NPASS Compound

Natural Product: NPC267340

Natural Product ID	NPC267340
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2E,4E,8E,10E,12E)-N-Isobutyl-2,4,8,10,12-Tetradecapentaenamide
IUPAC Name	(2E,4E,8E,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3086844
PubChem CID	5318518
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

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 47 46 0 0 0 0 0 0 0 0999 V2000 8.8448 2.8298 -1.3398 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5092 2.1847 -1.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0138 1.6313 -0.3460 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7166 0.9841 -0.3729 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2141 0.4272 0.7248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9122 -0.2044 0.6330 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3977 -0.7600 1.7039 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0896 -1.4103 1.6682 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5043 -1.3222 0.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1747 -2.0093 0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9617 -1.3821 0.0575 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2220 -2.1078 0.1376 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3564 -1.4841 -0.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6518 -2.1436 -0.0858 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7316 -1.6549 -0.3248 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3576 -0.5059 -0.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6873 0.8263 -0.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7093 1.8717 -1.0112 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2839 1.1140 0.9113 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6632 -3.5298 0.2971 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5918 2.0306 -1.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8621 3.5840 -0.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0652 3.2836 -2.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9379 2.1530 -2.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5734 1.6537 0.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1491 0.9559 -1.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7703 0.4466 1.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3974 -0.2051 -0.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9743 -0.7226 2.6217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1539 -2.5157 1.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3616 -0.9647 2.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3981 -0.2593 0.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1617 -1.7984 -0.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0983 -3.0497 0.6214 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8891 -0.3502 -0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2865 -3.1451 0.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2737 -0.4633 -0.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6751 -0.4946 -1.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3913 -0.4618 -0.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8210 0.9881 -1.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4755 1.9252 -0.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1984 2.8239 -1.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1769 1.4255 -1.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3574 1.7138 0.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 0.2139 1.5390 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0968 1.7193 1.3969 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4743 -3.8412 0.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 14 20 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 0 3 25 1 0 4 26 1 0 5 27 1 0 6 28 1 0 7 29 1 0 8 30 1 0 8 31 1 0 9 32 1 0 9 33 1 0 10 34 1 0 11 35 1 0 12 36 1 0 13 37 1 0 16 38 1 0 16 39 1 0 17 40 1 0 18 41 1 0 18 42 1 0 18 43 1 0 19 44 1 0 19 45 1 0 19 46 1 0 20 47 1 0 M END

Standard InCHIKey	KVUKDCFEXVWYBN-FMBIJHKPSA-N
Standard InCHI	InChI=1S/C18H27NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-18(20)19-16-17(2)3/h4-9,12-15,17H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8+,13-12+,15-14+
SMILES	C/C=C/C=C/C=C/CC/C=C/C=C/C(=NCC(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	273.21	Volume:	323.852 ? Van der Waals volume.
Dense:	0.844	LogP:	3.812 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.957 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.722 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	6.0
TPSA:	32.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.267	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.701	Fsp³:	0.389
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.653	Fluc inhibitor:	0.969 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.047 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.644	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.679	MDCK Permeability:	-4.696
Pgp-inhibitor:	0.713	Pgp-substrate:	0.642
PAMPA:	0.248 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.267	30% Bioavailability (F30%):	0.967
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.029
Plasma Protein Binding (PPB):	94.241%	Volume Distribution (VD):	-0.318
Fu:	7.019% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.947	BCRP inhibitor:	0.037
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.868	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.485	CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.056	CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.915	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.967 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.153

Half-life (T1/2):

0.712

ADMET: Toxicity

hERG Blockers:	0.123	hERG Blockers (10um):	0.233
Human Hepatotoxicity (H-HT):	0.949	Drug-induced Liver Injury (DILI):	0.862
AMES Toxicity:	0.931	Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.494	Skin Sensitization:	0.996
Carcinogencity:	0.84	Eye Corrosion:	0.022
Eye Irritation:	0.848	Respiratory Toxicity:	0.869
Drug-induced Neurotoxicity:	0.408	Ototoxicity:	0.595
Hematotoxicity:	0.394	Drug-induced Nephrotoxicity:	0.883
Genotoxicity:	0.496	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.017	Hek293 Cytotoxicity:	0.233
BCF:	1.427 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.232 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.471 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.046 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921433]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175626]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36786362]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37029634]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO7870	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9361	Aplophyllum villosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12591	Archaster typicus	Species	Archasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13555	Beaucarnea recurvata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4746	Centaurea arenaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12819	Clitocybe subilludens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9989	Cotylelobium scabriusculum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1326	Cratystylis conocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12367	Diospyros elliptifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11333	Trapa japonica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22899	Phaeotremella fagi	Species	Phaeotremellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8601	Petrosia volcano	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6386	Gutenbergia cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12233	Diospyros peregrina	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13042	Diospyros abyssinica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4746	Centaurea arenaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9361	Aplophyllum villosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1326	Cratystylis conocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22899	Phaeotremella fagi	Species	Phaeotremellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12367	Diospyros elliptifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13555	Beaucarnea recurvata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7870	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12819	Clitocybe subilludens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9989	Cotylelobium scabriusculum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12591	Archaster typicus	Species	Archasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6386	Gutenbergia cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8601	Petrosia volcano	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13042	Diospyros abyssinica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12233	Diospyros peregrina	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11333	Trapa japonica	Species	Lythraceae	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	Organism Name	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
Inhibition	10
Activity	9
EC50	1
IC50	2
Ratio IC50	1

Activity Type	# Activity
Individual protein	22
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	64.0	%	PMID[24175626]
NPT2766	Individual protein	Prostanoid EP2 receptor	Homo sapiens	Inhibition	=	-52.0	%	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	15.0	%	PMID[24175626]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	72.0	%	PMID[24175626]
NPT2766	Individual protein	Prostanoid EP2 receptor	Homo sapiens	Activity	=	7.0	%	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	5.0	%	PMID[24175626]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	41.7	nM	PMID[24175626]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	57.0	%	PMID[24175626]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	664.0	nM	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	37.0	%	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	100.0	nM	PMID[24175626]
NPT5622	Individual protein	Prolactin-releasing peptide receptor	Homo sapiens	Inhibition	=	52.0	%	PMID[24175626]
NPT5623	Individual protein	Probable G-protein coupled receptor 151	Homo sapiens	Activity	=	76.0	%	PMID[24175626]
NPT5624	Individual protein	Probable G-protein coupled receptor 132	Homo sapiens	Activity	=	61.0	%	PMID[24175626]
NPT5622	Individual protein	Prolactin-releasing peptide receptor	Homo sapiens	Activity	=	5.0	%	PMID[24175626]
NPT5620	Individual protein	Relaxin-3 receptor 1	Homo sapiens	Inhibition	=	-81.0	%	PMID[24175626]
NPT988	Individual protein	Histamine H4 receptor	Homo sapiens	Inhibition	=	-54.0	%	PMID[24175626]
NPT5620	Individual protein	Relaxin-3 receptor 1	Homo sapiens	Activity	=	18.0	%	PMID[24175626]
NPT988	Individual protein	Histamine H4 receptor	Homo sapiens	Activity	=	18.0	%	PMID[24175626]
NPT5621	Individual protein	Follicle stimulating hormone receptor	Homo sapiens	Inhibition	=	68.0	%	PMID[24175626]
NPT4120	Individual protein	G-protein coupled receptor 55	Homo sapiens	Activity	=	67.0	%	PMID[24175626]
NPT5621	Individual protein	Follicle stimulating hormone receptor	Homo sapiens	Activity	=	5.0	%	PMID[24175626]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	0.15	n.a.	PMID[24175626]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC267340 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	38964
0.1-0.2	10591
0.2-0.3	227
0.3-0.4	29
0.4-0.5	16
0.5-0.6	6
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC145032
0.9667	High Similarity	NPC304223
0.9667	High Similarity	NPC54542
0.9032	High Similarity	NPC307435
0.8438	Intermediate Similarity	NPC267692
0.8182	Intermediate Similarity	NPC243539
0.75	Intermediate Similarity	NPC303672
0.7429	Intermediate Similarity	NPC195986
0.7222	Intermediate Similarity	NPC104138
0.7222	Intermediate Similarity	NPC273023
0.7222	Intermediate Similarity	NPC24216
0.7222	Intermediate Similarity	NPC306420
0.7027	Intermediate Similarity	NPC261158
0.6923	Remote Similarity	NPC6795
0.6757	Remote Similarity	NPC269800
0.6757	Remote Similarity	NPC14234
0.675	Remote Similarity	NPC305288
0.675	Remote Similarity	NPC119655
0.675	Remote Similarity	NPC163912
0.6667	Remote Similarity	NPC167759
0.6667	Remote Similarity	NPC56028
0.6667	Remote Similarity	NPC123669
0.6286	Remote Similarity	NPC245650
0.6098	Remote Similarity	NPC297020
0.6047	Remote Similarity	NPC187315
0.5897	Remote Similarity	NPC132669
0.5897	Remote Similarity	NPC184014
0.561	Remote Similarity	NPC486662
0.5581	Remote Similarity	NPC471992
0.5116	Remote Similarity	NPC44193
0.5116	Remote Similarity	NPC246519

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC267340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7160
0.1-0.2	1964
0.2-0.3	26
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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