NPASS Compound

Structure

CID53240 OpenBabel06191715392D 38 38 0 0 1 0 0 0 0 0999 V2000 -9.2451 10.6550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3884 0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8473 4.7350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5748 -3.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3122 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2940 10.9640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5509 10.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7588 9.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0156 8.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4099 3.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2235 7.6695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1531 4.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6178 2.7276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4804 7.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9452 5.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8747 2.0585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 -0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0121 -2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5474 -0.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 -1.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6883 6.0222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1100 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0826 1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2690 -2.8833 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.3395 0.4112 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0337 0.7713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6394 5.7132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3179 -2.5743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 31 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 23 1 0 0 0 0 17 25 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 23 2 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 0 0 0 0 24 14 1 1 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 27 31 1 0 0 0 0 27 33 2 0 0 0 0 28 32 1 0 0 0 0 28 34 2 0 0 0 0 29 32 1 0 0 0 0 29 35 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.3
Volume:	573.074
LogP:	5.395
LogD:	3.956
LogS:	-5.179
# Rotatable Bonds:	21
TPSA:	90.23
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	4.345
Fsp3:	0.586
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.809
MDCK Permeability:	3.3638592867646366e-05
Pgp-inhibitor:	0.343
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.468
20% Bioavailability (F20%):	0.401
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	96.11487579345703%
Volume Distribution (VD):	0.392
Pgp-substrate:	4.960880756378174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.447
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	4.15
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.758
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.981
Carcinogencity:	0.582
Eye Corrosion:	0.006
Eye Irritation:	0.019
Respiratory Toxicity:	0.597

Download Data

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

Natural Product: NPC53240

Natural Product ID:	NPC53240
*Common Name:**	(E,7S)-N-[(E,2E)-2-(Chloromethylidene)-4-Methoxy-6-(3-Methoxy-5-Oxo-2H-Pyrrol-1-Yl)-6-Oxohex-4-Enyl]-7-Methoxy-N-Methyltetradec-4-Enamide
IUPAC Name:	(E,7S)-N-[(E,2E)-2-(chloromethylidene)-4-methoxy-6-(3-methoxy-5-oxo-2H-pyrrol-1-yl)-6-oxohex-4-enyl]-7-methoxy-N-methyltetradec-4-enamide
Synonyms:
Standard InCHIKey:	MCGPGUSLTPAGCR-RPPVKKOJSA-N
Standard InCHI:	InChI=1S/C29H45ClN2O6/c1-6-7-8-9-11-14-24(36-3)15-12-10-13-16-27(33)31(2)21-23(20-30)17-25(37-4)18-28(34)32-22-26(38-5)19-29(32)35/h10,12,18-20,24H,6-9,11,13-17,21-22H2,1-5H3/b12-10+,23-20+,25-18+/t24-/m0/s1
SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=O)N(C)C/C(=C/Cl)/C/C(=CC(=O)N1CC(=CC1=O)OC)/OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1357867
PubChem CID:	14779548
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

*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
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np960188t]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[12762793]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16595909]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO12302	Hebanthe paniculata	Species	Amaranthaceae	Eukaryota	n.a.	root	n.a.	PMID[19941264]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20795741]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12302	Hebanthe paniculata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13233	Solanum megacarpum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12302	Hebanthe paniculata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3396	Allium cernuum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16176	Citrus fusca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15140	Soja max	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21487	Eunicea flexuosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12135	Rhamnus triquetra	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	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
EC50	1
IC50	2
Potency	38

Activity Type	# Activity
Cell Line	1
Individual Protein	28
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	39810.7	nM	PMID[466043]
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	Potency	n.a.	3264.3	nM	PMID[466043]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	3264.3	nM	PMID[466043]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[466043]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	2058.8	nM	PMID[466043]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	1299.0	nM	PMID[466043]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[466043]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[466043]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	707.9	nM	PMID[466043]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[466043]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[466043]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	5804.8	nM	PMID[466043]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[466043]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[466043]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	501.2	nM	PMID[466043]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	12538.5	nM	PMID[466043]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	1835.6	nM	PMID[466043]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2310.9	nM	PMID[466043]
NPT585	Individual Protein	Nuclear receptor subfamily 0 group B member 1	Homo sapiens	IC50	>	277.93	nM	PMID[466043]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[466043]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[466043]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[466043]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[466043]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[466043]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	730.8	nM	PMID[466043]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	1987.2	nM	PMID[466043]
NPT2	Others	Unspecified		AC50	=	4120.0	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	2310.9	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	651.3	nM	PMID[466043]
NPT2	Others	Unspecified		AC50	=	5375.0	nM	PMID[466043]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[466043]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[466043]
NPT2	Others	Unspecified		EC50	=	1110.0	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	996.0	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	23109.3	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	9200.0	nM	PMID[466043]
NPT35	Others	n.a.		IC50	>	67539.0	nM	PMID[466043]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	5804.8	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[466043]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[466043]

☑ 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 NPC53240 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	71
0.1-0.2	972
0.2-0.3	21625
0.3-0.4	16106
0.4-0.5	3633
0.5-0.6	256
0.6-0.7	30
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC81195
0.7255	Intermediate Similarity	NPC233932
0.6809	Remote Similarity	NPC477523
0.6737	Remote Similarity	NPC477524
0.6727	Remote Similarity	NPC21324
0.6632	Remote Similarity	NPC209232
0.6481	Remote Similarity	NPC474244
0.6471	Remote Similarity	NPC47230
0.6471	Remote Similarity	NPC17143
0.6415	Remote Similarity	NPC52820
0.6392	Remote Similarity	NPC277341
0.6392	Remote Similarity	NPC226982
0.6374	Remote Similarity	NPC97614
0.6354	Remote Similarity	NPC471768
0.6339	Remote Similarity	NPC474099
0.6316	Remote Similarity	NPC46268
0.6273	Remote Similarity	NPC199831
0.6273	Remote Similarity	NPC68001
0.6273	Remote Similarity	NPC474827
0.6273	Remote Similarity	NPC474828
0.6239	Remote Similarity	NPC77703
0.6195	Remote Similarity	NPC476276
0.6154	Remote Similarity	NPC96272
0.6105	Remote Similarity	NPC34672
0.6071	Remote Similarity	NPC469604
0.604	Remote Similarity	NPC475975
0.6018	Remote Similarity	NPC476328
0.6	Remote Similarity	NPC477964
0.6	Remote Similarity	NPC473810
0.5948	Remote Similarity	NPC469603
0.5932	Remote Similarity	NPC469597
0.5897	Remote Similarity	NPC474411
0.5897	Remote Similarity	NPC474431
0.5888	Remote Similarity	NPC38172
0.5856	Remote Similarity	NPC316730
0.5856	Remote Similarity	NPC26597
0.5843	Remote Similarity	NPC252684
0.5841	Remote Similarity	NPC476877
0.5833	Remote Similarity	NPC470994
0.5825	Remote Similarity	NPC319913
0.5816	Remote Similarity	NPC325936
0.5804	Remote Similarity	NPC188785
0.5789	Remote Similarity	NPC476921
0.5776	Remote Similarity	NPC470072
0.5769	Remote Similarity	NPC322672
0.575	Remote Similarity	NPC474984
0.5745	Remote Similarity	NPC477688
0.5739	Remote Similarity	NPC476876
0.5714	Remote Similarity	NPC36254
0.5714	Remote Similarity	NPC324506
0.5714	Remote Similarity	NPC206660
0.5714	Remote Similarity	NPC473525
0.5701	Remote Similarity	NPC159568
0.5676	Remote Similarity	NPC241426
0.5676	Remote Similarity	NPC91036
0.5673	Remote Similarity	NPC475614
0.5673	Remote Similarity	NPC2640
0.5652	Remote Similarity	NPC205176
0.5652	Remote Similarity	NPC470073
0.5641	Remote Similarity	NPC207820
0.563	Remote Similarity	NPC476875
0.563	Remote Similarity	NPC58281
0.5619	Remote Similarity	NPC469860
0.5619	Remote Similarity	NPC469861
0.5619	Remote Similarity	NPC130436
0.5618	Remote Similarity	NPC133923
0.5603	Remote Similarity	NPC476926

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 NPC53240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	71
0.1-0.2	594
0.2-0.3	4621
0.3-0.4	3340
0.4-0.5	518
0.5-0.6	6
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5773	Remote Similarity	NPD1452	Discontinued
0.5703	Remote Similarity	NPD2079	Discontinued

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