NPASS Compound

Structure

CID47815 OpenBabel06191715382D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 -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 -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 3.4641 -0.0000 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 -1.7321 0.0000 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 1.7321 -0.0000 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 -2.5981 -0.5000 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 -0.5000 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 4.3301 1.5000 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 -0.0000 -3.0000 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 20 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	3.263
LogD:	2.825
LogS:	-3.623
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	2.224
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.764
MDCK Permeability:	1.3110925465298351e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.882
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	95.21680450439453%
Volume Distribution (VD):	0.729
Pgp-substrate:	6.592987537384033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	7.35
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.424
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.794
Carcinogencity:	0.276
Eye Corrosion:	0.008
Eye Irritation:	0.938
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC47815

Natural Product ID:	NPC47815
*Common Name:**	7-Hydroxy-2-(4-Hydroxyphenyl)-5-Methoxychromen-4-One
IUPAC Name:	7-hydroxy-2-(4-hydroxyphenyl)-5-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	YQABHAHJGSNVQR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-14-6-11(18)7-15-16(14)12(19)8-13(21-15)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES:	COc1cc(O)cc2c1c(=O)cc(o2)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL182265
PubChem CID:	5315202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO33252	heliotropium sinuatum	Species	Heliotropiaceae	Eukaryota	resinous exudate	n.a.	n.a.	PMID[15603945]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30088	Thevetia nerllfolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	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	57
Others	1

Activity Type	# Activity
Cell Line	57
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	64714.26	nM	PMID[500765]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	54954.09	nM	PMID[500765]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	71944.9	nM	PMID[500765]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	76559.66	nM	PMID[500765]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	29648.31	nM	PMID[500765]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	74644.88	nM	PMID[500765]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	71449.63	nM	PMID[500765]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	34355.79	nM	PMID[500765]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	37757.22	nM	PMID[500765]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	49317.38	nM	PMID[500765]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	22181.96	nM	PMID[500765]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	66069.34	nM	PMID[500765]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	47097.73	nM	PMID[500765]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	52844.53	nM	PMID[500765]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	14028.14	nM	PMID[500765]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	44360.86	nM	PMID[500765]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	67764.15	nM	PMID[500765]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	50350.06	nM	PMID[500765]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	83946.0	nM	PMID[500765]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	67452.8	nM	PMID[500765]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	64268.77	nM	PMID[500765]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	36224.3	nM	PMID[500765]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	47315.13	nM	PMID[500765]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	57016.43	nM	PMID[500765]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	68391.16	nM	PMID[500765]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	32658.78	nM	PMID[500765]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[500765]
NPT610	Others	Molecular identity unknown		Ratio	=	143.0	n.a.	PMID[500764]

☑ 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 NPC47815 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	453
0.1-0.2	1936
0.2-0.3	4943
0.3-0.4	12045
0.4-0.5	5395
0.5-0.6	4390
0.6-0.7	5772
0.7-0.8	4072
0.8-0.85	1835
0.85-0.9	1292
0.9-0.95	504
0.95-1	60

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124784
1.0	High Similarity	NPC473887
1.0	High Similarity	NPC29353
1.0	High Similarity	NPC127447
1.0	High Similarity	NPC234133
1.0	High Similarity	NPC194281
1.0	High Similarity	NPC231772
0.9924	High Similarity	NPC250266
0.9924	High Similarity	NPC266597
0.9847	High Similarity	NPC13408
0.9774	High Similarity	NPC152042
0.9774	High Similarity	NPC143799
0.9774	High Similarity	NPC241838
0.9774	High Similarity	NPC78913
0.9774	High Similarity	NPC18260
0.9769	High Similarity	NPC274121
0.9769	High Similarity	NPC50898
0.9769	High Similarity	NPC78540
0.9769	High Similarity	NPC213216
0.9701	High Similarity	NPC184536
0.9701	High Similarity	NPC146679
0.9701	High Similarity	NPC159275
0.9701	High Similarity	NPC241100
0.9701	High Similarity	NPC59951
0.9701	High Similarity	NPC269652
0.9701	High Similarity	NPC281207
0.9701	High Similarity	NPC103342
0.9701	High Similarity	NPC103904
0.9701	High Similarity	NPC230285
0.9699	High Similarity	NPC188947
0.9699	High Similarity	NPC99333
0.9699	High Similarity	NPC201395
0.9699	High Similarity	NPC280284
0.9695	High Similarity	NPC172262
0.963	High Similarity	NPC90582
0.963	High Similarity	NPC262094
0.963	High Similarity	NPC110969
0.963	High Similarity	NPC282300
0.963	High Similarity	NPC136840
0.9627	High Similarity	NPC301217
0.9627	High Similarity	NPC303633
0.9627	High Similarity	NPC53181
0.9627	High Similarity	NPC329203
0.9627	High Similarity	NPC216978
0.9627	High Similarity	NPC310135
0.9627	High Similarity	NPC222342
0.9627	High Similarity	NPC20709
0.9627	High Similarity	NPC96565
0.9627	High Similarity	NPC217186
0.9627	High Similarity	NPC55018
0.9627	High Similarity	NPC220062
0.9627	High Similarity	NPC225153
0.9627	High Similarity	NPC265871
0.9627	High Similarity	NPC274784
0.9627	High Similarity	NPC150648
0.9624	High Similarity	NPC290291
0.9624	High Similarity	NPC228661
0.9624	High Similarity	NPC188879
0.9624	High Similarity	NPC275055
0.9618	High Similarity	NPC57601
0.9615	High Similarity	NPC475589
0.9615	High Similarity	NPC31872
0.9615	High Similarity	NPC473584
0.9615	High Similarity	NPC113006
0.9615	High Similarity	NPC278556
0.9559	High Similarity	NPC226636
0.9559	High Similarity	NPC11561
0.9556	High Similarity	NPC6407
0.9556	High Similarity	NPC284550
0.9556	High Similarity	NPC129853
0.9556	High Similarity	NPC150522
0.9556	High Similarity	NPC76445
0.9556	High Similarity	NPC110228
0.9556	High Similarity	NPC270883
0.9556	High Similarity	NPC261227
0.9556	High Similarity	NPC188243
0.9556	High Similarity	NPC172986
0.9552	High Similarity	NPC124269
0.9552	High Similarity	NPC276905
0.9552	High Similarity	NPC118813
0.9549	High Similarity	NPC240593
0.9549	High Similarity	NPC187432
0.9549	High Similarity	NPC256042
0.9549	High Similarity	NPC281917
0.9549	High Similarity	NPC216361
0.9549	High Similarity	NPC116775
0.9542	High Similarity	NPC101294
0.9542	High Similarity	NPC129132
0.9542	High Similarity	NPC205468
0.9542	High Similarity	NPC87231
0.9542	High Similarity	NPC473655
0.9542	High Similarity	NPC25937
0.9542	High Similarity	NPC212631
0.9542	High Similarity	NPC10971
0.9542	High Similarity	NPC257756
0.9538	High Similarity	NPC137264
0.9538	High Similarity	NPC270369
0.9538	High Similarity	NPC5515
0.9489	High Similarity	NPC470216
0.9485	High Similarity	NPC3188
0.9485	High Similarity	NPC118840
0.9485	High Similarity	NPC4743
0.9485	High Similarity	NPC324386
0.9485	High Similarity	NPC147688
0.9485	High Similarity	NPC213322
0.9485	High Similarity	NPC205006
0.9485	High Similarity	NPC103362
0.9485	High Similarity	NPC312391
0.9485	High Similarity	NPC64908
0.9485	High Similarity	NPC156590
0.9481	High Similarity	NPC140890
0.9481	High Similarity	NPC261234
0.9478	High Similarity	NPC209560
0.9478	High Similarity	NPC294409
0.9478	High Similarity	NPC181124
0.9478	High Similarity	NPC162680
0.9478	High Similarity	NPC7013
0.9478	High Similarity	NPC243083
0.9478	High Similarity	NPC287246
0.9478	High Similarity	NPC12296
0.9478	High Similarity	NPC296490
0.9478	High Similarity	NPC13768
0.9478	High Similarity	NPC299379
0.9478	High Similarity	NPC303644
0.9478	High Similarity	NPC295261
0.9478	High Similarity	NPC79943
0.9478	High Similarity	NPC107586
0.9478	High Similarity	NPC116632
0.9478	High Similarity	NPC32441
0.9474	High Similarity	NPC239495
0.9474	High Similarity	NPC9985
0.947	High Similarity	NPC223457
0.947	High Similarity	NPC242294
0.947	High Similarity	NPC175098
0.947	High Similarity	NPC144051
0.947	High Similarity	NPC204960
0.947	High Similarity	NPC294593
0.947	High Similarity	NPC139813
0.947	High Similarity	NPC82225
0.947	High Similarity	NPC337373
0.947	High Similarity	NPC159623
0.947	High Similarity	NPC188646
0.947	High Similarity	NPC18877
0.947	High Similarity	NPC56031
0.947	High Similarity	NPC312318
0.947	High Similarity	NPC20560
0.947	High Similarity	NPC472365
0.947	High Similarity	NPC28753
0.947	High Similarity	NPC263670
0.947	High Similarity	NPC192304
0.9466	High Similarity	NPC262359
0.9466	High Similarity	NPC308037
0.9466	High Similarity	NPC64359
0.9466	High Similarity	NPC284424
0.9462	High Similarity	NPC115998
0.9462	High Similarity	NPC39753
0.942	High Similarity	NPC319752
0.942	High Similarity	NPC311741
0.942	High Similarity	NPC234629
0.942	High Similarity	NPC273538
0.942	High Similarity	NPC216538
0.9416	High Similarity	NPC167624
0.9416	High Similarity	NPC59739
0.9416	High Similarity	NPC76338
0.9416	High Similarity	NPC62840
0.9416	High Similarity	NPC220998
0.9416	High Similarity	NPC78803
0.9416	High Similarity	NPC228504
0.9416	High Similarity	NPC227579
0.9416	High Similarity	NPC161506
0.9416	High Similarity	NPC78
0.9416	High Similarity	NPC10937
0.9416	High Similarity	NPC223500
0.9416	High Similarity	NPC214236
0.9416	High Similarity	NPC328164
0.9416	High Similarity	NPC177354
0.9416	High Similarity	NPC64915
0.9416	High Similarity	NPC40833
0.9416	High Similarity	NPC1089
0.9416	High Similarity	NPC125855
0.9416	High Similarity	NPC182852
0.9416	High Similarity	NPC296917
0.9416	High Similarity	NPC200694
0.9416	High Similarity	NPC306829
0.9416	High Similarity	NPC66515
0.9416	High Similarity	NPC76372
0.9416	High Similarity	NPC148757
0.9416	High Similarity	NPC32739
0.9416	High Similarity	NPC166482
0.9416	High Similarity	NPC202981
0.9416	High Similarity	NPC473042
0.9416	High Similarity	NPC324134
0.9416	High Similarity	NPC107572
0.9416	High Similarity	NPC299080
0.9416	High Similarity	NPC265040
0.9416	High Similarity	NPC293852
0.9416	High Similarity	NPC37496
0.9416	High Similarity	NPC166934
0.9416	High Similarity	NPC194432
0.9416	High Similarity	NPC217083

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 NPC47815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	992
0.2-0.3	1535
0.3-0.4	2708
0.4-0.5	1837
0.5-0.6	1139
0.6-0.7	326
0.7-0.8	115
0.8-0.85	39
0.85-0.9	19
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9478	High Similarity	NPD1552	Clinical (unspecified phase)
0.9478	High Similarity	NPD1550	Clinical (unspecified phase)
0.942	High Similarity	NPD4378	Clinical (unspecified phase)
0.9407	High Similarity	NPD1549	Phase 2
0.9328	High Similarity	NPD1510	Phase 2
0.9318	High Similarity	NPD1240	Approved
0.9179	High Similarity	NPD1607	Approved
0.9143	High Similarity	NPD7410	Clinical (unspecified phase)
0.9118	High Similarity	NPD2796	Approved
0.9071	High Similarity	NPD1511	Approved
0.8944	High Similarity	NPD1512	Approved
0.8904	High Similarity	NPD2801	Approved
0.8836	High Similarity	NPD1934	Approved
0.8803	High Similarity	NPD6799	Approved
0.8776	High Similarity	NPD2393	Clinical (unspecified phase)
0.8767	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD3750	Approved
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8714	High Similarity	NPD970	Clinical (unspecified phase)
0.8699	High Similarity	NPD4380	Phase 2
0.8603	High Similarity	NPD6859	Clinical (unspecified phase)
0.86	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD1551	Phase 2
0.8533	High Similarity	NPD3882	Suspended
0.8523	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD3817	Phase 2
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.8392	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2800	Approved
0.837	Intermediate Similarity	NPD1203	Approved
0.8369	Intermediate Similarity	NPD3748	Approved
0.8367	Intermediate Similarity	NPD5403	Approved
0.8356	Intermediate Similarity	NPD5401	Approved
0.8355	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1548	Phase 1
0.8289	Intermediate Similarity	NPD7768	Phase 2
0.8269	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6166	Phase 2
0.8269	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1243	Approved
0.8252	Intermediate Similarity	NPD2344	Approved
0.8228	Intermediate Similarity	NPD7054	Approved
0.8228	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6651	Approved
0.8209	Intermediate Similarity	NPD422	Phase 1
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.8176	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD9717	Approved
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8121	Intermediate Similarity	NPD920	Approved
0.8095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7251	Discontinued
0.8074	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8071	Intermediate Similarity	NPD3268	Approved
0.8063	Intermediate Similarity	NPD7074	Phase 3
0.8058	Intermediate Similarity	NPD6832	Phase 2
0.8056	Intermediate Similarity	NPD2935	Discontinued
0.8029	Intermediate Similarity	NPD3225	Approved
0.8027	Intermediate Similarity	NPD2309	Approved
0.8025	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5402	Approved
0.7986	Intermediate Similarity	NPD7033	Discontinued
0.7986	Intermediate Similarity	NPD2799	Discontinued
0.7971	Intermediate Similarity	NPD2797	Approved
0.7958	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6099	Approved
0.7931	Intermediate Similarity	NPD6100	Approved
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2798	Approved
0.7911	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7898	Intermediate Similarity	NPD5494	Approved
0.7891	Intermediate Similarity	NPD2654	Approved
0.7888	Intermediate Similarity	NPD7286	Phase 2
0.7875	Intermediate Similarity	NPD7473	Discontinued
0.7867	Intermediate Similarity	NPD2532	Approved
0.7867	Intermediate Similarity	NPD2534	Approved
0.7867	Intermediate Similarity	NPD2533	Approved
0.7862	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4308	Phase 3
0.7842	Intermediate Similarity	NPD3267	Approved
0.7842	Intermediate Similarity	NPD3266	Approved
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD3226	Approved
0.7761	Intermediate Similarity	NPD9493	Approved
0.7744	Intermediate Similarity	NPD6559	Discontinued
0.7722	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7669	Intermediate Similarity	NPD1241	Discontinued
0.7655	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4288	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7626	Intermediate Similarity	NPD1608	Approved
0.7626	Intermediate Similarity	NPD3972	Approved
0.7625	Intermediate Similarity	NPD1247	Approved
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4307	Phase 2
0.758	Intermediate Similarity	NPD1465	Phase 2
0.7569	Intermediate Similarity	NPD411	Approved
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7558	Intermediate Similarity	NPD4363	Phase 3
0.7558	Intermediate Similarity	NPD4360	Phase 2
0.7552	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1019	Discontinued
0.7534	Intermediate Similarity	NPD5124	Phase 1
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7534	Intermediate Similarity	NPD447	Suspended
0.7534	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1481	Phase 2
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7448	Intermediate Similarity	NPD3764	Approved
0.7431	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1535	Discovery
0.7429	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD2296	Approved
0.741	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD1729	Discontinued
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1894	Discontinued
0.7383	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4625	Phase 3
0.7378	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4287	Approved
0.7324	Intermediate Similarity	NPD4749	Approved
0.7321	Intermediate Similarity	NPD6104	Discontinued
0.732	Intermediate Similarity	NPD2354	Approved
0.7303	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD6844	Discontinued
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD1876	Approved
0.7256	Intermediate Similarity	NPD5711	Approved
0.7256	Intermediate Similarity	NPD5710	Approved
0.7233	Intermediate Similarity	NPD5890	Approved
0.7233	Intermediate Similarity	NPD5889	Approved
0.723	Intermediate Similarity	NPD3142	Approved
0.723	Intermediate Similarity	NPD3140	Approved
0.7226	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD7213	Phase 3
0.7222	Intermediate Similarity	NPD1164	Approved
0.7222	Intermediate Similarity	NPD6971	Discontinued
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD7447	Phase 1
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2353	Approved
0.717	Intermediate Similarity	NPD6585	Discontinued
0.7169	Intermediate Similarity	NPD2403	Approved
0.7164	Intermediate Similarity	NPD9266	Approved
0.7164	Intermediate Similarity	NPD74	Approved
0.7161	Intermediate Similarity	NPD7440	Discontinued
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD3787	Discontinued
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7123	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5408	Approved
0.7105	Intermediate Similarity	NPD5405	Approved
0.7105	Intermediate Similarity	NPD5404	Approved
0.7105	Intermediate Similarity	NPD5406	Approved
0.7104	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD3887	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