NPASS Compound

Structure

CID197513 OpenBabel06191715582D 26 26 0 0 0 0 0 0 0 0999 V2000 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.8660 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 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 -0.8660 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 9.0000 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 0.0000 1.0000 0.0000 O 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 15 1 0 0 0 0 6 15 2 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 19 23 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:	360.19
Volume:	388.712
LogP:	3.076
LogD:	2.711
LogS:	-3.276
# Rotatable Bonds:	10
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	3.087
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	1.4527246094075963e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.683
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	90.74024963378906%
Volume Distribution (VD):	0.347
Pgp-substrate:	3.316983938217163%

ADMET: Metabolism

CYP1A2-inhibitor:	0.406
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.426
CYP2C9-substrate:	0.63
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.695
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	4.489
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.958
Carcinogencity:	0.02
Eye Corrosion:	0.053
Eye Irritation:	0.838
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC197513

Natural Product ID:	NPC197513
*Common Name:**	Ganomycin A
IUPAC Name:	(2Z,5E,9E)-2-[2-(2,5-dihydroxyphenyl)ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9-dienoic acid
Synonyms:
Standard InCHIKey:	YMBZMWGZXRRFEN-KPJMVHGFSA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-15(5-3-7-16(2)14-22)6-4-8-17(21(25)26)9-10-18-13-19(23)11-12-20(18)24/h6-7,9,11-13,22-24H,3-5,8,10,14H2,1-2H3,(H,25,26)/b15-6+,16-7+,17-9-
SMILES:	C/C(=CCC/C(=C/Cc1cc(ccc1O)O)/C(=O)O)/CC/C=C(C)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496059
PubChem CID:	9841824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757736]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378363]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[16378363]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804830]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11201	Barleria strigosa	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27375	Sphingomonas paucimobilis	Species	Sphingomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7245	Lamprometra klunzingeri	Species	Mariametridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14696	Frullania inflata	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12787	Phora hyperborea	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15560	Penicillium camemberti	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12142	Solanum nodiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13953	Gouania lupuloides	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14984	Agelenopsis aperta	Species	Agelenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	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
MIC	2
Others	9

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	19.0	mm	PMID[487822]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	15.0	mm	PMID[487822]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	16.0	mm	PMID[487822]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	24.0	mm	PMID[487822]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	16.0	mm	PMID[487822]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	25.0	mm	PMID[487822]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	4.0	mm	PMID[487822]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	IZ	=	15.0	mm	PMID[487822]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	IZ	=	15.0	mm	PMID[487822]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.5	ug.mL-1	PMID[487822]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[487822]

☑ 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 NPC197513 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	204
0.1-0.2	1035
0.2-0.3	3460
0.3-0.4	9292
0.4-0.5	10342
0.5-0.6	7524
0.6-0.7	8984
0.7-0.8	1681
0.8-0.85	145
0.85-0.9	23
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC228609
0.9273	High Similarity	NPC114918
0.9167	High Similarity	NPC98392
0.9083	High Similarity	NPC471535
0.9057	High Similarity	NPC93831
0.9052	High Similarity	NPC477151
0.9052	High Similarity	NPC132518
0.9009	High Similarity	NPC296144
0.9009	High Similarity	NPC28784
0.8929	High Similarity	NPC473931
0.8929	High Similarity	NPC474050
0.8929	High Similarity	NPC474114
0.8814	High Similarity	NPC477152
0.8761	High Similarity	NPC41851
0.8739	High Similarity	NPC208229
0.8727	High Similarity	NPC279887
0.8727	High Similarity	NPC68260
0.8655	High Similarity	NPC477153
0.8649	High Similarity	NPC26013
0.8649	High Similarity	NPC282855
0.8585	High Similarity	NPC152097
0.8583	High Similarity	NPC117794
0.8547	High Similarity	NPC476020
0.8534	High Similarity	NPC269414
0.8534	High Similarity	NPC160199
0.8512	High Similarity	NPC472592
0.8509	High Similarity	NPC190212
0.8505	High Similarity	NPC260775
0.8468	Intermediate Similarity	NPC123
0.8468	Intermediate Similarity	NPC474352
0.8468	Intermediate Similarity	NPC163169
0.8462	Intermediate Similarity	NPC206205
0.8426	Intermediate Similarity	NPC12931
0.8426	Intermediate Similarity	NPC130103
0.8426	Intermediate Similarity	NPC48730
0.8426	Intermediate Similarity	NPC70677
0.8426	Intermediate Similarity	NPC248396
0.8426	Intermediate Similarity	NPC129373
0.8426	Intermediate Similarity	NPC130756
0.8421	Intermediate Similarity	NPC26615
0.8417	Intermediate Similarity	NPC325301
0.8417	Intermediate Similarity	NPC327070
0.8411	Intermediate Similarity	NPC475078
0.8403	Intermediate Similarity	NPC165197
0.8396	Intermediate Similarity	NPC246679
0.8396	Intermediate Similarity	NPC257182
0.8362	Intermediate Similarity	NPC240163
0.8361	Intermediate Similarity	NPC167055
0.8361	Intermediate Similarity	NPC240744
0.8349	Intermediate Similarity	NPC94343
0.8333	Intermediate Similarity	NPC25168
0.8319	Intermediate Similarity	NPC473524
0.8305	Intermediate Similarity	NPC41567
0.8293	Intermediate Similarity	NPC474945
0.8293	Intermediate Similarity	NPC476022
0.8293	Intermediate Similarity	NPC474944
0.8291	Intermediate Similarity	NPC312800
0.8288	Intermediate Similarity	NPC303141
0.8288	Intermediate Similarity	NPC243677
0.8276	Intermediate Similarity	NPC81808
0.8273	Intermediate Similarity	NPC13426
0.8273	Intermediate Similarity	NPC235762
0.8273	Intermediate Similarity	NPC108497
0.8273	Intermediate Similarity	NPC471228
0.8264	Intermediate Similarity	NPC475192
0.8264	Intermediate Similarity	NPC297193
0.8257	Intermediate Similarity	NPC174911
0.8241	Intermediate Similarity	NPC474073
0.8241	Intermediate Similarity	NPC88420
0.8235	Intermediate Similarity	NPC160235
0.823	Intermediate Similarity	NPC31274
0.8226	Intermediate Similarity	NPC95034
0.8226	Intermediate Similarity	NPC142087
0.8214	Intermediate Similarity	NPC187913
0.8211	Intermediate Similarity	NPC287473
0.8208	Intermediate Similarity	NPC29373
0.8198	Intermediate Similarity	NPC475225
0.8189	Intermediate Similarity	NPC329427
0.8189	Intermediate Similarity	NPC317601
0.8182	Intermediate Similarity	NPC477685
0.8182	Intermediate Similarity	NPC80800
0.816	Intermediate Similarity	NPC476024
0.8158	Intermediate Similarity	NPC75272
0.8158	Intermediate Similarity	NPC471954
0.8151	Intermediate Similarity	NPC203124
0.8151	Intermediate Similarity	NPC309434
0.8148	Intermediate Similarity	NPC283711
0.8142	Intermediate Similarity	NPC34715
0.813	Intermediate Similarity	NPC469568
0.8125	Intermediate Similarity	NPC47284
0.812	Intermediate Similarity	NPC163154
0.8115	Intermediate Similarity	NPC49441
0.8108	Intermediate Similarity	NPC470202
0.8103	Intermediate Similarity	NPC302371
0.8099	Intermediate Similarity	NPC115188
0.8099	Intermediate Similarity	NPC179092
0.8099	Intermediate Similarity	NPC159760
0.8099	Intermediate Similarity	NPC292665
0.8099	Intermediate Similarity	NPC178395
0.8099	Intermediate Similarity	NPC244994
0.8099	Intermediate Similarity	NPC222876
0.8099	Intermediate Similarity	NPC26433
0.8099	Intermediate Similarity	NPC35856
0.8099	Intermediate Similarity	NPC301987
0.8099	Intermediate Similarity	NPC272454
0.8087	Intermediate Similarity	NPC183700
0.8083	Intermediate Similarity	NPC184579
0.8083	Intermediate Similarity	NPC233165
0.8083	Intermediate Similarity	NPC473767
0.808	Intermediate Similarity	NPC477212
0.808	Intermediate Similarity	NPC477211
0.808	Intermediate Similarity	NPC71525
0.808	Intermediate Similarity	NPC477214
0.808	Intermediate Similarity	NPC319422
0.807	Intermediate Similarity	NPC470039
0.8067	Intermediate Similarity	NPC125252
0.8067	Intermediate Similarity	NPC76308
0.8067	Intermediate Similarity	NPC325295
0.8053	Intermediate Similarity	NPC317592
0.8053	Intermediate Similarity	NPC53740
0.8053	Intermediate Similarity	NPC155072
0.8049	Intermediate Similarity	NPC275145
0.8047	Intermediate Similarity	NPC246693
0.8047	Intermediate Similarity	NPC110609
0.8047	Intermediate Similarity	NPC242358
0.8036	Intermediate Similarity	NPC323810
0.8036	Intermediate Similarity	NPC130817
0.8034	Intermediate Similarity	NPC148969
0.8033	Intermediate Similarity	NPC476165
0.803	Intermediate Similarity	NPC475045
0.8019	Intermediate Similarity	NPC312304
0.8017	Intermediate Similarity	NPC328485
0.8016	Intermediate Similarity	NPC473744
0.8	Intermediate Similarity	NPC474890
0.8	Intermediate Similarity	NPC306765
0.8	Intermediate Similarity	NPC245561
0.8	Intermediate Similarity	NPC326187
0.8	Intermediate Similarity	NPC273282
0.8	Intermediate Similarity	NPC49647
0.8	Intermediate Similarity	NPC136342
0.8	Intermediate Similarity	NPC295202
0.8	Intermediate Similarity	NPC227741
0.8	Intermediate Similarity	NPC161943
0.7984	Intermediate Similarity	NPC295406
0.7984	Intermediate Similarity	NPC472591
0.7984	Intermediate Similarity	NPC289572
0.7984	Intermediate Similarity	NPC157478
0.7984	Intermediate Similarity	NPC200422
0.7983	Intermediate Similarity	NPC281277
0.7983	Intermediate Similarity	NPC477453
0.7982	Intermediate Similarity	NPC320439
0.7982	Intermediate Similarity	NPC66834
0.7982	Intermediate Similarity	NPC233320
0.7967	Intermediate Similarity	NPC46634
0.7966	Intermediate Similarity	NPC285350
0.7966	Intermediate Similarity	NPC328593
0.7966	Intermediate Similarity	NPC33749
0.7966	Intermediate Similarity	NPC261453
0.7963	Intermediate Similarity	NPC81010
0.7963	Intermediate Similarity	NPC32977
0.7955	Intermediate Similarity	NPC475005
0.7955	Intermediate Similarity	NPC474943
0.7951	Intermediate Similarity	NPC470848
0.7951	Intermediate Similarity	NPC164852
0.7951	Intermediate Similarity	NPC470849
0.7946	Intermediate Similarity	NPC269212
0.7946	Intermediate Similarity	NPC304638
0.7937	Intermediate Similarity	NPC209959
0.7934	Intermediate Similarity	NPC141791
0.7934	Intermediate Similarity	NPC328459
0.7934	Intermediate Similarity	NPC263386
0.7934	Intermediate Similarity	NPC90522
0.7934	Intermediate Similarity	NPC98748
0.7931	Intermediate Similarity	NPC63345
0.7931	Intermediate Similarity	NPC222084
0.7928	Intermediate Similarity	NPC294741
0.7928	Intermediate Similarity	NPC253746
0.7928	Intermediate Similarity	NPC52472
0.7923	Intermediate Similarity	NPC474097
0.7923	Intermediate Similarity	NPC204582
0.792	Intermediate Similarity	NPC477213
0.792	Intermediate Similarity	NPC131799
0.7917	Intermediate Similarity	NPC278652
0.7917	Intermediate Similarity	NPC240664
0.7917	Intermediate Similarity	NPC320864
0.7913	Intermediate Similarity	NPC317305
0.7913	Intermediate Similarity	NPC224584
0.7899	Intermediate Similarity	NPC161304
0.7899	Intermediate Similarity	NPC23402
0.7899	Intermediate Similarity	NPC474967
0.7899	Intermediate Similarity	NPC233669
0.7895	Intermediate Similarity	NPC29989
0.7895	Intermediate Similarity	NPC294902
0.7895	Intermediate Similarity	NPC299405
0.7895	Intermediate Similarity	NPC471602
0.7895	Intermediate Similarity	NPC256463
0.7895	Intermediate Similarity	NPC469913
0.7895	Intermediate Similarity	NPC1786
0.7895	Intermediate Similarity	NPC306835
0.7895	Intermediate Similarity	NPC70843

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 NPC197513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	787
0.2-0.3	1538
0.3-0.4	2646
0.4-0.5	2119
0.5-0.6	1279
0.6-0.7	519
0.7-0.8	73
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD3496	Discontinued
0.8091	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD844	Approved
0.7879	Intermediate Similarity	NPD2935	Discontinued
0.7833	Intermediate Similarity	NPD9493	Approved
0.7759	Intermediate Similarity	NPD9266	Approved
0.7759	Intermediate Similarity	NPD74	Approved
0.7672	Intermediate Similarity	NPD9263	Approved
0.7672	Intermediate Similarity	NPD9267	Approved
0.7672	Intermediate Similarity	NPD9264	Approved
0.7658	Intermediate Similarity	NPD288	Approved
0.7581	Intermediate Similarity	NPD1778	Approved
0.7581	Intermediate Similarity	NPD4626	Approved
0.7561	Intermediate Similarity	NPD9545	Approved
0.7541	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7635	Approved
0.7478	Intermediate Similarity	NPD6647	Phase 2
0.7477	Intermediate Similarity	NPD2933	Approved
0.7477	Intermediate Similarity	NPD2934	Approved
0.7459	Intermediate Similarity	NPD6671	Approved
0.7419	Intermediate Similarity	NPD1759	Phase 1
0.7411	Intermediate Similarity	NPD2860	Approved
0.7411	Intermediate Similarity	NPD2859	Approved
0.7387	Intermediate Similarity	NPD845	Approved
0.7385	Intermediate Similarity	NPD5736	Approved
0.7377	Intermediate Similarity	NPD9281	Approved
0.7368	Intermediate Similarity	NPD3020	Approved
0.736	Intermediate Similarity	NPD5691	Approved
0.7339	Intermediate Similarity	NPD1758	Phase 1
0.7328	Intermediate Similarity	NPD9261	Approved
0.7321	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3134	Approved
0.7281	Intermediate Similarity	NPD9495	Approved
0.7266	Intermediate Similarity	NPD9717	Approved
0.7259	Intermediate Similarity	NPD6653	Approved
0.725	Intermediate Similarity	NPD4750	Phase 3
0.725	Intermediate Similarity	NPD3021	Approved
0.725	Intermediate Similarity	NPD3022	Approved
0.7241	Intermediate Similarity	NPD846	Approved
0.7241	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD1470	Approved
0.7231	Intermediate Similarity	NPD1164	Approved
0.7231	Intermediate Similarity	NPD2797	Approved
0.7227	Intermediate Similarity	NPD1358	Approved
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5585	Approved
0.7214	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1535	Discovery
0.7188	Intermediate Similarity	NPD1201	Approved
0.7185	Intermediate Similarity	NPD230	Phase 1
0.7185	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD256	Approved
0.7177	Intermediate Similarity	NPD255	Approved
0.7174	Intermediate Similarity	NPD7266	Discontinued
0.7167	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3019	Approved
0.7165	Intermediate Similarity	NPD2932	Approved
0.7164	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3136	Phase 2
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7132	Intermediate Similarity	NPD1481	Phase 2
0.7132	Intermediate Similarity	NPD9269	Phase 2
0.713	Intermediate Similarity	NPD111	Approved
0.7117	Intermediate Similarity	NPD9258	Approved
0.7117	Intermediate Similarity	NPD9256	Approved
0.7111	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD826	Approved
0.7111	Intermediate Similarity	NPD825	Approved
0.7109	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD1809	Phase 2
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD1203	Approved
0.7097	Intermediate Similarity	NPD9618	Approved
0.7097	Intermediate Similarity	NPD9614	Approved
0.7097	Intermediate Similarity	NPD2629	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.709	Intermediate Similarity	NPD411	Approved
0.7087	Intermediate Similarity	NPD9268	Approved
0.7068	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD258	Approved
0.7045	Intermediate Similarity	NPD257	Approved
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD520	Approved
0.7025	Intermediate Similarity	NPD2182	Approved
0.7023	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3091	Approved
0.7	Intermediate Similarity	NPD1445	Approved
0.7	Intermediate Similarity	NPD968	Approved
0.7	Intermediate Similarity	NPD1444	Approved
0.6992	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9568	Approved
0.6978	Remote Similarity	NPD6032	Approved
0.6975	Remote Similarity	NPD1237	Approved
0.697	Remote Similarity	NPD6362	Approved
0.6963	Remote Similarity	NPD6798	Discontinued
0.6963	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD2313	Discontinued
0.6963	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4359	Approved
0.6942	Remote Similarity	NPD2342	Discontinued
0.6934	Remote Similarity	NPD6355	Discontinued
0.6934	Remote Similarity	NPD555	Phase 2
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5536	Phase 2
0.6929	Remote Similarity	NPD6005	Phase 3
0.6929	Remote Similarity	NPD6002	Phase 3
0.6929	Remote Similarity	NPD9613	Approved
0.6929	Remote Similarity	NPD6004	Phase 3
0.6929	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2346	Discontinued
0.6929	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9616	Approved
0.6929	Remote Similarity	NPD9615	Approved
0.6923	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD422	Phase 1
0.6923	Remote Similarity	NPD1611	Approved
0.6917	Remote Similarity	NPD2798	Approved
0.6917	Remote Similarity	NPD1019	Discontinued
0.6917	Remote Similarity	NPD9697	Approved
0.6912	Remote Similarity	NPD259	Phase 1
0.6906	Remote Similarity	NPD2799	Discontinued
0.6906	Remote Similarity	NPD7033	Discontinued
0.6906	Remote Similarity	NPD4308	Phase 3
0.6901	Remote Similarity	NPD3400	Discontinued
0.6901	Remote Similarity	NPD4628	Phase 3
0.6894	Remote Similarity	NPD1283	Approved
0.688	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1241	Discontinued
0.6879	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD316	Approved
0.6875	Remote Similarity	NPD1894	Discontinued
0.6871	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1608	Approved
0.6867	Remote Similarity	NPD5402	Approved
0.6866	Remote Similarity	NPD9569	Approved
0.6866	Remote Similarity	NPD9494	Approved
0.6866	Remote Similarity	NPD2861	Phase 2
0.6866	Remote Similarity	NPD2237	Approved
0.6866	Remote Similarity	NPD4208	Discontinued
0.6864	Remote Similarity	NPD1242	Phase 1
0.6861	Remote Similarity	NPD943	Approved
0.6857	Remote Similarity	NPD9570	Approved
0.6857	Remote Similarity	NPD1551	Phase 2
0.6855	Remote Similarity	NPD228	Approved
0.6842	Remote Similarity	NPD3094	Phase 2
0.6833	Remote Similarity	NPD164	Approved
0.6829	Remote Similarity	NPD2067	Discontinued
0.6829	Remote Similarity	NPD1792	Phase 2
0.6825	Remote Similarity	NPD497	Approved
0.6825	Remote Similarity	NPD5951	Approved
0.6818	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1755	Approved
0.6815	Remote Similarity	NPD600	Approved
0.6815	Remote Similarity	NPD596	Approved
0.6809	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1653	Approved
0.6803	Remote Similarity	NPD290	Approved
0.6794	Remote Similarity	NPD3092	Approved
0.6794	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD9088	Approved
0.6791	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5647	Approved
0.6789	Remote Similarity	NPD9491	Approved
0.6788	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD839	Approved
0.6788	Remote Similarity	NPD840	Approved
0.6786	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1202	Approved
0.6783	Remote Similarity	NPD7003	Approved
0.6777	Remote Similarity	NPD5048	Discontinued
0.6774	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3095	Discontinued
0.6765	Remote Similarity	NPD7095	Approved
0.6759	Remote Similarity	NPD226	Approved
0.6757	Remote Similarity	NPD3455	Phase 2
0.6757	Remote Similarity	NPD9257	Approved
0.6757	Remote Similarity	NPD9259	Approved
0.675	Remote Similarity	NPD5765	Approved
0.675	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1929	Approved
0.675	Remote Similarity	NPD1930	Approved
0.6748	Remote Similarity	NPD2684	Approved
0.6746	Remote Similarity	NPD496	Approved
0.6746	Remote Similarity	NPD498	Approved
0.6746	Remote Similarity	NPD495	Approved
0.6744	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2979	Phase 3

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