NPASS Compound

Structure

CID160972 OpenBabel06191715532D 21 23 0 0 1 0 0 0 0 0999 V2000 2.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.6340 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 -0.8660 1.5000 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 2.8660 -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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8660 -1.5000 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	1.267
LogD:	0.912
LogS:	-2.758
# Rotatable Bonds:	1
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	3.205
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.5541982065769844e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.734

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	89.08236694335938%
Volume Distribution (VD):	0.722
Pgp-substrate:	7.100513458251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.531
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.522
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	2.13
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.09
AMES Toxicity:	0.282
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.884
Carcinogencity:	0.892
Eye Corrosion:	0.005
Eye Irritation:	0.908
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC160972

Natural Product ID:	NPC160972
*Common Name:**	Protoapigenone
IUPAC Name:	5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one
Synonyms:	Protoapigenone
Standard InCHIKey:	DLMOVPAUHQQYHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1-7,17-18,20H
SMILES:	C1=CC(C=CC1=O)(c1cc(=O)c2c(cc(cc2o1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL414890
PubChem CID:	11644907
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	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	8
EC50	3
IC50	25
Others	9
Potency	58

Activity Type	# Activity
Cell Line	18
Individual Protein	44
NON-MOLECULAR	5
Organism	4
Others	29
SINGLE PROTEIN	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8110.0	nM	PMID[568880]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1430.0	nM	PMID[568880]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3740.0	nM	PMID[568880]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13850.0	nM	PMID[568880]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	31622.8	nM	PMID[568882]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	35481.3	nM	PMID[568882]
NPT3256	Individual Protein	Serine/threonine-protein kinase WEE1	Homo sapiens	CC50	>	49750.0	nM	PMID[568882]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PMID[568882]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	1412.5	nM	PMID[568882]
NPT4854	Individual Protein	G2/mitotic-specific cyclin B1	Homo sapiens	EC50	>	1842.0	nM	PMID[568882]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[568882]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PMID[568882]
NPT1415	Individual Protein	Heat shock factor protein 1	Mus musculus	EC50	=	4281.0	nM	PMID[568882]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[568882]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	35481.3	nM	PMID[568882]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	22387.2	nM	PMID[568882]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[568882]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	223.9	nM	PMID[568882]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3981.1	nM	PMID[568882]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	0.00122	nM	PMID[568882]
NPT3256	Individual Protein	Serine/threonine-protein kinase WEE1	Homo sapiens	EC50	>	1842.0	nM	PMID[568882]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	3162.3	nM	PMID[568882]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[568882]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[568882]
NPT2892	Individual Protein	X-box-binding protein 1	Homo sapiens	IC50	=	3840.0	nM	PMID[568882]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[568882]
NPT2893	Individual Protein	DNA damage-inducible transcript 3 protein	Mus musculus	IC50	=	2580.0	nM	PMID[568882]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	3264.3	nM	PMID[568882]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5500.0	nM	PMID[568883]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1700.0	nM	PMID[568883]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	710.0	nM	PMID[568883]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	6130.0	nM	PMID[568883]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	7770.0	nM	PMID[568883]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	22090.0	nM	PMID[568883]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	3930.0	nM	PMID[568883]
NPT2015	Cell Line	U-266	Homo sapiens	IC50	=	7660.0	nM	PMID[568883]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	6790.0	nM	PMID[568883]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	8110.0	nM	PMID[568883]
NPT1357	Cell Line	H22	Mus musculus	Inhibition	<	5.0	%	PMID[568883]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[568882]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[568882]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[568882]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[568882]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	30131.3	nM	PMID[568882]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1458.1	nM	PMID[568882]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	4441.1	nM	PMID[568882]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	5591.1	nM	PMID[568882]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[568882]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[568882]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[568882]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[568882]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	7897.6	nM	PMID[568882]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	517.4	nM	PMID[568882]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	366.3	nM	PMID[568882]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[568882]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[568882]
NPT1654	Individual Protein	Urokinase-type plasminogen activator	Homo sapiens	Potency	n.a.	23280.9	nM	PMID[568882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2270.0	nM	PMID[568880]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	5847.9	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	=	14581.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	=	3874.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	=	5623.4	nM	PMID[568882]
NPT2	Others	Unspecified		CC50	n.a.	2605.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	32642.7	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	n.a.	3020.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	5804.8	nM	PMID[568882]
NPT2	Others	Unspecified		CC50	n.a.	5735.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	=	20500.0	nM	PMID[568882]
NPT2	Others	Unspecified		CC50	n.a.	3280.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	=	2210.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	>	80000.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	=	1620.0	nM	PMID[568882]
NPT2	Others	Unspecified		IC50	n.a.	2610.0	nM	PMID[568882]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	51.52	%	PMID[568883]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	36.9	%	PMID[568883]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[568882]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	70794.6	nM	PMID[568882]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[568882]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[568882]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[568882]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	20596.2	nM	PMID[568882]
NPT2	Others	Unspecified		AC50	=	32340.0	nM	PMID[568882]
NPT2	Others	Unspecified		AC50	=	5120.0	nM	PMID[568882]
NPT2	Others	Unspecified		AC50	=	4470.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	7079.5	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	5623.4	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	7307.8	nM	PMID[568882]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	16481.6	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[568882]
NPT2	Others	Unspecified		AC50	=	21440.0	nM	PMID[568882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	AC50	=	6310.0	nM	PMID[568882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	AC50	=	7090.0	nM	PMID[568882]
NPT2	Others	Unspecified		AC50	=	27070.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	14689.2	nM	PMID[568882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	AbsAC35_uM	=	8.15	uM	PMID[568882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	AC50	=	5130.0	nM	PMID[568882]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[568882]
NPT26245	SINGLE PROTEIN	Glutathione transferase omega 1	Homo sapiens	IC50	=	1600.0	nM	PMID[568884]

☑ 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 NPC160972 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	432
0.1-0.2	1886
0.2-0.3	4800
0.3-0.4	10907
0.4-0.5	6789
0.5-0.6	4143
0.6-0.7	5831
0.7-0.8	4072
0.8-0.85	2458
0.85-0.9	1253
0.9-0.95	125
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC172262
0.9398	High Similarity	NPC50898
0.9398	High Similarity	NPC78540
0.9398	High Similarity	NPC213216
0.9398	High Similarity	NPC274121
0.9398	High Similarity	NPC57601
0.9318	High Similarity	NPC5515
0.9318	High Similarity	NPC270369
0.9281	High Similarity	NPC242100
0.9281	High Similarity	NPC255133
0.9265	High Similarity	NPC299379
0.9265	High Similarity	NPC266597
0.9265	High Similarity	NPC250266
0.9259	High Similarity	NPC9985
0.9259	High Similarity	NPC239495
0.9259	High Similarity	NPC151113
0.9248	High Similarity	NPC31872
0.9248	High Similarity	NPC473584
0.9248	High Similarity	NPC475589
0.9248	High Similarity	NPC113006
0.9191	High Similarity	NPC231772
0.9191	High Similarity	NPC256042
0.9191	High Similarity	NPC47815
0.9191	High Similarity	NPC281917
0.9191	High Similarity	NPC13408
0.9191	High Similarity	NPC187432
0.9191	High Similarity	NPC29353
0.9191	High Similarity	NPC116775
0.9191	High Similarity	NPC194281
0.9191	High Similarity	NPC124784
0.9191	High Similarity	NPC234133
0.9191	High Similarity	NPC473887
0.9191	High Similarity	NPC127447
0.9191	High Similarity	NPC216361
0.9179	High Similarity	NPC10971
0.9179	High Similarity	NPC25937
0.9149	High Similarity	NPC229190
0.9137	High Similarity	NPC156590
0.9137	High Similarity	NPC147688
0.9137	High Similarity	NPC64908
0.9137	High Similarity	NPC118840
0.9137	High Similarity	NPC205006
0.9137	High Similarity	NPC150023
0.913	High Similarity	NPC473076
0.913	High Similarity	NPC471697
0.9124	High Similarity	NPC228661
0.9124	High Similarity	NPC275055
0.9124	High Similarity	NPC290291
0.9111	High Similarity	NPC223457
0.9111	High Similarity	NPC93756
0.9111	High Similarity	NPC108113
0.9098	High Similarity	NPC185497
0.9085	High Similarity	NPC168803
0.9078	High Similarity	NPC70136
0.9071	High Similarity	NPC11561
0.9071	High Similarity	NPC226636
0.9065	High Similarity	NPC172986
0.9065	High Similarity	NPC269652
0.9065	High Similarity	NPC235239
0.9065	High Similarity	NPC305355
0.9065	High Similarity	NPC475680
0.9065	High Similarity	NPC270883
0.9065	High Similarity	NPC281207
0.9065	High Similarity	NPC261227
0.9058	High Similarity	NPC188947
0.9058	High Similarity	NPC472460
0.9058	High Similarity	NPC329225
0.9058	High Similarity	NPC201395
0.9058	High Similarity	NPC99333
0.9058	High Similarity	NPC280284
0.9058	High Similarity	NPC470669
0.9058	High Similarity	NPC470668
0.9058	High Similarity	NPC147686
0.9044	High Similarity	NPC125920
0.9044	High Similarity	NPC248872
0.903	High Similarity	NPC137264
0.9023	High Similarity	NPC197425
0.9023	High Similarity	NPC60558
0.9014	High Similarity	NPC148011
0.9014	High Similarity	NPC1940
0.9007	High Similarity	NPC38219
0.9007	High Similarity	NPC279121
0.9	High Similarity	NPC103362
0.9	High Similarity	NPC110969
0.9	High Similarity	NPC136840
0.8993	High Similarity	NPC18260
0.8993	High Similarity	NPC469523
0.8993	High Similarity	NPC303633
0.8993	High Similarity	NPC55018
0.8993	High Similarity	NPC152042
0.8993	High Similarity	NPC96565
0.8993	High Similarity	NPC78913
0.8993	High Similarity	NPC143799
0.8993	High Similarity	NPC301217
0.8993	High Similarity	NPC23257
0.8993	High Similarity	NPC216978
0.8993	High Similarity	NPC261234
0.8993	High Similarity	NPC241838
0.8993	High Similarity	NPC220062
0.8986	High Similarity	NPC13768
0.8986	High Similarity	NPC295261
0.8986	High Similarity	NPC107586
0.8986	High Similarity	NPC188879
0.8986	High Similarity	NPC12296
0.8986	High Similarity	NPC296490
0.8986	High Similarity	NPC79943
0.8986	High Similarity	NPC32441
0.8986	High Similarity	NPC84585
0.8986	High Similarity	NPC254841
0.8986	High Similarity	NPC476480
0.8986	High Similarity	NPC243083
0.8986	High Similarity	NPC287246
0.8978	High Similarity	NPC234560
0.8978	High Similarity	NPC39426
0.8978	High Similarity	NPC60667
0.8966	High Similarity	NPC81474
0.8955	High Similarity	NPC115998
0.8955	High Similarity	NPC39753
0.8951	High Similarity	NPC74881
0.8951	High Similarity	NPC472918
0.8951	High Similarity	NPC51443
0.8951	High Similarity	NPC85773
0.8947	High Similarity	NPC186098
0.8947	High Similarity	NPC80694
0.8944	High Similarity	NPC234629
0.8944	High Similarity	NPC49130
0.8944	High Similarity	NPC208176
0.8944	High Similarity	NPC279417
0.8944	High Similarity	NPC311741
0.8944	High Similarity	NPC62290
0.8944	High Similarity	NPC4152
0.8944	High Similarity	NPC306607
0.8944	High Similarity	NPC326506
0.8944	High Similarity	NPC142731
0.8936	High Similarity	NPC293852
0.8936	High Similarity	NPC78803
0.8936	High Similarity	NPC175013
0.8936	High Similarity	NPC299080
0.8936	High Similarity	NPC217083
0.8936	High Similarity	NPC214236
0.8936	High Similarity	NPC59739
0.8936	High Similarity	NPC144499
0.8936	High Similarity	NPC62840
0.8929	High Similarity	NPC103904
0.8929	High Similarity	NPC150522
0.8929	High Similarity	NPC69769
0.8929	High Similarity	NPC241100
0.8929	High Similarity	NPC59951
0.8929	High Similarity	NPC184536
0.8929	High Similarity	NPC146679
0.8929	High Similarity	NPC471587
0.8929	High Similarity	NPC230285
0.8929	High Similarity	NPC103342
0.8929	High Similarity	NPC159275
0.8921	High Similarity	NPC118813
0.8921	High Similarity	NPC124269
0.8921	High Similarity	NPC131130
0.8913	High Similarity	NPC174999
0.8913	High Similarity	NPC87545
0.8913	High Similarity	NPC235428
0.8913	High Similarity	NPC187826
0.8913	High Similarity	NPC240593
0.8904	High Similarity	NPC285623
0.8904	High Similarity	NPC31627
0.8904	High Similarity	NPC327269
0.8904	High Similarity	NPC476238
0.8897	High Similarity	NPC212631
0.8897	High Similarity	NPC45873
0.8897	High Similarity	NPC129132
0.8897	High Similarity	NPC257756
0.8897	High Similarity	NPC205468
0.8897	High Similarity	NPC87231
0.8897	High Similarity	NPC203817
0.8897	High Similarity	NPC128216
0.8897	High Similarity	NPC267117
0.8889	High Similarity	NPC196277
0.8889	High Similarity	NPC43669
0.8889	High Similarity	NPC118726
0.8889	High Similarity	NPC211811
0.8889	High Similarity	NPC12367
0.8889	High Similarity	NPC272721
0.8881	High Similarity	NPC187907
0.8881	High Similarity	NPC329678
0.8881	High Similarity	NPC179271
0.8881	High Similarity	NPC20791
0.8873	High Similarity	NPC473813
0.8873	High Similarity	NPC473812
0.8873	High Similarity	NPC106985
0.8873	High Similarity	NPC219915
0.8873	High Similarity	NPC166138
0.8873	High Similarity	NPC18585
0.8872	High Similarity	NPC128428
0.8872	High Similarity	NPC475496
0.8872	High Similarity	NPC49852
0.8872	High Similarity	NPC22783
0.8872	High Similarity	NPC305518
0.8865	High Similarity	NPC282300
0.8865	High Similarity	NPC14871
0.8865	High Similarity	NPC3188
0.8865	High Similarity	NPC262094

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 NPC160972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	970
0.2-0.3	1745
0.3-0.4	2726
0.4-0.5	1785
0.5-0.6	1021
0.6-0.7	343
0.7-0.8	102
0.8-0.85	35
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD1549	Phase 2
0.9007	High Similarity	NPD1511	Approved
0.8986	High Similarity	NPD1552	Clinical (unspecified phase)
0.8986	High Similarity	NPD1550	Clinical (unspecified phase)
0.8978	High Similarity	NPD1510	Phase 2
0.8881	High Similarity	NPD1512	Approved
0.8824	High Similarity	NPD1240	Approved
0.8811	High Similarity	NPD7410	Clinical (unspecified phase)
0.8696	High Similarity	NPD1607	Approved
0.8681	High Similarity	NPD4378	Clinical (unspecified phase)
0.8639	High Similarity	NPD4380	Phase 2
0.8611	High Similarity	NPD6799	Approved
0.8591	High Similarity	NPD2801	Approved
0.8543	High Similarity	NPD4381	Clinical (unspecified phase)
0.8531	High Similarity	NPD3750	Approved
0.8523	High Similarity	NPD1934	Approved
0.8511	High Similarity	NPD2796	Approved
0.8421	Intermediate Similarity	NPD7075	Discontinued
0.84	Intermediate Similarity	NPD6801	Discontinued
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD5403	Approved
0.8299	Intermediate Similarity	NPD5401	Approved
0.8267	Intermediate Similarity	NPD6599	Discontinued
0.8252	Intermediate Similarity	NPD1551	Phase 2
0.8212	Intermediate Similarity	NPD7411	Suspended
0.8207	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD3748	Approved
0.8182	Intermediate Similarity	NPD3749	Approved
0.8175	Intermediate Similarity	NPD1203	Approved
0.817	Intermediate Similarity	NPD3817	Phase 2
0.8113	Intermediate Similarity	NPD3818	Discontinued
0.8088	Intermediate Similarity	NPD9717	Approved
0.8082	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD943	Approved
0.8027	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD422	Phase 1
0.7987	Intermediate Similarity	NPD6166	Phase 2
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6651	Approved
0.7901	Intermediate Similarity	NPD7472	Approved
0.7887	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7852	Intermediate Similarity	NPD1548	Phase 1
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD920	Approved
0.7823	Intermediate Similarity	NPD2344	Approved
0.7815	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2313	Discontinued
0.7758	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1465	Phase 2
0.7754	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD447	Suspended
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD919	Approved
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4628	Phase 3
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7635	Intermediate Similarity	NPD6099	Approved
0.7635	Intermediate Similarity	NPD6100	Approved
0.7625	Intermediate Similarity	NPD5494	Approved
0.7622	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2309	Approved
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7603	Intermediate Similarity	NPD230	Phase 1
0.7591	Intermediate Similarity	NPD9545	Approved
0.759	Intermediate Similarity	NPD6559	Discontinued
0.7589	Intermediate Similarity	NPD3225	Approved
0.7578	Intermediate Similarity	NPD6959	Discontinued
0.7578	Intermediate Similarity	NPD1247	Approved
0.7574	Intermediate Similarity	NPD9493	Approved
0.7568	Intermediate Similarity	NPD4308	Phase 3
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2799	Discontinued
0.7552	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.7517	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.7517	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7484	Intermediate Similarity	NPD4288	Approved
0.7483	Intermediate Similarity	NPD2654	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7483	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7455	Intermediate Similarity	NPD3751	Discontinued
0.745	Intermediate Similarity	NPD7033	Discontinued
0.744	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5953	Discontinued
0.7415	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1613	Approved
0.7413	Intermediate Similarity	NPD2797	Approved
0.741	Intermediate Similarity	NPD7286	Phase 2
0.7389	Intermediate Similarity	NPD3226	Approved
0.7386	Intermediate Similarity	NPD2354	Approved
0.7378	Intermediate Similarity	NPD3926	Phase 2
0.7368	Intermediate Similarity	NPD1652	Phase 2
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9494	Approved
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.7297	Intermediate Similarity	NPD4307	Phase 2
0.7292	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD3266	Approved
0.7279	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4908	Phase 1
0.726	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7237	Intermediate Similarity	NPD2346	Discontinued
0.7229	Intermediate Similarity	NPD2403	Approved
0.7215	Intermediate Similarity	NPD1653	Approved
0.7203	Intermediate Similarity	NPD9269	Phase 2
0.7203	Intermediate Similarity	NPD1608	Approved
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4287	Approved
0.7172	Intermediate Similarity	NPD1470	Approved
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9263	Approved
0.7164	Intermediate Similarity	NPD9264	Approved
0.7162	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD1729	Discontinued
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1201	Approved
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2353	Approved
0.7108	Intermediate Similarity	NPD3787	Discontinued
0.7089	Intermediate Similarity	NPD5049	Phase 3
0.7083	Intermediate Similarity	NPD3972	Approved
0.7076	Intermediate Similarity	NPD6104	Discontinued
0.707	Intermediate Similarity	NPD7390	Discontinued
0.7065	Intermediate Similarity	NPD7584	Approved
0.7055	Intermediate Similarity	NPD2296	Approved
0.7055	Intermediate Similarity	NPD1164	Approved
0.7042	Intermediate Similarity	NPD9268	Approved
0.7025	Intermediate Similarity	NPD4661	Approved
0.7025	Intermediate Similarity	NPD4662	Approved
0.7022	Intermediate Similarity	NPD4360	Phase 2
0.7022	Intermediate Similarity	NPD4363	Phase 3
0.7014	Intermediate Similarity	NPD1091	Approved
0.7013	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD17	Approved
0.6983	Remote Similarity	NPD4361	Phase 2
0.6983	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4625	Phase 3
0.6971	Remote Similarity	NPD8434	Phase 2
0.6968	Remote Similarity	NPD2424	Discontinued
0.6962	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3140	Approved
0.6954	Remote Similarity	NPD3142	Approved
0.6946	Remote Similarity	NPD7199	Phase 2
0.6943	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD3887	Approved
0.6941	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9281	Approved
0.6923	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6585	Discontinued
0.6912	Remote Similarity	NPD290	Approved
0.6908	Remote Similarity	NPD4340	Discontinued
0.6908	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD5710	Approved
0.6905	Remote Similarity	NPD5711	Approved
0.6897	Remote Similarity	NPD8312	Approved
0.6897	Remote Similarity	NPD8313	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