704
0.7-0.8	378
0.8-0.85	12
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC144419
0.8256	Intermediate Similarity	NPC130359
0.8256	Intermediate Similarity	NPC14901
0.8214	Intermediate Similarity	NPC307126
0.8214	Intermediate Similarity	NPC68303
0.8193	Intermediate Similarity	NPC144415
0.8118	Intermediate Similarity	NPC308412
0.8118	Intermediate Similarity	NPC210218
0.8118	Intermediate Similarity	NPC219498
0.8118	Intermediate Similarity	NPC204686
0.8118	Intermediate Similarity	NPC477015
0.8118	Intermediate Similarity	NPC134885
0.8118	Intermediate Similarity	NPC473687
0.8118	Intermediate Similarity	NPC134807
0.8095	Intermediate Similarity	NPC163093
0.8072	Intermediate Similarity	NPC475159
0.8072	Intermediate Similarity	NPC473529
0.8072	Intermediate Similarity	NPC473712
0.8072	Intermediate Similarity	NPC180363
0.8072	Intermediate Similarity	NPC65930
0.8072	Intermediate Similarity	NPC11332
0.8072	Intermediate Similarity	NPC94875
0.8072	Intermediate Similarity	NPC73310
0.8072	Intermediate Similarity	NPC131002
0.8072	Intermediate Similarity	NPC329829
0.8072	Intermediate Similarity	NPC473780
0.8072	Intermediate Similarity	NPC145914
0.8023	Intermediate Similarity	NPC178215
0.8	Intermediate Similarity	NPC120398
0.8	Intermediate Similarity	NPC477014
0.8	Intermediate Similarity	NPC1083
0.8	Intermediate Similarity	NPC182383
0.8	Intermediate Similarity	NPC82795
0.8	Intermediate Similarity	NPC110710
0.8	Intermediate Similarity	NPC283085
0.8	Intermediate Similarity	NPC107986
0.8	Intermediate Similarity	NPC286338
0.8	Intermediate Similarity	NPC223871
0.8	Intermediate Similarity	NPC471567
0.8	Intermediate Similarity	NPC103284
0.8	Intermediate Similarity	NPC231009
0.8	Intermediate Similarity	NPC473669
0.8	Intermediate Similarity	NPC66346
0.8	Intermediate Similarity	NPC132496
0.8	Intermediate Similarity	NPC473478
0.8	Intermediate Similarity	NPC477013
0.8	Intermediate Similarity	NPC473651
0.7976	Intermediate Similarity	NPC253801
0.7931	Intermediate Similarity	NPC280621
0.7931	Intermediate Similarity	NPC20339
0.7931	Intermediate Similarity	NPC233551
0.7931	Intermediate Similarity	NPC48338
0.7931	Intermediate Similarity	NPC21208
0.7931	Intermediate Similarity	NPC40376
0.7907	Intermediate Similarity	NPC62118
0.7907	Intermediate Similarity	NPC103523
0.7907	Intermediate Similarity	NPC134865
0.7907	Intermediate Similarity	NPC231096
0.7907	Intermediate Similarity	NPC279267
0.7907	Intermediate Similarity	NPC469483
0.7907	Intermediate Similarity	NPC477010
0.7907	Intermediate Similarity	NPC142117
0.7907	Intermediate Similarity	NPC69082
0.7907	Intermediate Similarity	NPC107717
0.7907	Intermediate Similarity	NPC47937
0.7907	Intermediate Similarity	NPC171174
0.7907	Intermediate Similarity	NPC114694
0.7907	Intermediate Similarity	NPC232555
0.7907	Intermediate Similarity	NPC112685
0.7907	Intermediate Similarity	NPC475581
0.7907	Intermediate Similarity	NPC240695
0.7882	Intermediate Similarity	NPC156804
0.7865	Intermediate Similarity	NPC327760
0.7841	Intermediate Similarity	NPC477016
0.7841	Intermediate Similarity	NPC280612
0.7841	Intermediate Similarity	NPC477017
0.7816	Intermediate Similarity	NPC477012
0.7791	Intermediate Similarity	NPC292809
0.7791	Intermediate Similarity	NPC39279
0.7791	Intermediate Similarity	NPC202055
0.7791	Intermediate Similarity	NPC473156
0.7791	Intermediate Similarity	NPC470400
0.7791	Intermediate Similarity	NPC235809
0.7791	Intermediate Similarity	NPC329615
0.7791	Intermediate Similarity	NPC77871
0.7791	Intermediate Similarity	NPC319036
0.7791	Intermediate Similarity	NPC475268
0.7791	Intermediate Similarity	NPC39167
0.7791	Intermediate Similarity	NPC25764
0.7791	Intermediate Similarity	NPC477018
0.7791	Intermediate Similarity	NPC322529
0.7791	Intermediate Similarity	NPC329838
0.7791	Intermediate Similarity	NPC9678
0.7791	Intermediate Similarity	NPC473671
0.7791	Intermediate Similarity	NPC100921
0.7778	Intermediate Similarity	NPC469692
0.7778	Intermediate Similarity	NPC469645
0.7765	Intermediate Similarity	NPC286770
0.7765	Intermediate Similarity	NPC284472
0.7765	Intermediate Similarity	NPC185256
0.7765	Intermediate Similarity	NPC229799
0.7753	Intermediate Similarity	NPC239517
0.7727	Intermediate Similarity	NPC39754
0.7727	Intermediate Similarity	NPC61257
0.7727	Intermediate Similarity	NPC171135
0.7727	Intermediate Similarity	NPC191929
0.7727	Intermediate Similarity	NPC320458
0.7727	Intermediate Similarity	NPC89001
0.7727	Intermediate Similarity	NPC274446
0.7727	Intermediate Similarity	NPC169511
0.7727	Intermediate Similarity	NPC242364
0.7727	Intermediate Similarity	NPC261952
0.7727	Intermediate Similarity	NPC81045
0.7727	Intermediate Similarity	NPC287164
0.7727	Intermediate Similarity	NPC133730
0.7727	Intermediate Similarity	NPC151403
0.7727	Intermediate Similarity	NPC320569
0.7727	Intermediate Similarity	NPC234077
0.7727	Intermediate Similarity	NPC473905
0.7727	Intermediate Similarity	NPC172821
0.7727	Intermediate Similarity	NPC100454
0.7701	Intermediate Similarity	NPC472009
0.7701	Intermediate Similarity	NPC309211
0.7701	Intermediate Similarity	NPC25703
0.7701	Intermediate Similarity	NPC241360
0.7701	Intermediate Similarity	NPC132940
0.7701	Intermediate Similarity	NPC293136
0.7701	Intermediate Similarity	NPC261721
0.7701	Intermediate Similarity	NPC219652
0.7701	Intermediate Similarity	NPC473840
0.7701	Intermediate Similarity	NPC282815
0.7692	Intermediate Similarity	NPC121825
0.7683	Intermediate Similarity	NPC125365
0.7683	Intermediate Similarity	NPC176329
0.7683	Intermediate Similarity	NPC49302
0.7683	Intermediate Similarity	NPC51809
0.7683	Intermediate Similarity	NPC474818
0.7667	Intermediate Similarity	NPC6099
0.7667	Intermediate Similarity	NPC114345
0.7667	Intermediate Similarity	NPC303230
0.7654	Intermediate Similarity	NPC329826
0.7654	Intermediate Similarity	NPC469414
0.7647	Intermediate Similarity	NPC475046
0.7647	Intermediate Similarity	NPC474959
0.7647	Intermediate Similarity	NPC11383
0.7647	Intermediate Similarity	NPC310450
0.764	Intermediate Similarity	NPC139418
0.764	Intermediate Similarity	NPC93794
0.764	Intermediate Similarity	NPC40066
0.764	Intermediate Similarity	NPC318963
0.764	Intermediate Similarity	NPC91067
0.764	Intermediate Similarity	NPC42598
0.764	Intermediate Similarity	NPC477011
0.764	Intermediate Similarity	NPC81778
0.764	Intermediate Similarity	NPC20621
0.764	Intermediate Similarity	NPC473504
0.7614	Intermediate Similarity	NPC473995
0.7614	Intermediate Similarity	NPC472007
0.7614	Intermediate Similarity	NPC159750
0.7614	Intermediate Similarity	NPC473649
0.7614	Intermediate Similarity	NPC20533
0.7614	Intermediate Similarity	NPC476583
0.7614	Intermediate Similarity	NPC258068
0.7614	Intermediate Similarity	NPC154097
0.7614	Intermediate Similarity	NPC470401
0.7595	Intermediate Similarity	NPC42526
0.759	Intermediate Similarity	NPC279214
0.759	Intermediate Similarity	NPC473471
0.759	Intermediate Similarity	NPC221095
0.7582	Intermediate Similarity	NPC11456
0.7561	Intermediate Similarity	NPC301207
0.7561	Intermediate Similarity	NPC49392
0.7561	Intermediate Similarity	NPC190400
0.7558	Intermediate Similarity	NPC475947
0.7556	Intermediate Similarity	NPC474232
0.7556	Intermediate Similarity	NPC475879
0.7556	Intermediate Similarity	NPC473904
0.7531	Intermediate Similarity	NPC474321
0.7529	Intermediate Similarity	NPC150502
0.7528	Intermediate Similarity	NPC472008
0.75	Intermediate Similarity	NPC469910
0.75	Intermediate Similarity	NPC99651
0.75	Intermediate Similarity	NPC84038
0.7471	Intermediate Similarity	NPC31086
0.7442	Intermediate Similarity	NPC475690
0.7439	Intermediate Similarity	NPC260396
0.7436	Intermediate Similarity	NPC104537
0.7436	Intermediate Similarity	NPC271921
0.7436	Intermediate Similarity	NPC22101
0.7436	Intermediate Similarity	NPC127091
0.7436	Intermediate Similarity	NPC148192
0.7436	Intermediate Similarity	NPC330426
0.7412	Intermediate Similarity	NPC91332
0.7412	Intermediate Similarity	NPC162741
0.7407	Intermediate Similarity	NPC474705
0.7396	Intermediate Similarity	NPC472753
0.7391	Intermediate Similarity	NPC295204
0.7391	Intermediate Similarity	NPC473723
0.7391	Intermediate Similarity	NPC475173
0.7391	Intermediate Similarity	NPC473561

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 NPC47653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	2610
0.2-0.3	3653
0.3-0.4	1849
0.4-0.5	615
0.5-0.6	140
0.6-0.7	33
0.7-0.8	1
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
0.7363	Intermediate Similarity	NPD6698	Approved
0.7363	Intermediate Similarity	NPD46	Approved
0.6989	Remote Similarity	NPD5785	Approved
0.6966	Remote Similarity	NPD7154	Phase 3
0.6915	Remote Similarity	NPD7983	Approved
0.6875	Remote Similarity	NPD3704	Approved
0.6827	Remote Similarity	NPD6371	Approved
0.6813	Remote Similarity	NPD5363	Approved
0.6757	Remote Similarity	NPD3728	Approved
0.6757	Remote Similarity	NPD3730	Approved
0.6701	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6632	Remote Similarity	NPD7838	Discovery
0.6629	Remote Similarity	NPD4252	Approved
0.6625	Remote Similarity	NPD3197	Phase 1
0.6623	Remote Similarity	NPD69	Approved
0.6623	Remote Similarity	NPD9119	Approved
0.6559	Remote Similarity	NPD5786	Approved
0.6556	Remote Similarity	NPD5369	Approved
0.6494	Remote Similarity	NPD9118	Approved
0.6484	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6686	Approved
0.6455	Remote Similarity	NPD7115	Discovery
0.6444	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5362	Discontinued
0.6344	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5778	Approved
0.6327	Remote Similarity	NPD5779	Approved
0.6304	Remote Similarity	NPD5209	Approved
0.6304	Remote Similarity	NPD6435	Approved
0.6296	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4271	Approved
0.6186	Remote Similarity	NPD5370	Suspended
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6101	Approved
0.6146	Remote Similarity	NPD4251	Approved
0.6146	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD7839	Suspended
0.6129	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4820	Approved
0.6087	Remote Similarity	NPD5368	Approved
0.6087	Remote Similarity	NPD4822	Approved
0.6087	Remote Similarity	NPD4821	Approved
0.6087	Remote Similarity	NPD4819	Approved
0.6061	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6411	Approved
0.6049	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6053	Discontinued
0.5946	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5282	Discontinued
0.5938	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD7637	Suspended
0.5897	Remote Similarity	NPD3194	Approved
0.5897	Remote Similarity	NPD3195	Phase 2
0.5897	Remote Similarity	NPD3196	Approved
0.5897	Remote Similarity	NPD4266	Approved
0.5897	Remote Similarity	NPD8080	Discontinued
0.5895	Remote Similarity	NPD5331	Approved
0.5895	Remote Similarity	NPD5332	Approved
0.5895	Remote Similarity	NPD6110	Phase 1
0.5889	Remote Similarity	NPD8039	Approved
0.5882	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7638	Approved
0.5851	Remote Similarity	NPD4790	Discontinued
0.5847	Remote Similarity	NPD7642	Approved
0.5823	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD8515	Approved
0.5812	Remote Similarity	NPD8444	Approved
0.5812	Remote Similarity	NPD8513	Phase 3
0.5812	Remote Similarity	NPD8516	Approved
0.5812	Remote Similarity	NPD8517	Approved
0.581	Remote Similarity	NPD7640	Approved
0.581	Remote Similarity	NPD7639	Approved
0.5802	Remote Similarity	NPD6109	Phase 1
0.5769	Remote Similarity	NPD3172	Approved
0.5769	Remote Similarity	NPD6083	Phase 2
0.5769	Remote Similarity	NPD6084	Phase 2
0.5765	Remote Similarity	NPD7341	Phase 2
0.5739	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7319	Approved
0.5714	Remote Similarity	NPD6927	Phase 3
0.5714	Remote Similarity	NPD7830	Approved
0.5714	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7829	Approved
0.5701	Remote Similarity	NPD7632	Discontinued
0.5699	Remote Similarity	NPD3732	Approved
0.5698	Remote Similarity	NPD7331	Phase 2
0.5696	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6399	Phase 3
0.5678	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD9120	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6412	Phase 2
0.5636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD2067	Discontinued
0.562	Remote Similarity	NPD7507	Approved

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