NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.09
Volume:	229.48
LogP:	3.473
LogD:	3.262
LogS:	-3.236
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.767
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.618
MDCK Permeability:	2.436486647638958e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	95.3705825805664%
Volume Distribution (VD):	0.788
Pgp-substrate:	3.8243212699890137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.22
CYP3A4-substrate:	0.304

ADMET: Excretion

Clearance (CL):	5.481
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.492
Drug-inuced Liver Injury (DILI):	0.329
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.407
Skin Sensitization:	0.222
Carcinogencity:	0.863
Eye Corrosion:	0.01
Eye Irritation:	0.51
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC151113

Natural Product ID:	NPC151113
*Common Name:**	Demethylencecalin
IUPAC Name:	1-(7-hydroxy-2,2-dimethylchromen-6-yl)ethanone
Synonyms:	7-Demethylencecalin; Demethylencecalin
Standard InCHIKey:	SVUVYHFYZBCYRF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O3/c1-8(14)10-6-9-4-5-13(2,3)16-12(9)7-11(10)15/h4-7,15H,1-3H3
SMILES:	CC(=O)c1cc2C=CC(C)(C)Oc2cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443462
PubChem CID:	100768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO3610	Strychnos panganensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542343]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	roots	n.a.	n.a.	PMID[14664512]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18662038]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25172742]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882437]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358640]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677276]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14553	Eupatorium semiserratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14553	Eupatorium semiserratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14553	Eupatorium semiserratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14553	Eupatorium semiserratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22725	Cirsium microspicatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26523	Alicyclobacillus acidocaldarius	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17285	Taraxacum udum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13648	Phialocephala fortinii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17194	Linum capitatum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8147	Calea hispida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3610	Strychnos panganensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11052	Helianthus hirsutus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16661	Duboisia myoporoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15368	Trifolium medium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9379	Cytisus caucasicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1178	Delphinium elisabethae	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6803	Heterotheca subaxillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13558	Mundulea suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15676	Tricholoma scalpturatum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10631	Gerbera lanuginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18310	Pecten jacobaeus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10414	Gram-negative bacterium	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
ED50	3
IC50	2
MIC	1
Others	7
Potency	9

Activity Type	# Activity
Cell Line	3
Individual Protein	10
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[487915]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[487915]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	10.0	ug ml-1	PMID[487915]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	22387.2	nM	PMID[487918]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	25118.9	nM	PMID[487918]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	25118.9	nM	PMID[487918]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	14125.4	nM	PMID[487918]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[487918]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[487918]
NPT140	Organism	Artemia	Artemia	LC50	=	31.0	ug.mL-1	PMID[487915]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	79.0	ug.mL-1	PMID[487915]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	27.0	ug.mL-1	PMID[487915]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	58.0	ug.mL-1	PMID[487915]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	66.6	%	PMID[487916]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	11.5	day	PMID[487916]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14125.4	nM	PMID[487918]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	FR50	=	0.4	n.a.	PMID[487919]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	17.6	ppm	PMID[487919]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	84.54	%	PMID[487920]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	88.13	%	PMID[487920]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[487918]

☑ 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 NPC151113 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	370
0.1-0.2	1783
0.2-0.3	4900
0.3-0.4	11675
0.4-0.5	5959
0.5-0.6	4156
0.6-0.7	6011
0.7-0.8	4796
0.8-0.85	1762
0.85-0.9	856
0.9-0.95	411
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC93756
0.9692	High Similarity	NPC108113
0.9627	High Similarity	NPC475680
0.9627	High Similarity	NPC305355
0.9624	High Similarity	NPC470668
0.9624	High Similarity	NPC470669
0.9618	High Similarity	NPC125920
0.9556	High Similarity	NPC147688
0.9556	High Similarity	NPC205006
0.9556	High Similarity	NPC156590
0.9556	High Similarity	NPC118840
0.9556	High Similarity	NPC64908
0.9552	High Similarity	NPC23257
0.9552	High Similarity	NPC473076
0.9545	High Similarity	NPC60667
0.9485	High Similarity	NPC11561
0.9485	High Similarity	NPC226636
0.9481	High Similarity	NPC270883
0.9481	High Similarity	NPC261227
0.9481	High Similarity	NPC471587
0.9481	High Similarity	NPC235239
0.9481	High Similarity	NPC172986
0.9478	High Similarity	NPC131130
0.9478	High Similarity	NPC201395
0.9474	High Similarity	NPC174999
0.9466	High Similarity	NPC229646
0.9462	High Similarity	NPC270369
0.9462	High Similarity	NPC5515
0.9416	High Similarity	NPC38219
0.9412	High Similarity	NPC110969
0.9412	High Similarity	NPC103362
0.9407	High Similarity	NPC220062
0.9407	High Similarity	NPC78913
0.9407	High Similarity	NPC55018
0.9407	High Similarity	NPC216978
0.9407	High Similarity	NPC301217
0.9407	High Similarity	NPC303633
0.9407	High Similarity	NPC18260
0.9407	High Similarity	NPC96565
0.9403	High Similarity	NPC332594
0.9403	High Similarity	NPC228661
0.9398	High Similarity	NPC101752
0.9394	High Similarity	NPC57601
0.9389	High Similarity	NPC31872
0.9389	High Similarity	NPC473584
0.9389	High Similarity	NPC475589
0.9348	High Similarity	NPC234629
0.9348	High Similarity	NPC311741
0.9343	High Similarity	NPC78803
0.9343	High Similarity	NPC62840
0.9343	High Similarity	NPC144499
0.9343	High Similarity	NPC217083
0.9343	High Similarity	NPC293852
0.9343	High Similarity	NPC299080
0.9343	High Similarity	NPC214236
0.9343	High Similarity	NPC162476
0.9343	High Similarity	NPC59739
0.9338	High Similarity	NPC150522
0.9338	High Similarity	NPC241100
0.9338	High Similarity	NPC159275
0.9338	High Similarity	NPC69769
0.9333	High Similarity	NPC470671
0.9333	High Similarity	NPC470672
0.9333	High Similarity	NPC474504
0.9333	High Similarity	NPC474487
0.9323	High Similarity	NPC172262
0.9318	High Similarity	NPC10971
0.9318	High Similarity	NPC25937
0.9275	High Similarity	NPC242100
0.9275	High Similarity	NPC219915
0.9275	High Similarity	NPC255133
0.9275	High Similarity	NPC166138
0.9275	High Similarity	NPC106985
0.9275	High Similarity	NPC18585
0.927	High Similarity	NPC282300
0.927	High Similarity	NPC3188
0.9265	High Similarity	NPC471697
0.9265	High Similarity	NPC217186
0.9265	High Similarity	NPC137009
0.9265	High Similarity	NPC53181
0.9265	High Similarity	NPC139554
0.9259	High Similarity	NPC160972
0.9259	High Similarity	NPC317119
0.9259	High Similarity	NPC250266
0.9259	High Similarity	NPC266597
0.9254	High Similarity	NPC9985
0.9254	High Similarity	NPC239495
0.9248	High Similarity	NPC213216
0.9248	High Similarity	NPC274121
0.9248	High Similarity	NPC50898
0.9248	High Similarity	NPC223457
0.9248	High Similarity	NPC78540
0.9242	High Similarity	NPC313618
0.9231	High Similarity	NPC80694
0.9231	High Similarity	NPC186098
0.9214	High Similarity	NPC104406
0.9214	High Similarity	NPC97716
0.9214	High Similarity	NPC201731
0.9214	High Similarity	NPC79469
0.9214	High Similarity	NPC237635
0.9214	High Similarity	NPC23728
0.9214	High Similarity	NPC110303
0.9214	High Similarity	NPC24673
0.9209	High Similarity	NPC278175
0.9209	High Similarity	NPC469953
0.9209	High Similarity	NPC209040
0.9209	High Similarity	NPC257236
0.9203	High Similarity	NPC200694
0.9203	High Similarity	NPC473042
0.9197	High Similarity	NPC477272
0.9191	High Similarity	NPC21350
0.9191	High Similarity	NPC124269
0.9185	High Similarity	NPC194281
0.9185	High Similarity	NPC1486
0.9185	High Similarity	NPC477242
0.9185	High Similarity	NPC124784
0.9185	High Similarity	NPC477244
0.9185	High Similarity	NPC234133
0.9185	High Similarity	NPC274109
0.9185	High Similarity	NPC168105
0.9185	High Similarity	NPC477243
0.9185	High Similarity	NPC249606
0.9185	High Similarity	NPC156910
0.9185	High Similarity	NPC186838
0.9185	High Similarity	NPC127447
0.9185	High Similarity	NPC187826
0.9185	High Similarity	NPC41461
0.9185	High Similarity	NPC25287
0.9185	High Similarity	NPC231772
0.9185	High Similarity	NPC150399
0.9185	High Similarity	NPC473887
0.9185	High Similarity	NPC66349
0.9185	High Similarity	NPC47815
0.9185	High Similarity	NPC240593
0.9185	High Similarity	NPC12165
0.9185	High Similarity	NPC98115
0.9185	High Similarity	NPC13408
0.9185	High Similarity	NPC29353
0.9179	High Similarity	NPC164136
0.9167	High Similarity	NPC250057
0.916	High Similarity	NPC60558
0.916	High Similarity	NPC187907
0.916	High Similarity	NPC230818
0.9149	High Similarity	NPC160821
0.9149	High Similarity	NPC132592
0.9149	High Similarity	NPC272194
0.9149	High Similarity	NPC266572
0.9149	High Similarity	NPC6511
0.9143	High Similarity	NPC475052
0.9143	High Similarity	NPC246948
0.9143	High Similarity	NPC111786
0.9143	High Similarity	NPC214774
0.9143	High Similarity	NPC195621
0.9143	High Similarity	NPC301276
0.9143	High Similarity	NPC88964
0.9143	High Similarity	NPC312973
0.9143	High Similarity	NPC83357
0.9143	High Similarity	NPC267375
0.9143	High Similarity	NPC20488
0.9143	High Similarity	NPC54577
0.9143	High Similarity	NPC142405
0.9143	High Similarity	NPC67805
0.9143	High Similarity	NPC176229
0.9143	High Similarity	NPC470647
0.9143	High Similarity	NPC477955
0.9143	High Similarity	NPC124729
0.9143	High Similarity	NPC329678
0.9137	High Similarity	NPC175504
0.9137	High Similarity	NPC316816
0.9137	High Similarity	NPC225884
0.9137	High Similarity	NPC9117
0.9137	High Similarity	NPC24821
0.9137	High Similarity	NPC150408
0.9137	High Similarity	NPC293053
0.9137	High Similarity	NPC214166
0.9137	High Similarity	NPC212932
0.9137	High Similarity	NPC68104
0.9137	High Similarity	NPC39329
0.9137	High Similarity	NPC75049
0.9137	High Similarity	NPC169591
0.9137	High Similarity	NPC257097
0.9137	High Similarity	NPC221432
0.9137	High Similarity	NPC143896
0.9137	High Similarity	NPC310130
0.9137	High Similarity	NPC478086
0.9137	High Similarity	NPC91560
0.9137	High Similarity	NPC164980
0.9137	High Similarity	NPC149026
0.9137	High Similarity	NPC190637
0.9137	High Similarity	NPC11700
0.913	High Similarity	NPC312391
0.913	High Similarity	NPC324386
0.913	High Similarity	NPC213322
0.913	High Similarity	NPC4743
0.913	High Similarity	NPC14871
0.9124	High Similarity	NPC295384
0.9124	High Similarity	NPC37206
0.9118	High Similarity	NPC153979
0.9118	High Similarity	NPC299379
0.9118	High Similarity	NPC188879

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 NPC151113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1022
0.2-0.3	1608
0.3-0.4	2710
0.4-0.5	1765
0.5-0.6	1131
0.6-0.7	371
0.7-0.8	127
0.8-0.85	39
0.85-0.9	6
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9242	High Similarity	NPD1240	Approved
0.9209	High Similarity	NPD7410	Clinical (unspecified phase)
0.9104	High Similarity	NPD1607	Approved
0.9071	High Similarity	NPD4378	Clinical (unspecified phase)
0.9051	High Similarity	NPD1549	Phase 2
0.8978	High Similarity	NPD1552	Clinical (unspecified phase)
0.8978	High Similarity	NPD1550	Clinical (unspecified phase)
0.8971	High Similarity	NPD1510	Phase 2
0.8768	High Similarity	NPD2796	Approved
0.8714	High Similarity	NPD1243	Approved
0.8601	High Similarity	NPD1511	Approved
0.8582	High Similarity	NPD2800	Approved
0.8571	High Similarity	NPD7411	Suspended
0.8511	High Similarity	NPD970	Clinical (unspecified phase)
0.8503	High Similarity	NPD4380	Phase 2
0.8483	Intermediate Similarity	NPD1512	Approved
0.8456	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD7075	Discontinued
0.8403	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD3750	Approved
0.8389	Intermediate Similarity	NPD6801	Discontinued
0.8345	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD920	Approved
0.8288	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6651	Approved
0.8271	Intermediate Similarity	NPD422	Phase 1
0.8267	Intermediate Similarity	NPD1934	Approved
0.8239	Intermediate Similarity	NPD1551	Phase 2
0.8212	Intermediate Similarity	NPD2801	Approved
0.8209	Intermediate Similarity	NPD9717	Approved
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2344	Approved
0.817	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD3749	Approved
0.8162	Intermediate Similarity	NPD1203	Approved
0.8138	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6599	Discontinued
0.8105	Intermediate Similarity	NPD3882	Suspended
0.8105	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3748	Approved
0.8042	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7959	Intermediate Similarity	NPD2309	Approved
0.7937	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2533	Approved
0.7919	Intermediate Similarity	NPD2534	Approved
0.7919	Intermediate Similarity	NPD2532	Approved
0.7917	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7887	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD919	Approved
0.7868	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6099	Approved
0.7862	Intermediate Similarity	NPD6100	Approved
0.784	Intermediate Similarity	NPD5953	Discontinued
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7836	Intermediate Similarity	NPD9545	Approved
0.7826	Intermediate Similarity	NPD7286	Phase 2
0.782	Intermediate Similarity	NPD9493	Approved
0.7815	Intermediate Similarity	NPD5403	Approved
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.78	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD1247	Approved
0.777	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3818	Discontinued
0.775	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6166	Phase 2
0.775	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1296	Phase 2
0.7744	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1241	Discontinued
0.7722	Intermediate Similarity	NPD5494	Approved
0.7714	Intermediate Similarity	NPD2798	Approved
0.7712	Intermediate Similarity	NPD3226	Approved
0.7671	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD1729	Discontinued
0.7643	Intermediate Similarity	NPD2797	Approved
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7622	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD411	Approved
0.7609	Intermediate Similarity	NPD1610	Phase 2
0.7607	Intermediate Similarity	NPD7054	Approved
0.7606	Intermediate Similarity	NPD6832	Phase 2
0.7593	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD447	Suspended
0.7586	Intermediate Similarity	NPD5124	Phase 1
0.7584	Intermediate Similarity	NPD2654	Approved
0.7576	Intermediate Similarity	NPD6559	Discontinued
0.7568	Intermediate Similarity	NPD2346	Discontinued
0.7561	Intermediate Similarity	NPD7472	Approved
0.7561	Intermediate Similarity	NPD7074	Phase 3
0.7554	Intermediate Similarity	NPD1608	Approved
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.7533	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1164	Approved
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD5402	Approved
0.7466	Intermediate Similarity	NPD230	Phase 1
0.7465	Intermediate Similarity	NPD1019	Discontinued
0.7447	Intermediate Similarity	NPD3225	Approved
0.7432	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7429	Intermediate Similarity	NPD3972	Approved
0.7425	Intermediate Similarity	NPD7808	Phase 3
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.7397	Intermediate Similarity	NPD4307	Phase 2
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD3266	Approved
0.7394	Intermediate Similarity	NPD3267	Approved
0.7391	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7390	Discontinued
0.7376	Intermediate Similarity	NPD4749	Approved
0.7362	Intermediate Similarity	NPD3926	Phase 2
0.7361	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4908	Phase 1
0.7358	Intermediate Similarity	NPD2296	Approved
0.7358	Intermediate Similarity	NPD4288	Approved
0.7357	Intermediate Similarity	NPD1201	Approved
0.7348	Intermediate Similarity	NPD9266	Approved
0.7348	Intermediate Similarity	NPD74	Approved
0.7338	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7321	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5710	Approved
0.7301	Intermediate Similarity	NPD5711	Approved
0.7299	Intermediate Similarity	NPD4363	Phase 3
0.7299	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9264	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9263	Approved
0.7262	Intermediate Similarity	NPD6104	Discontinued
0.726	Intermediate Similarity	NPD3764	Approved
0.7257	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4361	Phase 2
0.7255	Intermediate Similarity	NPD2354	Approved
0.7241	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6585	Discontinued
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7179	Intermediate Similarity	NPD5049	Phase 3
0.7174	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9494	Approved
0.717	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4287	Approved
0.7162	Intermediate Similarity	NPD3140	Approved
0.7162	Intermediate Similarity	NPD3142	Approved
0.7154	Intermediate Similarity	NPD940	Approved
0.7154	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7108	Intermediate Similarity	NPD2403	Approved
0.7105	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2353	Approved
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1876	Approved
0.7078	Intermediate Similarity	NPD7003	Approved
0.7063	Intermediate Similarity	NPD5889	Approved
0.7063	Intermediate Similarity	NPD5890	Approved
0.7059	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7049	Intermediate Similarity	NPD7584	Approved
0.7047	Intermediate Similarity	NPD1613	Approved
0.7047	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD5405	Approved
0.7039	Intermediate Similarity	NPD5404	Approved
0.7039	Intermediate Similarity	NPD5406	Approved
0.7013	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9697	Approved
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6671	Approved
0.6972	Remote Similarity	NPD1778	Approved
0.697	Remote Similarity	NPD9261	Approved
0.6966	Remote Similarity	NPD1283	Approved
0.6964	Remote Similarity	NPD3446	Phase 1
0.695	Remote Similarity	NPD1894	Discontinued
0.6944	Remote Similarity	NPD9269	Phase 2
0.6937	Remote Similarity	NPD5808	Clinical (unspecified phase)

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