NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.15
Volume:	255.048
LogP:	4.11
LogD:	3.748
LogS:	-4.617
# 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:	0.695
Synthetic Accessibility Score:	2.637
Fsp3:	0.4
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:	-4.536
MDCK Permeability:	1.6591488019912504e-05
Pgp-inhibitor:	0.766
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.135
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	94.69440460205078%
Volume Distribution (VD):	0.706
Pgp-substrate:	4.20523738861084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.832
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.909
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.366
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	10.658
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.259
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.925
Carcinogencity:	0.475
Eye Corrosion:	0.638
Eye Irritation:	0.985
Respiratory Toxicity:	0.769

Download Data

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

Natural Product: NPC17408

Natural Product ID:	NPC17408
*Common Name:**	Ar-Turmerone
IUPAC Name:	2-methyl-6-(4-methylphenyl)hept-2-en-4-one
Synonyms:	Ar-Turmerone
Standard InCHIKey:	NAAJVHHFAXWBOK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-9,13H,10H2,1-4H3
SMILES:	CC(=CC(=O)CC(C)c1ccc(C)cc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506948
PubChem CID:	558221
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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10785419]
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]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[18303853]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[18303853]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22932311]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23721280]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
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]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
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]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[p25172756]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	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[TCM_Taiwan]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15544	Cnidium monnieri	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	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
NPO24124	NPC17408	Other	Rhizome	327	74	580	mg/100g	Database [DUKE]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LD100	=	50.0	ug ml-1	PMID[453573]

☑ 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 NPC17408 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	285
0.1-0.2	1785
0.2-0.3	4874
0.3-0.4	15624
0.4-0.5	15142
0.5-0.6	4122
0.6-0.7	641
0.7-0.8	144
0.8-0.85	45
0.85-0.9	30
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285716
0.973	High Similarity	NPC103488
0.9103	High Similarity	NPC145053
0.8974	High Similarity	NPC157055
0.8974	High Similarity	NPC190567
0.8919	High Similarity	NPC74458
0.88	High Similarity	NPC285679
0.878	High Similarity	NPC160339
0.878	High Similarity	NPC307
0.875	High Similarity	NPC230068
0.8718	High Similarity	NPC36342
0.8718	High Similarity	NPC285470
0.8718	High Similarity	NPC2785
0.8706	High Similarity	NPC133461
0.8675	High Similarity	NPC69057
0.8659	High Similarity	NPC252067
0.8608	High Similarity	NPC139901
0.8608	High Similarity	NPC300205
0.8608	High Similarity	NPC151405
0.8605	High Similarity	NPC153885
0.859	High Similarity	NPC298023
0.859	High Similarity	NPC9796
0.859	High Similarity	NPC245966
0.8533	High Similarity	NPC95289
0.8506	High Similarity	NPC238219
0.85	High Similarity	NPC164086
0.85	High Similarity	NPC477703
0.85	High Similarity	NPC95868
0.8481	Intermediate Similarity	NPC76455
0.8481	Intermediate Similarity	NPC137847
0.8471	Intermediate Similarity	NPC298115
0.8415	Intermediate Similarity	NPC197581
0.8409	Intermediate Similarity	NPC260233
0.84	Intermediate Similarity	NPC98880
0.8395	Intermediate Similarity	NPC273033
0.8395	Intermediate Similarity	NPC12936
0.8391	Intermediate Similarity	NPC155232
0.8391	Intermediate Similarity	NPC323420
0.8391	Intermediate Similarity	NPC188844
0.8391	Intermediate Similarity	NPC1682
0.8375	Intermediate Similarity	NPC272260
0.8372	Intermediate Similarity	NPC277277
0.8372	Intermediate Similarity	NPC173413
0.8354	Intermediate Similarity	NPC329318
0.8353	Intermediate Similarity	NPC157778
0.8315	Intermediate Similarity	NPC185208
0.8315	Intermediate Similarity	NPC219573
0.8276	Intermediate Similarity	NPC284475
0.8272	Intermediate Similarity	NPC71664
0.8267	Intermediate Similarity	NPC311343
0.8235	Intermediate Similarity	NPC43945
0.8222	Intermediate Similarity	NPC239185
0.8193	Intermediate Similarity	NPC273758
0.8182	Intermediate Similarity	NPC59677
0.8171	Intermediate Similarity	NPC100039
0.8161	Intermediate Similarity	NPC110420
0.8161	Intermediate Similarity	NPC58872
0.8161	Intermediate Similarity	NPC303967
0.8161	Intermediate Similarity	NPC67585
0.814	Intermediate Similarity	NPC267262
0.814	Intermediate Similarity	NPC153308
0.8132	Intermediate Similarity	NPC134882
0.8132	Intermediate Similarity	NPC49994
0.8132	Intermediate Similarity	NPC75724
0.8118	Intermediate Similarity	NPC164526
0.8108	Intermediate Similarity	NPC198023
0.809	Intermediate Similarity	NPC289883
0.8077	Intermediate Similarity	NPC271437
0.8022	Intermediate Similarity	NPC265220
0.8	Intermediate Similarity	NPC123476
0.7976	Intermediate Similarity	NPC215008
0.7976	Intermediate Similarity	NPC39600
0.7975	Intermediate Similarity	NPC208075
0.7973	Intermediate Similarity	NPC88566
0.7957	Intermediate Similarity	NPC109514
0.7957	Intermediate Similarity	NPC476993
0.7955	Intermediate Similarity	NPC274455
0.7955	Intermediate Similarity	NPC19256
0.7955	Intermediate Similarity	NPC86670
0.7955	Intermediate Similarity	NPC70940
0.7952	Intermediate Similarity	NPC73978
0.7901	Intermediate Similarity	NPC179726
0.7865	Intermediate Similarity	NPC125226
0.7841	Intermediate Similarity	NPC418308
0.7841	Intermediate Similarity	NPC113307
0.7789	Intermediate Similarity	NPC247976
0.7765	Intermediate Similarity	NPC149263
0.7765	Intermediate Similarity	NPC324624
0.7763	Intermediate Similarity	NPC178527
0.7742	Intermediate Similarity	NPC145052
0.7727	Intermediate Similarity	NPC477693
0.7727	Intermediate Similarity	NPC477704
0.7722	Intermediate Similarity	NPC326200
0.7703	Intermediate Similarity	NPC135924
0.7703	Intermediate Similarity	NPC248705
0.7703	Intermediate Similarity	NPC54368
0.7667	Intermediate Similarity	NPC103346
0.764	Intermediate Similarity	NPC231591
0.7632	Intermediate Similarity	NPC155172
0.7632	Intermediate Similarity	NPC32312
0.7614	Intermediate Similarity	NPC322387
0.7609	Intermediate Similarity	NPC472880
0.7604	Intermediate Similarity	NPC471829
0.7604	Intermediate Similarity	NPC472691
0.7604	Intermediate Similarity	NPC475939
0.7604	Intermediate Similarity	NPC474866
0.7561	Intermediate Similarity	NPC78500
0.7558	Intermediate Similarity	NPC44830
0.7556	Intermediate Similarity	NPC84288
0.7553	Intermediate Similarity	NPC317280
0.7553	Intermediate Similarity	NPC329387
0.7551	Intermediate Similarity	NPC100767
0.7528	Intermediate Similarity	NPC473345
0.7526	Intermediate Similarity	NPC329282
0.75	Intermediate Similarity	NPC45756
0.7473	Intermediate Similarity	NPC476484
0.7471	Intermediate Similarity	NPC267704
0.7468	Intermediate Similarity	NPC16190
0.7468	Intermediate Similarity	NPC235059
0.7468	Intermediate Similarity	NPC169222
0.7467	Intermediate Similarity	NPC210849
0.7447	Intermediate Similarity	NPC226041
0.7444	Intermediate Similarity	NPC325709
0.7436	Intermediate Similarity	NPC267443
0.7436	Intermediate Similarity	NPC6107
0.7432	Intermediate Similarity	NPC8235
0.7416	Intermediate Similarity	NPC194326
0.7412	Intermediate Similarity	NPC127343
0.7407	Intermediate Similarity	NPC54269
0.74	Intermediate Similarity	NPC470252
0.7396	Intermediate Similarity	NPC472879
0.7396	Intermediate Similarity	NPC225079
0.7391	Intermediate Similarity	NPC77273
0.7386	Intermediate Similarity	NPC95965
0.7381	Intermediate Similarity	NPC50192
0.7374	Intermediate Similarity	NPC472699
0.7374	Intermediate Similarity	NPC185763
0.7374	Intermediate Similarity	NPC37914
0.7374	Intermediate Similarity	NPC472700
0.7374	Intermediate Similarity	NPC83409
0.7368	Intermediate Similarity	NPC29680
0.7363	Intermediate Similarity	NPC26224
0.7356	Intermediate Similarity	NPC288903
0.7326	Intermediate Similarity	NPC242628
0.732	Intermediate Similarity	NPC25458
0.732	Intermediate Similarity	NPC304873
0.7312	Intermediate Similarity	NPC291070
0.7312	Intermediate Similarity	NPC246757
0.7308	Intermediate Similarity	NPC113837
0.7308	Intermediate Similarity	NPC289915
0.73	Intermediate Similarity	NPC472695
0.73	Intermediate Similarity	NPC472696
0.73	Intermediate Similarity	NPC472683
0.73	Intermediate Similarity	NPC472701
0.7297	Intermediate Similarity	NPC212114
0.7297	Intermediate Similarity	NPC120441
0.7297	Intermediate Similarity	NPC300345
0.7297	Intermediate Similarity	NPC65873
0.7292	Intermediate Similarity	NPC54647
0.7292	Intermediate Similarity	NPC221825
0.7292	Intermediate Similarity	NPC476042
0.7283	Intermediate Similarity	NPC475059
0.7283	Intermediate Similarity	NPC187725
0.7283	Intermediate Similarity	NPC141607
0.7283	Intermediate Similarity	NPC475023
0.7273	Intermediate Similarity	NPC474910
0.7273	Intermediate Similarity	NPC471186
0.7273	Intermediate Similarity	NPC172483
0.7263	Intermediate Similarity	NPC103048
0.7263	Intermediate Similarity	NPC240042
0.7255	Intermediate Similarity	NPC265513
0.7255	Intermediate Similarity	NPC474057
0.7245	Intermediate Similarity	NPC329556
0.7245	Intermediate Similarity	NPC274443
0.7237	Intermediate Similarity	NPC238023
0.7237	Intermediate Similarity	NPC150196
0.7237	Intermediate Similarity	NPC310758
0.7216	Intermediate Similarity	NPC133809
0.7216	Intermediate Similarity	NPC128248
0.7216	Intermediate Similarity	NPC473325
0.7216	Intermediate Similarity	NPC136810
0.7204	Intermediate Similarity	NPC475057
0.7191	Intermediate Similarity	NPC294134
0.7184	Intermediate Similarity	NPC280789
0.7184	Intermediate Similarity	NPC292834
0.7162	Intermediate Similarity	NPC198841
0.7162	Intermediate Similarity	NPC269586
0.7159	Intermediate Similarity	NPC270507
0.7159	Intermediate Similarity	NPC285773
0.7158	Intermediate Similarity	NPC12695
0.7143	Intermediate Similarity	NPC329064
0.7143	Intermediate Similarity	NPC244427
0.7143	Intermediate Similarity	NPC222390
0.7129	Intermediate Similarity	NPC112903
0.7129	Intermediate Similarity	NPC470007
0.7128	Intermediate Similarity	NPC34243
0.7126	Intermediate Similarity	NPC303245
0.7115	Intermediate Similarity	NPC470253
0.7115	Intermediate Similarity	NPC93287
0.7113	Intermediate Similarity	NPC217621

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 NPC17408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	1049
0.2-0.3	1623
0.3-0.4	3379
0.4-0.5	1931
0.5-0.6	723
0.6-0.7	128
0.7-0.8	45
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD1507	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD942	Approved
0.8391	Intermediate Similarity	NPD7631	Approved
0.8276	Intermediate Similarity	NPD7609	Phase 3
0.8235	Intermediate Similarity	NPD650	Approved
0.8235	Intermediate Similarity	NPD1087	Approved
0.8222	Intermediate Similarity	NPD3495	Discontinued
0.809	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD2066	Phase 3
0.8	Intermediate Similarity	NPD1693	Approved
0.7955	Intermediate Similarity	NPD1090	Approved
0.7955	Intermediate Similarity	NPD1086	Approved
0.7955	Intermediate Similarity	NPD1089	Approved
0.7841	Intermediate Similarity	NPD800	Approved
0.7816	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1508	Approved
0.7778	Intermediate Similarity	NPD1088	Approved
0.7684	Intermediate Similarity	NPD2648	Phase 3
0.7684	Intermediate Similarity	NPD2196	Discontinued
0.7684	Intermediate Similarity	NPD2193	Phase 2
0.759	Intermediate Similarity	NPD227	Approved
0.759	Intermediate Similarity	NPD225	Approved
0.7556	Intermediate Similarity	NPD3672	Approved
0.7556	Intermediate Similarity	NPD3673	Approved
0.7527	Intermediate Similarity	NPD1843	Approved
0.75	Intermediate Similarity	NPD1563	Approved
0.7449	Intermediate Similarity	NPD1677	Discontinued
0.7444	Intermediate Similarity	NPD5346	Phase 2
0.7444	Intermediate Similarity	NPD5347	Phase 2
0.7419	Intermediate Similarity	NPD4094	Approved
0.734	Intermediate Similarity	NPD1989	Approved
0.7326	Intermediate Similarity	NPD226	Approved
0.732	Intermediate Similarity	NPD1932	Approved
0.7294	Intermediate Similarity	NPD9490	Approved
0.7283	Intermediate Similarity	NPD1239	Approved
0.7273	Intermediate Similarity	NPD2192	Approved
0.7273	Intermediate Similarity	NPD2197	Approved
0.7263	Intermediate Similarity	NPD1564	Approved
0.7263	Intermediate Similarity	NPD1565	Approved
0.7263	Intermediate Similarity	NPD1099	Approved
0.7263	Intermediate Similarity	NPD4657	Approved
0.7263	Intermediate Similarity	NPD4655	Approved
0.7263	Intermediate Similarity	NPD1566	Phase 3
0.7263	Intermediate Similarity	NPD1100	Approved
0.7255	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1929	Approved
0.7245	Intermediate Similarity	NPD1930	Approved
0.7228	Intermediate Similarity	NPD2329	Discontinued
0.7222	Intermediate Similarity	NPD4793	Discontinued
0.7191	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5909	Discontinued
0.7159	Intermediate Similarity	NPD9491	Approved
0.7159	Intermediate Similarity	NPD3971	Phase 1
0.7157	Intermediate Similarity	NPD1317	Discontinued
0.7143	Intermediate Similarity	NPD2171	Approved
0.7071	Intermediate Similarity	NPD3357	Discontinued
0.7053	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6049	Phase 2
0.7051	Intermediate Similarity	NPD675	Discontinued
0.7048	Intermediate Similarity	NPD7076	Approved
0.7048	Intermediate Similarity	NPD7077	Approved
0.7024	Intermediate Similarity	NPD9716	Approved
0.7	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6024	Approved
0.697	Remote Similarity	NPD6027	Approved
0.6952	Remote Similarity	NPD6858	Approved
0.6952	Remote Similarity	NPD7094	Approved
0.69	Remote Similarity	NPD6647	Phase 2
0.6869	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD466	Approved
0.6829	Remote Similarity	NPD1673	Approved
0.6789	Remote Similarity	NPD7610	Discontinued
0.6774	Remote Similarity	NPD1101	Approved
0.6739	Remote Similarity	NPD9257	Approved
0.6739	Remote Similarity	NPD9259	Approved
0.6737	Remote Similarity	NPD1007	Discontinued
0.6727	Remote Similarity	NPD7009	Phase 2
0.6701	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD253	Approved
0.6634	Remote Similarity	NPD813	Approved
0.6634	Remote Similarity	NPD4803	Discontinued
0.6627	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3317	Approved
0.6604	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1761	Approved
0.6602	Remote Similarity	NPD1767	Approved
0.6602	Remote Similarity	NPD1765	Approved
0.6602	Remote Similarity	NPD1763	Approved
0.6602	Remote Similarity	NPD1766	Approved
0.66	Remote Similarity	NPD742	Approved
0.6598	Remote Similarity	NPD1202	Approved
0.6549	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD1245	Approved
0.6514	Remote Similarity	NPD5951	Approved
0.6509	Remote Similarity	NPD2067	Discontinued
0.6505	Remote Similarity	NPD164	Approved
0.65	Remote Similarity	NPD5926	Approved
0.6489	Remote Similarity	NPD1282	Approved
0.6471	Remote Similarity	NPD292	Approved
0.6471	Remote Similarity	NPD294	Approved
0.6465	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5836	Discontinued
0.6458	Remote Similarity	NPD9258	Approved
0.6458	Remote Similarity	NPD9256	Approved
0.6449	Remote Similarity	NPD3644	Approved
0.6449	Remote Similarity	NPD3642	Approved
0.6449	Remote Similarity	NPD3643	Approved
0.6436	Remote Similarity	NPD7798	Approved
0.6436	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1409	Phase 3
0.6415	Remote Similarity	NPD2182	Approved
0.6415	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5765	Approved
0.6381	Remote Similarity	NPD6685	Approved
0.6374	Remote Similarity	NPD3035	Approved
0.6364	Remote Similarity	NPD2319	Discontinued
0.6364	Remote Similarity	NPD1246	Approved
0.6364	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4814	Discontinued
0.6355	Remote Similarity	NPD664	Approved
0.6337	Remote Similarity	NPD9495	Approved
0.6337	Remote Similarity	NPD4263	Approved
0.6337	Remote Similarity	NPD4813	Approved
0.633	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4169	Approved
0.6304	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4170	Approved
0.6293	Remote Similarity	NPD3972	Approved
0.6286	Remote Similarity	NPD5048	Discontinued
0.6286	Remote Similarity	NPD1018	Approved
0.6275	Remote Similarity	NPD1238	Approved
0.6273	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD2652	Approved
0.6273	Remote Similarity	NPD2650	Approved
0.6264	Remote Similarity	NPD3903	Approved
0.6264	Remote Similarity	NPD3981	Approved
0.6264	Remote Similarity	NPD3979	Approved
0.6264	Remote Similarity	NPD3904	Approved
0.6263	Remote Similarity	NPD845	Approved
0.6263	Remote Similarity	NPD1066	Discontinued
0.6261	Remote Similarity	NPD4879	Approved
0.625	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD288	Approved
0.6238	Remote Similarity	NPD9566	Approved
0.6237	Remote Similarity	NPD4635	Approved
0.6237	Remote Similarity	NPD2001	Discontinued
0.6228	Remote Similarity	NPD1651	Approved
0.6228	Remote Similarity	NPD3024	Approved
0.6228	Remote Similarity	NPD3025	Approved
0.6222	Remote Similarity	NPD79	Approved
0.6222	Remote Similarity	NPD9564	Approved
0.6222	Remote Similarity	NPD9563	Approved
0.6216	Remote Similarity	NPD1073	Approved
0.6216	Remote Similarity	NPD2508	Discontinued
0.6216	Remote Similarity	NPD1023	Approved
0.6216	Remote Similarity	NPD1021	Approved
0.6216	Remote Similarity	NPD1074	Approved
0.6216	Remote Similarity	NPD1075	Approved
0.6216	Remote Similarity	NPD1711	Phase 2
0.6216	Remote Similarity	NPD1020	Approved
0.6216	Remote Similarity	NPD1022	Approved
0.6214	Remote Similarity	NPD5630	Phase 1
0.6207	Remote Similarity	NPD6287	Discontinued
0.6204	Remote Similarity	NPD1756	Approved
0.6204	Remote Similarity	NPD4233	Approved
0.6204	Remote Similarity	NPD3581	Discontinued
0.6204	Remote Similarity	NPD1752	Approved
0.6204	Remote Similarity	NPD4234	Approved
0.62	Remote Similarity	NPD9260	Approved
0.6186	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2932	Approved
0.6174	Remote Similarity	NPD2345	Approved
0.6174	Remote Similarity	NPD3019	Approved
0.6174	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4544	Approved
0.6167	Remote Similarity	NPD7084	Phase 3
0.6154	Remote Similarity	NPD1475	Approved
0.6154	Remote Similarity	NPD4878	Approved
0.6154	Remote Similarity	NPD590	Approved
0.6154	Remote Similarity	NPD589	Approved
0.6139	Remote Similarity	NPD844	Approved
0.6136	Remote Similarity	NPD9592	Approved
0.6136	Remote Similarity	NPD4058	Approved
0.6136	Remote Similarity	NPD9593	Approved
0.6136	Remote Similarity	NPD4687	Approved
0.6136	Remote Similarity	NPD9590	Approved
0.6136	Remote Similarity	NPD9594	Approved
0.6136	Remote Similarity	NPD9589	Approved
0.6136	Remote Similarity	NPD80	Approved
0.6136	Remote Similarity	NPD9588	Approved
0.6136	Remote Similarity	NPD9591	Approved
0.6126	Remote Similarity	NPD1370	Approved
0.6126	Remote Similarity	NPD1374	Approved
0.6126	Remote Similarity	NPD1371	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