NPASS Compound

Structure

CID164697 OpenBabel06191715532D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.2202 0.5070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0746 -0.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2257 -3.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 1.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8359 -1.4482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5076 0.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5084 -2.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6716 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6718 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5082 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6718 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3437 -0.9649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5078 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6720 -0.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9002 1.3634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5908 -2.7109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 -1.4660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2099 -1.4647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5078 1.4830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8363 1.4824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8359 -1.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 9 1 0 0 0 0 5 10 2 0 0 0 0 6 14 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 20 2 0 0 0 0 9 11 2 0 0 0 0 9 21 1 0 0 0 0 10 18 1 0 0 0 0 10 25 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 24 2 0 0 0 0 18 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	2.324
LogD:	0.752
LogS:	-2.886
# Rotatable Bonds:	2
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	4.248
Fsp3:	0.333
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:	-4.883
MDCK Permeability:	2.1458870833157562e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	92.93888854980469%
Volume Distribution (VD):	0.428
Pgp-substrate:	4.099302768707275%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	10.015
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.463
Carcinogencity:	0.687
Eye Corrosion:	0.038
Eye Irritation:	0.87
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC164697

Natural Product ID:	NPC164697
*Common Name:**	(-)-Usnic Acid
IUPAC Name:	(9bS)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one
Synonyms:	(+)-Usnic Acid; (-)-Usnic Acid
Standard InCHIKey:	WEYVVCKOOFYHRW-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3/t18-/m1/s1
SMILES:	CC(=O)C1=C(O)C=C2[C@](C1=O)(C)c1c(O)c(C)c(c(c1O2)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461903
PubChem CID:	442614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*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
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO40010	Alectoria sarmentosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964789]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20304	Astragalus pectinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17423	Solanum coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19943	Fleischmannia hymenophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18807	Coffea pseudozanguebariae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13015	Pilosella officinarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20689	Roystonea regia	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2258	Johnius belangerii	Species	Sciaenidae	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
ED50	4
IC50	7
Others	12
Potency	10

Activity Type	# Activity
Cell Line	8
Individual Protein	9
NON-MOLECULAR	3
Organism	6
Others	6
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	17400.0	nM	PMID[521271]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	45900.0	nM	PMID[521271]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	51700.0	nM	PMID[521271]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	21800.0	nM	PMID[521271]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	19700.0	nM	PMID[521271]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	=	50118.7	nM	PMID[521272]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	28183.8	nM	PMID[521272]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	31622.8	nM	PMID[521273]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[521272]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	6.3	nM	PMID[521273]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CTD50	=	209.3	uM	PMID[521274]
NPT168	Cell Line	P388	Mus musculus	T/C	=	141.0	%	PMID[521276]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CTD50	=	133.7	uM	PMID[521277]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[521278]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	25.0	ug ml-1	PMID[521270]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	6.25	ug ml-1	PMID[521270]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	50.0	ug ml-1	PMID[521270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	35100.0	nM	PMID[521271]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[521272]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	12589.3	nM	PMID[521272]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	12589.3	nM	PMID[521272]
NPT2	Others	Unspecified		Potency	=	35481.3	nM	PMID[521272]
NPT2	Others	Unspecified		Selectivity Index	=	14.4	n.a.	PMID[521274]
NPT742	Organism	Influenza A virus	Influenza A virus	ED50	=	14.5	uM	PMID[521274]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	ED50	=	1.2	uM	PMID[521275]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	ED50	=	8.6	uM	PMID[521275]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	35.0	%	PMID[521276]
NPT35	Others	n.a.		solubility	<	10.0	mg	PMID[521276]
NPT35	Others	n.a.		solubility	=	20.0	mg	PMID[521276]
NPT35	Others	n.a.		LogP	=	2.88	n.a.	PMID[521276]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	13.1	uM	PMID[521277]
NPT2	Others	Unspecified		Selectivity Index	=	10.2	n.a.	PMID[521277]

☑ 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 NPC164697 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	385
0.1-0.2	1639
0.2-0.3	3977
0.3-0.4	9604
0.4-0.5	9633
0.5-0.6	4457
0.6-0.7	6277
0.7-0.8	4867
0.8-0.85	1517
0.85-0.9	306
0.9-0.95	30
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289660
1.0	High Similarity	NPC82920
0.9926	High Similarity	NPC111201
0.9925	High Similarity	NPC270913
0.9149	High Similarity	NPC96791
0.9149	High Similarity	NPC470636
0.9149	High Similarity	NPC226942
0.9137	High Similarity	NPC268178
0.9137	High Similarity	NPC54820
0.9137	High Similarity	NPC180501
0.9078	High Similarity	NPC316911
0.9078	High Similarity	NPC316560
0.9014	High Similarity	NPC321629
0.9014	High Similarity	NPC323884
0.9014	High Similarity	NPC326193
0.9014	High Similarity	NPC321148
0.9014	High Similarity	NPC325346
0.8973	High Similarity	NPC321896
0.8973	High Similarity	NPC476185
0.8951	High Similarity	NPC262935
0.8951	High Similarity	NPC11700
0.8951	High Similarity	NPC251182
0.8951	High Similarity	NPC172182
0.8944	High Similarity	NPC74397
0.8921	High Similarity	NPC101752
0.8904	High Similarity	NPC471114
0.8889	High Similarity	NPC117716
0.8889	High Similarity	NPC206212
0.8889	High Similarity	NPC470674
0.8889	High Similarity	NPC470673
0.8889	High Similarity	NPC71184
0.8881	High Similarity	NPC472344
0.8873	High Similarity	NPC477272
0.8865	High Similarity	NPC470671
0.8865	High Similarity	NPC131130
0.8865	High Similarity	NPC474487
0.8865	High Similarity	NPC474504
0.8865	High Similarity	NPC470672
0.8865	High Similarity	NPC477055
0.8865	High Similarity	NPC477056
0.8865	High Similarity	NPC183639
0.8865	High Similarity	NPC199458
0.8857	High Similarity	NPC174999
0.8803	High Similarity	NPC241975
0.8803	High Similarity	NPC19476
0.8794	High Similarity	NPC131782
0.8794	High Similarity	NPC474624
0.8794	High Similarity	NPC138047
0.8784	High Similarity	NPC476162
0.8777	High Similarity	NPC108113
0.8777	High Similarity	NPC93756
0.8776	High Similarity	NPC226644
0.8776	High Similarity	NPC178202
0.8776	High Similarity	NPC37226
0.8776	High Similarity	NPC317492
0.8767	High Similarity	NPC300988
0.8767	High Similarity	NPC308200
0.8767	High Similarity	NPC10990
0.875	High Similarity	NPC112829
0.875	High Similarity	NPC276565
0.875	High Similarity	NPC294432
0.875	High Similarity	NPC313368
0.875	High Similarity	NPC470556
0.8742	High Similarity	NPC196448
0.8741	High Similarity	NPC11056
0.8732	High Similarity	NPC254168
0.8732	High Similarity	NPC470083
0.8732	High Similarity	NPC272844
0.8732	High Similarity	NPC470669
0.8732	High Similarity	NPC248995
0.8732	High Similarity	NPC470668
0.8732	High Similarity	NPC219584
0.8725	High Similarity	NPC470353
0.8725	High Similarity	NPC5871
0.8723	High Similarity	NPC470983
0.8723	High Similarity	NPC470982
0.8723	High Similarity	NPC156910
0.8716	High Similarity	NPC78335
0.8716	High Similarity	NPC476509
0.8716	High Similarity	NPC230713
0.8714	High Similarity	NPC125920
0.8707	High Similarity	NPC39195
0.8707	High Similarity	NPC135325
0.8707	High Similarity	NPC168085
0.8707	High Similarity	NPC145467
0.8705	High Similarity	NPC215875
0.8705	High Similarity	NPC285054
0.8705	High Similarity	NPC15834
0.8705	High Similarity	NPC10971
0.8699	High Similarity	NPC82534
0.8699	High Similarity	NPC210826
0.869	High Similarity	NPC184738
0.869	High Similarity	NPC470909
0.869	High Similarity	NPC473813
0.869	High Similarity	NPC470553
0.869	High Similarity	NPC293053
0.869	High Similarity	NPC24821
0.869	High Similarity	NPC9117
0.869	High Similarity	NPC18886
0.869	High Similarity	NPC474939
0.869	High Similarity	NPC96216
0.869	High Similarity	NPC307895
0.869	High Similarity	NPC212932
0.869	High Similarity	NPC5990
0.869	High Similarity	NPC190637
0.869	High Similarity	NPC33653
0.869	High Similarity	NPC473812
0.8681	High Similarity	NPC171870
0.8675	High Similarity	NPC160015
0.8675	High Similarity	NPC474386
0.8675	High Similarity	NPC247677
0.8671	High Similarity	NPC96565
0.8671	High Similarity	NPC220062
0.8671	High Similarity	NPC55018
0.8671	High Similarity	NPC137009
0.8671	High Similarity	NPC53181
0.8671	High Similarity	NPC139554
0.8671	High Similarity	NPC301217
0.8671	High Similarity	NPC472343
0.8671	High Similarity	NPC37206
0.8671	High Similarity	NPC23257
0.8671	High Similarity	NPC216978
0.8671	High Similarity	NPC303633
0.8671	High Similarity	NPC240305
0.8671	High Similarity	NPC217186
0.8667	High Similarity	NPC213608
0.8667	High Similarity	NPC235333
0.8667	High Similarity	NPC1477
0.8662	High Similarity	NPC322301
0.8662	High Similarity	NPC255801
0.8658	High Similarity	NPC170169
0.8658	High Similarity	NPC473131
0.8658	High Similarity	NPC470675
0.8652	High Similarity	NPC60667
0.8643	High Similarity	NPC16197
0.8639	High Similarity	NPC202494
0.8639	High Similarity	NPC12148
0.8639	High Similarity	NPC130581
0.8633	High Similarity	NPC27490
0.863	High Similarity	NPC216538
0.863	High Similarity	NPC472446
0.863	High Similarity	NPC224714
0.863	High Similarity	NPC297788
0.863	High Similarity	NPC234629
0.863	High Similarity	NPC326500
0.863	High Similarity	NPC271288
0.863	High Similarity	NPC311144
0.863	High Similarity	NPC273538
0.863	High Similarity	NPC75694
0.863	High Similarity	NPC288910
0.863	High Similarity	NPC470890
0.863	High Similarity	NPC476055
0.863	High Similarity	NPC133060
0.863	High Similarity	NPC472447
0.863	High Similarity	NPC311741
0.863	High Similarity	NPC118059
0.863	High Similarity	NPC470554
0.8623	High Similarity	NPC186628
0.8623	High Similarity	NPC84772
0.8621	High Similarity	NPC200694
0.8621	High Similarity	NPC204469
0.8621	High Similarity	NPC473042
0.8621	High Similarity	NPC144499
0.8618	High Similarity	NPC260902
0.8618	High Similarity	NPC270044
0.8618	High Similarity	NPC296957
0.8611	High Similarity	NPC221173
0.8611	High Similarity	NPC270883
0.8611	High Similarity	NPC69769
0.8611	High Similarity	NPC469818
0.8611	High Similarity	NPC241100
0.8611	High Similarity	NPC159275
0.8611	High Similarity	NPC172986
0.8611	High Similarity	NPC261227
0.8611	High Similarity	NPC471587
0.8609	High Similarity	NPC470344
0.8609	High Similarity	NPC148938
0.8609	High Similarity	NPC297531
0.8609	High Similarity	NPC213936
0.8609	High Similarity	NPC471116
0.8601	High Similarity	NPC201395
0.8591	High Similarity	NPC470908
0.8591	High Similarity	NPC472421
0.8591	High Similarity	NPC321387
0.8591	High Similarity	NPC327059
0.8591	High Similarity	NPC29777
0.8591	High Similarity	NPC471115
0.8591	High Similarity	NPC227122
0.8582	High Similarity	NPC144027
0.8582	High Similarity	NPC103842
0.8582	High Similarity	NPC236974
0.8581	High Similarity	NPC475055
0.8581	High Similarity	NPC186397
0.8581	High Similarity	NPC37135
0.8571	High Similarity	NPC299011
0.8571	High Similarity	NPC473135
0.8571	High Similarity	NPC178343
0.8571	High Similarity	NPC220418
0.8571	High Similarity	NPC470910
0.8571	High Similarity	NPC187282

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 NPC164697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	1031
0.2-0.3	1896
0.3-0.4	2733
0.4-0.5	1862
0.5-0.6	894
0.6-0.7	267
0.7-0.8	105
0.8-0.85	11
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9925	High Similarity	NPD2800	Approved
0.8913	High Similarity	NPD6651	Approved
0.863	High Similarity	NPD4378	Clinical (unspecified phase)
0.863	High Similarity	NPD2532	Approved
0.863	High Similarity	NPD2534	Approved
0.863	High Similarity	NPD2533	Approved
0.8378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD1549	Phase 2
0.8041	Intermediate Similarity	NPD1243	Approved
0.8027	Intermediate Similarity	NPD2344	Approved
0.8026	Intermediate Similarity	NPD920	Approved
0.8014	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.7973	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3882	Suspended
0.7959	Intermediate Similarity	NPD2796	Approved
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7949	Intermediate Similarity	NPD2801	Approved
0.7947	Intermediate Similarity	NPD1511	Approved
0.7937	Intermediate Similarity	NPD5711	Approved
0.7937	Intermediate Similarity	NPD5710	Approved
0.7935	Intermediate Similarity	NPD7411	Suspended
0.7911	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD7075	Discontinued
0.7885	Intermediate Similarity	NPD1934	Approved
0.7871	Intermediate Similarity	NPD6599	Discontinued
0.7867	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD1512	Approved
0.7834	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2309	Approved
0.7812	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.777	Intermediate Similarity	NPD2799	Discontinued
0.7748	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7768	Phase 2
0.773	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD6100	Approved
0.7712	Intermediate Similarity	NPD6799	Approved
0.7688	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.7603	Intermediate Similarity	NPD2313	Discontinued
0.76	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD7286	Phase 2
0.759	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.7566	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2403	Approved
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3226	Approved
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7455	Intermediate Similarity	NPD3926	Phase 2
0.7453	Intermediate Similarity	NPD3817	Phase 2
0.7451	Intermediate Similarity	NPD2654	Approved
0.7439	Intermediate Similarity	NPD1247	Approved
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7372	Intermediate Similarity	NPD7390	Discontinued
0.7337	Intermediate Similarity	NPD7074	Phase 3
0.7317	Intermediate Similarity	NPD919	Approved
0.7292	Intermediate Similarity	NPD9717	Approved
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD7054	Approved
0.7267	Intermediate Similarity	NPD943	Approved
0.726	Intermediate Similarity	NPD1203	Approved
0.7254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2296	Approved
0.7235	Intermediate Similarity	NPD1729	Discontinued
0.7235	Intermediate Similarity	NPD7472	Approved
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6797	Phase 2
0.7176	Intermediate Similarity	NPD5844	Phase 1
0.7172	Intermediate Similarity	NPD3972	Approved
0.7151	Intermediate Similarity	NPD7251	Discontinued
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5403	Approved
0.7123	Intermediate Similarity	NPD4749	Approved
0.7114	Intermediate Similarity	NPD4908	Phase 1
0.711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7808	Phase 3
0.7105	Intermediate Similarity	NPD447	Suspended
0.7105	Intermediate Similarity	NPD230	Phase 1
0.7097	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6002	Phase 3
0.7097	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD6005	Phase 3
0.7097	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD4363	Phase 3
0.7095	Intermediate Similarity	NPD4360	Phase 2
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7078	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6696	Suspended
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7062	Intermediate Similarity	NPD4287	Approved
0.7052	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6104	Discontinued
0.7045	Intermediate Similarity	NPD8434	Phase 2
0.7027	Intermediate Similarity	NPD2797	Approved
0.702	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD6832	Phase 2
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1610	Phase 2
0.6968	Remote Similarity	NPD7033	Discontinued
0.6954	Remote Similarity	NPD4625	Phase 3
0.6951	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2424	Discontinued
0.6939	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6280	Approved
0.6909	Remote Similarity	NPD6279	Approved
0.6908	Remote Similarity	NPD411	Approved
0.6908	Remote Similarity	NPD1296	Phase 2
0.6871	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4308	Phase 3
0.6855	Remote Similarity	NPD7003	Approved
0.6831	Remote Similarity	NPD1241	Discontinued
0.6828	Remote Similarity	NPD9545	Approved
0.6828	Remote Similarity	NPD1548	Phase 1
0.6821	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5408	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6811	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD37	Approved
0.6806	Remote Similarity	NPD9493	Approved
0.6805	Remote Similarity	NPD6234	Discontinued
0.68	Remote Similarity	NPD1164	Approved
0.68	Remote Similarity	NPD3267	Approved
0.68	Remote Similarity	NPD1470	Approved
0.68	Remote Similarity	NPD3266	Approved
0.6796	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4967	Phase 2
0.6786	Remote Similarity	NPD4965	Approved
0.6786	Remote Similarity	NPD4966	Approved
0.6784	Remote Similarity	NPD6808	Phase 2
0.6776	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3446	Phase 1
0.6757	Remote Similarity	NPD1201	Approved
0.6755	Remote Similarity	NPD1019	Discontinued
0.6739	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD17	Approved
0.6733	Remote Similarity	NPD3225	Approved
0.6733	Remote Similarity	NPD1876	Approved
0.6733	Remote Similarity	NPD8651	Approved
0.6728	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7199	Phase 2
0.6724	Remote Similarity	NPD3751	Discontinued
0.669	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8312	Approved
0.6685	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6273	Approved
0.6646	Remote Similarity	NPD5049	Phase 3
0.6627	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1778	Approved
0.6604	Remote Similarity	NPD4477	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