NPASS Compound

Structure

CID261548 OpenBabel06191716062D 26 28 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	3.32
LogD:	2.691
LogS:	-4.462
# Rotatable Bonds:	5
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.241
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	4.6316650696098804e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	79.66610717773438%
Volume Distribution (VD):	0.917
Pgp-substrate:	17.567195892333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.803
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.658
CYP2C19-substrate:	0.432
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	6.023
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.455
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.098
Carcinogencity:	0.031
Eye Corrosion:	0.004
Eye Irritation:	0.107
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC261548

Natural Product ID:	NPC261548
*Common Name:**	2-(3,4-Dimethoxyphenyl)-3-Hydroxy-5,7-Dimethoxychromen-4-One
IUPAC Name:	2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxychromen-4-one
Synonyms:	NSC-102049
Standard InCHIKey:	AAASNKNLMQBKFV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-11-8-14(25-4)16-15(9-11)26-19(18(21)17(16)20)10-5-6-12(23-2)13(7-10)24-3/h5-9,21H,1-4H3
SMILES:	COc1cc(OC)c2c(c1)oc(c(c2=O)O)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL74675
PubChem CID:	97142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	60
IC50	5
Others	7
Potency	16

Activity Type	# Activity
Cell Line	62
Individual Protein	16
Organism	1
Others	7
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	=	6600.0	nM	PMID[487069]
NPT171	Cell Line	MRC5	Homo sapiens	CC50	=	20000.0	nM	PMID[487070]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	11220.2	nM	PMID[487072]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[487072]
NPT1226	Individual Protein	Caspase-7	Homo sapiens	Potency	=	25118.9	nM	PMID[487072]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7079.5	nM	PMID[487072]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PMID[487072]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	39810.7	nM	PMID[487072]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	15848.9	nM	PMID[487072]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	31622.8	nM	PMID[487072]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	2511.9	nM	PMID[487072]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	47752.93	nM	PMID[487073]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	6280.58	nM	PMID[487073]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	11117.32	nM	PMID[487073]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	4355.12	nM	PMID[487073]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	8851.16	nM	PMID[487073]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	2992.26	nM	PMID[487073]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	3475.36	nM	PMID[487073]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	8279.42	nM	PMID[487073]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	16069.41	nM	PMID[487073]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	28054.34	nM	PMID[487073]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	5956.62	nM	PMID[487073]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	5248.07	nM	PMID[487073]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	3564.51	nM	PMID[487073]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	10327.61	nM	PMID[487073]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	2890.68	nM	PMID[487073]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	3990.25	nM	PMID[487073]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	4943.11	nM	PMID[487073]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2864.18	nM	PMID[487073]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	3828.25	nM	PMID[487073]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	10256.52	nM	PMID[487073]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	10256.52	nM	PMID[487073]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	3334.26	nM	PMID[487073]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	5284.45	nM	PMID[487073]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	11246.05	nM	PMID[487073]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	7798.3	nM	PMID[487073]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	4226.69	nM	PMID[487073]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	9397.23	nM	PMID[487073]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	7294.58	nM	PMID[487073]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	5188.0	nM	PMID[487073]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	4720.63	nM	PMID[487073]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	606.74	nM	PMID[487073]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	3784.43	nM	PMID[487073]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	755.09	nM	PMID[487073]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	5847.9	nM	PMID[487073]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	7585.78	nM	PMID[487073]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	4255.98	nM	PMID[487073]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	3076.1	nM	PMID[487073]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	4943.11	nM	PMID[487073]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	4111.5	nM	PMID[487073]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	4017.91	nM	PMID[487073]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	7144.96	nM	PMID[487073]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	3917.42	nM	PMID[487073]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	4965.92	nM	PMID[487073]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	13551.89	nM	PMID[487073]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	3427.68	nM	PMID[487073]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	3935.5	nM	PMID[487073]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	22594.36	nM	PMID[487073]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	4102.04	nM	PMID[487073]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	5370.32	nM	PMID[487073]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	4864.07	nM	PMID[487073]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[487073]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	6870.68	nM	PMID[487073]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	5248.07	nM	PMID[487073]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	3097.42	nM	PMID[487073]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	9397.23	nM	PMID[487073]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	28183.83	nM	PMID[487073]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25176.77	nM	PMID[487073]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	8994.98	nM	PMID[487073]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	4841.72	nM	PMID[487073]
NPT1460	Cell Line	L929	Mus musculus	IC50	>	100000.0	nM	PMID[487074]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	FC	=	3.3	n.a.	PMID[487074]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	FC	=	6.0	n.a.	PMID[487074]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	FC	=	0.7	n.a.	PMID[487074]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5173.5	nM	PMID[487072]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[487072]
NPT518	Protein Complex	Tubulin	Homo sapiens	IC50	>	40000.0	nM	PMID[487069]
NPT518	Protein Complex	Tubulin	Homo sapiens	Inhibition	=	0.0	%	PMID[487069]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	26000.0	nM	PMID[487070]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	0.77	n.a.	PMID[487070]
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PMID[487072]
NPT2	Others	Unspecified		Potency	=	19952.6	nM	PMID[487072]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[487074]
NPT2	Others	Unspecified		FC	=	1.7	n.a.	PMID[487074]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[487072]

☑ 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 NPC261548 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	1867
0.2-0.3	4835
0.3-0.4	10962
0.4-0.5	6548
0.5-0.6	3674
0.6-0.7	4925
0.7-0.8	4881
0.8-0.85	2178
0.85-0.9	1384
0.9-0.95	700
0.95-1	308

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC50728
0.986	High Similarity	NPC166753
0.9792	High Similarity	NPC236769
0.979	High Similarity	NPC159103
0.9724	High Similarity	NPC134677
0.9722	High Similarity	NPC219330
0.972	High Similarity	NPC195202
0.9718	High Similarity	NPC310259
0.9658	High Similarity	NPC86485
0.9658	High Similarity	NPC236223
0.9658	High Similarity	NPC270620
0.9658	High Similarity	NPC78326
0.9658	High Similarity	NPC179126
0.9655	High Similarity	NPC252933
0.9655	High Similarity	NPC76376
0.9655	High Similarity	NPC200740
0.9655	High Similarity	NPC54394
0.9655	High Similarity	NPC125062
0.965	High Similarity	NPC299923
0.965	High Similarity	NPC62536
0.965	High Similarity	NPC33265
0.965	High Similarity	NPC12200
0.9645	High Similarity	NPC9966
0.9645	High Similarity	NPC70853
0.9592	High Similarity	NPC189960
0.9592	High Similarity	NPC32557
0.9589	High Similarity	NPC301123
0.9589	High Similarity	NPC82325
0.9589	High Similarity	NPC55205
0.9589	High Similarity	NPC279989
0.9577	High Similarity	NPC113089
0.9574	High Similarity	NPC29536
0.9527	High Similarity	NPC49824
0.9527	High Similarity	NPC265511
0.9527	High Similarity	NPC178854
0.9524	High Similarity	NPC162351
0.9524	High Similarity	NPC246204
0.9524	High Similarity	NPC58382
0.9521	High Similarity	NPC133953
0.9521	High Similarity	NPC28274
0.9521	High Similarity	NPC226973
0.9521	High Similarity	NPC208043
0.9521	High Similarity	NPC50403
0.9521	High Similarity	NPC308451
0.9517	High Similarity	NPC137062
0.9517	High Similarity	NPC69752
0.9517	High Similarity	NPC87125
0.9517	High Similarity	NPC270465
0.9517	High Similarity	NPC223579
0.9517	High Similarity	NPC287101
0.9517	High Similarity	NPC328119
0.9517	High Similarity	NPC183950
0.9517	High Similarity	NPC52005
0.9517	High Similarity	NPC48479
0.9517	High Similarity	NPC177298
0.951	High Similarity	NPC136278
0.9463	High Similarity	NPC224137
0.9463	High Similarity	NPC101830
0.9463	High Similarity	NPC189179
0.9463	High Similarity	NPC75215
0.9463	High Similarity	NPC110070
0.9463	High Similarity	NPC93376
0.9463	High Similarity	NPC227192
0.9463	High Similarity	NPC203891
0.9459	High Similarity	NPC44079
0.9459	High Similarity	NPC26227
0.9459	High Similarity	NPC201451
0.9456	High Similarity	NPC123886
0.9456	High Similarity	NPC39732
0.9456	High Similarity	NPC60972
0.9452	High Similarity	NPC188871
0.9452	High Similarity	NPC259058
0.9452	High Similarity	NPC149127
0.9452	High Similarity	NPC306821
0.9452	High Similarity	NPC201547
0.9452	High Similarity	NPC286342
0.9448	High Similarity	NPC120464
0.9444	High Similarity	NPC14958
0.9444	High Similarity	NPC40818
0.9444	High Similarity	NPC106461
0.9444	High Similarity	NPC215932
0.9444	High Similarity	NPC110639
0.94	High Similarity	NPC22472
0.94	High Similarity	NPC18772
0.94	High Similarity	NPC176300
0.94	High Similarity	NPC19687
0.94	High Similarity	NPC105242
0.94	High Similarity	NPC288669
0.94	High Similarity	NPC7846
0.94	High Similarity	NPC18607
0.94	High Similarity	NPC25495
0.94	High Similarity	NPC115798
0.94	High Similarity	NPC9609
0.94	High Similarity	NPC143828
0.94	High Similarity	NPC191459
0.94	High Similarity	NPC4481
0.94	High Similarity	NPC300943
0.94	High Similarity	NPC152166
0.94	High Similarity	NPC204854
0.94	High Similarity	NPC130894
0.94	High Similarity	NPC261004
0.94	High Similarity	NPC253634
0.9396	High Similarity	NPC98661
0.9396	High Similarity	NPC55619
0.9396	High Similarity	NPC247017
0.9396	High Similarity	NPC200388
0.9396	High Similarity	NPC303255
0.9396	High Similarity	NPC474520
0.9396	High Similarity	NPC266960
0.9396	High Similarity	NPC43243
0.9396	High Similarity	NPC292107
0.9396	High Similarity	NPC100916
0.9396	High Similarity	NPC245546
0.9392	High Similarity	NPC274327
0.9392	High Similarity	NPC183878
0.9392	High Similarity	NPC176775
0.9392	High Similarity	NPC47781
0.9392	High Similarity	NPC255350
0.9392	High Similarity	NPC69394
0.9392	High Similarity	NPC231018
0.9392	High Similarity	NPC145379
0.9392	High Similarity	NPC22519
0.9392	High Similarity	NPC160951
0.9388	High Similarity	NPC260895
0.9388	High Similarity	NPC474170
0.9388	High Similarity	NPC474388
0.9388	High Similarity	NPC472535
0.9384	High Similarity	NPC181250
0.9379	High Similarity	NPC108406
0.9379	High Similarity	NPC117463
0.9379	High Similarity	NPC205522
0.9379	High Similarity	NPC85233
0.9375	High Similarity	NPC471590
0.9362	High Similarity	NPC276905
0.9333	High Similarity	NPC471479
0.9333	High Similarity	NPC287979
0.9333	High Similarity	NPC163524
0.9333	High Similarity	NPC235215
0.9333	High Similarity	NPC472438
0.9333	High Similarity	NPC174908
0.9333	High Similarity	NPC7973
0.9333	High Similarity	NPC471515
0.9333	High Similarity	NPC78302
0.9333	High Similarity	NPC29841
0.9333	High Similarity	NPC176665
0.9333	High Similarity	NPC67876
0.9333	High Similarity	NPC305663
0.9329	High Similarity	NPC196439
0.9329	High Similarity	NPC201136
0.9329	High Similarity	NPC92659
0.9329	High Similarity	NPC146165
0.9329	High Similarity	NPC4455
0.9329	High Similarity	NPC163780
0.9329	High Similarity	NPC138360
0.9329	High Similarity	NPC280339
0.9329	High Similarity	NPC213622
0.9329	High Similarity	NPC227325
0.9329	High Similarity	NPC167815
0.9329	High Similarity	NPC20830
0.9329	High Similarity	NPC183597
0.9329	High Similarity	NPC133392
0.9329	High Similarity	NPC256612
0.9329	High Similarity	NPC128863
0.9329	High Similarity	NPC80534
0.9329	High Similarity	NPC50715
0.9329	High Similarity	NPC56786
0.9329	High Similarity	NPC2476
0.9324	High Similarity	NPC241498
0.9324	High Similarity	NPC162313
0.9324	High Similarity	NPC120163
0.9324	High Similarity	NPC222830
0.9324	High Similarity	NPC293183
0.9324	High Similarity	NPC188203
0.9324	High Similarity	NPC157784
0.9324	High Similarity	NPC275836
0.9324	High Similarity	NPC239128
0.9324	High Similarity	NPC57030
0.9324	High Similarity	NPC83508
0.9324	High Similarity	NPC100887
0.9324	High Similarity	NPC471982
0.9324	High Similarity	NPC301323
0.9324	High Similarity	NPC212678
0.9324	High Similarity	NPC187498
0.9324	High Similarity	NPC63187
0.9324	High Similarity	NPC25270
0.9324	High Similarity	NPC131624
0.9324	High Similarity	NPC71334
0.9324	High Similarity	NPC156222
0.9324	High Similarity	NPC37684
0.9324	High Similarity	NPC275722
0.9324	High Similarity	NPC198826
0.9324	High Similarity	NPC256283
0.932	High Similarity	NPC177839
0.932	High Similarity	NPC338131
0.931	High Similarity	NPC302408
0.931	High Similarity	NPC283002
0.931	High Similarity	NPC20791
0.931	High Similarity	NPC179271
0.9306	High Similarity	NPC23955
0.9306	High Similarity	NPC293201

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 NPC261548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	967
0.2-0.3	1790
0.3-0.4	2657
0.4-0.5	1764
0.5-0.6	1002
0.6-0.7	389
0.7-0.8	118
0.8-0.85	36
0.85-0.9	14
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9459	High Similarity	NPD3817	Phase 2
0.9392	High Similarity	NPD2801	Approved
0.931	High Similarity	NPD1512	Approved
0.9195	High Similarity	NPD1934	Approved
0.9172	High Similarity	NPD1511	Approved
0.9139	High Similarity	NPD3882	Suspended
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.9007	High Similarity	NPD2393	Clinical (unspecified phase)
0.8974	High Similarity	NPD6168	Clinical (unspecified phase)
0.8974	High Similarity	NPD6167	Clinical (unspecified phase)
0.8974	High Similarity	NPD6166	Phase 2
0.8784	High Similarity	NPD6799	Approved
0.8704	High Similarity	NPD7808	Phase 3
0.8696	High Similarity	NPD6797	Phase 2
0.869	High Similarity	NPD2796	Approved
0.8688	High Similarity	NPD7054	Approved
0.8642	High Similarity	NPD7251	Discontinued
0.8636	High Similarity	NPD7096	Clinical (unspecified phase)
0.8634	High Similarity	NPD7472	Approved
0.8625	High Similarity	NPD3818	Discontinued
0.8599	High Similarity	NPD5494	Approved
0.8589	High Similarity	NPD4338	Clinical (unspecified phase)
0.8519	High Similarity	NPD7074	Phase 3
0.8503	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1550	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1510	Phase 2
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD6801	Discontinued
0.8446	Intermediate Similarity	NPD1549	Phase 2
0.8442	Intermediate Similarity	NPD6599	Discontinued
0.8442	Intermediate Similarity	NPD4380	Phase 2
0.8438	Intermediate Similarity	NPD3926	Phase 2
0.8428	Intermediate Similarity	NPD1247	Approved
0.8418	Intermediate Similarity	NPD919	Approved
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8375	Intermediate Similarity	NPD6232	Discontinued
0.8355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1240	Approved
0.8344	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD5403	Approved
0.8235	Intermediate Similarity	NPD5401	Approved
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1607	Approved
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5844	Phase 1
0.8113	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD447	Suspended
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7974	Intermediate Similarity	NPD3750	Approved
0.7973	Intermediate Similarity	NPD943	Approved
0.7937	Intermediate Similarity	NPD1465	Phase 2
0.7919	Intermediate Similarity	NPD1933	Approved
0.7881	Intermediate Similarity	NPD3748	Approved
0.7879	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1551	Phase 2
0.7823	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2800	Approved
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7763	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1613	Approved
0.7733	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7711	Intermediate Similarity	NPD3787	Discontinued
0.7683	Intermediate Similarity	NPD3749	Approved
0.7682	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD2534	Approved
0.7658	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD2533	Approved
0.7651	Intermediate Similarity	NPD3027	Phase 3
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3751	Discontinued
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7597	Intermediate Similarity	NPD6099	Approved
0.7597	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7578	Intermediate Similarity	NPD3226	Approved
0.7568	Intermediate Similarity	NPD2798	Approved
0.7566	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7548	Intermediate Similarity	NPD2344	Approved
0.7517	Intermediate Similarity	NPD3018	Phase 2
0.7516	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD2403	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5536	Phase 2
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD3268	Approved
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6190	Approved
0.7466	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5242	Approved
0.7452	Intermediate Similarity	NPD2654	Approved
0.7439	Intermediate Similarity	NPD37	Approved
0.7434	Intermediate Similarity	NPD6233	Phase 2
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD9717	Approved
0.7415	Intermediate Similarity	NPD1608	Approved
0.7412	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD9494	Approved
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD2797	Approved
0.7378	Intermediate Similarity	NPD6386	Approved
0.7378	Intermediate Similarity	NPD6385	Approved
0.7375	Intermediate Similarity	NPD7390	Discontinued
0.7365	Intermediate Similarity	NPD2983	Phase 2
0.7365	Intermediate Similarity	NPD2982	Phase 2
0.7358	Intermediate Similarity	NPD2309	Approved
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7349	Intermediate Similarity	NPD5353	Approved
0.7347	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD6844	Discontinued
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD3225	Approved
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD411	Approved
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2354	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7233	Intermediate Similarity	NPD1652	Phase 2
0.723	Intermediate Similarity	NPD1610	Phase 2
0.7225	Intermediate Similarity	NPD2163	Approved
0.7222	Intermediate Similarity	NPD3146	Approved
0.7222	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1471	Phase 3
0.7211	Intermediate Similarity	NPD17	Approved
0.7198	Intermediate Similarity	NPD4363	Phase 3
0.7198	Intermediate Similarity	NPD4360	Phase 2
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.719	Intermediate Similarity	NPD7095	Approved
0.7181	Intermediate Similarity	NPD3972	Approved
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD6971	Discontinued
0.7159	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD9268	Approved
0.7107	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2353	Approved
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7101	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4062	Phase 3
0.7093	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD4625	Phase 3
0.7073	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5049	Phase 3
0.7067	Intermediate Similarity	NPD9269	Phase 2
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4361	Phase 2
0.7062	Intermediate Similarity	NPD7039	Approved
0.7062	Intermediate Similarity	NPD7038	Approved
0.7051	Intermediate Similarity	NPD4060	Phase 1
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD8127	Discontinued
0.7029	Intermediate Similarity	NPD7228	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