NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	146.04
Volume:	151.506
LogP:	2.026
LogD:	2.412
LogS:	-3.053
# Rotatable Bonds:	1
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	2.53
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.332
MDCK Permeability:	1.5278445061994717e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.245
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.739
Plasma Protein Binding (PPB):	91.51627349853516%
Volume Distribution (VD):	1.618
Pgp-substrate:	7.785925388336182%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.661
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.392
CYP2D6-inhibitor:	0.134
CYP2D6-substrate:	0.646
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	8.377
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.549
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.071
Carcinogencity:	0.907
Eye Corrosion:	0.639
Eye Irritation:	0.989
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC115859

Natural Product ID:	NPC115859
*Common Name:**	Cyclopenta[C]Pyran-7-Carbaldehyde
IUPAC Name:	cyclopenta[c]pyran-7-carbaldehyde
Synonyms:
Standard InCHIKey:	VRMFZTBAWYVGGB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O2/c10-5-8-2-1-7-3-4-11-6-9(7)8/h1-6H
SMILES:	O=Cc1ccc2c1cocc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1996335
PubChem CID:	390664
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes

*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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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	57

Activity Type	# Activity
Cell Line	57

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[573237]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573237]

☑ 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 NPC115859 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	609
0.1-0.2	2508
0.2-0.3	6353
0.3-0.4	12099
0.4-0.5	5505
0.5-0.6	9792
0.6-0.7	5401
0.7-0.8	408
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8983	High Similarity	NPC137710
0.8862	High Similarity	NPC141059
0.878	High Similarity	NPC83301
0.8583	High Similarity	NPC206007
0.8583	High Similarity	NPC475092
0.8281	Intermediate Similarity	NPC50583
0.8264	Intermediate Similarity	NPC316062
0.8182	Intermediate Similarity	NPC205523
0.8175	Intermediate Similarity	NPC118853
0.8145	Intermediate Similarity	NPC246214
0.811	Intermediate Similarity	NPC471074
0.811	Intermediate Similarity	NPC473885
0.8049	Intermediate Similarity	NPC312525
0.8049	Intermediate Similarity	NPC217180
0.8033	Intermediate Similarity	NPC150895
0.8031	Intermediate Similarity	NPC188377
0.8031	Intermediate Similarity	NPC65735
0.8	Intermediate Similarity	NPC54626
0.7967	Intermediate Similarity	NPC59035
0.7967	Intermediate Similarity	NPC45536
0.7967	Intermediate Similarity	NPC79202
0.7951	Intermediate Similarity	NPC252004
0.7941	Intermediate Similarity	NPC233707
0.7934	Intermediate Similarity	NPC22678
0.791	Intermediate Similarity	NPC209858
0.7886	Intermediate Similarity	NPC28054
0.7881	Intermediate Similarity	NPC42471
0.7874	Intermediate Similarity	NPC314329
0.7863	Intermediate Similarity	NPC59502
0.7795	Intermediate Similarity	NPC79557
0.7795	Intermediate Similarity	NPC97566
0.7778	Intermediate Similarity	NPC35744
0.776	Intermediate Similarity	NPC227660
0.7752	Intermediate Similarity	NPC141252
0.7752	Intermediate Similarity	NPC11799
0.7724	Intermediate Similarity	NPC53953
0.771	Intermediate Similarity	NPC184391
0.7705	Intermediate Similarity	NPC57879
0.7704	Intermediate Similarity	NPC106247
0.7698	Intermediate Similarity	NPC243704
0.7692	Intermediate Similarity	NPC107846
0.7687	Intermediate Similarity	NPC473982
0.7674	Intermediate Similarity	NPC16922
0.7671	Intermediate Similarity	NPC471863
0.766	Intermediate Similarity	NPC117674
0.7647	Intermediate Similarity	NPC324117
0.7647	Intermediate Similarity	NPC265793
0.7638	Intermediate Similarity	NPC201284
0.7634	Intermediate Similarity	NPC74612
0.7634	Intermediate Similarity	NPC470858
0.7634	Intermediate Similarity	NPC224657
0.7619	Intermediate Similarity	NPC144745
0.7619	Intermediate Similarity	NPC208906
0.7615	Intermediate Similarity	NPC243269
0.7612	Intermediate Similarity	NPC477645
0.7609	Intermediate Similarity	NPC472376
0.7606	Intermediate Similarity	NPC93241
0.7606	Intermediate Similarity	NPC247221
0.7606	Intermediate Similarity	NPC27798
0.7597	Intermediate Similarity	NPC317217
0.7597	Intermediate Similarity	NPC477967
0.7581	Intermediate Similarity	NPC279916
0.7561	Intermediate Similarity	NPC105249
0.7561	Intermediate Similarity	NPC23332
0.7559	Intermediate Similarity	NPC21831
0.7559	Intermediate Similarity	NPC187547
0.7559	Intermediate Similarity	NPC32298
0.7557	Intermediate Similarity	NPC179354
0.7552	Intermediate Similarity	NPC208584
0.7536	Intermediate Similarity	NPC473268
0.7536	Intermediate Similarity	NPC278832
0.7536	Intermediate Similarity	NPC307401
0.7536	Intermediate Similarity	NPC64157
0.7519	Intermediate Similarity	NPC329707
0.75	Intermediate Similarity	NPC54243
0.75	Intermediate Similarity	NPC281398
0.75	Intermediate Similarity	NPC138139
0.75	Intermediate Similarity	NPC224418
0.75	Intermediate Similarity	NPC23086
0.75	Intermediate Similarity	NPC471006
0.75	Intermediate Similarity	NPC470740
0.75	Intermediate Similarity	NPC473626
0.75	Intermediate Similarity	NPC216810
0.75	Intermediate Similarity	NPC473969
0.75	Intermediate Similarity	NPC46536
0.7483	Intermediate Similarity	NPC56731
0.7482	Intermediate Similarity	NPC130976
0.7481	Intermediate Similarity	NPC477038
0.7481	Intermediate Similarity	NPC245395
0.7481	Intermediate Similarity	NPC477965
0.7481	Intermediate Similarity	NPC178382
0.7481	Intermediate Similarity	NPC136340
0.748	Intermediate Similarity	NPC469954
0.748	Intermediate Similarity	NPC183648
0.748	Intermediate Similarity	NPC45104
0.7465	Intermediate Similarity	NPC27220
0.7462	Intermediate Similarity	NPC471549
0.7462	Intermediate Similarity	NPC473379
0.7459	Intermediate Similarity	NPC471521
0.7459	Intermediate Similarity	NPC473356
0.7458	Intermediate Similarity	NPC156768
0.7444	Intermediate Similarity	NPC83178
0.7444	Intermediate Similarity	NPC319140
0.7444	Intermediate Similarity	NPC95567
0.7444	Intermediate Similarity	NPC177925
0.7431	Intermediate Similarity	NPC246903
0.7429	Intermediate Similarity	NPC202260
0.7429	Intermediate Similarity	NPC265181
0.7422	Intermediate Similarity	NPC171023
0.7422	Intermediate Similarity	NPC293424
0.7413	Intermediate Similarity	NPC158871
0.7413	Intermediate Similarity	NPC166858
0.7413	Intermediate Similarity	NPC51146
0.741	Intermediate Similarity	NPC215109
0.741	Intermediate Similarity	NPC170604
0.7407	Intermediate Similarity	NPC66246
0.7407	Intermediate Similarity	NPC45947
0.7407	Intermediate Similarity	NPC939
0.7407	Intermediate Similarity	NPC170546
0.7402	Intermediate Similarity	NPC474987
0.7402	Intermediate Similarity	NPC476031
0.7402	Intermediate Similarity	NPC470860
0.7402	Intermediate Similarity	NPC476014
0.7398	Intermediate Similarity	NPC177331
0.7391	Intermediate Similarity	NPC274876
0.7388	Intermediate Similarity	NPC477040
0.7388	Intermediate Similarity	NPC161322
0.7388	Intermediate Similarity	NPC477966
0.7388	Intermediate Similarity	NPC207294
0.7388	Intermediate Similarity	NPC476917
0.7388	Intermediate Similarity	NPC112706
0.7388	Intermediate Similarity	NPC327527
0.7388	Intermediate Similarity	NPC477123
0.7388	Intermediate Similarity	NPC477039
0.7388	Intermediate Similarity	NPC298884
0.7385	Intermediate Similarity	NPC295317
0.7383	Intermediate Similarity	NPC25351
0.7381	Intermediate Similarity	NPC292036
0.7379	Intermediate Similarity	NPC190572
0.7379	Intermediate Similarity	NPC308799
0.7372	Intermediate Similarity	NPC293253
0.7365	Intermediate Similarity	NPC156244
0.7364	Intermediate Similarity	NPC4898
0.7361	Intermediate Similarity	NPC290038
0.7357	Intermediate Similarity	NPC177262
0.7353	Intermediate Similarity	NPC282230
0.7353	Intermediate Similarity	NPC298190
0.7353	Intermediate Similarity	NPC278787
0.7353	Intermediate Similarity	NPC183348
0.7348	Intermediate Similarity	NPC182646
0.7344	Intermediate Similarity	NPC131801
0.7344	Intermediate Similarity	NPC217423
0.7344	Intermediate Similarity	NPC240664
0.7338	Intermediate Similarity	NPC204592
0.7333	Intermediate Similarity	NPC89886
0.7329	Intermediate Similarity	NPC93666
0.7329	Intermediate Similarity	NPC61284
0.7329	Intermediate Similarity	NPC113428
0.7329	Intermediate Similarity	NPC198427
0.7319	Intermediate Similarity	NPC200718
0.7315	Intermediate Similarity	NPC67654
0.7315	Intermediate Similarity	NPC24232
0.7313	Intermediate Similarity	NPC246392
0.7313	Intermediate Similarity	NPC290955
0.7313	Intermediate Similarity	NPC237868
0.731	Intermediate Similarity	NPC478166
0.7308	Intermediate Similarity	NPC230951
0.7305	Intermediate Similarity	NPC62735
0.7299	Intermediate Similarity	NPC141549
0.7299	Intermediate Similarity	NPC15083
0.7299	Intermediate Similarity	NPC125153
0.7299	Intermediate Similarity	NPC470976
0.7299	Intermediate Similarity	NPC279596
0.7299	Intermediate Similarity	NPC470977
0.7299	Intermediate Similarity	NPC196979
0.7297	Intermediate Similarity	NPC144010
0.7297	Intermediate Similarity	NPC472406
0.7293	Intermediate Similarity	NPC75557
0.7293	Intermediate Similarity	NPC71274
0.7293	Intermediate Similarity	NPC4012
0.7293	Intermediate Similarity	NPC471559
0.7293	Intermediate Similarity	NPC474829
0.7292	Intermediate Similarity	NPC218712
0.7292	Intermediate Similarity	NPC307346
0.7292	Intermediate Similarity	NPC267004
0.7292	Intermediate Similarity	NPC261733
0.7287	Intermediate Similarity	NPC166591
0.7287	Intermediate Similarity	NPC152159
0.7287	Intermediate Similarity	NPC87466
0.7287	Intermediate Similarity	NPC291619
0.7287	Intermediate Similarity	NPC254958
0.7286	Intermediate Similarity	NPC163029
0.7286	Intermediate Similarity	NPC42400
0.7279	Intermediate Similarity	NPC95526
0.7279	Intermediate Similarity	NPC21460
0.7279	Intermediate Similarity	NPC476925
0.7279	Intermediate Similarity	NPC306788
0.7273	Intermediate Similarity	NPC263337
0.7273	Intermediate Similarity	NPC69403
0.7273	Intermediate Similarity	NPC291189

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 NPC115859 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	558
0.1-0.2	994
0.2-0.3	1702
0.3-0.4	2926
0.4-0.5	1828
0.5-0.6	875
0.6-0.7	247
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7969	Intermediate Similarity	NPD1876	Approved
0.7941	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1241	Discontinued
0.7554	Intermediate Similarity	NPD2344	Approved
0.7431	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1471	Phase 3
0.7413	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD3972	Approved
0.7211	Intermediate Similarity	NPD920	Approved
0.7206	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD17	Approved
0.7101	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD6280	Approved
0.7086	Intermediate Similarity	NPD6279	Approved
0.7083	Intermediate Similarity	NPD1238	Approved
0.7063	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD2798	Approved
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.704	Intermediate Similarity	NPD2182	Approved
0.7027	Intermediate Similarity	NPD6273	Approved
0.7015	Intermediate Similarity	NPD9717	Approved
0.7015	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD3140	Approved
0.7	Intermediate Similarity	NPD3142	Approved
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD2796	Approved
0.6993	Remote Similarity	NPD1551	Phase 2
0.6993	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD164	Approved
0.6985	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD1243	Approved
0.695	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2346	Discontinued
0.694	Remote Similarity	NPD1281	Approved
0.6935	Remote Similarity	NPD9697	Approved
0.6923	Remote Similarity	NPD3748	Approved
0.6918	Remote Similarity	NPD4628	Phase 3
0.6897	Remote Similarity	NPD1549	Phase 2
0.6894	Remote Similarity	NPD1894	Discontinued
0.6875	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3869	Phase 3
0.6867	Remote Similarity	NPD3873	Phase 3
0.6861	Remote Similarity	NPD3266	Approved
0.6861	Remote Similarity	NPD3267	Approved
0.6861	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD5585	Approved
0.6831	Remote Similarity	NPD4622	Approved
0.6831	Remote Similarity	NPD1933	Approved
0.6831	Remote Similarity	NPD4618	Approved
0.6831	Remote Similarity	NPD6355	Discontinued
0.6828	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4308	Phase 3
0.6788	Remote Similarity	NPD1283	Approved
0.6776	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2296	Approved
0.6772	Remote Similarity	NPD1247	Approved
0.6767	Remote Similarity	NPD9545	Approved
0.6752	Remote Similarity	NPD919	Approved
0.6746	Remote Similarity	NPD3134	Approved
0.6738	Remote Similarity	NPD411	Approved
0.6738	Remote Similarity	NPD3764	Approved
0.6736	Remote Similarity	NPD5689	Approved
0.6736	Remote Similarity	NPD5688	Approved
0.6735	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6808	Phase 2
0.6713	Remote Similarity	NPD447	Suspended
0.6693	Remote Similarity	NPD1358	Approved
0.6692	Remote Similarity	NPD9092	Discovery
0.6691	Remote Similarity	NPD5647	Approved
0.669	Remote Similarity	NPD8032	Phase 2
0.669	Remote Similarity	NPD1510	Phase 2
0.6689	Remote Similarity	NPD3750	Approved
0.6688	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2897	Discontinued
0.6644	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3887	Approved
0.6643	Remote Similarity	NPD2979	Phase 3
0.6643	Remote Similarity	NPD1240	Approved
0.6642	Remote Similarity	NPD1481	Phase 2
0.6641	Remote Similarity	NPD2684	Approved
0.6625	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3268	Approved
0.6617	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD9493	Approved
0.6614	Remote Similarity	NPD968	Approved
0.6603	Remote Similarity	NPD5761	Phase 2
0.6603	Remote Similarity	NPD5760	Phase 2
0.6599	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2353	Approved
0.6594	Remote Similarity	NPD4359	Approved
0.6593	Remote Similarity	NPD5691	Approved
0.6584	Remote Similarity	NPD3926	Phase 2
0.6577	Remote Similarity	NPD7003	Approved
0.6569	Remote Similarity	NPD1535	Discovery
0.6565	Remote Similarity	NPD5535	Approved
0.6564	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5977	Approved
0.6561	Remote Similarity	NPD5978	Approved
0.6558	Remote Similarity	NPD3226	Approved
0.6554	Remote Similarity	NPD5958	Discontinued
0.6552	Remote Similarity	NPD1607	Approved
0.6544	Remote Similarity	NPD1778	Approved
0.6541	Remote Similarity	NPD7157	Approved
0.6541	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4476	Approved
0.6531	Remote Similarity	NPD2935	Discontinued
0.6531	Remote Similarity	NPD4477	Approved
0.6525	Remote Similarity	NPD2861	Phase 2
0.6525	Remote Similarity	NPD454	Approved
0.6524	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4662	Approved
0.6513	Remote Similarity	NPD4661	Approved
0.6508	Remote Similarity	NPD9261	Approved
0.6503	Remote Similarity	NPD6798	Discontinued
0.65	Remote Similarity	NPD5494	Approved
0.65	Remote Similarity	NPD6362	Approved
0.6497	Remote Similarity	NPD7819	Suspended
0.6496	Remote Similarity	NPD9257	Approved
0.6496	Remote Similarity	NPD3496	Discontinued
0.6496	Remote Similarity	NPD9259	Approved
0.649	Remote Similarity	NPD7440	Discontinued
0.6486	Remote Similarity	NPD6004	Phase 3
0.6486	Remote Similarity	NPD6005	Phase 3
0.6486	Remote Similarity	NPD6002	Phase 3
0.6486	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5327	Phase 3
0.6467	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1237	Approved
0.6452	Remote Similarity	NPD2649	Approved
0.6452	Remote Similarity	NPD2651	Approved
0.6449	Remote Similarity	NPD1610	Phase 2
0.6449	Remote Similarity	NPD1611	Approved
0.6447	Remote Similarity	NPD6799	Approved
0.6444	Remote Similarity	NPD5536	Phase 2
0.6442	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7843	Approved
0.6438	Remote Similarity	NPD6653	Approved
0.6434	Remote Similarity	NPD290	Approved
0.6433	Remote Similarity	NPD7577	Discontinued
0.6433	Remote Similarity	NPD6844	Discontinued
0.6429	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2354	Approved
0.6419	Remote Similarity	NPD2438	Suspended
0.6419	Remote Similarity	NPD2531	Phase 2
0.6415	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7768	Phase 2
0.641	Remote Similarity	NPD6599	Discontinued
0.6407	Remote Similarity	NPD6559	Discontinued
0.6405	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5401	Approved
0.6398	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1202	Approved
0.6392	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1296	Phase 2
0.6389	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1470	Approved
0.6369	Remote Similarity	NPD7411	Suspended
0.6358	Remote Similarity	NPD4110	Phase 3
0.6358	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7033	Discontinued
0.635	Remote Similarity	NPD3444	Approved
0.635	Remote Similarity	NPD3445	Approved
0.635	Remote Similarity	NPD3443	Approved
0.6345	Remote Similarity	NPD4870	Approved
0.6345	Remote Similarity	NPD4062	Phase 3
0.6345	Remote Similarity	NPD6233	Phase 2
0.6336	Remote Similarity	NPD2067	Discontinued
0.6333	Remote Similarity	NPD4534	Discontinued
0.6333	Remote Similarity	NPD2424	Discontinued
0.6329	Remote Similarity	NPD1934	Approved
0.6323	Remote Similarity	NPD5403	Approved
0.6316	Remote Similarity	NPD821	Approved
0.6316	Remote Similarity	NPD8434	Phase 2
0.6312	Remote Similarity	NPD3225	Approved
0.6312	Remote Similarity	NPD3882	Suspended
0.6312	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6764	Approved
0.631	Remote Similarity	NPD6765	Approved
0.6309	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD9264	Approved
0.6308	Remote Similarity	NPD9267	Approved
0.6308	Remote Similarity	NPD9263	Approved
0.6306	Remote Similarity	NPD4380	Phase 2
0.6304	Remote Similarity	NPD4626	Approved
0.6301	Remote Similarity	NPD4140	Approved
0.6296	Remote Similarity	NPD2557	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