NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	282.198
LogP:	3.805
LogD:	3.322
LogS:	-3.425
# Rotatable Bonds:	3
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.068
Fsp3:	0.118
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:	-4.854
MDCK Permeability:	1.5118433111638296e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	98.65584564208984%
Volume Distribution (VD):	0.69
Pgp-substrate:	1.2374770641326904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.642
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	3.792
Half-life (T1/2):	0.567

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.295
AMES Toxicity:	0.72
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.263
Skin Sensitization:	0.928
Carcinogencity:	0.631
Eye Corrosion:	0.023
Eye Irritation:	0.968
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC39753

Natural Product ID:	NPC39753
*Common Name:**	5-Hydroxy-2-(2-Phenylethyl)Chromen-4-One
IUPAC Name:	5-hydroxy-2-(2-phenylethyl)chromen-4-one
Synonyms:
Standard InCHIKey:	OLLHYYCQHNBTQC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O3/c18-14-7-4-8-16-17(14)15(19)11-13(20-16)10-9-12-5-2-1-3-6-12/h1-8,11,18H,9-10H2
SMILES:	Oc1cccc2c1c(=O)cc(o2)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479683
PubChem CID:	11536299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO33572	Imperata cylindrical	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24582985]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	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
IC50	1
Ki	3
Others	38
Potency	5

Activity Type	# Activity
Individual Protein	42
NON-MOLECULAR	1
Others	3
PROTEIN COMPLEX GROUP	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[508269]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[508269]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[508269]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[508269]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	IC50	=	8912.51	nM	PMID[508270]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	6.9	%	PMID[508270]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Activity	=	0.6	%	PMID[508270]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	Ki	=	2511.89	nM	PMID[508270]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	2454.71	nM	PMID[508270]
NPT2776	Individual Protein	Serotonin 1e (5-HT1e) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[508270]
NPT2777	Individual Protein	Translocator protein	Homo sapiens	Inhibition	=	2.8	%	PMID[508270]
NPT266	Individual Protein	Muscarinic acetylcholine receptor M5	Homo sapiens	Inhibition	=	19.3	%	PMID[508270]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	Inhibition	=	1.8	%	PMID[508270]
NPT228	Individual Protein	Norepinephrine transporter	Homo sapiens	Inhibition	=	34.6	%	PMID[508270]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	Inhibition	=	1.4	%	PMID[508270]
NPT224	Individual Protein	Alpha-2c adrenergic receptor	Homo sapiens	Inhibition	=	32.7	%	PMID[508270]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	22.2	%	PMID[508270]
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	Inhibition	=	2.1	%	PMID[508270]
NPT1789	Individual Protein	Alpha-1b adrenergic receptor	Homo sapiens	Inhibition	=	2.9	%	PMID[508270]
NPT1788	Individual Protein	Alpha-1a adrenergic receptor	Homo sapiens	Inhibition	=	16.9	%	PMID[508270]
NPT251	Individual Protein	Histamine H1 receptor	Homo sapiens	Inhibition	=	13.0	%	PMID[508270]
NPT1811	Individual Protein	Dopamine D5 receptor	Homo sapiens	Inhibition	=	0.4	%	PMID[508270]
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Inhibition	=	24.7	%	PMID[508270]
NPT295	Individual Protein	Serotonin transporter	Homo sapiens	Inhibition	=	28.9	%	PMID[508270]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	35.9	%	PMID[508270]
NPT294	Individual Protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Inhibition	=	5.8	%	PMID[508270]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	Inhibition	=	61.7	%	PMID[508270]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Inhibition	=	4.8	%	PMID[508270]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	62.6	%	PMID[508270]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	14.2	%	PMID[508270]
NPT2776	Individual Protein	Serotonin 1e (5-HT1e) receptor	Homo sapiens	Inhibition	=	55.1	%	PMID[508270]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Inhibition	=	4.8	%	PMID[508271]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	62.6	%	PMID[508271]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	14.2	%	PMID[508271]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	6.9	%	PMID[508271]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Inhibition	=	4.8	%	PMID[508273]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	14.2	%	PMID[508273]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	62.6	%	PMID[508273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	67.0	%	PMID[508268]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[508269]
NPT22674	PROTEIN COMPLEX GROUP	Glutamate [NMDA] receptor	Homo sapiens	Inhibition	=	17.4	%	PMID[508270]
NPT2	Others	Unspecified		Inhibition	=	0.1	%	PMID[508270]
NPT2	Others	Unspecified		Inhibition	=	36.8	%	PMID[508270]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	Inhibition	=	15.9	%	PMID[508270]
NPT974	Individual Protein	Serotonin 1d (5-HT1d) receptor	Homo sapiens	Inhibition	=	4.3	%	PMID[508270]
NPT973	Individual Protein	Serotonin 1b (5-HT1b) receptor	Homo sapiens	Inhibition	=	3.7	%	PMID[508270]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Inhibition	=	5.4	%	PMID[508270]

☑ 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 NPC39753 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	435
0.1-0.2	2029
0.2-0.3	5362
0.3-0.4	12361
0.4-0.5	4929
0.5-0.6	4848
0.6-0.7	5734
0.7-0.8	4046
0.8-0.85	1734
0.85-0.9	999
0.9-0.95	187
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC115998
0.9919	High Similarity	NPC137264
0.9919	High Similarity	NPC197425
0.9683	High Similarity	NPC113006
0.9606	High Similarity	NPC128216
0.96	High Similarity	NPC187907
0.9531	High Similarity	NPC50898
0.9531	High Similarity	NPC274121
0.9531	High Similarity	NPC78540
0.9531	High Similarity	NPC57601
0.9531	High Similarity	NPC213216
0.9462	High Similarity	NPC473887
0.9462	High Similarity	NPC234133
0.9462	High Similarity	NPC47815
0.9462	High Similarity	NPC124784
0.9462	High Similarity	NPC29353
0.9462	High Similarity	NPC13408
0.9462	High Similarity	NPC194281
0.9462	High Similarity	NPC127447
0.9462	High Similarity	NPC231772
0.9457	High Similarity	NPC248872
0.9457	High Similarity	NPC172262
0.944	High Similarity	NPC41721
0.9389	High Similarity	NPC266597
0.9389	High Similarity	NPC228661
0.9389	High Similarity	NPC250266
0.9355	High Similarity	NPC193805
0.9318	High Similarity	NPC201395
0.9313	High Similarity	NPC281917
0.9313	High Similarity	NPC116775
0.9313	High Similarity	NPC187432
0.9313	High Similarity	NPC256042
0.9313	High Similarity	NPC216361
0.9286	High Similarity	NPC22783
0.9248	High Similarity	NPC78913
0.9248	High Similarity	NPC55018
0.9248	High Similarity	NPC152042
0.9248	High Similarity	NPC18260
0.9248	High Similarity	NPC301217
0.9248	High Similarity	NPC220062
0.9248	High Similarity	NPC303633
0.9248	High Similarity	NPC96565
0.9248	High Similarity	NPC143799
0.9248	High Similarity	NPC241838
0.9248	High Similarity	NPC216978
0.9242	High Similarity	NPC299379
0.9242	High Similarity	NPC275055
0.9242	High Similarity	NPC290291
0.9237	High Similarity	NPC9985
0.9237	High Similarity	NPC239495
0.9179	High Similarity	NPC475680
0.9179	High Similarity	NPC59951
0.9179	High Similarity	NPC269652
0.9179	High Similarity	NPC281207
0.9179	High Similarity	NPC241100
0.9179	High Similarity	NPC103342
0.9179	High Similarity	NPC184536
0.9179	High Similarity	NPC103904
0.9179	High Similarity	NPC230285
0.9179	High Similarity	NPC159275
0.9179	High Similarity	NPC172986
0.9179	High Similarity	NPC261227
0.9179	High Similarity	NPC270883
0.9179	High Similarity	NPC305355
0.9179	High Similarity	NPC146679
0.9173	High Similarity	NPC99333
0.9173	High Similarity	NPC118813
0.9173	High Similarity	NPC280284
0.9173	High Similarity	NPC188947
0.9167	High Similarity	NPC240593
0.9154	High Similarity	NPC10971
0.9147	High Similarity	NPC5515
0.9147	High Similarity	NPC270369
0.9111	High Similarity	NPC136840
0.9111	High Similarity	NPC147688
0.9111	High Similarity	NPC156590
0.9111	High Similarity	NPC64908
0.9111	High Similarity	NPC282300
0.9111	High Similarity	NPC118840
0.9111	High Similarity	NPC90582
0.9111	High Similarity	NPC14871
0.9111	High Similarity	NPC205006
0.9111	High Similarity	NPC262094
0.9111	High Similarity	NPC110969
0.9104	High Similarity	NPC310135
0.9104	High Similarity	NPC274784
0.9104	High Similarity	NPC53181
0.9104	High Similarity	NPC222342
0.9104	High Similarity	NPC20709
0.9104	High Similarity	NPC265871
0.9104	High Similarity	NPC261234
0.9104	High Similarity	NPC217186
0.9104	High Similarity	NPC329203
0.9104	High Similarity	NPC150648
0.9104	High Similarity	NPC225153
0.9098	High Similarity	NPC287246
0.9098	High Similarity	NPC476480
0.9098	High Similarity	NPC13768
0.9098	High Similarity	NPC188879
0.9098	High Similarity	NPC107586
0.9098	High Similarity	NPC295261
0.9098	High Similarity	NPC296490
0.9098	High Similarity	NPC32441
0.9098	High Similarity	NPC84585
0.9098	High Similarity	NPC12296
0.9098	High Similarity	NPC243083
0.9098	High Similarity	NPC79943
0.9077	High Similarity	NPC31872
0.9077	High Similarity	NPC186097
0.9077	High Similarity	NPC475009
0.9077	High Similarity	NPC308037
0.9077	High Similarity	NPC475008
0.9077	High Similarity	NPC64359
0.9077	High Similarity	NPC473584
0.9077	High Similarity	NPC278556
0.9077	High Similarity	NPC284424
0.9077	High Similarity	NPC475589
0.907	High Similarity	NPC228184
0.9044	High Similarity	NPC200694
0.9044	High Similarity	NPC1534
0.9044	High Similarity	NPC78803
0.9044	High Similarity	NPC217083
0.9044	High Similarity	NPC62840
0.9044	High Similarity	NPC214236
0.9044	High Similarity	NPC293852
0.9044	High Similarity	NPC59739
0.9044	High Similarity	NPC299080
0.9044	High Similarity	NPC473042
0.9044	High Similarity	NPC11561
0.9044	High Similarity	NPC226636
0.9037	High Similarity	NPC76445
0.9037	High Similarity	NPC150522
0.9037	High Similarity	NPC284550
0.9037	High Similarity	NPC6407
0.9037	High Similarity	NPC69769
0.9037	High Similarity	NPC110228
0.9037	High Similarity	NPC235239
0.9037	High Similarity	NPC129853
0.9037	High Similarity	NPC188243
0.903	High Similarity	NPC124269
0.903	High Similarity	NPC18457
0.903	High Similarity	NPC329225
0.903	High Similarity	NPC276905
0.903	High Similarity	NPC147686
0.903	High Similarity	NPC472460
0.9008	High Similarity	NPC205468
0.9008	High Similarity	NPC25937
0.9008	High Similarity	NPC101294
0.9008	High Similarity	NPC473655
0.9008	High Similarity	NPC212631
0.9008	High Similarity	NPC87231
0.9008	High Similarity	NPC257756
0.9008	High Similarity	NPC129132
0.8978	High Similarity	NPC9117
0.8978	High Similarity	NPC212932
0.8978	High Similarity	NPC38219
0.8978	High Similarity	NPC190637
0.8978	High Similarity	NPC24821
0.8978	High Similarity	NPC293053
0.8978	High Similarity	NPC11700
0.8978	High Similarity	NPC470216
0.8978	High Similarity	NPC219915
0.8971	High Similarity	NPC324386
0.8971	High Similarity	NPC103362
0.8971	High Similarity	NPC213322
0.8971	High Similarity	NPC4743
0.8971	High Similarity	NPC3188
0.8971	High Similarity	NPC312391
0.8963	High Similarity	NPC316480
0.8963	High Similarity	NPC140890
0.8955	High Similarity	NPC162680
0.8955	High Similarity	NPC7013
0.8955	High Similarity	NPC160972
0.8955	High Similarity	NPC209560
0.8955	High Similarity	NPC181124
0.8955	High Similarity	NPC254841
0.8955	High Similarity	NPC294409
0.8955	High Similarity	NPC116632
0.8955	High Similarity	NPC303644
0.8947	High Similarity	NPC151113
0.8947	High Similarity	NPC39426
0.8947	High Similarity	NPC234560
0.8939	High Similarity	NPC18877
0.8939	High Similarity	NPC56031
0.8939	High Similarity	NPC294593
0.8939	High Similarity	NPC204960
0.8939	High Similarity	NPC242294
0.8939	High Similarity	NPC20560
0.8939	High Similarity	NPC312318
0.8939	High Similarity	NPC263670
0.8939	High Similarity	NPC93756
0.8939	High Similarity	NPC472365
0.8939	High Similarity	NPC192304
0.8939	High Similarity	NPC292998
0.8939	High Similarity	NPC188646
0.8939	High Similarity	NPC139813
0.8939	High Similarity	NPC82225
0.8939	High Similarity	NPC159623
0.8939	High Similarity	NPC337373
0.8939	High Similarity	NPC28753

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 NPC39753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	997
0.2-0.3	1474
0.3-0.4	2753
0.4-0.5	1920
0.5-0.6	1107
0.6-0.7	298
0.7-0.8	114
0.8-0.85	36
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD1552	Clinical (unspecified phase)
0.9098	High Similarity	NPD1550	Clinical (unspecified phase)
0.903	High Similarity	NPD1549	Phase 2
0.8947	High Similarity	NPD1510	Phase 2
0.8931	High Similarity	NPD1240	Approved
0.8913	High Similarity	NPD4378	Clinical (unspecified phase)
0.8841	High Similarity	NPD1511	Approved
0.8797	High Similarity	NPD1607	Approved
0.8777	High Similarity	NPD7410	Clinical (unspecified phase)
0.8759	High Similarity	NPD3750	Approved
0.8741	High Similarity	NPD1551	Phase 2
0.8741	High Similarity	NPD2796	Approved
0.8714	High Similarity	NPD1512	Approved
0.8682	High Similarity	NPD1203	Approved
0.8521	High Similarity	NPD5403	Approved
0.8511	High Similarity	NPD5401	Approved
0.8425	Intermediate Similarity	NPD2801	Approved
0.8394	Intermediate Similarity	NPD3748	Approved
0.8372	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD2313	Discontinued
0.8357	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1934	Approved
0.8346	Intermediate Similarity	NPD1548	Phase 1
0.8345	Intermediate Similarity	NPD4380	Phase 2
0.831	Intermediate Similarity	NPD6799	Approved
0.8308	Intermediate Similarity	NPD9717	Approved
0.8299	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD2797	Approved
0.8255	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD422	Phase 1
0.8214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD2798	Approved
0.8182	Intermediate Similarity	NPD3225	Approved
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD5402	Approved
0.8108	Intermediate Similarity	NPD6801	Discontinued
0.8088	Intermediate Similarity	NPD3268	Approved
0.8088	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD6832	Phase 2
0.8067	Intermediate Similarity	NPD7768	Phase 2
0.8067	Intermediate Similarity	NPD3882	Suspended
0.8054	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7819	Suspended
0.8028	Intermediate Similarity	NPD2800	Approved
0.8028	Intermediate Similarity	NPD1243	Approved
0.8014	Intermediate Similarity	NPD2344	Approved
0.8	Intermediate Similarity	NPD4308	Phase 3
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7973	Intermediate Similarity	NPD6599	Discontinued
0.7955	Intermediate Similarity	NPD1610	Phase 2
0.7943	Intermediate Similarity	NPD6099	Approved
0.7943	Intermediate Similarity	NPD6100	Approved
0.7907	Intermediate Similarity	NPD9493	Approved
0.7902	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2799	Discontinued
0.7862	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3267	Approved
0.7852	Intermediate Similarity	NPD3266	Approved
0.7834	Intermediate Similarity	NPD3818	Discontinued
0.7821	Intermediate Similarity	NPD6166	Phase 2
0.7821	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1201	Approved
0.7817	Intermediate Similarity	NPD2935	Discontinued
0.7793	Intermediate Similarity	NPD2309	Approved
0.7786	Intermediate Similarity	NPD1933	Approved
0.7785	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7054	Approved
0.7785	Intermediate Similarity	NPD3226	Approved
0.7762	Intermediate Similarity	NPD2346	Discontinued
0.7755	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7033	Discontinued
0.7742	Intermediate Similarity	NPD6959	Discontinued
0.7736	Intermediate Similarity	NPD7472	Approved
0.773	Intermediate Similarity	NPD6651	Approved
0.7724	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD943	Approved
0.7714	Intermediate Similarity	NPD4307	Phase 2
0.7698	Intermediate Similarity	NPD411	Approved
0.7698	Intermediate Similarity	NPD1296	Phase 2
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7681	Intermediate Similarity	NPD4908	Phase 1
0.766	Intermediate Similarity	NPD447	Suspended
0.766	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD920	Approved
0.7647	Intermediate Similarity	NPD4288	Approved
0.764	Intermediate Similarity	NPD7251	Discontinued
0.763	Intermediate Similarity	NPD1608	Approved
0.7626	Intermediate Similarity	NPD4625	Phase 3
0.7625	Intermediate Similarity	NPD7074	Phase 3
0.7597	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7808	Phase 3
0.7591	Intermediate Similarity	NPD1470	Approved
0.7574	Intermediate Similarity	NPD4749	Approved
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD9266	Approved
0.7559	Intermediate Similarity	NPD74	Approved
0.7554	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD1241	Discontinued
0.7536	Intermediate Similarity	NPD1019	Discontinued
0.7531	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1481	Phase 2
0.7482	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9263	Approved
0.748	Intermediate Similarity	NPD9267	Approved
0.748	Intermediate Similarity	NPD9264	Approved
0.7469	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD6232	Discontinued
0.7453	Intermediate Similarity	NPD7286	Phase 2
0.7452	Intermediate Similarity	NPD5494	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7426	Intermediate Similarity	NPD1535	Discovery
0.7415	Intermediate Similarity	NPD2654	Approved
0.7407	Intermediate Similarity	NPD17	Approved
0.74	Intermediate Similarity	NPD2532	Approved
0.74	Intermediate Similarity	NPD2534	Approved
0.74	Intermediate Similarity	NPD2533	Approved
0.7391	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD9545	Approved
0.7388	Intermediate Similarity	NPD1894	Discontinued
0.7375	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD1465	Phase 2
0.7343	Intermediate Similarity	NPD1613	Approved
0.7343	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1164	Approved
0.7305	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5124	Phase 1
0.7292	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6844	Discontinued
0.7285	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4661	Approved
0.7285	Intermediate Similarity	NPD4662	Approved
0.7279	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD919	Approved
0.7266	Intermediate Similarity	NPD968	Approved
0.7246	Intermediate Similarity	NPD3972	Approved
0.7226	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7390	Discontinued
0.7208	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3926	Phase 2
0.7203	Intermediate Similarity	NPD6798	Discontinued
0.7203	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2296	Approved
0.7188	Intermediate Similarity	NPD9697	Approved
0.7188	Intermediate Similarity	NPD1247	Approved
0.7165	Intermediate Similarity	NPD9261	Approved
0.7161	Intermediate Similarity	NPD6585	Discontinued
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7118	Intermediate Similarity	NPD4287	Approved
0.7115	Intermediate Similarity	NPD5889	Approved
0.7115	Intermediate Similarity	NPD5890	Approved
0.7113	Intermediate Similarity	NPD2861	Phase 2
0.711	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4361	Phase 2
0.7095	Intermediate Similarity	NPD5405	Approved
0.7095	Intermediate Similarity	NPD5404	Approved
0.7095	Intermediate Similarity	NPD5408	Approved
0.7095	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD1729	Discontinued
0.709	Intermediate Similarity	NPD9281	Approved
0.7086	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7047	Intermediate Similarity	NPD1471	Phase 3
0.7039	Intermediate Similarity	NPD7440	Discontinued
0.7037	Intermediate Similarity	NPD6671	Approved
0.7034	Intermediate Similarity	NPD6233	Phase 2
0.7029	Intermediate Similarity	NPD1778	Approved
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.702	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD2366	Approved
0.7	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD955	Approved
0.6993	Remote Similarity	NPD7213	Phase 3
0.6993	Remote Similarity	NPD7212	Phase 2
0.6974	Remote Similarity	NPD2354	Approved
0.6953	Remote Similarity	NPD846	Approved
0.6953	Remote Similarity	NPD940	Approved
0.6948	Remote Similarity	NPD7447	Phase 1
0.6947	Remote Similarity	NPD290	Approved
0.6947	Remote Similarity	NPD9265	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