NPASS Compound

Structure

CID250769 OpenBabel06191716052D 21 24 0 0 1 0 0 0 0 0999 V2000 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3549 3.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7617 3.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6962 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7562 3.8442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 0.8660 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 8 1 6 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	279.199
LogP:	3.547
LogD:	3.109
LogS:	-4.541
# Rotatable Bonds:	3
TPSA:	65.11
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	3.265
Fsp3:	0.312
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:	-4.765
MDCK Permeability:	2.3230208171298727e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.777
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	89.54808807373047%
Volume Distribution (VD):	0.79
Pgp-substrate:	9.87384033203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.616
CYP2C19-substrate:	0.181
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.452
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.763
CYP3A4-inhibitor:	0.324
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	10.182
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.299
Carcinogencity:	0.616
Eye Corrosion:	0.003
Eye Irritation:	0.531
Respiratory Toxicity:	0.573

Download Data

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

Natural Product: NPC250769

Natural Product ID:	NPC250769
*Common Name:**	4-[[(2R)-3,3-Dimethyloxiran-2-Yl]Methoxy]Furo[3,2-G]Chromen-7-One
IUPAC Name:	4-[[(2R)-3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	QTAGQHZOLRFCBU-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3/t13-/m1/s1
SMILES:	CC1(C)[C@@H](COc2c3ccc(=O)oc3cc3c2cco3)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1609439
PubChem CID:	928465
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO11147	Spongia hispida	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479380]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO22063	Solanum lycocarpum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17249729]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO30686	Citrus hystrix	Species	Rutaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[20964319]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15022	Baccharis flabellata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18926	Tephrosia lupinifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14231	Senecio barba-johannis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11147	Spongia hispida	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15022	Baccharis flabellata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19012	Gasteria bicolor	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15484	Adlumia fungosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16778	Leptospermum liversidgei	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22063	Solanum lycocarpum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2
Potency	8

Activity Type	# Activity
Cell Line	2
Individual Protein	5
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	6309.6	nM	PMID[450030]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[450030]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[450030]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[450030]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	103.9	%	PMID[450031]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	59.3	%	PMID[450031]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[450030]
NPT2	Others	Unspecified		Potency	=	183.6	nM	PMID[450030]
NPT2	Others	Unspecified		Potency	n.a.	12995.3	nM	PMID[450030]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[450030]

☑ 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 NPC250769 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	454
0.1-0.2	2035
0.2-0.3	5201
0.3-0.4	11198
0.4-0.5	7290
0.5-0.6	5242
0.6-0.7	5355
0.7-0.8	5212
0.8-0.85	492
0.85-0.9	173
0.9-0.95	41
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295608
1.0	High Similarity	NPC278010
0.9797	High Similarity	NPC131725
0.9527	High Similarity	NPC88445
0.9524	High Similarity	NPC304443
0.9524	High Similarity	NPC74539
0.9477	High Similarity	NPC95472
0.9477	High Similarity	NPC239270
0.9477	High Similarity	NPC303210
0.9463	High Similarity	NPC191104
0.9416	High Similarity	NPC14822
0.9351	High Similarity	NPC49009
0.9351	High Similarity	NPC169
0.9257	High Similarity	NPC246903
0.9245	High Similarity	NPC144288
0.9236	High Similarity	NPC173149
0.9236	High Similarity	NPC179015
0.9221	High Similarity	NPC269495
0.92	High Similarity	NPC266743
0.9128	High Similarity	NPC208584
0.9122	High Similarity	NPC166858
0.9122	High Similarity	NPC51146
0.9122	High Similarity	NPC313036
0.9097	High Similarity	NPC270044
0.9079	High Similarity	NPC155882
0.9067	High Similarity	NPC190572
0.8987	High Similarity	NPC78612
0.8987	High Similarity	NPC234536
0.8981	High Similarity	NPC243509
0.8954	High Similarity	NPC148423
0.8954	High Similarity	NPC135303
0.8938	High Similarity	NPC210460
0.8938	High Similarity	NPC193881
0.8938	High Similarity	NPC155264
0.8938	High Similarity	NPC67450
0.8931	High Similarity	NPC179464
0.8926	High Similarity	NPC254010
0.8924	High Similarity	NPC216092
0.8919	High Similarity	NPC262635
0.8917	High Similarity	NPC33320
0.891	High Similarity	NPC470625
0.8896	High Similarity	NPC98028
0.8882	High Similarity	NPC198427
0.8874	High Similarity	NPC171656
0.8859	High Similarity	NPC470856
0.8841	High Similarity	NPC224165
0.8841	High Similarity	NPC53917
0.8839	High Similarity	NPC130015
0.8839	High Similarity	NPC38361
0.8824	High Similarity	NPC306788
0.8808	High Similarity	NPC76657
0.8792	High Similarity	NPC472515
0.8788	High Similarity	NPC325176
0.8782	High Similarity	NPC41719
0.8774	High Similarity	NPC472407
0.8773	High Similarity	NPC51404
0.8766	High Similarity	NPC164299
0.875	High Similarity	NPC294365
0.875	High Similarity	NPC470857
0.8726	High Similarity	NPC279218
0.8726	High Similarity	NPC108937
0.8726	High Similarity	NPC233776
0.8718	High Similarity	NPC263676
0.871	High Similarity	NPC472406
0.8704	High Similarity	NPC323137
0.8684	High Similarity	NPC17262
0.8675	High Similarity	NPC107244
0.8671	High Similarity	NPC109967
0.8671	High Similarity	NPC78554
0.8671	High Similarity	NPC469936
0.8671	High Similarity	NPC474738
0.8671	High Similarity	NPC129053
0.8671	High Similarity	NPC321372
0.8671	High Similarity	NPC474609
0.8671	High Similarity	NPC475797
0.8667	High Similarity	NPC136095
0.8667	High Similarity	NPC233956
0.8667	High Similarity	NPC72455
0.8659	High Similarity	NPC120220
0.8659	High Similarity	NPC281835
0.8658	High Similarity	NPC253616
0.8642	High Similarity	NPC329215
0.8642	High Similarity	NPC204088
0.8642	High Similarity	NPC259007
0.8625	High Similarity	NPC74749
0.8625	High Similarity	NPC43971
0.8625	High Similarity	NPC19554
0.8616	High Similarity	NPC260902
0.8616	High Similarity	NPC296957
0.8606	High Similarity	NPC472584
0.86	High Similarity	NPC36414
0.8599	High Similarity	NPC31627
0.8599	High Similarity	NPC476238
0.8599	High Similarity	NPC327269
0.8591	High Similarity	NPC268081
0.8591	High Similarity	NPC472516
0.859	High Similarity	NPC180351
0.859	High Similarity	NPC472421
0.858	High Similarity	NPC65846
0.8571	High Similarity	NPC264293
0.8562	High Similarity	NPC476350
0.8562	High Similarity	NPC476349
0.8553	High Similarity	NPC247677
0.8553	High Similarity	NPC160015
0.8553	High Similarity	NPC19860
0.8544	High Similarity	NPC122365
0.8535	High Similarity	NPC474744
0.8535	High Similarity	NPC474772
0.8535	High Similarity	NPC116604
0.8535	High Similarity	NPC471675
0.8535	High Similarity	NPC472423
0.8535	High Similarity	NPC290671
0.8533	High Similarity	NPC103001
0.8526	High Similarity	NPC317492
0.8526	High Similarity	NPC37226
0.8526	High Similarity	NPC226644
0.8519	High Similarity	NPC219861
0.8509	High Similarity	NPC304839
0.8509	High Similarity	NPC260296
0.8509	High Similarity	NPC220582
0.8509	High Similarity	NPC115432
0.8506	High Similarity	NPC316535
0.85	High Similarity	NPC65504
0.8491	Intermediate Similarity	NPC474542
0.8485	Intermediate Similarity	NPC41853
0.8481	Intermediate Similarity	NPC67654
0.8481	Intermediate Similarity	NPC288534
0.8481	Intermediate Similarity	NPC256141
0.8481	Intermediate Similarity	NPC285623
0.8481	Intermediate Similarity	NPC473996
0.8471	Intermediate Similarity	NPC321387
0.8471	Intermediate Similarity	NPC327059
0.8471	Intermediate Similarity	NPC470908
0.8467	Intermediate Similarity	NPC29638
0.8466	Intermediate Similarity	NPC155640
0.8466	Intermediate Similarity	NPC15819
0.8466	Intermediate Similarity	NPC472581
0.8462	Intermediate Similarity	NPC168085
0.8457	Intermediate Similarity	NPC30655
0.8457	Intermediate Similarity	NPC74854
0.8457	Intermediate Similarity	NPC92589
0.8457	Intermediate Similarity	NPC45124
0.8447	Intermediate Similarity	NPC50430
0.8447	Intermediate Similarity	NPC244750
0.8442	Intermediate Similarity	NPC184702
0.8435	Intermediate Similarity	NPC472517
0.8431	Intermediate Similarity	NPC297985
0.8428	Intermediate Similarity	NPC186507
0.8428	Intermediate Similarity	NPC472462
0.8428	Intermediate Similarity	NPC213608
0.8428	Intermediate Similarity	NPC1477
0.8424	Intermediate Similarity	NPC167479
0.8424	Intermediate Similarity	NPC320789
0.8421	Intermediate Similarity	NPC473209
0.8421	Intermediate Similarity	NPC11566
0.8418	Intermediate Similarity	NPC472580
0.8418	Intermediate Similarity	NPC156244
0.8418	Intermediate Similarity	NPC470380
0.8418	Intermediate Similarity	NPC170169
0.8418	Intermediate Similarity	NPC472636
0.8415	Intermediate Similarity	NPC136641
0.8411	Intermediate Similarity	NPC38153
0.8408	Intermediate Similarity	NPC37208
0.8408	Intermediate Similarity	NPC296030
0.8408	Intermediate Similarity	NPC221868
0.8408	Intermediate Similarity	NPC39929
0.8405	Intermediate Similarity	NPC193998
0.8397	Intermediate Similarity	NPC129650
0.8397	Intermediate Similarity	NPC282335
0.8397	Intermediate Similarity	NPC12148
0.8397	Intermediate Similarity	NPC202494
0.8397	Intermediate Similarity	NPC14875
0.8397	Intermediate Similarity	NPC218300
0.8397	Intermediate Similarity	NPC471285
0.8397	Intermediate Similarity	NPC130581
0.8389	Intermediate Similarity	NPC247743
0.8389	Intermediate Similarity	NPC307412
0.8389	Intermediate Similarity	NPC55149
0.8387	Intermediate Similarity	NPC297788
0.8387	Intermediate Similarity	NPC179970
0.8385	Intermediate Similarity	NPC19097
0.8383	Intermediate Similarity	NPC475964
0.8378	Intermediate Similarity	NPC470859
0.8378	Intermediate Similarity	NPC175159
0.8375	Intermediate Similarity	NPC198490
0.8375	Intermediate Similarity	NPC477530
0.8375	Intermediate Similarity	NPC469934
0.8366	Intermediate Similarity	NPC472409
0.8365	Intermediate Similarity	NPC477957
0.8365	Intermediate Similarity	NPC40033
0.8365	Intermediate Similarity	NPC253872
0.8365	Intermediate Similarity	NPC5871
0.8364	Intermediate Similarity	NPC53640
0.8364	Intermediate Similarity	NPC472895
0.8354	Intermediate Similarity	NPC474735
0.8354	Intermediate Similarity	NPC91288
0.8354	Intermediate Similarity	NPC230713
0.8354	Intermediate Similarity	NPC78335
0.8344	Intermediate Similarity	NPC34376
0.8344	Intermediate Similarity	NPC272194

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 NPC250769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1026
0.2-0.3	2025
0.3-0.4	2774
0.4-0.5	1806
0.5-0.6	799
0.6-0.7	220
0.7-0.8	99
0.8-0.85	6
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9524	High Similarity	NPD920	Approved
0.9257	High Similarity	NPD642	Clinical (unspecified phase)
0.9122	High Similarity	NPD643	Clinical (unspecified phase)
0.8919	High Similarity	NPD1243	Approved
0.8917	High Similarity	NPD919	Approved
0.8571	High Similarity	NPD1247	Approved
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD5494	Approved
0.816	Intermediate Similarity	NPD3749	Approved
0.816	Intermediate Similarity	NPD7075	Discontinued
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.8038	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD1549	Phase 2
0.7866	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2800	Approved
0.7831	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5401	Approved
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3926	Phase 2
0.7806	Intermediate Similarity	NPD1510	Phase 2
0.7806	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7716	Intermediate Similarity	NPD5403	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7674	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7662	Intermediate Similarity	NPD1240	Approved
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2801	Approved
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7632	Intermediate Similarity	NPD6832	Phase 2
0.763	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5844	Phase 1
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2344	Approved
0.758	Intermediate Similarity	NPD2799	Discontinued
0.7564	Intermediate Similarity	NPD1607	Approved
0.7562	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6232	Discontinued
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1511	Approved
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7471	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7443	Intermediate Similarity	NPD5953	Discontinued
0.7442	Intermediate Similarity	NPD6808	Phase 2
0.7439	Intermediate Similarity	NPD1512	Approved
0.7421	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD3226	Approved
0.7407	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD1019	Discontinued
0.736	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2403	Approved
0.7356	Intermediate Similarity	NPD6166	Phase 2
0.7356	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1465	Phase 2
0.733	Intermediate Similarity	NPD7054	Approved
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.7308	Intermediate Similarity	NPD1296	Phase 2
0.7288	Intermediate Similarity	NPD7074	Phase 3
0.7288	Intermediate Similarity	NPD7472	Approved
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD447	Suspended
0.7278	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7247	Intermediate Similarity	NPD6797	Phase 2
0.7237	Intermediate Similarity	NPD9717	Approved
0.7213	Intermediate Similarity	NPD4287	Approved
0.7208	Intermediate Similarity	NPD1203	Approved
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7207	Intermediate Similarity	NPD7251	Discontinued
0.7195	Intermediate Similarity	NPD3887	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7176	Intermediate Similarity	NPD6279	Approved
0.7176	Intermediate Similarity	NPD6280	Approved
0.7175	Intermediate Similarity	NPD3751	Discontinued
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7808	Phase 3
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.7125	Intermediate Similarity	NPD6651	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8285	Discontinued
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD2353	Approved
0.7055	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7043	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5760	Phase 2
0.7035	Intermediate Similarity	NPD5761	Phase 2
0.7018	Intermediate Similarity	NPD5889	Approved
0.7018	Intermediate Similarity	NPD5890	Approved
0.7012	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD1729	Discontinued
0.6994	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD3268	Approved
0.697	Remote Similarity	NPD1652	Phase 2
0.6962	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6585	Discontinued
0.6957	Remote Similarity	NPD6355	Discontinued
0.6943	Remote Similarity	NPD2798	Approved
0.6935	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD17	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1241	Discontinued
0.6901	Remote Similarity	NPD7458	Discontinued
0.6897	Remote Similarity	NPD4288	Approved
0.6897	Remote Similarity	NPD2296	Approved
0.6894	Remote Similarity	NPD943	Approved
0.6893	Remote Similarity	NPD7199	Phase 2
0.6886	Remote Similarity	NPD2354	Approved
0.6879	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD411	Approved
0.6875	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD6798	Discontinued
0.6864	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4967	Phase 2
0.6857	Remote Similarity	NPD4966	Approved
0.6857	Remote Similarity	NPD4965	Approved
0.6848	Remote Similarity	NPD6002	Phase 3
0.6848	Remote Similarity	NPD8312	Approved
0.6848	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD6005	Phase 3
0.6848	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6004	Phase 3
0.6848	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8455	Phase 2
0.6837	Remote Similarity	NPD7584	Approved
0.6831	Remote Similarity	NPD6764	Approved
0.6831	Remote Similarity	NPD6765	Approved
0.6829	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5049	Phase 3
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD6385	Approved
0.6816	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3225	Approved
0.6805	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9545	Approved
0.6795	Remote Similarity	NPD3972	Approved
0.6795	Remote Similarity	NPD1608	Approved
0.6789	Remote Similarity	NPD4363	Phase 3
0.6789	Remote Similarity	NPD4360	Phase 2
0.6788	Remote Similarity	NPD2438	Suspended
0.678	Remote Similarity	NPD6234	Discontinued
0.6774	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4361	Phase 2
0.6751	Remote Similarity	NPD7583	Approved
0.6739	Remote Similarity	NPD7685	Pre-registration
0.6728	Remote Similarity	NPD6233	Phase 2
0.6725	Remote Similarity	NPD6273	Approved
0.6717	Remote Similarity	NPD7585	Approved
0.6709	Remote Similarity	NPD1876	Approved
0.67	Remote Similarity	NPD7783	Phase 2
0.67	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2979	Phase 3
0.6685	Remote Similarity	NPD4575	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