Structure

Physi-Chem Properties

Molecular Weight:  224.11
Volume:  217.89
LogP:  1.126
LogD:  1.483
LogS:  -1.187
# Rotatable Bonds:  7
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.674
Synthetic Accessibility Score:  2.889
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.637
MDCK Permeability:  2.533460792619735e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.052
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.466
Plasma Protein Binding (PPB):  93.5051498413086%
Volume Distribution (VD):  0.389
Pgp-substrate:  5.4484686851501465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.367
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.882
CYP2C9-inhibitor:  0.076
CYP2C9-substrate:  0.944
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.156
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.041

ADMET: Excretion

Clearance (CL):  3.536
Half-life (T1/2):  0.134

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.674
Drug-inuced Liver Injury (DILI):  0.063
AMES Toxicity:  0.308
Rat Oral Acute Toxicity:  0.055
Maximum Recommended Daily Dose:  0.079
Skin Sensitization:  0.951
Carcinogencity:  0.855
Eye Corrosion:  0.995
Eye Irritation:  0.986
Respiratory Toxicity:  0.985

Download Data

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

  Natural Product: NPC473568

Natural Product ID:  NPC473568
Common Name*:   2,6-Dimethylheptylsulfate
IUPAC Name:   2,6-dimethylheptyl hydrogen sulfate
Synonyms:   2,6-Dimethylheptylsulfate
Standard InCHIKey:  LICTUMJMBMBMQH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H20O4S/c1-8(2)5-4-6-9(3)7-13-14(10,11)12/h8-9H,4-7H2,1-3H3,(H,10,11,12)
SMILES:  CC(COS(=O)(=O)O)CCCC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445873
PubChem CID:   21630867
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000403] Organic sulfuric acids and derivatives
        • [CHEMONTID:0003455] Sulfuric acid esters
          • [CHEMONTID:0001185] Sulfuric acid monoesters

*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
NPO21633 Halocynthia roretzi Species Pyuridae Eukaryota n.a. n.a. n.a. PMID[7853012]
NPO21633 Halocynthia roretzi Species Pyuridae 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
NPT1845 Organism Vibrio alginolyticus Vibrio alginolyticus IZ = 12.0 mm PMID[458386]
NPT5959 Organism Umbelopsis ramanniana Umbelopsis ramanniana IZ = 10.0 mm PMID[458386]

☑ 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 NPC473568 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 NPC469714
1.0 High Similarity NPC469712
0.8049 Intermediate Similarity NPC474126
0.8049 Intermediate Similarity NPC474125
0.7778 Intermediate Similarity NPC272426
0.7368 Intermediate Similarity NPC474120
0.7368 Intermediate Similarity NPC474089
0.725 Intermediate Similarity NPC177022
0.6923 Remote Similarity NPC283682
0.6905 Remote Similarity NPC221022
0.6857 Remote Similarity NPC474048
0.6364 Remote Similarity NPC160261
0.6364 Remote Similarity NPC469759
0.6279 Remote Similarity NPC316546
0.625 Remote Similarity NPC249754
0.619 Remote Similarity NPC61665
0.619 Remote Similarity NPC328441
0.617 Remote Similarity NPC215358
0.6154 Remote Similarity NPC147096
0.6154 Remote Similarity NPC163556
0.6154 Remote Similarity NPC225783
0.6154 Remote Similarity NPC24506
0.6154 Remote Similarity NPC185041
0.6154 Remote Similarity NPC236797
0.6154 Remote Similarity NPC112242
0.6053 Remote Similarity NPC279895
0.6042 Remote Similarity NPC87439
0.6042 Remote Similarity NPC473914
0.6 Remote Similarity NPC126915
0.5957 Remote Similarity NPC144891
0.5918 Remote Similarity NPC198540
0.5918 Remote Similarity NPC287550
0.5918 Remote Similarity NPC147343
0.5918 Remote Similarity NPC176309
0.5918 Remote Similarity NPC84030
0.5918 Remote Similarity NPC223468
0.5854 Remote Similarity NPC193062
0.5854 Remote Similarity NPC152759
0.5854 Remote Similarity NPC72324
0.5854 Remote Similarity NPC139131
0.5854 Remote Similarity NPC205141
0.5854 Remote Similarity NPC147054
0.5854 Remote Similarity NPC66124
0.5854 Remote Similarity NPC12231
0.5854 Remote Similarity NPC319034
0.5854 Remote Similarity NPC1748
0.5854 Remote Similarity NPC291158
0.5854 Remote Similarity NPC185538
0.5854 Remote Similarity NPC181516
0.5854 Remote Similarity NPC272998
0.5833 Remote Similarity NPC55023
0.5814 Remote Similarity NPC474914
0.5814 Remote Similarity NPC474392
0.58 Remote Similarity NPC13105
0.5789 Remote Similarity NPC39869
0.5789 Remote Similarity NPC125506
0.5789 Remote Similarity NPC276332
0.5769 Remote Similarity NPC307022
0.5714 Remote Similarity NPC77550
0.5714 Remote Similarity NPC108441
0.5714 Remote Similarity NPC308301
0.5714 Remote Similarity NPC314679
0.5714 Remote Similarity NPC286498
0.5682 Remote Similarity NPC74352
0.5682 Remote Similarity NPC14608
0.5652 Remote Similarity NPC152008
0.561 Remote Similarity NPC122962
0.561 Remote Similarity NPC267243
0.56 Remote Similarity NPC21844

  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 NPC473568 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
0.8974 High Similarity NPD1462 Approved
0.8462 Intermediate Similarity NPD1460 Approved
0.7778 Intermediate Similarity NPD1461 Approved
0.7778 Intermediate Similarity NPD907 Approved
0.7778 Intermediate Similarity NPD908 Approved
0.5918 Remote Similarity NPD384 Approved
0.5918 Remote Similarity NPD385 Approved
0.587 Remote Similarity NPD9426 Discontinued
0.5854 Remote Similarity NPD5383 Approved
0.5854 Remote Similarity NPD2272 Approved
0.5789 Remote Similarity NPD4280 Approved
0.5714 Remote Similarity NPD386 Approved
0.5714 Remote Similarity NPD388 Approved
0.5714 Remote Similarity NPD634 Phase 3
0.5652 Remote Similarity NPD7536 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