Structure

Physi-Chem Properties

Molecular Weight:  234.09
Volume:  229.913
LogP:  -0.06
LogD:  0.463
LogS:  -2.118
# Rotatable Bonds:  8
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.398
Synthetic Accessibility Score:  2.839
Fsp3:  0.6
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:  -5.084
MDCK Permeability:  2.2676176740787923e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.426
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  96.00521087646484%
Volume Distribution (VD):  0.432
Pgp-substrate:  2.644455909729004%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.247
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.275
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.958
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.319
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  3.756
Half-life (T1/2):  0.85

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.634
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.544
Rat Oral Acute Toxicity:  0.027
Maximum Recommended Daily Dose:  0.655
Skin Sensitization:  0.958
Carcinogencity:  0.928
Eye Corrosion:  0.991
Eye Irritation:  0.986
Respiratory Toxicity:  0.982

Download Data

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

  Natural Product: NPC171978

Natural Product ID:  NPC171978
Common Name*:   (4Z,7E)-4,7-Decadienyl Sulfate
IUPAC Name:   [(4Z,7E)-deca-4,7-dienyl] hydrogen sulfate
Synonyms:   (4Z,7E)-4,7-Decadienyl Sulfate
Standard InCHIKey:  IUFFPMSLKYCSDC-FDTUMDBZSA-N
Standard InCHI:  InChI=1S/C10H18O4S/c1-2-3-4-5-6-7-8-9-10-14-15(11,12)13/h3-4,6-7H,2,5,8-10H2,1H3,(H,11,12,13)/b4-3+,7-6-
SMILES:  CC/C=C/C/C=CCCCOS(=O)(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460438
PubChem CID:   10331598
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[490208]
NPT5959 Organism Umbelopsis ramanniana Umbelopsis ramanniana IZ = 10.0 mm PMID[490208]

☑ 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 NPC171978 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 NPC277382
0.9474 High Similarity NPC469713
0.8919 High Similarity NPC195109
0.7317 Intermediate Similarity NPC34873
0.7317 Intermediate Similarity NPC40434
0.6744 Remote Similarity NPC15934
0.6585 Remote Similarity NPC58957
0.6522 Remote Similarity NPC252978
0.65 Remote Similarity NPC197356
0.65 Remote Similarity NPC63121
0.6383 Remote Similarity NPC108195
0.6364 Remote Similarity NPC182840
0.6364 Remote Similarity NPC103213
0.6364 Remote Similarity NPC255042
0.6364 Remote Similarity NPC29091
0.6341 Remote Similarity NPC250734
0.6304 Remote Similarity NPC206906
0.6304 Remote Similarity NPC304151
0.625 Remote Similarity NPC160628
0.625 Remote Similarity NPC140501
0.625 Remote Similarity NPC329424
0.625 Remote Similarity NPC221379
0.625 Remote Similarity NPC276825
0.625 Remote Similarity NPC76976
0.6222 Remote Similarity NPC103236
0.6222 Remote Similarity NPC27444
0.6222 Remote Similarity NPC123357
0.6222 Remote Similarity NPC329762
0.62 Remote Similarity NPC302310
0.617 Remote Similarity NPC116934
0.617 Remote Similarity NPC270796
0.6136 Remote Similarity NPC226511
0.6087 Remote Similarity NPC33489
0.6087 Remote Similarity NPC269823
0.6078 Remote Similarity NPC291437
0.6078 Remote Similarity NPC328784
0.6078 Remote Similarity NPC474460
0.6047 Remote Similarity NPC75204
0.6042 Remote Similarity NPC138935
0.6 Remote Similarity NPC33761
0.6 Remote Similarity NPC318549
0.5962 Remote Similarity NPC71053
0.5962 Remote Similarity NPC151782
0.5962 Remote Similarity NPC59408
0.5957 Remote Similarity NPC187922
0.5957 Remote Similarity NPC68889
0.5957 Remote Similarity NPC67761
0.5957 Remote Similarity NPC180871
0.5957 Remote Similarity NPC88079
0.5957 Remote Similarity NPC287397
0.5957 Remote Similarity NPC298710
0.5957 Remote Similarity NPC256766
0.5957 Remote Similarity NPC67920
0.5957 Remote Similarity NPC149668
0.5957 Remote Similarity NPC108494
0.5957 Remote Similarity NPC213538
0.5957 Remote Similarity NPC194586
0.5957 Remote Similarity NPC51758
0.5957 Remote Similarity NPC209279
0.5957 Remote Similarity NPC57923
0.5957 Remote Similarity NPC208936
0.5918 Remote Similarity NPC24824
0.5918 Remote Similarity NPC165651
0.5918 Remote Similarity NPC210560
0.5918 Remote Similarity NPC269074
0.5918 Remote Similarity NPC117572
0.5909 Remote Similarity NPC279300
0.5897 Remote Similarity NPC138325
0.5882 Remote Similarity NPC98284
0.5882 Remote Similarity NPC31194
0.5882 Remote Similarity NPC85079
0.5882 Remote Similarity NPC153538
0.5882 Remote Similarity NPC207815
0.5882 Remote Similarity NPC248884
0.587 Remote Similarity NPC323278
0.587 Remote Similarity NPC12319
0.587 Remote Similarity NPC56917
0.587 Remote Similarity NPC18205
0.5849 Remote Similarity NPC35756
0.5814 Remote Similarity NPC72258
0.58 Remote Similarity NPC19834
0.58 Remote Similarity NPC124183
0.58 Remote Similarity NPC157096
0.58 Remote Similarity NPC55063
0.58 Remote Similarity NPC35141
0.58 Remote Similarity NPC180575
0.5778 Remote Similarity NPC155880
0.5778 Remote Similarity NPC92863
0.5769 Remote Similarity NPC225974
0.5769 Remote Similarity NPC288381
0.5769 Remote Similarity NPC20934
0.5769 Remote Similarity NPC72699
0.575 Remote Similarity NPC34671
0.575 Remote Similarity NPC138113
0.5745 Remote Similarity NPC188596
0.5741 Remote Similarity NPC284224
0.5741 Remote Similarity NPC475723
0.5714 Remote Similarity NPC101616
0.5714 Remote Similarity NPC12907
0.5686 Remote Similarity NPC91495
0.5682 Remote Similarity NPC277288
0.5682 Remote Similarity NPC79544
0.5682 Remote Similarity NPC213767
0.566 Remote Similarity NPC129263
0.566 Remote Similarity NPC55383
0.566 Remote Similarity NPC474495
0.566 Remote Similarity NPC93639
0.566 Remote Similarity NPC473672
0.566 Remote Similarity NPC29234
0.5652 Remote Similarity NPC217923
0.5652 Remote Similarity NPC57011
0.5636 Remote Similarity NPC49059
0.5636 Remote Similarity NPC110732
0.5636 Remote Similarity NPC300121
0.5636 Remote Similarity NPC256209
0.5636 Remote Similarity NPC137538
0.5625 Remote Similarity NPC46248
0.5625 Remote Similarity NPC249801
0.5614 Remote Similarity NPC323436
0.561 Remote Similarity NPC60288
0.56 Remote Similarity NPC47946
0.56 Remote Similarity NPC474362
0.56 Remote Similarity NPC474202
0.56 Remote Similarity NPC26600
0.56 Remote Similarity NPC239754

  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 NPC171978 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
0.6383 Remote Similarity NPD6096 Approved
0.6383 Remote Similarity NPD6097 Approved
0.625 Remote Similarity NPD4265 Approved
0.617 Remote Similarity NPD5326 Phase 3
0.6 Remote Similarity NPD5343 Approved
0.5918 Remote Similarity NPD39 Approved
0.5918 Remote Similarity NPD4222 Approved
0.5769 Remote Similarity NPD2268 Discontinued
0.56 Remote Similarity NPD3174 Discontinued

  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