NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.12
Volume:	170.557
LogP:	2.549
LogD:	2.243
LogS:	-3.081
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	4.584
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.487
MDCK Permeability:	2.371493428654503e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.975
Plasma Protein Binding (PPB):	51.75977325439453%
Volume Distribution (VD):	1.073
Pgp-substrate:	41.713844299316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.5
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.737
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	17.016
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.127
Carcinogencity:	0.061
Eye Corrosion:	0.92
Eye Irritation:	0.969
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC294440

Natural Product ID:	NPC294440
*Common Name:**	2,2,3-Trimethylbicyclo[2.2.1]Heptan-5-One
IUPAC Name:	2,2,3-trimethylbicyclo[2.2.1]heptan-5-one
Synonyms:
Standard InCHIKey:	TZAXGXBLCOILBQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H16O/c1-6-8-4-7(5-9(8)11)10(6,2)3/h6-8H,4-5H2,1-3H3
SMILES:	CC1C2CC(CC2=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1972894
PubChem CID:	376006
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9546	Cinamomum cassia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	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
GI50	55

Activity Type	# Activity
Cell Line	55

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[487904]

☑ 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 NPC294440 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	648
0.1-0.2	16779
0.2-0.3	13209
0.3-0.4	8645
0.4-0.5	2827
0.5-0.6	507
0.6-0.7	63
0.7-0.8	9
0.8-0.85	0
0.85-0.9	1
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC293343
0.9778	High Similarity	NPC258672
0.9778	High Similarity	NPC247786
0.9362	High Similarity	NPC274182
0.9333	High Similarity	NPC40249
0.9333	High Similarity	NPC131981
0.9333	High Similarity	NPC173996
0.8723	High Similarity	NPC20017
0.8511	High Similarity	NPC285814
0.8511	High Similarity	NPC83187
0.8511	High Similarity	NPC98246
0.7955	Intermediate Similarity	NPC223315
0.7925	Intermediate Similarity	NPC184819
0.7857	Intermediate Similarity	NPC270042
0.7778	Intermediate Similarity	NPC474105
0.7778	Intermediate Similarity	NPC151464
0.7778	Intermediate Similarity	NPC143597
0.7736	Intermediate Similarity	NPC53245
0.7736	Intermediate Similarity	NPC288296
0.766	Intermediate Similarity	NPC18397
0.75	Intermediate Similarity	NPC171783
0.7391	Intermediate Similarity	NPC141634
0.7288	Intermediate Similarity	NPC472306
0.7234	Intermediate Similarity	NPC215118
0.7234	Intermediate Similarity	NPC45270
0.7234	Intermediate Similarity	NPC135077
0.7234	Intermediate Similarity	NPC59570
0.7018	Intermediate Similarity	NPC49575
0.7018	Intermediate Similarity	NPC55004
0.7018	Intermediate Similarity	NPC267626
0.6885	Remote Similarity	NPC128608
0.6852	Remote Similarity	NPC236623
0.6833	Remote Similarity	NPC213152
0.6724	Remote Similarity	NPC230823
0.6667	Remote Similarity	NPC307063
0.6667	Remote Similarity	NPC200258
0.6667	Remote Similarity	NPC96812
0.6667	Remote Similarity	NPC107704
0.6667	Remote Similarity	NPC168824
0.6667	Remote Similarity	NPC25853
0.6667	Remote Similarity	NPC189917
0.6667	Remote Similarity	NPC39462
0.6667	Remote Similarity	NPC43300
0.6613	Remote Similarity	NPC212210
0.661	Remote Similarity	NPC266295
0.661	Remote Similarity	NPC94991
0.661	Remote Similarity	NPC30215
0.6567	Remote Similarity	NPC248567
0.6567	Remote Similarity	NPC52667
0.65	Remote Similarity	NPC259261
0.6491	Remote Similarity	NPC319589
0.6462	Remote Similarity	NPC20610
0.6462	Remote Similarity	NPC473225
0.6452	Remote Similarity	NPC165695
0.6418	Remote Similarity	NPC197701
0.6406	Remote Similarity	NPC323005
0.6377	Remote Similarity	NPC132064
0.6364	Remote Similarity	NPC477857
0.6364	Remote Similarity	NPC182815
0.6364	Remote Similarity	NPC474962
0.6364	Remote Similarity	NPC116906
0.6364	Remote Similarity	NPC321646
0.6349	Remote Similarity	NPC473902
0.6333	Remote Similarity	NPC127798
0.6308	Remote Similarity	NPC475523
0.6304	Remote Similarity	NPC248190
0.629	Remote Similarity	NPC475795
0.6269	Remote Similarity	NPC282593
0.6269	Remote Similarity	NPC159577
0.6269	Remote Similarity	NPC35734
0.6269	Remote Similarity	NPC40574
0.6269	Remote Similarity	NPC214770
0.6269	Remote Similarity	NPC108131
0.6269	Remote Similarity	NPC477856
0.6269	Remote Similarity	NPC307176
0.625	Remote Similarity	NPC157518
0.625	Remote Similarity	NPC69245
0.6207	Remote Similarity	NPC202146
0.6207	Remote Similarity	NPC32222
0.6197	Remote Similarity	NPC74685
0.6197	Remote Similarity	NPC169389
0.6197	Remote Similarity	NPC475932
0.6176	Remote Similarity	NPC110615
0.6176	Remote Similarity	NPC473267
0.6176	Remote Similarity	NPC305501
0.6176	Remote Similarity	NPC320549
0.6176	Remote Similarity	NPC58057
0.6176	Remote Similarity	NPC223187
0.6176	Remote Similarity	NPC5701
0.6176	Remote Similarity	NPC115023
0.6176	Remote Similarity	NPC156277
0.6176	Remote Similarity	NPC234707
0.6176	Remote Similarity	NPC151018
0.6176	Remote Similarity	NPC470078
0.617	Remote Similarity	NPC121215
0.6167	Remote Similarity	NPC192427
0.6154	Remote Similarity	NPC166362
0.6154	Remote Similarity	NPC268736
0.6154	Remote Similarity	NPC141777
0.6154	Remote Similarity	NPC42060
0.6154	Remote Similarity	NPC477931
0.6154	Remote Similarity	NPC227670
0.6143	Remote Similarity	NPC155441
0.6136	Remote Similarity	NPC196434
0.6136	Remote Similarity	NPC79887
0.6136	Remote Similarity	NPC221192
0.6136	Remote Similarity	NPC153439
0.6136	Remote Similarity	NPC222997
0.6136	Remote Similarity	NPC42403
0.6136	Remote Similarity	NPC29561
0.6136	Remote Similarity	NPC4962
0.6129	Remote Similarity	NPC127582
0.6129	Remote Similarity	NPC84218
0.6129	Remote Similarity	NPC478126
0.6119	Remote Similarity	NPC6120
0.6119	Remote Similarity	NPC131892
0.6119	Remote Similarity	NPC321732
0.6119	Remote Similarity	NPC213178
0.6119	Remote Similarity	NPC196197
0.6119	Remote Similarity	NPC324607
0.6119	Remote Similarity	NPC139397
0.6119	Remote Similarity	NPC327728
0.6111	Remote Similarity	NPC228911
0.6087	Remote Similarity	NPC474228
0.6087	Remote Similarity	NPC470045
0.6087	Remote Similarity	NPC474123
0.6087	Remote Similarity	NPC310766
0.6087	Remote Similarity	NPC303613
0.6087	Remote Similarity	NPC251705
0.6087	Remote Similarity	NPC470044
0.6087	Remote Similarity	NPC232112
0.6061	Remote Similarity	NPC478180
0.6061	Remote Similarity	NPC130459
0.6061	Remote Similarity	NPC474221
0.6032	Remote Similarity	NPC60565
0.6032	Remote Similarity	NPC83088
0.6029	Remote Similarity	NPC260040
0.6029	Remote Similarity	NPC265782
0.6029	Remote Similarity	NPC2634
0.6029	Remote Similarity	NPC251929
0.6029	Remote Similarity	NPC476731
0.6	Remote Similarity	NPC20603
0.6	Remote Similarity	NPC255021
0.6	Remote Similarity	NPC159497
0.6	Remote Similarity	NPC309852
0.6	Remote Similarity	NPC254340
0.6	Remote Similarity	NPC472854
0.6	Remote Similarity	NPC168982
0.5968	Remote Similarity	NPC143834
0.5942	Remote Similarity	NPC89310
0.5942	Remote Similarity	NPC126642
0.5942	Remote Similarity	NPC472309
0.5942	Remote Similarity	NPC54123
0.5938	Remote Similarity	NPC32285
0.5938	Remote Similarity	NPC197238
0.5938	Remote Similarity	NPC202118
0.5926	Remote Similarity	NPC229403
0.5915	Remote Similarity	NPC125767
0.5915	Remote Similarity	NPC21220
0.5915	Remote Similarity	NPC293803
0.5915	Remote Similarity	NPC201263
0.5915	Remote Similarity	NPC273366
0.5915	Remote Similarity	NPC255650
0.5915	Remote Similarity	NPC97534
0.5915	Remote Similarity	NPC174964
0.5915	Remote Similarity	NPC195155
0.5915	Remote Similarity	NPC72444
0.5915	Remote Similarity	NPC472311
0.5909	Remote Similarity	NPC198118
0.5909	Remote Similarity	NPC295442
0.5909	Remote Similarity	NPC38859
0.5909	Remote Similarity	NPC176171
0.5902	Remote Similarity	NPC115385
0.5902	Remote Similarity	NPC150713
0.5902	Remote Similarity	NPC29976
0.5882	Remote Similarity	NPC319671
0.5882	Remote Similarity	NPC476734
0.5882	Remote Similarity	NPC162867
0.5882	Remote Similarity	NPC469677
0.5882	Remote Similarity	NPC64466
0.5882	Remote Similarity	NPC475952
0.5882	Remote Similarity	NPC469941
0.5882	Remote Similarity	NPC252032
0.5882	Remote Similarity	NPC61702
0.5873	Remote Similarity	NPC66145
0.587	Remote Similarity	NPC225318
0.587	Remote Similarity	NPC268596
0.587	Remote Similarity	NPC76608
0.587	Remote Similarity	NPC149101
0.587	Remote Similarity	NPC16578
0.5846	Remote Similarity	NPC475124
0.5846	Remote Similarity	NPC469662
0.5846	Remote Similarity	NPC285371
0.5846	Remote Similarity	NPC6697
0.5833	Remote Similarity	NPC218357
0.5833	Remote Similarity	NPC472486
0.5833	Remote Similarity	NPC5767
0.5833	Remote Similarity	NPC472487
0.5833	Remote Similarity	NPC475742
0.5833	Remote Similarity	NPC69408

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 NPC294440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1043
0.1-0.2	6012
0.2-0.3	1480
0.3-0.4	412
0.4-0.5	154
0.5-0.6	45
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD344	Approved
0.9333	High Similarity	NPD345	Approved
0.9333	High Similarity	NPD343	Approved
0.6774	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5360	Phase 3
0.6406	Remote Similarity	NPD4224	Phase 2
0.6269	Remote Similarity	NPD4747	Approved
0.6269	Remote Similarity	NPD4789	Approved
0.6212	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4758	Discontinued
0.6176	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5276	Approved
0.6176	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6081	Approved
0.6119	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD4137	Phase 3
0.6119	Remote Similarity	NPD3698	Phase 2
0.6029	Remote Similarity	NPD4245	Approved
0.6029	Remote Similarity	NPD4691	Approved
0.6029	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD5733	Approved
0.6	Remote Similarity	NPD4687	Approved
0.5962	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD5777	Approved
0.5775	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD3198	Approved
0.5694	Remote Similarity	NPD3703	Phase 2
0.5694	Remote Similarity	NPD3702	Approved
0.5676	Remote Similarity	NPD5364	Discontinued
0.5636	Remote Similarity	NPD634	Phase 3
0.5616	Remote Similarity	NPD6117	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