NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	257.684
LogP:	4.59
LogD:	3.44
LogS:	-4.291
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	3.99
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.514
MDCK Permeability:	1.8113018086296506e-05
Pgp-inhibitor:	0.204
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	88.0990219116211%
Volume Distribution (VD):	2.531
Pgp-substrate:	9.945935249328613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	15.273
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.884
Carcinogencity:	0.963
Eye Corrosion:	0.925
Eye Irritation:	0.964
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC32351

Natural Product ID:	NPC32351
*Common Name:**	Turmerone
IUPAC Name:	(6S)-2-methyl-6-(4-methylcyclohexa-1,4-dien-1-yl)hept-2-en-4-one
Synonyms:
Standard InCHIKey:	FZPYMZUVXJUAQA-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5,8-9,13H,6-7,10H2,1-4H3/t13-/m0/s1
SMILES:	CC(=CC(=O)C[C@@H](C1=CCC(=CC1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2272665
PubChem CID:	14367555
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
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11551759]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21214467]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[26661932]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	Radix	n.a.	n.a.	PMID[29236488]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30920	Acacia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19855	Oxalis acetosella	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19855	Oxalis acetosella	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3634	Robinia pseudoacacia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19855	Oxalis acetosella	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7191	Mimosa pudica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25160	Goniothalamus borneensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3532	Tridentata marginata	n.a.	n.a.	n.a.	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Unit	Reference
NPT2564	Organism	Blumeria graminis	Blumeria graminis	Activity	=	%	PMID[572869]
NPT829	Organism	Puccinia recondita	Puccinia recondita	Activity	=	%	PMID[572869]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Activity	=	%	PMID[572869]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Activity	=	%	PMID[572869]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Activity	=	%	PMID[572869]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	Activity	=	%	PMID[572869]

☑ 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 NPC32351 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	211
0.1-0.2	4404
0.2-0.3	18664
0.3-0.4	11477
0.4-0.5	5601
0.5-0.6	1855
0.6-0.7	365
0.7-0.8	87
0.8-0.85	21
0.85-0.9	4
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC268564
0.9167	High Similarity	NPC163984
0.9167	High Similarity	NPC176819
0.9167	High Similarity	NPC58970
0.9149	High Similarity	NPC91962
0.898	High Similarity	NPC64866
0.8936	High Similarity	NPC14917
0.8936	High Similarity	NPC236355
0.8936	High Similarity	NPC4079
0.8913	High Similarity	NPC25771
0.8846	High Similarity	NPC473733
0.8696	High Similarity	NPC292463
0.8542	High Similarity	NPC262558
0.8542	High Similarity	NPC8610
0.8519	High Similarity	NPC311852
0.8364	Intermediate Similarity	NPC276764
0.8364	Intermediate Similarity	NPC472304
0.8333	Intermediate Similarity	NPC166788
0.8302	Intermediate Similarity	NPC275472
0.8269	Intermediate Similarity	NPC45283
0.8269	Intermediate Similarity	NPC23117
0.8269	Intermediate Similarity	NPC474141
0.8269	Intermediate Similarity	NPC37644
0.8235	Intermediate Similarity	NPC27438
0.8214	Intermediate Similarity	NPC127582
0.8182	Intermediate Similarity	NPC308108
0.8182	Intermediate Similarity	NPC56905
0.8182	Intermediate Similarity	NPC27610
0.8182	Intermediate Similarity	NPC170799
0.8113	Intermediate Similarity	NPC209431
0.8113	Intermediate Similarity	NPC100809
0.8077	Intermediate Similarity	NPC471751
0.807	Intermediate Similarity	NPC213152
0.8039	Intermediate Similarity	NPC228776
0.8	Intermediate Similarity	NPC193695
0.8	Intermediate Similarity	NPC115385
0.7959	Intermediate Similarity	NPC191337
0.7931	Intermediate Similarity	NPC165695
0.7925	Intermediate Similarity	NPC14002
0.7917	Intermediate Similarity	NPC301972
0.7857	Intermediate Similarity	NPC94991
0.7857	Intermediate Similarity	NPC266295
0.7843	Intermediate Similarity	NPC145311
0.7818	Intermediate Similarity	NPC20603
0.78	Intermediate Similarity	NPC276009
0.78	Intermediate Similarity	NPC195246
0.78	Intermediate Similarity	NPC22098
0.78	Intermediate Similarity	NPC100380
0.7797	Intermediate Similarity	NPC6697
0.7797	Intermediate Similarity	NPC475124
0.7797	Intermediate Similarity	NPC212210
0.7797	Intermediate Similarity	NPC285371
0.7797	Intermediate Similarity	NPC150162
0.7778	Intermediate Similarity	NPC202850
0.7778	Intermediate Similarity	NPC5626
0.7778	Intermediate Similarity	NPC63396
0.7755	Intermediate Similarity	NPC477686
0.7719	Intermediate Similarity	NPC285594
0.7719	Intermediate Similarity	NPC259261
0.7719	Intermediate Similarity	NPC143834
0.7719	Intermediate Similarity	NPC96551
0.7692	Intermediate Similarity	NPC116906
0.7692	Intermediate Similarity	NPC15325
0.7692	Intermediate Similarity	NPC118788
0.7667	Intermediate Similarity	NPC251118
0.7627	Intermediate Similarity	NPC32285
0.7627	Intermediate Similarity	NPC288253
0.7593	Intermediate Similarity	NPC296311
0.7586	Intermediate Similarity	NPC25853
0.7544	Intermediate Similarity	NPC30215
0.75	Intermediate Similarity	NPC4638
0.7458	Intermediate Similarity	NPC97322
0.7451	Intermediate Similarity	NPC471752
0.7419	Intermediate Similarity	NPC475523
0.7391	Intermediate Similarity	NPC185839
0.7377	Intermediate Similarity	NPC470329
0.7368	Intermediate Similarity	NPC192427
0.7368	Intermediate Similarity	NPC49575
0.7368	Intermediate Similarity	NPC267626
0.7368	Intermediate Similarity	NPC55004
0.7368	Intermediate Similarity	NPC230823
0.7333	Intermediate Similarity	NPC197238
0.7333	Intermediate Similarity	NPC167256
0.7333	Intermediate Similarity	NPC202118
0.7321	Intermediate Similarity	NPC188789
0.7302	Intermediate Similarity	NPC260474
0.7302	Intermediate Similarity	NPC188292
0.7302	Intermediate Similarity	NPC310992
0.7302	Intermediate Similarity	NPC155198
0.7302	Intermediate Similarity	NPC87141
0.7292	Intermediate Similarity	NPC111474
0.7292	Intermediate Similarity	NPC113082
0.7273	Intermediate Similarity	NPC69898
0.7273	Intermediate Similarity	NPC295777
0.7234	Intermediate Similarity	NPC155880
0.7234	Intermediate Similarity	NPC92863
0.7234	Intermediate Similarity	NPC180840
0.7222	Intermediate Similarity	NPC236623
0.7213	Intermediate Similarity	NPC473902
0.7213	Intermediate Similarity	NPC469662
0.72	Intermediate Similarity	NPC216921
0.72	Intermediate Similarity	NPC106819
0.7188	Intermediate Similarity	NPC256846
0.7188	Intermediate Similarity	NPC469914
0.7188	Intermediate Similarity	NPC474060
0.7188	Intermediate Similarity	NPC139397
0.7174	Intermediate Similarity	NPC38497
0.7167	Intermediate Similarity	NPC475795
0.7167	Intermediate Similarity	NPC60565
0.7143	Intermediate Similarity	NPC250539
0.7091	Intermediate Similarity	NPC216407
0.7083	Intermediate Similarity	NPC217923
0.7077	Intermediate Similarity	NPC35734
0.7077	Intermediate Similarity	NPC2634
0.7077	Intermediate Similarity	NPC260040
0.7077	Intermediate Similarity	NPC307176
0.7077	Intermediate Similarity	NPC159577
0.7077	Intermediate Similarity	NPC265782
0.7077	Intermediate Similarity	NPC282593
0.7077	Intermediate Similarity	NPC251929
0.7059	Intermediate Similarity	NPC114841
0.7021	Intermediate Similarity	NPC190810
0.7021	Intermediate Similarity	NPC34764
0.7021	Intermediate Similarity	NPC76145
0.7018	Intermediate Similarity	NPC200258
0.6981	Remote Similarity	NPC324812
0.697	Remote Similarity	NPC181204
0.697	Remote Similarity	NPC54123
0.697	Remote Similarity	NPC474562
0.697	Remote Similarity	NPC115023
0.697	Remote Similarity	NPC190035
0.6949	Remote Similarity	NPC60772
0.6923	Remote Similarity	NPC136473
0.6909	Remote Similarity	NPC234829
0.6909	Remote Similarity	NPC30433
0.6909	Remote Similarity	NPC477458
0.6875	Remote Similarity	NPC139717
0.6875	Remote Similarity	NPC297643
0.6875	Remote Similarity	NPC290350
0.6875	Remote Similarity	NPC4370
0.6875	Remote Similarity	NPC269985
0.6875	Remote Similarity	NPC229262
0.6866	Remote Similarity	NPC470045
0.6866	Remote Similarity	NPC109576
0.6866	Remote Similarity	NPC56747
0.6866	Remote Similarity	NPC130016
0.6866	Remote Similarity	NPC276336
0.6866	Remote Similarity	NPC470044
0.6866	Remote Similarity	NPC186042
0.6866	Remote Similarity	NPC180015
0.6866	Remote Similarity	NPC474228
0.6866	Remote Similarity	NPC303613
0.6866	Remote Similarity	NPC251705
0.6842	Remote Similarity	NPC95581
0.6833	Remote Similarity	NPC473494
0.6825	Remote Similarity	NPC61473
0.6825	Remote Similarity	NPC474304
0.6825	Remote Similarity	NPC474329
0.6818	Remote Similarity	NPC151045
0.6818	Remote Similarity	NPC246722
0.6786	Remote Similarity	NPC22182
0.678	Remote Similarity	NPC165808
0.6774	Remote Similarity	NPC477707
0.6774	Remote Similarity	NPC477830
0.6774	Remote Similarity	NPC57463
0.6774	Remote Similarity	NPC151728
0.6774	Remote Similarity	NPC472306
0.6774	Remote Similarity	NPC190049
0.6774	Remote Similarity	NPC322457
0.6769	Remote Similarity	NPC142754
0.6769	Remote Similarity	NPC469679
0.6769	Remote Similarity	NPC82477
0.6769	Remote Similarity	NPC20610
0.6769	Remote Similarity	NPC39157
0.6769	Remote Similarity	NPC469688
0.6769	Remote Similarity	NPC296697
0.6765	Remote Similarity	NPC215050
0.6765	Remote Similarity	NPC309852
0.6739	Remote Similarity	NPC12889
0.6731	Remote Similarity	NPC471753
0.6727	Remote Similarity	NPC474391
0.6719	Remote Similarity	NPC100719
0.6719	Remote Similarity	NPC323005
0.6719	Remote Similarity	NPC166791
0.6719	Remote Similarity	NPC322035
0.6719	Remote Similarity	NPC197089
0.6716	Remote Similarity	NPC234707
0.6716	Remote Similarity	NPC133253
0.6716	Remote Similarity	NPC225467
0.6716	Remote Similarity	NPC5701
0.6716	Remote Similarity	NPC21944
0.6667	Remote Similarity	NPC65650
0.6667	Remote Similarity	NPC476346
0.6667	Remote Similarity	NPC114236
0.6667	Remote Similarity	NPC477449
0.6667	Remote Similarity	NPC474400
0.6667	Remote Similarity	NPC182815
0.6667	Remote Similarity	NPC473171
0.6667	Remote Similarity	NPC477448
0.6667	Remote Similarity	NPC293803

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 NPC32351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	3537
0.2-0.3	3998
0.3-0.4	995
0.4-0.5	299
0.5-0.6	88
0.6-0.7	19
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD287	Approved
0.7258	Intermediate Similarity	NPD7331	Phase 2
0.7188	Intermediate Similarity	NPD4137	Phase 3
0.7083	Intermediate Similarity	NPD5783	Phase 3
0.7077	Intermediate Similarity	NPD4747	Approved
0.7077	Intermediate Similarity	NPD4691	Approved
0.7021	Intermediate Similarity	NPD319	Phase 1
0.697	Remote Similarity	NPD5276	Approved
0.6825	Remote Similarity	NPD7341	Phase 2
0.6769	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4687	Approved
0.6765	Remote Similarity	NPD5733	Approved
0.6765	Remote Similarity	NPD4058	Approved
0.6724	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8779	Phase 3
0.6216	Remote Similarity	NPD4695	Discontinued
0.6094	Remote Similarity	NPD4193	Approved
0.6094	Remote Similarity	NPD4191	Approved
0.6094	Remote Similarity	NPD4194	Approved
0.6094	Remote Similarity	NPD4192	Approved
0.6053	Remote Similarity	NPD4223	Phase 3
0.6053	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD3174	Discontinued
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD8028	Phase 2
0.5902	Remote Similarity	NPD342	Phase 1
0.5897	Remote Similarity	NPD3666	Approved
0.5897	Remote Similarity	NPD4197	Approved
0.5897	Remote Similarity	NPD3133	Approved
0.5897	Remote Similarity	NPD3665	Phase 1
0.5823	Remote Similarity	NPD5329	Approved
0.5763	Remote Similarity	NPD29	Approved
0.5763	Remote Similarity	NPD28	Approved
0.575	Remote Similarity	NPD5690	Phase 2
0.575	Remote Similarity	NPD6684	Approved
0.575	Remote Similarity	NPD4689	Approved
0.575	Remote Similarity	NPD7521	Approved
0.575	Remote Similarity	NPD4693	Phase 3
0.575	Remote Similarity	NPD6409	Approved
0.575	Remote Similarity	NPD3618	Phase 1
0.575	Remote Similarity	NPD4519	Discontinued
0.575	Remote Similarity	NPD7146	Approved
0.575	Remote Similarity	NPD4623	Approved
0.575	Remote Similarity	NPD4690	Approved
0.575	Remote Similarity	NPD4138	Approved
0.575	Remote Similarity	NPD5330	Approved
0.575	Remote Similarity	NPD5279	Phase 3
0.575	Remote Similarity	NPD4694	Approved
0.575	Remote Similarity	NPD5205	Approved
0.575	Remote Similarity	NPD5280	Approved
0.575	Remote Similarity	NPD4688	Approved
0.575	Remote Similarity	NPD7334	Approved
0.5738	Remote Similarity	NPD539	Approved
0.5735	Remote Similarity	NPD3704	Approved
0.5733	Remote Similarity	NPD3617	Approved
0.569	Remote Similarity	NPD3173	Approved
0.5679	Remote Similarity	NPD3573	Approved
0.5652	Remote Similarity	NPD3709	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3667	Approved
0.5625	Remote Similarity	NPD1694	Approved
0.561	Remote Similarity	NPD5208	Approved
0.561	Remote Similarity	NPD6903	Approved
0.561	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6672	Approved
0.561	Remote Similarity	NPD5737	Approved
0.561	Remote Similarity	NPD4518	Approved
0.5606	Remote Similarity	NPD368	Approved
0.56	Remote Similarity	NPD4756	Discovery

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