NPASS Compound

Structure

CID193358 OpenBabel06191715582D 28 32 0 0 1 0 0 0 0 0999 V2000 0.0002 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0408 -0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3609 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2003 -1.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5204 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0410 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3611 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8400 -1.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3601 -0.9710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6801 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6799 -0.9707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -0.9704 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2007 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5208 -1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3603 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6803 -0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6801 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5202 -1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5205 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2009 1.5018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5210 -2.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5200 -2.4558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8408 -2.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5207 1.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8400 1.4851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 20 27 2 0 0 0 0 21 22 1 0 0 0 0 21 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.08
Volume:	370.026
LogP:	4.596
LogD:	2.827
LogS:	-4.099
# Rotatable Bonds:	0
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	3.645
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.476
MDCK Permeability:	1.278876698052045e-05
Pgp-inhibitor:	0.082
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.226
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.86504364013672%
Volume Distribution (VD):	0.348
Pgp-substrate:	1.4571999311447144%

ADMET: Metabolism

CYP1A2-inhibitor:	0.855
CYP1A2-substrate:	0.664
CYP2C19-inhibitor:	0.293
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.835
CYP2C9-substrate:	0.704
CYP2D6-inhibitor:	0.425
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	3.208
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.849
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.828
Carcinogencity:	0.813
Eye Corrosion:	0.003
Eye Irritation:	0.507
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC193358

Natural Product ID:	NPC193358
*Common Name:**	Zeylanone
IUPAC Name:	n.a.
Synonyms:	Zeylanone
Standard InCHIKey:	XVMQJJJRMHQCGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H14O6/c1-22-12(19(26)16-10(21(22)28)5-3-7-14(16)24)8-11-17(22)20(27)15-9(18(11)25)4-2-6-13(15)23/h2-7,12,23-24H,8H2,1H3
SMILES:	Oc1cccc2c1C(=O)C1=C(C2=O)CC2C1(C)C(=O)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470457
PubChem CID:	5276618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	PMID[16078700]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23848163]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13608	Plumbago zeylanica	Species	Plumbaginaceae	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	8
Others	8

Activity Type	# Activity
Cell Line	4
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[533037]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	14.5	ug ml-1	PMID[533037]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[533037]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[533037]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	=	50.0	ug.mL-1	PMID[533037]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	>	800.0	ug ml-1	PMID[533037]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	6.0	ug.mL-1	PMID[533037]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	>	800.0	ug ml-1	PMID[533037]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IC50	=	50.0	ug.mL-1	PMID[533037]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	400.0	ug ml-1	PMID[533037]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	IC50	=	200.0	ug.mL-1	PMID[533037]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	Activity	>	800.0	ug ml-1	PMID[533037]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3.0	ug.mL-1	PMID[533037]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	10.0	ug.mL-1	PMID[533037]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Activity	=	100.0	ug ml-1	PMID[533037]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	10.0	ug.mL-1	PMID[533037]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	500.0	ug ml-1	PMID[533037]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IC50	=	30.0	ug.mL-1	PMID[533037]
NPT21	Organism	Aspergillus niger	Aspergillus niger	Activity	>	800.0	ug ml-1	PMID[533037]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	3.0	ug ml-1	PMID[533037]

☑ 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 NPC193358 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	349
0.1-0.2	1548
0.2-0.3	3070
0.3-0.4	8518
0.4-0.5	10969
0.5-0.6	6637
0.6-0.7	9076
0.7-0.8	2215
0.8-0.85	246
0.85-0.9	54
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.903	High Similarity	NPC53896
0.903	High Similarity	NPC115458
0.9015	High Similarity	NPC34414
0.9015	High Similarity	NPC146647
0.8992	High Similarity	NPC375356
0.8931	High Similarity	NPC3224
0.8915	High Similarity	NPC300274
0.8897	High Similarity	NPC80035
0.8881	High Similarity	NPC244699
0.8855	High Similarity	NPC103540
0.8849	High Similarity	NPC96421
0.8832	High Similarity	NPC272268
0.8815	High Similarity	NPC58685
0.8806	High Similarity	NPC55949
0.8797	High Similarity	NPC282923
0.8797	High Similarity	NPC48248
0.8788	High Similarity	NPC96915
0.8779	High Similarity	NPC142956
0.8759	High Similarity	NPC283088
0.875	High Similarity	NPC225051
0.8731	High Similarity	NPC99731
0.8731	High Similarity	NPC25736
0.8722	High Similarity	NPC471530
0.8705	High Similarity	NPC13715
0.8686	High Similarity	NPC50924
0.8682	High Similarity	NPC206778
0.8682	High Similarity	NPC285829
0.8667	High Similarity	NPC475741
0.8647	High Similarity	NPC306765
0.8626	High Similarity	NPC307174
0.8603	High Similarity	NPC17083
0.8603	High Similarity	NPC205992
0.8571	High Similarity	NPC4214
0.8561	High Similarity	NPC474813
0.8561	High Similarity	NPC472308
0.8561	High Similarity	NPC155211
0.8551	High Similarity	NPC288089
0.8529	High Similarity	NPC199253
0.8529	High Similarity	NPC136588
0.8511	High Similarity	NPC26924
0.8507	High Similarity	NPC474106
0.8507	High Similarity	NPC231774
0.85	High Similarity	NPC245923
0.85	High Similarity	NPC36868
0.8496	Intermediate Similarity	NPC173978
0.8496	Intermediate Similarity	NPC310540
0.8462	Intermediate Similarity	NPC193555
0.8451	Intermediate Similarity	NPC315578
0.8429	Intermediate Similarity	NPC474311
0.8417	Intermediate Similarity	NPC472262
0.8417	Intermediate Similarity	NPC161964
0.8417	Intermediate Similarity	NPC287604
0.8406	Intermediate Similarity	NPC70622
0.8394	Intermediate Similarity	NPC31799
0.8392	Intermediate Similarity	NPC91019
0.8392	Intermediate Similarity	NPC477275
0.8392	Intermediate Similarity	NPC106519
0.8372	Intermediate Similarity	NPC108288
0.8369	Intermediate Similarity	NPC305060
0.8369	Intermediate Similarity	NPC118366
0.8358	Intermediate Similarity	NPC234890
0.8358	Intermediate Similarity	NPC74507
0.8346	Intermediate Similarity	NPC91478
0.8345	Intermediate Similarity	NPC52407
0.8345	Intermediate Similarity	NPC79627
0.8345	Intermediate Similarity	NPC294226
0.8333	Intermediate Similarity	NPC474517
0.8333	Intermediate Similarity	NPC72669
0.8322	Intermediate Similarity	NPC181560
0.8322	Intermediate Similarity	NPC169452
0.8321	Intermediate Similarity	NPC276238
0.8309	Intermediate Similarity	NPC84672
0.8309	Intermediate Similarity	NPC69424
0.8309	Intermediate Similarity	NPC72667
0.8309	Intermediate Similarity	NPC176130
0.8309	Intermediate Similarity	NPC78364
0.8298	Intermediate Similarity	NPC141934
0.8286	Intermediate Similarity	NPC12070
0.8286	Intermediate Similarity	NPC44437
0.8276	Intermediate Similarity	NPC66593
0.8273	Intermediate Similarity	NPC246693
0.8273	Intermediate Similarity	NPC110609
0.8273	Intermediate Similarity	NPC242358
0.8271	Intermediate Similarity	NPC120545
0.8261	Intermediate Similarity	NPC108129
0.8252	Intermediate Similarity	NPC138099
0.8252	Intermediate Similarity	NPC1268
0.8252	Intermediate Similarity	NPC242994
0.8248	Intermediate Similarity	NPC96024
0.8248	Intermediate Similarity	NPC237225
0.8239	Intermediate Similarity	NPC475957
0.8239	Intermediate Similarity	NPC53414
0.8239	Intermediate Similarity	NPC471905
0.8239	Intermediate Similarity	NPC53206
0.8235	Intermediate Similarity	NPC71610
0.8235	Intermediate Similarity	NPC254492
0.8231	Intermediate Similarity	NPC477453
0.8231	Intermediate Similarity	NPC143685
0.8227	Intermediate Similarity	NPC258502
0.8227	Intermediate Similarity	NPC249272
0.8214	Intermediate Similarity	NPC171968
0.8214	Intermediate Similarity	NPC477139
0.8214	Intermediate Similarity	NPC114183
0.8207	Intermediate Similarity	NPC19631
0.8207	Intermediate Similarity	NPC239136
0.8207	Intermediate Similarity	NPC69755
0.8194	Intermediate Similarity	NPC225243
0.8188	Intermediate Similarity	NPC171460
0.8182	Intermediate Similarity	NPC477849
0.8182	Intermediate Similarity	NPC91887
0.8182	Intermediate Similarity	NPC46242
0.8182	Intermediate Similarity	NPC473479
0.8182	Intermediate Similarity	NPC51531
0.8182	Intermediate Similarity	NPC157284
0.8182	Intermediate Similarity	NPC5014
0.8182	Intermediate Similarity	NPC165191
0.8182	Intermediate Similarity	NPC297797
0.8182	Intermediate Similarity	NPC28592
0.8182	Intermediate Similarity	NPC61398
0.8182	Intermediate Similarity	NPC114333
0.8182	Intermediate Similarity	NPC289358
0.8182	Intermediate Similarity	NPC473779
0.8182	Intermediate Similarity	NPC42384
0.8182	Intermediate Similarity	NPC232178
0.8182	Intermediate Similarity	NPC416
0.8182	Intermediate Similarity	NPC149773
0.8182	Intermediate Similarity	NPC50615
0.8182	Intermediate Similarity	NPC469857
0.8182	Intermediate Similarity	NPC245760
0.8182	Intermediate Similarity	NPC23667
0.8176	Intermediate Similarity	NPC162751
0.8176	Intermediate Similarity	NPC52161
0.8169	Intermediate Similarity	NPC254847
0.8156	Intermediate Similarity	NPC270899
0.8156	Intermediate Similarity	NPC202225
0.8154	Intermediate Similarity	NPC161304
0.8151	Intermediate Similarity	NPC471682
0.8151	Intermediate Similarity	NPC478164
0.8151	Intermediate Similarity	NPC53016
0.8151	Intermediate Similarity	NPC199936
0.8138	Intermediate Similarity	NPC246638
0.8138	Intermediate Similarity	NPC124365
0.8134	Intermediate Similarity	NPC154696
0.8133	Intermediate Similarity	NPC315520
0.8129	Intermediate Similarity	NPC198305
0.8129	Intermediate Similarity	NPC117609
0.8125	Intermediate Similarity	NPC294330
0.8121	Intermediate Similarity	NPC106524
0.8121	Intermediate Similarity	NPC290695
0.812	Intermediate Similarity	NPC318552
0.812	Intermediate Similarity	NPC190501
0.8116	Intermediate Similarity	NPC95537
0.8112	Intermediate Similarity	NPC53001
0.8108	Intermediate Similarity	NPC314437
0.8102	Intermediate Similarity	NPC51037
0.8102	Intermediate Similarity	NPC160499
0.8102	Intermediate Similarity	NPC1991
0.8099	Intermediate Similarity	NPC22222
0.8099	Intermediate Similarity	NPC477596
0.8099	Intermediate Similarity	NPC281513
0.8099	Intermediate Similarity	NPC161632
0.8088	Intermediate Similarity	NPC68756
0.8088	Intermediate Similarity	NPC152525
0.8088	Intermediate Similarity	NPC199273
0.8085	Intermediate Similarity	NPC254603
0.8085	Intermediate Similarity	NPC314048
0.8082	Intermediate Similarity	NPC477209
0.8082	Intermediate Similarity	NPC469520
0.8082	Intermediate Similarity	NPC73061
0.8082	Intermediate Similarity	NPC474300
0.8082	Intermediate Similarity	NPC257644
0.8074	Intermediate Similarity	NPC176208
0.8071	Intermediate Similarity	NPC93015
0.8071	Intermediate Similarity	NPC471851
0.8069	Intermediate Similarity	NPC473527
0.806	Intermediate Similarity	NPC259703
0.806	Intermediate Similarity	NPC32322
0.8058	Intermediate Similarity	NPC278928
0.8058	Intermediate Similarity	NPC303910
0.8056	Intermediate Similarity	NPC469680
0.8056	Intermediate Similarity	NPC87723
0.8056	Intermediate Similarity	NPC471974
0.8056	Intermediate Similarity	NPC469681
0.8056	Intermediate Similarity	NPC61590
0.8042	Intermediate Similarity	NPC86524
0.8042	Intermediate Similarity	NPC7464
0.8041	Intermediate Similarity	NPC471683
0.8041	Intermediate Similarity	NPC12402
0.8041	Intermediate Similarity	NPC478160
0.8028	Intermediate Similarity	NPC166480
0.8028	Intermediate Similarity	NPC477594
0.8028	Intermediate Similarity	NPC282780
0.8027	Intermediate Similarity	NPC476473
0.8015	Intermediate Similarity	NPC198014
0.8015	Intermediate Similarity	NPC477153
0.8015	Intermediate Similarity	NPC135062
0.8015	Intermediate Similarity	NPC275145
0.8014	Intermediate Similarity	NPC309430
0.8014	Intermediate Similarity	NPC305845
0.8014	Intermediate Similarity	NPC204045

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 NPC193358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	953
0.2-0.3	1244
0.3-0.4	2603
0.4-0.5	2371
0.5-0.6	1162
0.6-0.7	446
0.7-0.8	53
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD1470	Approved
0.855	High Similarity	NPD1201	Approved
0.8372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD3019	Approved
0.812	Intermediate Similarity	NPD2932	Approved
0.7862	Intermediate Similarity	NPD5404	Approved
0.7862	Intermediate Similarity	NPD5405	Approved
0.7862	Intermediate Similarity	NPD5406	Approved
0.7862	Intermediate Similarity	NPD5408	Approved
0.7829	Intermediate Similarity	NPD3226	Approved
0.7793	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD3300	Phase 2
0.7664	Intermediate Similarity	NPD3026	Approved
0.7664	Intermediate Similarity	NPD3023	Approved
0.7647	Intermediate Similarity	NPD3025	Approved
0.7647	Intermediate Similarity	NPD3024	Approved
0.7616	Intermediate Similarity	NPD7390	Discontinued
0.7566	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2798	Approved
0.7417	Intermediate Similarity	NPD7003	Approved
0.7407	Intermediate Similarity	NPD5951	Approved
0.7397	Intermediate Similarity	NPD943	Approved
0.7394	Intermediate Similarity	NPD1164	Approved
0.7379	Intermediate Similarity	NPD3764	Approved
0.7338	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7329	Intermediate Similarity	NPD6663	Approved
0.7324	Intermediate Similarity	NPD1876	Approved
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD8166	Discontinued
0.7292	Intermediate Similarity	NPD5736	Approved
0.729	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7266	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2313	Discontinued
0.725	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4059	Approved
0.7194	Intermediate Similarity	NPD3091	Approved
0.7183	Intermediate Similarity	NPD4878	Approved
0.7143	Intermediate Similarity	NPD2342	Discontinued
0.7143	Intermediate Similarity	NPD2309	Approved
0.7122	Intermediate Similarity	NPD7610	Discontinued
0.709	Intermediate Similarity	NPD9266	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.7086	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3750	Approved
0.7066	Intermediate Similarity	NPD7473	Discontinued
0.705	Intermediate Similarity	NPD9493	Approved
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9264	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7007	Intermediate Similarity	NPD7635	Approved
0.6993	Remote Similarity	NPD3092	Approved
0.6988	Remote Similarity	NPD6232	Discontinued
0.6974	Remote Similarity	NPD1510	Phase 2
0.6972	Remote Similarity	NPD3095	Discontinued
0.6972	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1607	Approved
0.6951	Remote Similarity	NPD3749	Approved
0.695	Remote Similarity	NPD7009	Phase 2
0.6933	Remote Similarity	NPD1240	Approved
0.6918	Remote Similarity	NPD3094	Phase 2
0.6918	Remote Similarity	NPD1203	Approved
0.6913	Remote Similarity	NPD3268	Approved
0.6903	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7819	Suspended
0.6867	Remote Similarity	NPD8032	Phase 2
0.6859	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8150	Discontinued
0.6852	Remote Similarity	NPD7411	Suspended
0.6849	Remote Similarity	NPD1283	Approved
0.6846	Remote Similarity	NPD288	Approved
0.6846	Remote Similarity	NPD7008	Discontinued
0.6842	Remote Similarity	NPD1930	Approved
0.6842	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1929	Approved
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3972	Approved
0.6826	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4879	Approved
0.6795	Remote Similarity	NPD2800	Approved
0.6792	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7028	Phase 2
0.6786	Remote Similarity	NPD9281	Approved
0.6782	Remote Similarity	NPD8313	Approved
0.6782	Remote Similarity	NPD8312	Approved
0.6763	Remote Similarity	NPD5027	Approved
0.6763	Remote Similarity	NPD5029	Approved
0.6763	Remote Similarity	NPD5031	Approved
0.6755	Remote Similarity	NPD7961	Discontinued
0.6753	Remote Similarity	NPD3748	Approved
0.6753	Remote Similarity	NPD4308	Phase 3
0.6752	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3020	Approved
0.6731	Remote Similarity	NPD1549	Phase 2
0.6724	Remote Similarity	NPD4954	Approved
0.6724	Remote Similarity	NPD5028	Approved
0.6724	Remote Similarity	NPD4955	Approved
0.6724	Remote Similarity	NPD36	Approved
0.6724	Remote Similarity	NPD5026	Approved
0.6724	Remote Similarity	NPD5034	Approved
0.6716	Remote Similarity	NPD9261	Approved
0.6712	Remote Similarity	NPD9717	Approved
0.671	Remote Similarity	NPD6099	Approved
0.671	Remote Similarity	NPD6100	Approved
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3266	Approved
0.6689	Remote Similarity	NPD3267	Approved
0.6689	Remote Similarity	NPD411	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4380	Phase 2
0.6687	Remote Similarity	NPD2534	Approved
0.6687	Remote Similarity	NPD2532	Approved
0.6687	Remote Similarity	NPD2533	Approved
0.6687	Remote Similarity	NPD7768	Phase 2
0.6685	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD5033	Approved
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD4750	Phase 3
0.6667	Remote Similarity	NPD3022	Approved
0.6644	Remote Similarity	NPD4624	Approved
0.6644	Remote Similarity	NPD1281	Approved
0.6642	Remote Similarity	NPD1932	Approved
0.6641	Remote Similarity	NPD844	Approved
0.6627	Remote Similarity	NPD2296	Approved
0.6625	Remote Similarity	NPD1511	Approved
0.6619	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6844	Discontinued
0.6606	Remote Similarity	NPD1934	Approved
0.6603	Remote Similarity	NPD1551	Phase 2
0.6594	Remote Similarity	NPD2329	Discontinued
0.6592	Remote Similarity	NPD6836	Approved
0.6591	Remote Similarity	NPD3495	Discontinued
0.6587	Remote Similarity	NPD3882	Suspended
0.6573	Remote Similarity	NPD5037	Approved
0.6573	Remote Similarity	NPD5038	Approved
0.6573	Remote Similarity	NPD8434	Phase 2
0.6568	Remote Similarity	NPD5494	Approved
0.6566	Remote Similarity	NPD2801	Approved
0.6566	Remote Similarity	NPD5761	Phase 2
0.6566	Remote Similarity	NPD5760	Phase 2
0.6558	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6832	Phase 2
0.6554	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4093	Discontinued
0.6552	Remote Similarity	NPD4956	Approved
0.6543	Remote Similarity	NPD1512	Approved
0.6541	Remote Similarity	NPD4628	Phase 3
0.6534	Remote Similarity	NPD5032	Approved
0.6529	Remote Similarity	NPD8127	Discontinued
0.6527	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5036	Approved
0.6516	Remote Similarity	NPD6651	Approved
0.6516	Remote Similarity	NPD4097	Suspended
0.6515	Remote Similarity	NPD2860	Approved
0.6515	Remote Similarity	NPD2859	Approved
0.6513	Remote Similarity	NPD5156	Approved
0.6513	Remote Similarity	NPD5155	Approved
0.6507	Remote Similarity	NPD2286	Discontinued
0.6507	Remote Similarity	NPD4626	Approved
0.6497	Remote Similarity	NPD5035	Approved
0.6497	Remote Similarity	NPD2796	Approved
0.6494	Remote Similarity	NPD4140	Approved
0.6494	Remote Similarity	NPD6020	Phase 2
0.6494	Remote Similarity	NPD4307	Phase 2
0.6493	Remote Similarity	NPD2066	Phase 3
0.6489	Remote Similarity	NPD845	Approved
0.6486	Remote Similarity	NPD1608	Approved
0.6485	Remote Similarity	NPD6599	Discontinued
0.6484	Remote Similarity	NPD6212	Phase 3
0.6484	Remote Similarity	NPD6213	Phase 3
0.6484	Remote Similarity	NPD6214	Clinical (unspecified phase)

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