NPASS Compound

Natural Product: NPC469760

Natural Product ID	NPC469760
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N-[2-(1H-Indol-3-Yl)Ethyl]Pentadecanamide
IUPAC Name	N-[2-(1H-indol-3-yl)ethyl]pentadecanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1170470
PubChem CID	46897117
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

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 68 69 0 0 0 0 0 0 0 0999 V2000 -7.2819 -3.8496 1.7641 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6255 -2.4126 1.5612 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6874 -1.4747 2.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1756 -0.0863 2.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4795 1.0395 2.6213 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 1.3999 2.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5804 1.7802 1.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5245 0.7615 -0.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5467 -0.3568 0.2958 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1284 0.1707 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6521 0.8460 -0.8200 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2171 1.3230 -0.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3272 2.0201 -1.7684 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 2.4967 -1.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 1.4234 -1.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4072 0.2024 -1.2184 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0638 1.8021 -1.0284 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0994 0.8320 -0.7399 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2855 -0.1749 -1.8543 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3776 -1.0944 -1.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2974 -2.3736 -0.9425 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5426 -2.7828 -0.7040 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4374 -1.8205 -1.0198 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8292 -1.7465 -0.9604 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4645 -0.5814 -1.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7789 0.5141 -1.8416 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3856 0.4074 -1.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7258 -0.7374 -1.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1967 -3.9572 2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9191 -4.3790 2.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3716 -4.3793 0.7851 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4732 -2.1490 0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6624 -2.1437 1.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6565 -1.6511 2.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8556 -1.7055 3.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2406 -0.0836 2.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4112 -0.0534 0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5920 0.9090 3.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1209 1.9753 2.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4310 0.6077 2.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8742 2.2918 3.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1024 2.7087 0.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5087 2.1751 1.1666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5087 0.3241 -0.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2390 1.2799 -0.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7528 -0.8379 1.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6170 -1.1179 -0.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0046 0.8244 1.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4835 -0.7335 0.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6078 0.1841 -1.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2263 1.7713 -1.0529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2364 2.1023 0.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3755 0.4972 -0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2657 1.3574 -2.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3087 2.9408 -1.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7349 3.2806 -0.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0964 3.0398 -2.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 2.8430 -1.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8896 0.3099 0.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0552 1.3807 -0.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3583 -0.7255 -2.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5811 0.3132 -2.8040 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4089 -2.9499 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8298 -3.7156 -0.3236 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4038 -2.5892 -0.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5426 -0.5428 -1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3021 1.4087 -2.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8207 1.2522 -2.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 20 1 0 28 23 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 21 63 1 0 22 64 1 0 24 65 1 0 25 66 1 0 26 67 1 0 27 68 1 0 M END

Standard InCHIKey	BBQOSPPWYMINSN-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C25H40N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-18-25(28)26-20-19-22-21-27-24-17-15-14-16-23(22)24/h14-17,21,27H,2-13,18-20H2,1H3,(H,26,28)
SMILES	CCCCCCCCCCCCCCC(=O)NCCC1=CNC2=CC=CC=C21

Calculated Properties

Physi-Chem Properties

Molecular Weight:	384.31	Volume:	441.445 ? Van der Waals volume.
Dense:	0.871	LogP:	6.853 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.445 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.699 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	11.0
TPSA:	44.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.303	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.03	Fsp³:	0.64
MCE-18:	10.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.747	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.507 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.123

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.116	MDCK Permeability:	-4.821
Pgp-inhibitor:	0.036	Pgp-substrate:	0.816
PAMPA:	0.005 ? 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):	0.842
20% Bioavailability (F20%):	0.733	30% Bioavailability (F30%):	0.943
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204	MRP1:	0.598
Plasma Protein Binding (PPB):	99.016%	Volume Distribution (VD):	0.749
Fu:	0.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.256
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.459
BSEP inhibitor:	0.978

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.033	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.101	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

5.514

Half-life (T1/2):

0.458

ADMET: Toxicity

hERG Blockers:	0.687	hERG Blockers (10um):	0.874
Human Hepatotoxicity (H-HT):	0.576	Drug-induced Liver Injury (DILI):	0.138
AMES Toxicity:	0.136	Rat Oral Acute Toxicity:	0.264
Maximum Recommended Daily Dose:	0.531	Skin Sensitization:	0.951
Carcinogencity:	0.26	Eye Corrosion:	0.019
Eye Irritation:	0.867	Respiratory Toxicity:	0.949
Drug-induced Neurotoxicity:	0.185	Ototoxicity:	0.357
Hematotoxicity:	0.161	Drug-induced Nephrotoxicity:	0.215
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.55	Hek293 Cytotoxicity:	0.2
BCF:	1.169 ? 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:	4.749 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.13 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.963 ? 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
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20579892]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23513739]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26920282]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Activity	2

Activity Type	# Activity
Cell line	2

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4564	Cell line	Neurons	n.a.	Activity	=	99.3	%	PMID[25681711]
NPT4564	Cell line	Neurons	n.a.	Activity	=	139.0	%	PMID[11473410]

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 NPC469760 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	30688
0.1-0.2	17560
0.2-0.3	1155
0.3-0.4	320
0.4-0.5	101
0.5-0.6	25
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469786
0.8235	Intermediate Similarity	NPC608269
0.8214	Intermediate Similarity	NPC469762
0.678	Remote Similarity	NPC605381
0.6441	Remote Similarity	NPC476460
0.5968	Remote Similarity	NPC259644
0.5968	Remote Similarity	NPC70922
0.5968	Remote Similarity	NPC211572
0.5968	Remote Similarity	NPC75540
0.5968	Remote Similarity	NPC212376
0.5968	Remote Similarity	NPC469765
0.5968	Remote Similarity	NPC80597
0.5968	Remote Similarity	NPC25008
0.5968	Remote Similarity	NPC73952
0.5357	Remote Similarity	NPC310665
0.5246	Remote Similarity	NPC602373
0.5211	Remote Similarity	NPC469763
0.5161	Remote Similarity	NPC314002
0.5161	Remote Similarity	NPC606242
0.5152	Remote Similarity	NPC611116
0.5147	Remote Similarity	NPC105818
0.5085	Remote Similarity	NPC600736
0.5079	Remote Similarity	NPC469780
0.5079	Remote Similarity	NPC469761
0.5079	Remote Similarity	NPC469783
0.5079	Remote Similarity	NPC469766
0.5079	Remote Similarity	NPC469779
0.5079	Remote Similarity	NPC469768
0.5079	Remote Similarity	NPC469784
0.5079	Remote Similarity	NPC602670

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4164
0.1-0.2	4801
0.2-0.3	129
0.3-0.4	48
0.4-0.5	8
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