Structure

Physi-Chem Properties

Molecular Weight:  254.26
Volume:  308.742
LogP:  6.524
LogD:  4.673
LogS:  -6.227
# Rotatable Bonds:  14
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.344
Synthetic Accessibility Score:  1.742
Fsp3:  0.941
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:  -4.732
MDCK Permeability:  1.012794382404536e-05
Pgp-inhibitor:  0.018
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.509
Plasma Protein Binding (PPB):  98.20846557617188%
Volume Distribution (VD):  1.467
Pgp-substrate:  1.3256471157073975%

ADMET: Metabolism

CYP1A2-inhibitor:  0.324
CYP1A2-substrate:  0.22
CYP2C19-inhibitor:  0.36
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.183
CYP2C9-substrate:  0.945
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.126
CYP3A4-inhibitor:  0.281
CYP3A4-substrate:  0.056

ADMET: Excretion

Clearance (CL):  5.759
Half-life (T1/2):  0.496

ADMET: Toxicity

hERG Blockers:  0.177
Human Hepatotoxicity (H-HT):  0.038
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.839
Carcinogencity:  0.043
Eye Corrosion:  0.923
Eye Irritation:  0.957
Respiratory Toxicity:  0.925

Download Data

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

  Natural Product: NPC225318

Natural Product ID:  NPC225318
Common Name*:   Heptadecan-9-One
IUPAC Name:   heptadecan-9-one
Synonyms:  
Standard InCHIKey:  WTJKUFMLQFLJOT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H34O/c1-3-5-7-9-11-13-15-17(18)16-14-12-10-8-6-4-2/h3-16H2,1-2H3
SMILES:  CCCCCCCCC(=O)CCCCCCCC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2398215
PubChem CID:   10887
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones

*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
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26650 Terminalia chebula Species Combretaceae 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
NPT862 Individual Protein Epoxide hydratase Homo sapiens IC50 > 100000.0 nM PMID[450960]

☑ 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 NPC225318 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
1.0 High Similarity NPC149101
1.0 High Similarity NPC16578
1.0 High Similarity NPC76608
0.931 High Similarity NPC42403
0.931 High Similarity NPC29561
0.931 High Similarity NPC221192
0.931 High Similarity NPC79887
0.931 High Similarity NPC153439
0.931 High Similarity NPC196434
0.931 High Similarity NPC222997
0.931 High Similarity NPC4962
0.9 High Similarity NPC168982
0.8966 High Similarity NPC295442
0.8966 High Similarity NPC198118
0.8966 High Similarity NPC38859
0.871 High Similarity NPC268596
0.8182 Intermediate Similarity NPC49615
0.8065 Intermediate Similarity NPC158107
0.7931 Intermediate Similarity NPC66624
0.7714 Intermediate Similarity NPC301919
0.7667 Intermediate Similarity NPC79591
0.7576 Intermediate Similarity NPC261991
0.7576 Intermediate Similarity NPC254713
0.7576 Intermediate Similarity NPC179831
0.7576 Intermediate Similarity NPC262505
0.7576 Intermediate Similarity NPC49151
0.7297 Intermediate Similarity NPC223315
0.725 Intermediate Similarity NPC74845
0.7105 Intermediate Similarity NPC141634
0.7073 Intermediate Similarity NPC469781
0.7 Intermediate Similarity NPC30338
0.6923 Remote Similarity NPC12156
0.6923 Remote Similarity NPC28598
0.6923 Remote Similarity NPC135077
0.6923 Remote Similarity NPC215118
0.6923 Remote Similarity NPC45270
0.6923 Remote Similarity NPC59570
0.6923 Remote Similarity NPC161097
0.6897 Remote Similarity NPC32603
0.6829 Remote Similarity NPC317128
0.6774 Remote Similarity NPC129976
0.6765 Remote Similarity NPC321646
0.675 Remote Similarity NPC196924
0.675 Remote Similarity NPC307783
0.675 Remote Similarity NPC171736
0.675 Remote Similarity NPC216630
0.675 Remote Similarity NPC209970
0.675 Remote Similarity NPC149184
0.6667 Remote Similarity NPC47363
0.6667 Remote Similarity NPC33928
0.6667 Remote Similarity NPC287231
0.6667 Remote Similarity NPC32279
0.6585 Remote Similarity NPC18397
0.6585 Remote Similarity NPC67462
0.6585 Remote Similarity NPC236579
0.6585 Remote Similarity NPC203531
0.6579 Remote Similarity NPC69245
0.6552 Remote Similarity NPC141986
0.6486 Remote Similarity NPC156630
0.6429 Remote Similarity NPC76051
0.641 Remote Similarity NPC201622
0.641 Remote Similarity NPC305660
0.641 Remote Similarity NPC22903
0.641 Remote Similarity NPC54980
0.6364 Remote Similarity NPC328497
0.6364 Remote Similarity NPC100997
0.6364 Remote Similarity NPC324004
0.6333 Remote Similarity NPC222945
0.6279 Remote Similarity NPC8219
0.625 Remote Similarity NPC301696
0.625 Remote Similarity NPC31551
0.625 Remote Similarity NPC219536
0.625 Remote Similarity NPC14227
0.625 Remote Similarity NPC301585
0.625 Remote Similarity NPC201844
0.625 Remote Similarity NPC261080
0.625 Remote Similarity NPC113928
0.625 Remote Similarity NPC154186
0.625 Remote Similarity NPC279026
0.6222 Remote Similarity NPC106872
0.6207 Remote Similarity NPC147212
0.619 Remote Similarity NPC301528
0.619 Remote Similarity NPC129972
0.619 Remote Similarity NPC71317
0.619 Remote Similarity NPC473674
0.617 Remote Similarity NPC477458
0.6154 Remote Similarity NPC220061
0.6136 Remote Similarity NPC12438
0.6136 Remote Similarity NPC30195
0.6129 Remote Similarity NPC254524
0.6129 Remote Similarity NPC185768
0.6098 Remote Similarity NPC250028
0.6098 Remote Similarity NPC165533
0.6098 Remote Similarity NPC149299
0.6098 Remote Similarity NPC256163
0.6098 Remote Similarity NPC40597
0.6061 Remote Similarity NPC59581
0.6053 Remote Similarity NPC218357
0.6047 Remote Similarity NPC171783
0.6047 Remote Similarity NPC19305
0.6047 Remote Similarity NPC255837
0.6 Remote Similarity NPC131981
0.6 Remote Similarity NPC44363
0.6 Remote Similarity NPC98246
0.6 Remote Similarity NPC173996
0.6 Remote Similarity NPC21844
0.6 Remote Similarity NPC285814
0.6 Remote Similarity NPC163751
0.6 Remote Similarity NPC110234
0.6 Remote Similarity NPC83187
0.6 Remote Similarity NPC40249
0.5957 Remote Similarity NPC55678
0.5957 Remote Similarity NPC474391
0.5957 Remote Similarity NPC90904
0.5952 Remote Similarity NPC103286
0.5952 Remote Similarity NPC141914
0.5952 Remote Similarity NPC53541
0.5952 Remote Similarity NPC163746
0.587 Remote Similarity NPC294440
0.587 Remote Similarity NPC477878
0.587 Remote Similarity NPC324793
0.5862 Remote Similarity NPC239406
0.5862 Remote Similarity NPC26229
0.5862 Remote Similarity NPC77249
0.5862 Remote Similarity NPC154477
0.5862 Remote Similarity NPC211453
0.5862 Remote Similarity NPC26974
0.5854 Remote Similarity NPC80234
0.5854 Remote Similarity NPC183424
0.5854 Remote Similarity NPC223249
0.5854 Remote Similarity NPC214610
0.5854 Remote Similarity NPC118968
0.5854 Remote Similarity NPC294085
0.5833 Remote Similarity NPC287811
0.5789 Remote Similarity NPC248190
0.5778 Remote Similarity NPC52700
0.5778 Remote Similarity NPC105329
0.5778 Remote Similarity NPC145045
0.5778 Remote Similarity NPC63182
0.5778 Remote Similarity NPC239754
0.5758 Remote Similarity NPC227197
0.5758 Remote Similarity NPC307594
0.5745 Remote Similarity NPC26253
0.5745 Remote Similarity NPC293343
0.5745 Remote Similarity NPC247786
0.5745 Remote Similarity NPC145311
0.5745 Remote Similarity NPC258672
0.5745 Remote Similarity NPC304162
0.5714 Remote Similarity NPC471607
0.5714 Remote Similarity NPC48930
0.5686 Remote Similarity NPC184819
0.5686 Remote Similarity NPC307063
0.5652 Remote Similarity NPC326957
0.5641 Remote Similarity NPC121215
0.5625 Remote Similarity NPC116906
0.561 Remote Similarity NPC155880
0.561 Remote Similarity NPC268826
0.561 Remote Similarity NPC92863

  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 NPC225318 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
0.7297 Intermediate Similarity NPD3206 Approved
0.675 Remote Similarity NPD2270 Approved
0.6667 Remote Similarity NPD2699 Approved
0.6279 Remote Similarity NPD3199 Clinical (unspecified phase)
0.625 Remote Similarity NPD633 Phase 3
0.625 Remote Similarity NPD9448 Phase 2
0.6 Remote Similarity NPD344 Approved
0.6 Remote Similarity NPD345 Approved
0.6 Remote Similarity NPD343 Approved
0.587 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5854 Remote Similarity NPD9655 Approved
0.5814 Remote Similarity NPD387 Clinical (unspecified phase)

  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