NPASS Compound

Structure

CID205265 OpenBabel06191715592D 24 27 0 0 1 0 0 0 0 0999 V2000 5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2923 -2.4781 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 -2.5981 -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 4.1369 -1.0000 0.0000 C 0 0 3 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 -2.5981 -0.5000 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 2.5981 -0.5000 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 2.5981 -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 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 18 1 0 0 0 0 7 23 1 0 0 0 0 8 14 1 0 0 0 0 8 17 2 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	319.945
LogP:	3.718
LogD:	2.318
LogS:	-4.016
# Rotatable Bonds:	0
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	3.531
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995
MDCK Permeability:	1.868770232249517e-05
Pgp-inhibitor:	0.292
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	95.72525787353516%
Volume Distribution (VD):	0.716
Pgp-substrate:	9.67530345916748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.868
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.671
CYP2D6-inhibitor:	0.218
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	2.37
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.714
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.885
Carcinogencity:	0.639
Eye Corrosion:	0.004
Eye Irritation:	0.901
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC205265

Natural Product ID:	NPC205265
*Common Name:**	Toxyloxanthone C
IUPAC Name:	4,8,9-trihydroxy-2,3,3-trimethyl-2H-furo[3,2-b]xanthen-5-one
Synonyms:	toxyloxanthone C
Standard InCHIKey:	UMGNGSNVYJDUQS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-7-18(2,3)13-11(23-7)6-10-12(16(13)22)14(20)8-4-5-9(19)15(21)17(8)24-10/h4-7,19,21-22H,1-3H3
SMILES:	CC1C(C)(C)c2c(cc3c(c(=O)c4ccc(c(c4o3)O)O)c2O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459022
PubChem CID:	5495919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
AC50	1
EC50	7
MIC	8
Others	1
Potency	17

Activity Type	# Activity
Cell Line	1
Individual Protein	15
Organism	11
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	5887.0	nM	PMID[573387]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	>	150000.0	nM	PMID[573387]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[573387]
NPT1273	Individual Protein	ATP-dependent molecular chaperone HSP82	Candida albicans (strain WO-1) (Yeast)	EC50	=	14444.0	nM	PMID[573387]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[573387]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[573387]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[573387]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[573387]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[573387]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	19952.6	nM	PMID[573387]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[573387]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[573387]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[573387]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[573387]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[573386]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	128.0	ug.mL-1	PMID[573386]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	128.0	ug.mL-1	PMID[573386]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9.0	mm	PMID[573386]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	8.0	ug.mL-1	PMID[573386]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	8.0	ug.mL-1	PMID[573386]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	8.0	ug.mL-1	PMID[573386]
NPT925	Organism	Emericella nidulans	Emericella nidulans	MIC	=	8.0	ug.mL-1	PMID[573386]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	8066.0	nM	PMID[573387]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	5906.0	nM	PMID[573387]
NPT2	Others	Unspecified		EC50	>	38000.0	nM	PMID[573387]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[573387]
NPT2	Others	Unspecified		EC50	>	150000.0	nM	PMID[573387]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	AC50	=	38042.0	nM	PMID[573387]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[573387]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[573387]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[573387]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[573387]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[573387]

☑ 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 NPC205265 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	439
0.1-0.2	1801
0.2-0.3	3953
0.3-0.4	10081
0.4-0.5	8240
0.5-0.6	3760
0.6-0.7	5158
0.7-0.8	5014
0.8-0.85	2327
0.85-0.9	1315
0.9-0.95	585
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472281
0.9935	High Similarity	NPC472277
0.9871	High Similarity	NPC18100
0.9747	High Similarity	NPC288813
0.9686	High Similarity	NPC472276
0.9675	High Similarity	NPC219867
0.9675	High Similarity	NPC180011
0.9618	High Similarity	NPC472278
0.9618	High Similarity	NPC124038
0.9618	High Similarity	NPC473313
0.9618	High Similarity	NPC329669
0.961	High Similarity	NPC115853
0.9557	High Similarity	NPC108433
0.9557	High Similarity	NPC300053
0.9551	High Similarity	NPC476283
0.9551	High Similarity	NPC472624
0.9548	High Similarity	NPC187745
0.9548	High Similarity	NPC304008
0.9548	High Similarity	NPC161960
0.9548	High Similarity	NPC291508
0.9497	High Similarity	NPC235610
0.949	High Similarity	NPC57715
0.9484	High Similarity	NPC291878
0.9484	High Similarity	NPC195796
0.9484	High Similarity	NPC35038
0.9484	High Similarity	NPC278778
0.9434	High Similarity	NPC326520
0.9434	High Similarity	NPC473286
0.943	High Similarity	NPC81679
0.943	High Similarity	NPC472635
0.9427	High Similarity	NPC188433
0.9427	High Similarity	NPC328102
0.9427	High Similarity	NPC36217
0.9423	High Similarity	NPC299520
0.9423	High Similarity	NPC472598
0.9423	High Similarity	NPC79053
0.9423	High Similarity	NPC27337
0.9423	High Similarity	NPC474055
0.9423	High Similarity	NPC129684
0.9419	High Similarity	NPC117992
0.9419	High Similarity	NPC230149
0.9419	High Similarity	NPC168247
0.9419	High Similarity	NPC45849
0.9419	High Similarity	NPC200761
0.9419	High Similarity	NPC256925
0.9419	High Similarity	NPC470327
0.9419	High Similarity	NPC57674
0.9419	High Similarity	NPC152951
0.9419	High Similarity	NPC477503
0.9379	High Similarity	NPC165456
0.9375	High Similarity	NPC119589
0.9375	High Similarity	NPC170245
0.9371	High Similarity	NPC306321
0.9371	High Similarity	NPC319200
0.9371	High Similarity	NPC303460
0.9371	High Similarity	NPC187491
0.9371	High Similarity	NPC220313
0.9367	High Similarity	NPC187354
0.9367	High Similarity	NPC134783
0.9367	High Similarity	NPC472275
0.9367	High Similarity	NPC234644
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC185258
0.9363	High Similarity	NPC235448
0.9363	High Similarity	NPC172770
0.9359	High Similarity	NPC209614
0.9359	High Similarity	NPC470328
0.9359	High Similarity	NPC472626
0.9355	High Similarity	NPC33051
0.9355	High Similarity	NPC227337
0.9355	High Similarity	NPC192083
0.9355	High Similarity	NPC49402
0.9355	High Similarity	NPC273462
0.9355	High Similarity	NPC70433
0.9355	High Similarity	NPC18727
0.9355	High Similarity	NPC213896
0.9321	High Similarity	NPC131866
0.9313	High Similarity	NPC62261
0.9308	High Similarity	NPC474034
0.9308	High Similarity	NPC474033
0.9308	High Similarity	NPC201800
0.9308	High Similarity	NPC474150
0.9308	High Similarity	NPC474162
0.9308	High Similarity	NPC476247
0.9304	High Similarity	NPC287328
0.9304	High Similarity	NPC192686
0.9304	High Similarity	NPC118256
0.9304	High Similarity	NPC119209
0.9304	High Similarity	NPC282009
0.9299	High Similarity	NPC99597
0.9299	High Similarity	NPC223787
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC262286
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC36852
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC78225
0.9299	High Similarity	NPC162869
0.9299	High Similarity	NPC210084
0.9295	High Similarity	NPC255807
0.9295	High Similarity	NPC226025
0.9295	High Similarity	NPC321779
0.9295	High Similarity	NPC31018
0.929	High Similarity	NPC236637
0.929	High Similarity	NPC302950
0.929	High Similarity	NPC257648
0.929	High Similarity	NPC477231
0.929	High Similarity	NPC106976
0.929	High Similarity	NPC219582
0.9259	High Similarity	NPC152477
0.9259	High Similarity	NPC242395
0.9255	High Similarity	NPC128293
0.9255	High Similarity	NPC277480
0.9255	High Similarity	NPC173292
0.925	High Similarity	NPC273959
0.925	High Similarity	NPC475985
0.925	High Similarity	NPC186686
0.9245	High Similarity	NPC471499
0.9245	High Similarity	NPC474038
0.9245	High Similarity	NPC472634
0.9245	High Similarity	NPC26326
0.9245	High Similarity	NPC472632
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC32694
0.9245	High Similarity	NPC471210
0.9241	High Similarity	NPC210459
0.9241	High Similarity	NPC55738
0.9241	High Similarity	NPC204879
0.9241	High Similarity	NPC22192
0.9236	High Similarity	NPC472455
0.9236	High Similarity	NPC472916
0.9236	High Similarity	NPC68093
0.9236	High Similarity	NPC235165
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC255106
0.9236	High Similarity	NPC138243
0.9236	High Similarity	NPC470600
0.9231	High Similarity	NPC469550
0.9231	High Similarity	NPC74924
0.9231	High Similarity	NPC298692
0.9226	High Similarity	NPC31363
0.9207	High Similarity	NPC310794
0.9202	High Similarity	NPC279209
0.9202	High Similarity	NPC102277
0.9198	High Similarity	NPC247973
0.9198	High Similarity	NPC150131
0.9193	High Similarity	NPC37183
0.9193	High Similarity	NPC293319
0.9187	High Similarity	NPC83922
0.9187	High Similarity	NPC472964
0.9187	High Similarity	NPC472448
0.9187	High Similarity	NPC261470
0.9187	High Similarity	NPC220912
0.9182	High Similarity	NPC45146
0.9182	High Similarity	NPC80375
0.9182	High Similarity	NPC228785
0.9182	High Similarity	NPC472630
0.9182	High Similarity	NPC470326
0.9182	High Similarity	NPC56085
0.9182	High Similarity	NPC472902
0.9182	High Similarity	NPC14353
0.9182	High Similarity	NPC174953
0.9182	High Similarity	NPC299436
0.9182	High Similarity	NPC321399
0.9182	High Similarity	NPC472631
0.9182	High Similarity	NPC476980
0.9182	High Similarity	NPC475784
0.9182	High Similarity	NPC235018
0.9177	High Similarity	NPC472914
0.9177	High Similarity	NPC284820
0.9177	High Similarity	NPC472911
0.9177	High Similarity	NPC52530
0.9177	High Similarity	NPC245758
0.9177	High Similarity	NPC52889
0.9177	High Similarity	NPC136674
0.9177	High Similarity	NPC472910
0.9177	High Similarity	NPC222814
0.9177	High Similarity	NPC471479
0.9177	High Similarity	NPC469584
0.9177	High Similarity	NPC471515
0.9177	High Similarity	NPC474681
0.9177	High Similarity	NPC218313
0.9177	High Similarity	NPC196448
0.9177	High Similarity	NPC473272
0.9177	High Similarity	NPC67876
0.9177	High Similarity	NPC471209
0.9177	High Similarity	NPC181960
0.9177	High Similarity	NPC96167
0.9177	High Similarity	NPC472913
0.9172	High Similarity	NPC67396
0.9172	High Similarity	NPC37392
0.9172	High Similarity	NPC234255
0.9172	High Similarity	NPC2928
0.9172	High Similarity	NPC200246
0.9172	High Similarity	NPC472280
0.9172	High Similarity	NPC113906
0.9167	High Similarity	NPC161277

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 NPC205265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	950
0.2-0.3	1876
0.3-0.4	2615
0.4-0.5	1831
0.5-0.6	935
0.6-0.7	381
0.7-0.8	116
0.8-0.85	34
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD2393	Clinical (unspecified phase)
0.929	High Similarity	NPD1934	Approved
0.9114	High Similarity	NPD3882	Suspended
0.9062	High Similarity	NPD5494	Approved
0.8987	High Similarity	NPD2801	Approved
0.8963	High Similarity	NPD3818	Discontinued
0.8841	High Similarity	NPD6167	Clinical (unspecified phase)
0.8841	High Similarity	NPD6166	Phase 2
0.8841	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD4380	Phase 2
0.8654	High Similarity	NPD1511	Approved
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8631	High Similarity	NPD7074	Phase 3
0.8589	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD7054	Approved
0.8544	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD7472	Approved
0.8519	High Similarity	NPD7096	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD2800	Approved
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6232	Discontinued
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD6797	Phase 2
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8314	Intermediate Similarity	NPD6559	Discontinued
0.8314	Intermediate Similarity	NPD7251	Discontinued
0.8293	Intermediate Similarity	NPD1465	Phase 2
0.8266	Intermediate Similarity	NPD7808	Phase 3
0.8221	Intermediate Similarity	NPD6599	Discontinued
0.8214	Intermediate Similarity	NPD1247	Approved
0.8205	Intermediate Similarity	NPD2796	Approved
0.8171	Intermediate Similarity	NPD7411	Suspended
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.814	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD919	Approved
0.8075	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3749	Approved
0.7927	Intermediate Similarity	NPD920	Approved
0.7917	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD4628	Phase 3
0.7885	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1613	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.787	Intermediate Similarity	NPD7768	Phase 2
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5403	Approved
0.7702	Intermediate Similarity	NPD2344	Approved
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.768	Intermediate Similarity	NPD8434	Phase 2
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6651	Approved
0.767	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD3750	Approved
0.7661	Intermediate Similarity	NPD4965	Approved
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD4966	Approved
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6100	Approved
0.764	Intermediate Similarity	NPD6099	Approved
0.7627	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD3226	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1243	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD5401	Approved
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7561	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7542	Intermediate Similarity	NPD5953	Discontinued
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.753	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD9494	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6190	Approved
0.7391	Intermediate Similarity	NPD1933	Approved
0.7362	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.733	Intermediate Similarity	NPD6776	Approved
0.733	Intermediate Similarity	NPD6779	Approved
0.733	Intermediate Similarity	NPD6780	Approved
0.733	Intermediate Similarity	NPD6781	Approved
0.733	Intermediate Similarity	NPD6777	Approved
0.733	Intermediate Similarity	NPD6778	Approved
0.733	Intermediate Similarity	NPD6782	Approved
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5242	Approved
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7292	Intermediate Similarity	NPD2494	Approved
0.7292	Intermediate Similarity	NPD2493	Approved
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2403	Approved
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7907	Approved
0.7229	Intermediate Similarity	NPD2424	Discontinued
0.7228	Intermediate Similarity	NPD4665	Approved
0.7228	Intermediate Similarity	NPD4111	Phase 1
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7213	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3452	Approved
0.7202	Intermediate Similarity	NPD3450	Approved
0.72	Intermediate Similarity	NPD5353	Approved
0.7198	Intermediate Similarity	NPD1729	Discontinued
0.7194	Intermediate Similarity	NPD7584	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD4583	Approved
0.7179	Intermediate Similarity	NPD4582	Approved
0.7175	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6273	Approved
0.7128	Intermediate Similarity	NPD7698	Approved
0.7128	Intermediate Similarity	NPD4002	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD4004	Approved
0.7128	Intermediate Similarity	NPD7697	Approved
0.7125	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.709	Intermediate Similarity	NPD2488	Approved
0.709	Intermediate Similarity	NPD2490	Approved
0.7088	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD2973	Approved
0.7083	Intermediate Similarity	NPD2974	Approved
0.7083	Intermediate Similarity	NPD2975	Approved
0.7081	Intermediate Similarity	NPD6832	Phase 2
0.7077	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7071	Intermediate Similarity	NPD7701	Phase 2
0.7068	Intermediate Similarity	NPD6535	Approved
0.7068	Intermediate Similarity	NPD6534	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