Structure

Physi-Chem Properties

Molecular Weight:  208.08
Volume:  197.958
LogP:  -0.474
LogD:  -0.158
LogS:  -1.166
# 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:  0.394
Synthetic Accessibility Score:  2.547
Fsp3:  0.75
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:  -5.007
MDCK Permeability:  2.026339279836975e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.265
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.103
Plasma Protein Binding (PPB):  86.30855560302734%
Volume Distribution (VD):  0.466
Pgp-substrate:  14.22474193572998%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.555
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.622
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.917
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.272
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  4.837
Half-life (T1/2):  0.738

ADMET: Toxicity

hERG Blockers:  0.089
Human Hepatotoxicity (H-HT):  0.227
Drug-inuced Liver Injury (DILI):  0.018
AMES Toxicity:  0.804
Rat Oral Acute Toxicity:  0.205
Maximum Recommended Daily Dose:  0.163
Skin Sensitization:  0.945
Carcinogencity:  0.912
Eye Corrosion:  0.991
Eye Irritation:  0.989
Respiratory Toxicity:  0.981

Download Data

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

  Natural Product: NPC469713

Natural Product ID:  NPC469713
Common Name*:   (E)-5-Octenyl Sulfate
IUPAC Name:   [(Z)-oct-5-enyl] hydrogen sulfate
Synonyms:   (E)-5-Octenyl Sulfate
Standard InCHIKey:  VWHWMQCIWRGWAE-ARJAWSKDSA-N
Standard InCHI:  InChI=1S/C8H16O4S/c1-2-3-4-5-6-7-8-12-13(9,10)11/h3-4H,2,5-8H2,1H3,(H,9,10,11)/b4-3-
SMILES:  CC/C=CCCCCOS(=O)(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1162329
PubChem CID:   10058896
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
NPO18164 Halocynthia papillosa Species Pyuridae Eukaryota n.a. mediterranean n.a. PMID[11087619]
NPO18164 Halocynthia papillosa 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
NPT3470 Cell Line WEHI-164 Mus musculus IC50 = 12.2 ug.mL-1 PMID[536529]
NPT76 Cell Line C6 Rattus norvegicus IC50 = 515.2 ug.mL-1 PMID[536529]

☑ 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 NPC469713 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
0.9474 High Similarity NPC171978
0.9474 High Similarity NPC277382
0.8462 Intermediate Similarity NPC195109
0.7805 Intermediate Similarity NPC34873
0.7805 Intermediate Similarity NPC40434
0.6957 Remote Similarity NPC252978
0.6818 Remote Similarity NPC15934
0.6667 Remote Similarity NPC76976
0.6667 Remote Similarity NPC140501
0.6458 Remote Similarity NPC108195
0.6444 Remote Similarity NPC103213
0.6444 Remote Similarity NPC255042
0.6444 Remote Similarity NPC182840
0.6444 Remote Similarity NPC29091
0.6383 Remote Similarity NPC206906
0.6383 Remote Similarity NPC304151
0.6327 Remote Similarity NPC210560
0.6327 Remote Similarity NPC117572
0.6327 Remote Similarity NPC24824
0.6327 Remote Similarity NPC221379
0.6327 Remote Similarity NPC276825
0.6327 Remote Similarity NPC165651
0.6327 Remote Similarity NPC160628
0.6316 Remote Similarity NPC329424
0.6304 Remote Similarity NPC329762
0.6304 Remote Similarity NPC27444
0.6304 Remote Similarity NPC103236
0.6279 Remote Similarity NPC58957
0.6275 Remote Similarity NPC207815
0.6275 Remote Similarity NPC98284
0.6275 Remote Similarity NPC302310
0.625 Remote Similarity NPC116934
0.619 Remote Similarity NPC63121
0.619 Remote Similarity NPC197356
0.617 Remote Similarity NPC269823
0.617 Remote Similarity NPC33489
0.6154 Remote Similarity NPC291437
0.6154 Remote Similarity NPC474460
0.6154 Remote Similarity NPC328784
0.6122 Remote Similarity NPC138935
0.6087 Remote Similarity NPC33761
0.6078 Remote Similarity NPC318549
0.6078 Remote Similarity NPC91495
0.6047 Remote Similarity NPC250734
0.6042 Remote Similarity NPC256766
0.6042 Remote Similarity NPC249801
0.6042 Remote Similarity NPC180871
0.6042 Remote Similarity NPC213538
0.6042 Remote Similarity NPC51758
0.6042 Remote Similarity NPC149668
0.6042 Remote Similarity NPC67920
0.6042 Remote Similarity NPC108494
0.6042 Remote Similarity NPC88079
0.6042 Remote Similarity NPC208936
0.6042 Remote Similarity NPC46248
0.6042 Remote Similarity NPC194586
0.6042 Remote Similarity NPC287397
0.6042 Remote Similarity NPC67761
0.6042 Remote Similarity NPC209279
0.6042 Remote Similarity NPC298710
0.6042 Remote Similarity NPC68889
0.6038 Remote Similarity NPC473672
0.6038 Remote Similarity NPC71053
0.6038 Remote Similarity NPC474495
0.6038 Remote Similarity NPC59408
0.6038 Remote Similarity NPC129263
0.6038 Remote Similarity NPC151782
0.6 Remote Similarity NPC256209
0.6 Remote Similarity NPC269074
0.6 Remote Similarity NPC138325
0.6 Remote Similarity NPC110732
0.6 Remote Similarity NPC49059
0.6 Remote Similarity NPC137538
0.6 Remote Similarity NPC279300
0.5965 Remote Similarity NPC323436
0.5962 Remote Similarity NPC62755
0.5962 Remote Similarity NPC85079
0.5962 Remote Similarity NPC234597
0.5962 Remote Similarity NPC163345
0.5962 Remote Similarity NPC149821
0.5962 Remote Similarity NPC248884
0.5962 Remote Similarity NPC5413
0.5962 Remote Similarity NPC153538
0.5962 Remote Similarity NPC31194
0.5957 Remote Similarity NPC323278
0.5957 Remote Similarity NPC12319
0.5957 Remote Similarity NPC18205
0.5957 Remote Similarity NPC123357
0.5926 Remote Similarity NPC35756
0.5918 Remote Similarity NPC270796
0.5918 Remote Similarity NPC269862
0.5893 Remote Similarity NPC52264
0.5893 Remote Similarity NPC227135
0.5893 Remote Similarity NPC242930
0.5893 Remote Similarity NPC281590
0.5893 Remote Similarity NPC317899
0.5882 Remote Similarity NPC124183
0.5882 Remote Similarity NPC35141
0.5882 Remote Similarity NPC42304
0.5882 Remote Similarity NPC19834
0.5882 Remote Similarity NPC180575
0.5882 Remote Similarity NPC55063
0.5882 Remote Similarity NPC157096
0.587 Remote Similarity NPC92863
0.587 Remote Similarity NPC155880
0.587 Remote Similarity NPC226511
0.5854 Remote Similarity NPC138113
0.5854 Remote Similarity NPC34671
0.5849 Remote Similarity NPC289388
0.5849 Remote Similarity NPC59051
0.5849 Remote Similarity NPC20934
0.5849 Remote Similarity NPC72699
0.5849 Remote Similarity NPC225974
0.5849 Remote Similarity NPC288381
0.5833 Remote Similarity NPC188596
0.5818 Remote Similarity NPC475723
0.5818 Remote Similarity NPC474496
0.5818 Remote Similarity NPC217188
0.5818 Remote Similarity NPC26102
0.5818 Remote Similarity NPC187361
0.5818 Remote Similarity NPC477724
0.5818 Remote Similarity NPC34577
0.5818 Remote Similarity NPC284224
0.58 Remote Similarity NPC101616
0.58 Remote Similarity NPC12907
0.5789 Remote Similarity NPC324224
0.5789 Remote Similarity NPC327388
0.5789 Remote Similarity NPC472808
0.5778 Remote Similarity NPC79544
0.5778 Remote Similarity NPC75204
0.5778 Remote Similarity NPC213767
0.5769 Remote Similarity NPC207292
0.5763 Remote Similarity NPC318306
0.5763 Remote Similarity NPC329249
0.5745 Remote Similarity NPC217923
0.5745 Remote Similarity NPC57011
0.5741 Remote Similarity NPC93639
0.5741 Remote Similarity NPC48162
0.5741 Remote Similarity NPC200772
0.5741 Remote Similarity NPC55383
0.5741 Remote Similarity NPC29234
0.5741 Remote Similarity NPC244452
0.5741 Remote Similarity NPC28205
0.5714 Remote Similarity NPC187922
0.5714 Remote Similarity NPC300121
0.5714 Remote Similarity NPC473532
0.5714 Remote Similarity NPC57923
0.5714 Remote Similarity NPC60288
0.569 Remote Similarity NPC323597
0.569 Remote Similarity NPC52012
0.569 Remote Similarity NPC470970
0.569 Remote Similarity NPC211752
0.569 Remote Similarity NPC323498
0.5686 Remote Similarity NPC474202
0.5686 Remote Similarity NPC239754
0.5686 Remote Similarity NPC26600
0.5686 Remote Similarity NPC47946
0.5686 Remote Similarity NPC474362
0.5667 Remote Similarity NPC81896
0.5667 Remote Similarity NPC258788
0.5667 Remote Similarity NPC328311
0.5667 Remote Similarity NPC321919
0.566 Remote Similarity NPC471276
0.566 Remote Similarity NPC125122
0.566 Remote Similarity NPC471280
0.566 Remote Similarity NPC135698
0.566 Remote Similarity NPC91765
0.566 Remote Similarity NPC267110
0.566 Remote Similarity NPC471275
0.5652 Remote Similarity NPC216416
0.5652 Remote Similarity NPC185839
0.5636 Remote Similarity NPC281245
0.5636 Remote Similarity NPC92114
0.5636 Remote Similarity NPC40417
0.5636 Remote Similarity NPC294358
0.5636 Remote Similarity NPC142092
0.5636 Remote Similarity NPC170167
0.5625 Remote Similarity NPC56917
0.5614 Remote Similarity NPC200845
0.5614 Remote Similarity NPC475353
0.5614 Remote Similarity NPC473725
0.5614 Remote Similarity NPC10316
0.5614 Remote Similarity NPC477726
0.5614 Remote Similarity NPC473735
0.5614 Remote Similarity NPC477725
0.5614 Remote Similarity NPC28779
0.5614 Remote Similarity NPC473721
0.5614 Remote Similarity NPC128061
0.5614 Remote Similarity NPC474913
0.5614 Remote Similarity NPC473896
0.5614 Remote Similarity NPC223677
0.5614 Remote Similarity NPC473910
0.56 Remote Similarity NPC106819

  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 NPC469713 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
0.6667 Remote Similarity NPD4265 Approved
0.64 Remote Similarity NPD5343 Approved
0.6327 Remote Similarity NPD4222 Approved
0.6122 Remote Similarity NPD6097 Approved
0.6122 Remote Similarity NPD6096 Approved
0.6 Remote Similarity NPD3174 Discontinued
0.6 Remote Similarity NPD39 Approved
0.5962 Remote Similarity NPD3173 Approved
0.5918 Remote Similarity NPD5326 Phase 3
0.5849 Remote Similarity NPD2268 Discontinued
0.5625 Remote Similarity NPD1153 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