Structure

Physi-Chem Properties

Molecular Weight:  297.3
Volume:  354.331
LogP:  6.736
LogD:  4.247
LogS:  -4.285
# Rotatable Bonds:  17
TPSA:  29.1
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.348
Synthetic Accessibility Score:  1.786
Fsp3:  0.947
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.792
MDCK Permeability:  1.2705743756669108e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.577
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.244
Plasma Protein Binding (PPB):  97.40613555908203%
Volume Distribution (VD):  1.11
Pgp-substrate:  1.5510019063949585%

ADMET: Metabolism

CYP1A2-inhibitor:  0.19
CYP1A2-substrate:  0.223
CYP2C19-inhibitor:  0.455
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.18
CYP2C9-substrate:  0.863
CYP2D6-inhibitor:  0.5
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.405
CYP3A4-substrate:  0.063

ADMET: Excretion

Clearance (CL):  4.849
Half-life (T1/2):  0.304

ADMET: Toxicity

hERG Blockers:  0.318
Human Hepatotoxicity (H-HT):  0.041
Drug-inuced Liver Injury (DILI):  0.121
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.011
Skin Sensitization:  0.928
Carcinogencity:  0.045
Eye Corrosion:  0.047
Eye Irritation:  0.801
Respiratory Toxicity:  0.524

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  Natural Product: NPC241279

Natural Product ID:  NPC241279
Common Name*:   Hexadecanoic Acid Propylamide
IUPAC Name:   N-propylhexadecanamide
Synonyms:   Hexadecanoic Acid Propylamide
Standard InCHIKey:  HBMSIPLIFIVUKZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H39NO/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21)20-18-4-2/h3-18H2,1-2H3,(H,20,21)
SMILES:  CCCCCCCCCCCCCCCC(=NCCC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL35286
PubChem CID:   10379895
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
NPO21005 Baphia nitida Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(92)80059-N]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. DOI[10.1016/S0040-4039(00)86970-1]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. PMID[10869195]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. stem n.a. PMID[16508191]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[17340534]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. stem n.a. PMID[21469695]
NPO19192 Sinocalamus affinis Species n.a. n.a. skin-removed stems Pingle Town, Sichuang Province, China 2008-AUG PMID[21469695]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. PMID[22690646]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[23397723]
NPO20739 Jungermannia hyalina Species Jungermanniaceae Eukaryota n.a. Guangxi Zhuang Autonomous Region, China n.a. PMID[25856683]
NPO21618 Ircinia oros Species Irciniidae Eukaryota n.a. n.a. n.a. PMID[28840725]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. PMID[31182315]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[31276403]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota Fruits n.a. n.a. PMID[3760884]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6736970]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875576]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6875577]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[6875577]
NPO20671 Selliguea feei Species Polypodiaceae Eukaryota Rhizomes n.a. n.a. PMID[8254348]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11966 Euphorbia kamerunica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8678 Trillium camschatcense Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19901 Emilia sonchifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20931 Simaba multiflora Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21088 Litsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19192 Sinocalamus affinis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20671 Selliguea feei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20813 Myrmica sabuleti Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2854 Gymnosporia senegalensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21365 Ligularia muliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20051 Gardenia collinsae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21679 Nuphar lutea Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17515 Pronephrium triphyllum Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3777 Stevia chamaedrys Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11622.1 Shuteria involucrata var. vestita Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19017 Prangos pabularia Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19986 Crataegus davisii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21618 Ircinia oros Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16907 Pentzia incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3237 Mytilus edulis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4343 Guanomyces polythrix Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20212 Callistemon viminalis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14136 Acherontia atropus Species Sphingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15216 Encephalartos altensteinii Species Zamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16454 Crinum erubescens Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18620 Grindelia acutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14330 Agave aurea Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16044 Cupressus lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20612 Ursinia abrotanifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11966 Euphorbia kamerunica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20408 Ajuga spectabilis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19488 Trifolium subterraneum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20739 Jungermannia hyalina Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19773 Xenorhabdus bovienii Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13260 Eria foetida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20872 Melampodium heterophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21550 Achillea macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21005 Baphia nitida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22510 Eupatorium havanense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20340 Pausinystalia mayumbensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8678 Trillium camschatcense Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17256 Kobresia nepalensis Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21426 Alstroemeria revoluta Species Alstroemeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20546 Cissus pallidiflorus Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21231 Astragalus tragacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18096 Excoecaria oppositifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21486 Marrubium alysson Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21289 Teucrium oxylepis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26840 Litsea aciculata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19622 Euphorbia marginata Species Euphorbiaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT232 Individual Protein Cannabinoid CB1 receptor Homo sapiens Inhibition = 14.4 % PMID[473982]
NPT1287 Individual Protein Cannabinoid CB2 receptor Homo sapiens Inhibition = 6.1 % PMID[473982]
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 2754.23 nM PMID[473982]
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = 49.0 % PMID[473982]

☑ 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 NPC241279 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8837 High Similarity NPC289484
0.8837 High Similarity NPC319709
0.85 High Similarity NPC28394
0.85 High Similarity NPC31557
0.8261 Intermediate Similarity NPC329181
0.8261 Intermediate Similarity NPC319110
0.8 Intermediate Similarity NPC277333
0.74 Intermediate Similarity NPC270041
0.7037 Intermediate Similarity NPC216415
0.7037 Intermediate Similarity NPC476537
0.6977 Remote Similarity NPC111686
0.6909 Remote Similarity NPC325550
0.6909 Remote Similarity NPC326524
0.6909 Remote Similarity NPC329003
0.675 Remote Similarity NPC95174
0.6727 Remote Similarity NPC321030
0.6667 Remote Similarity NPC145627
0.66 Remote Similarity NPC80350
0.6585 Remote Similarity NPC139131
0.6585 Remote Similarity NPC291158
0.6585 Remote Similarity NPC185538
0.6585 Remote Similarity NPC272998
0.6585 Remote Similarity NPC205141
0.6585 Remote Similarity NPC181516
0.6552 Remote Similarity NPC316674
0.6538 Remote Similarity NPC49494
0.6538 Remote Similarity NPC188341
0.6364 Remote Similarity NPC150560
0.6346 Remote Similarity NPC261571
0.6341 Remote Similarity NPC126915
0.6279 Remote Similarity NPC97967
0.625 Remote Similarity NPC326521
0.619 Remote Similarity NPC152759
0.619 Remote Similarity NPC12231
0.6182 Remote Similarity NPC242930
0.6136 Remote Similarity NPC474914
0.6136 Remote Similarity NPC474392
0.6129 Remote Similarity NPC470110
0.6129 Remote Similarity NPC195165
0.6098 Remote Similarity NPC112242
0.6098 Remote Similarity NPC147096
0.6098 Remote Similarity NPC225783
0.6098 Remote Similarity NPC236797
0.6098 Remote Similarity NPC163556
0.6098 Remote Similarity NPC185041
0.6098 Remote Similarity NPC24506
0.6078 Remote Similarity NPC180402
0.6078 Remote Similarity NPC87359
0.6066 Remote Similarity NPC474402
0.6032 Remote Similarity NPC475808
0.6032 Remote Similarity NPC474298
0.6032 Remote Similarity NPC28348
0.6032 Remote Similarity NPC473985
0.6032 Remote Similarity NPC474299
0.6 Remote Similarity NPC74352
0.5968 Remote Similarity NPC470109
0.5938 Remote Similarity NPC103712
0.5938 Remote Similarity NPC291196
0.5932 Remote Similarity NPC477644
0.5926 Remote Similarity NPC123814
0.5926 Remote Similarity NPC474322
0.5862 Remote Similarity NPC325734
0.5846 Remote Similarity NPC477200
0.5814 Remote Similarity NPC72324
0.5814 Remote Similarity NPC193062
0.5814 Remote Similarity NPC66124
0.5814 Remote Similarity NPC145895
0.5814 Remote Similarity NPC1748
0.5814 Remote Similarity NPC319034
0.5806 Remote Similarity NPC470108
0.5789 Remote Similarity NPC471605
0.5789 Remote Similarity NPC471443
0.5769 Remote Similarity NPC121062
0.5769 Remote Similarity NPC29222
0.5769 Remote Similarity NPC96966
0.5745 Remote Similarity NPC221022
0.5714 Remote Similarity NPC471917
0.569 Remote Similarity NPC472578
0.5672 Remote Similarity NPC43219
0.5652 Remote Similarity NPC25237
0.5636 Remote Similarity NPC137327
0.561 Remote Similarity NPC279895

  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 NPC241279 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8837 High Similarity NPD3211 Approved
0.7778 Intermediate Similarity NPD1152 Phase 2
0.6875 Remote Similarity NPD379 Clinical (unspecified phase)
0.6585 Remote Similarity NPD2272 Approved
0.6585 Remote Similarity NPD5383 Approved
0.6154 Remote Similarity NPD3214 Discontinued
0.6087 Remote Similarity NPD9453 Phase 3
0.6078 Remote Similarity NPD362 Phase 1
0.6 Remote Similarity NPD1830 Clinical (unspecified phase)
0.5968 Remote Similarity NPD5380 Approved
0.5926 Remote Similarity NPD3215 Phase 1
0.5849 Remote Similarity NPD324 Approved
0.5769 Remote Similarity NPD4840 Approved
0.5758 Remote Similarity NPD3187 Discontinued
0.5758 Remote Similarity NPD6944 Clinical (unspecified phase)
0.5636 Remote Similarity NPD611 Approved
0.5636 Remote Similarity NPD609 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