NPASS Compound

Structure

CID9743 OpenBabel06191715332D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 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 -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 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 -2.5981 1.5000 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 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 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -2.5981 2.5000 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 -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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 6 1 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 6 1 6 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.06
Volume:	285.403
LogP:	0.449
LogD:	-0.142
LogS:	-2.662
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	3.546
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.055
MDCK Permeability:	4.002155492344173e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.678

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	85.44282531738281%
Volume Distribution (VD):	0.681
Pgp-substrate:	15.909717559814453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.11
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	9.517
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.544
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.423
Skin Sensitization:	0.932
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.911
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC9743

Natural Product ID:	NPC9743
*Common Name:**	(+)-Epitaxifolin
IUPAC Name:	(2S,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	CXQWRCVTCMQVQX-GJZGRUSLSA-N
Standard InCHI:	InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15-/m0/s1
SMILES:	Oc1cc2O[C@@H](c3ccc(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL9249
PubChem CID:	443758
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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
AC50	2
Others	9
Potency	13

Activity Type	# Activity
Individual Protein	14
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	=	1584.9	nM	PMID[545701]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	25118.9	nM	PMID[545701]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	12589.3	nM	PMID[545701]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	31.6	nM	PMID[545701]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	5011.9	nM	PMID[545701]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	10000.0	nM	PMID[545701]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	10000.0	nM	PMID[545701]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	15848.93	nM	PMID[545701]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.0	%	PMID[545699]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	2.1	%	PMID[545699]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	11.0	%	PMID[545699]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	21.7	%	PMID[545699]
NPT2	Others	Unspecified		Inhibition	=	3.5	%	PMID[545700]
NPT2	Others	Unspecified		Inhibition	=	6.8	%	PMID[545700]
NPT2	Others	Unspecified		Inhibition	=	6.9	%	PMID[545700]
NPT2	Others	Unspecified		Inhibition	=	13.7	%	PMID[545700]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[545700]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	12589.3	nM	PMID[545701]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	22.4	nM	PMID[545701]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	28183.8	nM	PMID[545701]
NPT2	Others	Unspecified		Potency	n.a.	6510.4	nM	PMID[545701]

☑ 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 NPC9743 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	458
0.1-0.2	1766
0.2-0.3	4623
0.3-0.4	10685
0.4-0.5	6885
0.5-0.6	3638
0.6-0.7	4802
0.7-0.8	5415
0.8-0.85	2627
0.85-0.9	1369
0.9-0.95	374
0.95-1	55

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246162
1.0	High Similarity	NPC260491
1.0	High Similarity	NPC36835
1.0	High Similarity	NPC61506
1.0	High Similarity	NPC240476
0.9932	High Similarity	NPC256346
0.9932	High Similarity	NPC246328
0.9932	High Similarity	NPC27532
0.9932	High Similarity	NPC325028
0.9863	High Similarity	NPC19721
0.9797	High Similarity	NPC326037
0.9797	High Similarity	NPC13858
0.9797	High Similarity	NPC320825
0.9797	High Similarity	NPC201837
0.9732	High Similarity	NPC52530
0.9724	High Similarity	NPC294852
0.9724	High Similarity	NPC188679
0.9724	High Similarity	NPC321011
0.9724	High Similarity	NPC218569
0.9667	High Similarity	NPC22192
0.9664	High Similarity	NPC471500
0.9664	High Similarity	NPC250922
0.9662	High Similarity	NPC141212
0.9658	High Similarity	NPC1612
0.9658	High Similarity	NPC183959
0.9655	High Similarity	NPC21835
0.9603	High Similarity	NPC263449
0.9603	High Similarity	NPC287328
0.9603	High Similarity	NPC282009
0.9603	High Similarity	NPC470183
0.96	High Similarity	NPC471515
0.96	High Similarity	NPC471479
0.9595	High Similarity	NPC236637
0.9595	High Similarity	NPC302950
0.9595	High Similarity	NPC219582
0.9539	High Similarity	NPC308992
0.9539	High Similarity	NPC471499
0.9539	High Similarity	NPC289771
0.9533	High Similarity	NPC474638
0.953	High Similarity	NPC18727
0.9527	High Similarity	NPC204515
0.9517	High Similarity	NPC142731
0.9517	High Similarity	NPC279417
0.9517	High Similarity	NPC326506
0.9517	High Similarity	NPC49130
0.9517	High Similarity	NPC4152
0.9517	High Similarity	NPC306607
0.9517	High Similarity	NPC62290
0.9517	High Similarity	NPC208176
0.9474	High Similarity	NPC471744
0.9474	High Similarity	NPC470326
0.947	High Similarity	NPC474055
0.947	High Similarity	NPC472598
0.947	High Similarity	NPC67876
0.9467	High Similarity	NPC321779
0.9456	High Similarity	NPC3036
0.9456	High Similarity	NPC119059
0.9452	High Similarity	NPC1940
0.9452	High Similarity	NPC20791
0.9452	High Similarity	NPC179271
0.9452	High Similarity	NPC148011
0.9416	High Similarity	NPC472625
0.9412	High Similarity	NPC112418
0.9412	High Similarity	NPC173137
0.9408	High Similarity	NPC53545
0.9408	High Similarity	NPC55738
0.9408	High Similarity	NPC117418
0.9404	High Similarity	NPC255106
0.9404	High Similarity	NPC291878
0.9404	High Similarity	NPC35038
0.9404	High Similarity	NPC195796
0.9404	High Similarity	NPC278778
0.9404	High Similarity	NPC235165
0.94	High Similarity	NPC192083
0.94	High Similarity	NPC213896
0.9396	High Similarity	NPC125062
0.9396	High Similarity	NPC252933
0.9396	High Similarity	NPC54394
0.9396	High Similarity	NPC200740
0.9392	High Similarity	NPC105512
0.9392	High Similarity	NPC270465
0.9392	High Similarity	NPC87125
0.9388	High Similarity	NPC176869
0.9388	High Similarity	NPC95864
0.9388	High Similarity	NPC3779
0.9388	High Similarity	NPC44721
0.9388	High Similarity	NPC40086
0.9388	High Similarity	NPC476182
0.9388	High Similarity	NPC211466
0.9388	High Similarity	NPC74881
0.9388	High Similarity	NPC51443
0.9388	High Similarity	NPC122828
0.9355	High Similarity	NPC7688
0.9355	High Similarity	NPC72787
0.9355	High Similarity	NPC58223
0.9355	High Similarity	NPC7154
0.9355	High Similarity	NPC36916
0.9355	High Similarity	NPC36
0.9355	High Similarity	NPC125039
0.9351	High Similarity	NPC471745
0.9351	High Similarity	NPC211107
0.9342	High Similarity	NPC99597
0.9342	High Similarity	NPC162869
0.9342	High Similarity	NPC27337
0.9342	High Similarity	NPC156057
0.9342	High Similarity	NPC210084
0.9342	High Similarity	NPC475267
0.9342	High Similarity	NPC474208
0.9342	High Similarity	NPC48208
0.9342	High Similarity	NPC291508
0.9342	High Similarity	NPC474836
0.9338	High Similarity	NPC477503
0.9338	High Similarity	NPC470327
0.9338	High Similarity	NPC45849
0.9338	High Similarity	NPC200761
0.9338	High Similarity	NPC67396
0.9333	High Similarity	NPC199100
0.9333	High Similarity	NPC279989
0.9333	High Similarity	NPC55205
0.9333	High Similarity	NPC180234
0.9333	High Similarity	NPC472912
0.9333	High Similarity	NPC260979
0.9333	High Similarity	NPC106976
0.9333	High Similarity	NPC120537
0.9333	High Similarity	NPC82325
0.9329	High Similarity	NPC188871
0.9329	High Similarity	NPC61620
0.9329	High Similarity	NPC62042
0.9329	High Similarity	NPC338131
0.9329	High Similarity	NPC149127
0.9329	High Similarity	NPC29231
0.9329	High Similarity	NPC286342
0.9324	High Similarity	NPC272721
0.9324	High Similarity	NPC43669
0.9324	High Similarity	NPC196277
0.9324	High Similarity	NPC276930
0.932	High Similarity	NPC169749
0.9315	High Similarity	NPC279121
0.9295	High Similarity	NPC471213
0.9286	High Similarity	NPC474038
0.9286	High Similarity	NPC472632
0.9286	High Similarity	NPC472634
0.9286	High Similarity	NPC26326
0.9286	High Similarity	NPC142252
0.9286	High Similarity	NPC158188
0.9281	High Similarity	NPC152904
0.9276	High Similarity	NPC470328
0.9276	High Similarity	NPC209614
0.9276	High Similarity	NPC24640
0.9276	High Similarity	NPC472626
0.9272	High Similarity	NPC179126
0.9272	High Similarity	NPC469550
0.9272	High Similarity	NPC270620
0.9272	High Similarity	NPC88645
0.9272	High Similarity	NPC298692
0.9272	High Similarity	NPC78326
0.9272	High Similarity	NPC167091
0.9272	High Similarity	NPC236223
0.9272	High Similarity	NPC292214
0.9272	High Similarity	NPC74924
0.9272	High Similarity	NPC206238
0.9272	High Similarity	NPC271779
0.9267	High Similarity	NPC262039
0.9267	High Similarity	NPC262038
0.9267	High Similarity	NPC251110
0.9267	High Similarity	NPC254412
0.9267	High Similarity	NPC28274
0.9267	High Similarity	NPC50403
0.9267	High Similarity	NPC260895
0.9267	High Similarity	NPC278476
0.9267	High Similarity	NPC31363
0.9267	High Similarity	NPC225731
0.9267	High Similarity	NPC133953
0.9267	High Similarity	NPC319910
0.9262	High Similarity	NPC223579
0.9262	High Similarity	NPC287101
0.9262	High Similarity	NPC183950
0.9262	High Similarity	NPC137062
0.9262	High Similarity	NPC159103
0.9262	High Similarity	NPC52005
0.9262	High Similarity	NPC195351
0.9257	High Similarity	NPC108406
0.9257	High Similarity	NPC77378
0.9252	High Similarity	NPC70136
0.9247	High Similarity	NPC175013
0.9241	High Similarity	NPC182421
0.9236	High Similarity	NPC42892
0.9236	High Similarity	NPC160156
0.9236	High Similarity	NPC92565
0.9236	High Similarity	NPC260266
0.9231	High Similarity	NPC277205
0.9231	High Similarity	NPC224280
0.9231	High Similarity	NPC62261
0.9231	High Similarity	NPC475888
0.9226	High Similarity	NPC127782
0.9226	High Similarity	NPC472635
0.9226	High Similarity	NPC300537
0.9226	High Similarity	NPC472964
0.9226	High Similarity	NPC474033
0.9226	High Similarity	NPC476247

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 NPC9743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	924
0.2-0.3	1904
0.3-0.4	2567
0.4-0.5	1724
0.5-0.6	955
0.6-0.7	464
0.7-0.8	121
0.8-0.85	33
0.85-0.9	12
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9595	High Similarity	NPD1934	Approved
0.9452	High Similarity	NPD1512	Approved
0.94	High Similarity	NPD2393	Clinical (unspecified phase)
0.9355	High Similarity	NPD6167	Clinical (unspecified phase)
0.9355	High Similarity	NPD6166	Phase 2
0.9355	High Similarity	NPD6168	Clinical (unspecified phase)
0.9315	High Similarity	NPD1511	Approved
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.9026	High Similarity	NPD3882	Suspended
0.902	High Similarity	NPD2801	Approved
0.8973	High Similarity	NPD1549	Phase 2
0.8944	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD7251	Discontinued
0.8882	High Similarity	NPD7074	Phase 3
0.8875	High Similarity	NPD3818	Discontinued
0.8839	High Similarity	NPD3817	Phase 2
0.8834	High Similarity	NPD4338	Clinical (unspecified phase)
0.8824	High Similarity	NPD4380	Phase 2
0.882	High Similarity	NPD7054	Approved
0.8782	High Similarity	NPD4868	Clinical (unspecified phase)
0.8765	High Similarity	NPD7472	Approved
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8726	High Similarity	NPD4381	Clinical (unspecified phase)
0.8726	High Similarity	NPD7075	Discontinued
0.872	High Similarity	NPD7808	Phase 3
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.8639	High Similarity	NPD1510	Phase 2
0.8621	High Similarity	NPD1612	Clinical (unspecified phase)
0.8621	High Similarity	NPD1613	Approved
0.8598	High Similarity	NPD7993	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6801	Discontinued
0.8431	Intermediate Similarity	NPD6799	Approved
0.8385	Intermediate Similarity	NPD5494	Approved
0.8367	Intermediate Similarity	NPD943	Approved
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD5402	Approved
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2796	Approved
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8276	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD5403	Approved
0.8258	Intermediate Similarity	NPD5401	Approved
0.8255	Intermediate Similarity	NPD1607	Approved
0.825	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD1247	Approved
0.811	Intermediate Similarity	NPD6959	Discontinued
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8098	Intermediate Similarity	NPD919	Approved
0.8063	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8026	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3751	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.7885	Intermediate Similarity	NPD3750	Approved
0.7844	Intermediate Similarity	NPD3787	Discontinued
0.7834	Intermediate Similarity	NPD6190	Approved
0.7818	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7764	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD447	Suspended
0.7707	Intermediate Similarity	NPD2800	Approved
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7598	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD920	Approved
0.7593	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD9494	Approved
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2344	Approved
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6798	Discontinued
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7394	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD37	Approved
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7356	Intermediate Similarity	NPD7228	Approved
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.733	Intermediate Similarity	NPD5953	Discontinued
0.7325	Intermediate Similarity	NPD6651	Approved
0.7322	Intermediate Similarity	NPD4360	Phase 2
0.7322	Intermediate Similarity	NPD4363	Phase 3
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7312	Intermediate Similarity	NPD6780	Approved
0.7312	Intermediate Similarity	NPD6777	Approved
0.7312	Intermediate Similarity	NPD6776	Approved
0.7312	Intermediate Similarity	NPD6779	Approved
0.7312	Intermediate Similarity	NPD6778	Approved
0.7312	Intermediate Similarity	NPD6781	Approved
0.7312	Intermediate Similarity	NPD6782	Approved
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD1652	Phase 2
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD6233	Phase 2
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD9717	Approved
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7196	Intermediate Similarity	NPD7435	Discontinued
0.7195	Intermediate Similarity	NPD7390	Discontinued
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7584	Approved
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.716	Intermediate Similarity	NPD6844	Discontinued
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD8455	Phase 2
0.7105	Intermediate Similarity	NPD7697	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7698	Approved
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7089	Intermediate Similarity	NPD4060	Phase 1
0.7086	Intermediate Similarity	NPD5242	Approved
0.7078	Intermediate Similarity	NPD1470	Approved
0.7076	Intermediate Similarity	NPD5353	Approved
0.7073	Intermediate Similarity	NPD2354	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7067	Intermediate Similarity	NPD9268	Approved
0.7062	Intermediate Similarity	NPD2163	Approved
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4661	Approved
0.7048	Intermediate Similarity	NPD4662	Approved
0.7047	Intermediate Similarity	NPD7701	Phase 2
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7043	Intermediate Similarity	NPD6534	Approved
0.7043	Intermediate Similarity	NPD6535	Approved
0.7039	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD1471	Phase 3
0.7032	Intermediate Similarity	NPD2798	Approved
0.702	Intermediate Similarity	NPD17	Approved
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7013	Intermediate Similarity	NPD3225	Approved
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7005	Intermediate Similarity	NPD4361	Phase 2
0.7005	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9545	Approved
0.6977	Remote Similarity	NPD4288	Approved
0.6974	Remote Similarity	NPD7874	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