NPASS Compound

Structure

CID321011 OpenBabel06191716152D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 3 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	2.118
LogD:	2.307
LogS:	-3.827
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	2.994
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.189
MDCK Permeability:	6.052525804989273e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	93.32046508789062%
Volume Distribution (VD):	0.561
Pgp-substrate:	6.160038948059082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.325
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.513
CYP2D6-substrate:	0.429
CYP3A4-inhibitor:	0.693
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	19.889
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.577
Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.951
Carcinogencity:	0.395
Eye Corrosion:	0.005
Eye Irritation:	0.941
Respiratory Toxicity:	0.248

Download Data

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

Natural Product: NPC321011

Natural Product ID:	NPC321011
*Common Name:**	2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-2,3-Dihydrochromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:	5,7,3',5'-Tetrahydroxyflavanone
Standard InCHIKey:	SBHXYTNGIZCORC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2
SMILES:	C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL307893
PubChem CID:	11095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	leaves	n.a.	n.a.	PMID[20634065]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	flower buds	n.a.	n.a.	PMID[25987378]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[27792321]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30692	Prunus amygdalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1439	Mentha longifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1439	Mentha longifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30692	Prunus amygdalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31378	Scutellaria balcalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1439	Mentha longifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1439	Mentha longifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15768	Lyonia ovalifolia	Species	Ericaceae	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
EC50	4
IC50	8
Others	27
Potency	40

Activity Type	# Activity
Individual Protein	45
Organism	4
Others	30

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	35481.3	nM	PMID[480940]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[480941]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[480941]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[480940]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	=	15848.9	nM	PMID[480940]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PMID[480941]
NPT52	Individual Protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Potency	=	11220.2	nM	PMID[480940]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	39810.7	nM	PMID[480940]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	7.9	nM	PMID[480941]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	12589.3	nM	PMID[480941]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PMID[480941]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PMID[480941]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	12589.3	nM	PMID[480940]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[480941]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	35481.3	nM	PMID[480940]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[480940]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[480941]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[480941]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[480940]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[480940]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4610.9	nM	PMID[480940]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[480941]
NPT1634	Individual Protein	Myeloperoxidase	Homo sapiens	Inhibition	=	40.0	%	PMID[480943]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	53.4	%	PMID[480944]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[480940]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[480941]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	9.3	%	PMID[480945]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.1	%	PMID[480945]
NPT1720	Individual Protein	Plasminogen	Homo sapiens	Inhibition	=	20.7	%	PMID[480945]
NPT1443	Individual Protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	Inhibition	=	20.64	%	PMID[480946]
NPT2	Others	Unspecified		IC50	=	4230.0	nM	PMID[480940]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	31622.8	nM	PMID[480941]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	10000.0	nM	PMID[480941]
NPT798	Individual Protein	Alkaline phosphatase placental-like	Homo sapiens	EC50	=	60300.0	nM	PMID[480940]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[480940]
NPT801	Individual Protein	Intestinal alkaline phosphatase	Homo sapiens	EC50	=	50400.0	nM	PMID[480940]
NPT802	Individual Protein	Alkaline phosphatase, tissue-nonspecific isozyme	Homo sapiens	EC50	=	81800.0	nM	PMID[480940]
NPT799	Individual Protein	Intestinal alkaline phosphatase	Mus musculus	EC50	n.a.	54100.0	nM	PMID[480940]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[480940]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[480940]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[480940]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[480940]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[480940]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[480940]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[480941]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[480940]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[480940]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[480943]
NPT2	Others	Unspecified		IC50	=	1400.0	nM	PMID[480943]
NPT2	Others	Unspecified		IC50	=	4000.0	nM	PMID[480943]
NPT2	Others	Unspecified		IC50	=	15500.0	nM	PMID[480943]
NPT2	Others	Unspecified		IC50	=	18000.0	nM	PMID[480943]
NPT27	Others	Unspecified		Activity	>	98.0	%	PMID[480943]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	75686.3	nM	PMID[480940]
NPT27	Others	Unspecified		Activity	=	100.9	%	PMID[480945]
NPT27	Others	Unspecified		Activity	=	108.3	%	PMID[480945]
NPT2	Others	Unspecified		IC50	=	48000.0	nM	PMID[480945]
NPT2	Others	Unspecified		Inhibition	=	61.1	%	PMID[480945]
NPT2	Others	Unspecified		Inhibition	=	42.5	%	PMID[480945]
NPT2	Others	Unspecified		Inhibition	=	37.2	%	PMID[480945]
NPT2	Others	Unspecified		Inhibition	=	10.3	%	PMID[480945]
NPT2	Others	Unspecified		Inhibition	=	5.8	%	PMID[480945]
NPT27	Others	Unspecified		Activity	=	88.2	%	PMID[480945]
NPT27	Others	Unspecified		Activity	=	72.6	%	PMID[480945]
NPT27	Others	Unspecified		Activity	=	55.9	%	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.97	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.66	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.38	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.94	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.36	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.29	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.67	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.55	n.a.	PMID[480945]
NPT610	Others	Molecular identity unknown		Ratio	=	0.43	n.a.	PMID[480945]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[480947]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[480947]

☑ 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 NPC321011 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	442
0.1-0.2	1787
0.2-0.3	4611
0.3-0.4	11029
0.4-0.5	6494
0.5-0.6	3520
0.6-0.7	4780
0.7-0.8	5493
0.8-0.85	2534
0.85-0.9	1586
0.9-0.95	355
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188679
1.0	High Similarity	NPC294852
0.993	High Similarity	NPC183959
0.993	High Similarity	NPC1612
0.9792	High Similarity	NPC204515
0.9724	High Similarity	NPC219582
0.9724	High Similarity	NPC61506
0.9724	High Similarity	NPC302950
0.9724	High Similarity	NPC246162
0.9724	High Similarity	NPC36835
0.9724	High Similarity	NPC260491
0.9724	High Similarity	NPC236637
0.9724	High Similarity	NPC9743
0.9724	High Similarity	NPC240476
0.972	High Similarity	NPC3036
0.9658	High Similarity	NPC325028
0.9658	High Similarity	NPC192083
0.9658	High Similarity	NPC213896
0.9658	High Similarity	NPC18727
0.9658	High Similarity	NPC256346
0.9658	High Similarity	NPC27532
0.9658	High Similarity	NPC246328
0.9653	High Similarity	NPC105512
0.965	High Similarity	NPC95864
0.9592	High Similarity	NPC321779
0.9592	High Similarity	NPC67396
0.9589	High Similarity	NPC106976
0.9589	High Similarity	NPC19721
0.9586	High Similarity	NPC62042
0.9583	High Similarity	NPC119059
0.9583	High Similarity	NPC276930
0.9577	High Similarity	NPC279121
0.9527	High Similarity	NPC291878
0.9527	High Similarity	NPC201837
0.9527	High Similarity	NPC320825
0.9527	High Similarity	NPC35038
0.9527	High Similarity	NPC195796
0.9527	High Similarity	NPC24640
0.9527	High Similarity	NPC471500
0.9527	High Similarity	NPC255106
0.9527	High Similarity	NPC326037
0.9527	High Similarity	NPC235165
0.9527	High Similarity	NPC278778
0.9527	High Similarity	NPC13858
0.9524	High Similarity	NPC141212
0.9524	High Similarity	NPC298692
0.9524	High Similarity	NPC74924
0.9514	High Similarity	NPC108406
0.951	High Similarity	NPC70136
0.9507	High Similarity	NPC175013
0.9504	High Similarity	NPC182421
0.9463	High Similarity	NPC52530
0.9463	High Similarity	NPC162869
0.9463	High Similarity	NPC99597
0.9463	High Similarity	NPC472598
0.9463	High Similarity	NPC27337
0.9463	High Similarity	NPC471479
0.9463	High Similarity	NPC474055
0.9463	High Similarity	NPC474836
0.9463	High Similarity	NPC156057
0.9463	High Similarity	NPC475267
0.9463	High Similarity	NPC210084
0.9463	High Similarity	NPC471515
0.9463	High Similarity	NPC48208
0.9463	High Similarity	NPC471209
0.9463	High Similarity	NPC291508
0.9463	High Similarity	NPC474208
0.9459	High Similarity	NPC477503
0.9459	High Similarity	NPC45849
0.9459	High Similarity	NPC200761
0.9459	High Similarity	NPC470327
0.9456	High Similarity	NPC180234
0.9456	High Similarity	NPC260979
0.9456	High Similarity	NPC120537
0.9456	High Similarity	NPC199100
0.9456	High Similarity	NPC472912
0.9452	High Similarity	NPC29231
0.9452	High Similarity	NPC61620
0.9452	High Similarity	NPC338131
0.9448	High Similarity	NPC43669
0.9448	High Similarity	NPC272721
0.9448	High Similarity	NPC194856
0.9448	High Similarity	NPC196277
0.9448	High Similarity	NPC218569
0.9444	High Similarity	NPC20791
0.9444	High Similarity	NPC179271
0.9441	High Similarity	NPC242893
0.9441	High Similarity	NPC38065
0.94	High Similarity	NPC210459
0.94	High Similarity	NPC117418
0.94	High Similarity	NPC53545
0.94	High Similarity	NPC22192
0.9396	High Similarity	NPC474638
0.9396	High Similarity	NPC209614
0.9396	High Similarity	NPC470328
0.9396	High Similarity	NPC472626
0.9396	High Similarity	NPC250922
0.9392	High Similarity	NPC469550
0.9392	High Similarity	NPC167091
0.9392	High Similarity	NPC88645
0.9392	High Similarity	NPC292214
0.9392	High Similarity	NPC206238
0.9392	High Similarity	NPC271779
0.9388	High Similarity	NPC251110
0.9388	High Similarity	NPC31363
0.9384	High Similarity	NPC87125
0.9384	High Similarity	NPC287101
0.9384	High Similarity	NPC52005
0.9384	High Similarity	NPC183950
0.9384	High Similarity	NPC223579
0.9384	High Similarity	NPC270465
0.9384	High Similarity	NPC137062
0.9379	High Similarity	NPC21835
0.9379	High Similarity	NPC51443
0.9379	High Similarity	NPC239312
0.9379	High Similarity	NPC74881
0.9379	High Similarity	NPC207729
0.9379	High Similarity	NPC275772
0.9379	High Similarity	NPC130230
0.9379	High Similarity	NPC77378
0.9371	High Similarity	NPC73028
0.9338	High Similarity	NPC471744
0.9338	High Similarity	NPC36217
0.9338	High Similarity	NPC118256
0.9338	High Similarity	NPC470183
0.9338	High Similarity	NPC321399
0.9338	High Similarity	NPC287328
0.9338	High Similarity	NPC192686
0.9338	High Similarity	NPC119209
0.9338	High Similarity	NPC282009
0.9338	High Similarity	NPC472624
0.9338	High Similarity	NPC263449
0.9333	High Similarity	NPC472910
0.9333	High Similarity	NPC222814
0.9333	High Similarity	NPC299520
0.9333	High Similarity	NPC223787
0.9333	High Similarity	NPC96167
0.9333	High Similarity	NPC129684
0.9333	High Similarity	NPC245758
0.9333	High Similarity	NPC472914
0.9333	High Similarity	NPC472911
0.9333	High Similarity	NPC67876
0.9333	High Similarity	NPC472913
0.9329	High Similarity	NPC2928
0.9329	High Similarity	NPC37392
0.9329	High Similarity	NPC226025
0.9324	High Similarity	NPC477231
0.9324	High Similarity	NPC161277
0.9324	High Similarity	NPC257648
0.9324	High Similarity	NPC39007
0.9324	High Similarity	NPC101996
0.932	High Similarity	NPC149127
0.932	High Similarity	NPC286342
0.932	High Similarity	NPC184136
0.932	High Similarity	NPC188871
0.932	High Similarity	NPC3825
0.932	High Similarity	NPC88804
0.932	High Similarity	NPC248102
0.9315	High Similarity	NPC118726
0.9315	High Similarity	NPC12367
0.9315	High Similarity	NPC218490
0.9315	High Similarity	NPC120464
0.931	High Similarity	NPC169749
0.9291	High Similarity	NPC32441
0.9291	High Similarity	NPC243083
0.9291	High Similarity	NPC13768
0.9291	High Similarity	NPC12296
0.9291	High Similarity	NPC295261
0.9291	High Similarity	NPC296490
0.9291	High Similarity	NPC79943
0.9291	High Similarity	NPC107586
0.9291	High Similarity	NPC287246
0.9276	High Similarity	NPC158188
0.9276	High Similarity	NPC472632
0.9276	High Similarity	NPC471210
0.9276	High Similarity	NPC112418
0.9276	High Similarity	NPC142252
0.9276	High Similarity	NPC471499
0.9276	High Similarity	NPC308992
0.9276	High Similarity	NPC289771
0.9276	High Similarity	NPC173137
0.9276	High Similarity	NPC474038
0.9276	High Similarity	NPC26326
0.9276	High Similarity	NPC472634
0.9272	High Similarity	NPC85121
0.9272	High Similarity	NPC95936
0.9272	High Similarity	NPC250214
0.9272	High Similarity	NPC329091
0.9272	High Similarity	NPC55738
0.9267	High Similarity	NPC472916
0.9257	High Similarity	NPC260895
0.9257	High Similarity	NPC149614
0.9257	High Similarity	NPC202157
0.9257	High Similarity	NPC125062
0.9257	High Similarity	NPC252933
0.9257	High Similarity	NPC54394
0.9257	High Similarity	NPC200740
0.9257	High Similarity	NPC171010
0.9257	High Similarity	NPC117579
0.9252	High Similarity	NPC177298

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 NPC321011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	918
0.2-0.3	1817
0.3-0.4	2613
0.4-0.5	1687
0.5-0.6	1028
0.6-0.7	478
0.7-0.8	117
0.8-0.85	32
0.85-0.9	15
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9724	High Similarity	NPD1934	Approved
0.9658	High Similarity	NPD2393	Clinical (unspecified phase)
0.9577	High Similarity	NPD1511	Approved
0.9444	High Similarity	NPD1512	Approved
0.9291	High Similarity	NPD1550	Clinical (unspecified phase)
0.9291	High Similarity	NPD1552	Clinical (unspecified phase)
0.9225	High Similarity	NPD1549	Phase 2
0.9133	High Similarity	NPD2801	Approved
0.9097	High Similarity	NPD6166	Phase 2
0.9097	High Similarity	NPD6168	Clinical (unspecified phase)
0.9097	High Similarity	NPD6167	Clinical (unspecified phase)
0.8889	High Similarity	NPD4868	Clinical (unspecified phase)
0.8889	High Similarity	NPD3882	Suspended
0.8881	High Similarity	NPD1510	Phase 2
0.8868	High Similarity	NPD7074	Phase 3
0.8861	High Similarity	NPD3818	Discontinued
0.8808	High Similarity	NPD4380	Phase 2
0.8805	High Similarity	NPD7054	Approved
0.875	High Similarity	NPD7472	Approved
0.8725	High Similarity	NPD4378	Clinical (unspecified phase)
0.871	High Similarity	NPD4381	Clinical (unspecified phase)
0.8701	High Similarity	NPD3817	Phase 2
0.8696	High Similarity	NPD6797	Phase 2
0.8642	High Similarity	NPD7251	Discontinued
0.8601	High Similarity	NPD943	Approved
0.8601	High Similarity	NPD1612	Clinical (unspecified phase)
0.8601	High Similarity	NPD1613	Approved
0.8601	High Similarity	NPD1240	Approved
0.859	High Similarity	NPD7075	Discontinued
0.8589	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD2796	Approved
0.8516	High Similarity	NPD7096	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1607	Approved
0.8481	Intermediate Similarity	NPD5494	Approved
0.8476	Intermediate Similarity	NPD7808	Phase 3
0.8462	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD1465	Phase 2
0.838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD6799	Approved
0.8269	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6801	Discontinued
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8163	Intermediate Similarity	NPD230	Phase 1
0.8148	Intermediate Similarity	NPD6232	Discontinued
0.8121	Intermediate Similarity	NPD5844	Phase 1
0.8113	Intermediate Similarity	NPD5402	Approved
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8092	Intermediate Similarity	NPD3750	Approved
0.8089	Intermediate Similarity	NPD6599	Discontinued
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.8013	Intermediate Similarity	NPD5403	Approved
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1247	Approved
0.7963	Intermediate Similarity	NPD919	Approved
0.7958	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2800	Approved
0.7891	Intermediate Similarity	NPD3027	Phase 3
0.784	Intermediate Similarity	NPD7768	Phase 2
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD1610	Phase 2
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.78	Intermediate Similarity	NPD447	Suspended
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7763	Intermediate Similarity	NPD3748	Approved
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.774	Intermediate Similarity	NPD1203	Approved
0.7738	Intermediate Similarity	NPD3751	Discontinued
0.7736	Intermediate Similarity	NPD1653	Approved
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD6100	Approved
0.7677	Intermediate Similarity	NPD1243	Approved
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7673	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9494	Approved
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3787	Discontinued
0.76	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD6190	Approved
0.7578	Intermediate Similarity	NPD3226	Approved
0.7566	Intermediate Similarity	NPD1933	Approved
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7199	Phase 2
0.7534	Intermediate Similarity	NPD9269	Phase 2
0.753	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD6651	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2309	Approved
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7415	Intermediate Similarity	NPD1608	Approved
0.7415	Intermediate Similarity	NPD9717	Approved
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2861	Phase 2
0.7389	Intermediate Similarity	NPD4360	Phase 2
0.7389	Intermediate Similarity	NPD4363	Phase 3
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7390	Discontinued
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7365	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6832	Phase 2
0.7347	Intermediate Similarity	NPD422	Phase 1
0.7347	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD37	Approved
0.7326	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD5710	Approved
0.7294	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1470	Approved
0.726	Intermediate Similarity	NPD9268	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.7255	Intermediate Similarity	NPD3268	Approved
0.7255	Intermediate Similarity	NPD411	Approved
0.7233	Intermediate Similarity	NPD1652	Phase 2
0.7229	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2798	Approved
0.7213	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD17	Approved
0.72	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD4308	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD2797	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7133	Intermediate Similarity	NPD4749	Approved
0.7125	Intermediate Similarity	NPD2654	Approved
0.7115	Intermediate Similarity	NPD5124	Phase 1
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7266	Discontinued
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6779	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD6233	Phase 2
0.7093	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7072	Intermediate Similarity	NPD4287	Approved
0.7068	Intermediate Similarity	NPD8151	Discontinued
0.7067	Intermediate Similarity	NPD1481	Phase 2
0.7065	Intermediate Similarity	NPD4361	Phase 2
0.7065	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD9493	Approved
0.7045	Intermediate Similarity	NPD1729	Discontinued
0.7039	Intermediate Similarity	NPD3267	Approved
0.7039	Intermediate Similarity	NPD3266	Approved
0.7032	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4662	Approved
0.7012	Intermediate Similarity	NPD4661	Approved
0.7011	Intermediate Similarity	NPD2403	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