Structure

Physi-Chem Properties

Molecular Weight:  538.41
Volume:  571.956
LogP:  3.173
LogD:  3.128
LogS:  -3.06
# Rotatable Bonds:  34
TPSA:  94.07
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.122
Synthetic Accessibility Score:  2.291
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.735
MDCK Permeability:  1.438988147128839e-05
Pgp-inhibitor:  0.465
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.0
20% Bioavailability (F20%):  0.096
30% Bioavailability (F30%):  0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  87.89025115966797%
Volume Distribution (VD):  0.554
Pgp-substrate:  3.8905446529388428%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.049
CYP2C19-inhibitor:  0.06
CYP2C19-substrate:  0.046
CYP2C9-inhibitor:  0.175
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.002
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.057

ADMET: Excretion

Clearance (CL):  4.647
Half-life (T1/2):  0.219

ADMET: Toxicity

hERG Blockers:  0.997
Human Hepatotoxicity (H-HT):  0.011
Drug-inuced Liver Injury (DILI):  0.0
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.964
Carcinogencity:  0.612
Eye Corrosion:  0.045
Eye Irritation:  0.968
Respiratory Toxicity:  0.002

Download Data

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

  Natural Product: NPC152008

Natural Product ID:  NPC152008
Common Name*:   2-[2-[2-[2-[2-[2-[2-(2-Dodecoxyethoxy)Ethoxy]Ethoxy]Ethoxy]Ethoxy]Ethoxy]Ethoxy]Ethanol
IUPAC Name:   2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol
Synonyms:  
Standard InCHIKey:  YYELLDKEOUKVIQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C28H58O9/c1-2-3-4-5-6-7-8-9-10-11-13-30-15-17-32-19-21-34-23-25-36-27-28-37-26-24-35-22-20-33-18-16-31-14-12-29/h29H,2-28H2,1H3
SMILES:  CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501722
PubChem CID:   123921
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0001167] Dialkyl ethers
            • [CHEMONTID:0003338] Polyethylene glycols

*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
NPO26967 Phallus impudicus Species Phallaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26967 Phallus impudicus Species Phallaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26967 Phallus impudicus Species Phallaceae 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
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 59000.0 nM PMID[476123]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 29000.0 nM PMID[476123]
NPT2 Others Unspecified Ratio IC50 = 2.0 n.a. PMID[476123]

☑ 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 NPC152008 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
0.9459 High Similarity NPC197039
0.7727 Intermediate Similarity NPC62014
0.7632 Intermediate Similarity NPC12231
0.7632 Intermediate Similarity NPC185538
0.7632 Intermediate Similarity NPC181516
0.7632 Intermediate Similarity NPC205141
0.7632 Intermediate Similarity NPC139131
0.7632 Intermediate Similarity NPC291158
0.7632 Intermediate Similarity NPC152759
0.7632 Intermediate Similarity NPC272998
0.75 Intermediate Similarity NPC474914
0.75 Intermediate Similarity NPC474392
0.7447 Intermediate Similarity NPC26253
0.7391 Intermediate Similarity NPC8597
0.7368 Intermediate Similarity NPC126915
0.7317 Intermediate Similarity NPC74352
0.725 Intermediate Similarity NPC97967
0.7105 Intermediate Similarity NPC163556
0.7105 Intermediate Similarity NPC112242
0.7105 Intermediate Similarity NPC147096
0.7105 Intermediate Similarity NPC185041
0.7105 Intermediate Similarity NPC24506
0.7105 Intermediate Similarity NPC225783
0.7105 Intermediate Similarity NPC236797
0.7059 Intermediate Similarity NPC53463
0.7059 Intermediate Similarity NPC23155
0.7059 Intermediate Similarity NPC289979
0.7059 Intermediate Similarity NPC469937
0.7059 Intermediate Similarity NPC320588
0.7027 Intermediate Similarity NPC238135
0.7 Intermediate Similarity NPC474120
0.7 Intermediate Similarity NPC474089
0.6905 Remote Similarity NPC128996
0.6792 Remote Similarity NPC148424
0.675 Remote Similarity NPC319034
0.675 Remote Similarity NPC72324
0.675 Remote Similarity NPC193062
0.675 Remote Similarity NPC66124
0.675 Remote Similarity NPC1748
0.6727 Remote Similarity NPC174485
0.6667 Remote Similarity NPC322148
0.6607 Remote Similarity NPC477757
0.6607 Remote Similarity NPC477755
0.6607 Remote Similarity NPC477763
0.6607 Remote Similarity NPC477762
0.6607 Remote Similarity NPC477753
0.6607 Remote Similarity NPC477750
0.6591 Remote Similarity NPC221022
0.6591 Remote Similarity NPC471282
0.6585 Remote Similarity NPC139569
0.6579 Remote Similarity NPC279895
0.65 Remote Similarity NPC122962
0.65 Remote Similarity NPC272426
0.65 Remote Similarity NPC267243
0.6486 Remote Similarity NPC317724
0.6486 Remote Similarity NPC329496
0.6486 Remote Similarity NPC128335
0.6486 Remote Similarity NPC230452
0.6458 Remote Similarity NPC30195
0.6458 Remote Similarity NPC12438
0.6429 Remote Similarity NPC470363
0.6429 Remote Similarity NPC474627
0.6429 Remote Similarity NPC328786
0.6429 Remote Similarity NPC86545
0.6429 Remote Similarity NPC223374
0.6429 Remote Similarity NPC196442
0.6429 Remote Similarity NPC201338
0.6429 Remote Similarity NPC301398
0.6364 Remote Similarity NPC472025
0.6275 Remote Similarity NPC55678
0.625 Remote Similarity NPC469781
0.6216 Remote Similarity NPC304786
0.62 Remote Similarity NPC106872
0.619 Remote Similarity NPC286498
0.617 Remote Similarity NPC203531
0.617 Remote Similarity NPC474126
0.617 Remote Similarity NPC236579
0.617 Remote Similarity NPC474125
0.6167 Remote Similarity NPC190418
0.6167 Remote Similarity NPC471761
0.6167 Remote Similarity NPC471760
0.6154 Remote Similarity NPC287811
0.6136 Remote Similarity NPC177022
0.6087 Remote Similarity NPC469759
0.6087 Remote Similarity NPC266553
0.6087 Remote Similarity NPC160261
0.6078 Remote Similarity NPC82512
0.6071 Remote Similarity NPC474577
0.6066 Remote Similarity NPC477752
0.6066 Remote Similarity NPC477756
0.6066 Remote Similarity NPC477751
0.6066 Remote Similarity NPC477764
0.6034 Remote Similarity NPC472026
0.6 Remote Similarity NPC319709
0.6 Remote Similarity NPC328497
0.6 Remote Similarity NPC289484
0.6 Remote Similarity NPC476702
0.6 Remote Similarity NPC110884
0.6 Remote Similarity NPC324004
0.5968 Remote Similarity NPC206601
0.5968 Remote Similarity NPC477761
0.5968 Remote Similarity NPC477754
0.5968 Remote Similarity NPC477758
0.5968 Remote Similarity NPC477760
0.5968 Remote Similarity NPC477759
0.5957 Remote Similarity NPC53541
0.5952 Remote Similarity NPC147054
0.5946 Remote Similarity NPC237965
0.5946 Remote Similarity NPC318912
0.5932 Remote Similarity NPC17455
0.5918 Remote Similarity NPC215358
0.5918 Remote Similarity NPC287231
0.5918 Remote Similarity NPC47363
0.5909 Remote Similarity NPC80641
0.5902 Remote Similarity NPC238646
0.5897 Remote Similarity NPC272307
0.5873 Remote Similarity NPC67099
0.5873 Remote Similarity NPC50228
0.5873 Remote Similarity NPC97736
0.5849 Remote Similarity NPC100096
0.5849 Remote Similarity NPC233726
0.5849 Remote Similarity NPC124963
0.5849 Remote Similarity NPC23134
0.5849 Remote Similarity NPC326533
0.5833 Remote Similarity NPC235788
0.5833 Remote Similarity NPC144829
0.5818 Remote Similarity NPC303727
0.5814 Remote Similarity NPC227267
0.5814 Remote Similarity NPC283682
0.58 Remote Similarity NPC473914
0.58 Remote Similarity NPC76976
0.5789 Remote Similarity NPC275462
0.5789 Remote Similarity NPC213764
0.5781 Remote Similarity NPC285003
0.5781 Remote Similarity NPC241265
0.5781 Remote Similarity NPC211428
0.575 Remote Similarity NPC223195
0.575 Remote Similarity NPC159845
0.5745 Remote Similarity NPC149299
0.5745 Remote Similarity NPC256163
0.5745 Remote Similarity NPC250028
0.5745 Remote Similarity NPC161097
0.5745 Remote Similarity NPC40597
0.5745 Remote Similarity NPC28598
0.5745 Remote Similarity NPC12156
0.5745 Remote Similarity NPC165533
0.5714 Remote Similarity NPC22101
0.5714 Remote Similarity NPC469925
0.5714 Remote Similarity NPC104537
0.5714 Remote Similarity NPC271921
0.5714 Remote Similarity NPC127091
0.5714 Remote Similarity NPC148192
0.5714 Remote Similarity NPC40965
0.5714 Remote Similarity NPC70756
0.5714 Remote Similarity NPC330426
0.5714 Remote Similarity NPC320240
0.5714 Remote Similarity NPC473829
0.5714 Remote Similarity NPC29721
0.5714 Remote Similarity NPC76051
0.5714 Remote Similarity NPC475443
0.5714 Remote Similarity NPC286842
0.5692 Remote Similarity NPC470268
0.5692 Remote Similarity NPC321873
0.5692 Remote Similarity NPC52268
0.5692 Remote Similarity NPC53760
0.569 Remote Similarity NPC290179
0.569 Remote Similarity NPC34877
0.569 Remote Similarity NPC317023
0.5686 Remote Similarity NPC230789
0.5686 Remote Similarity NPC277475
0.5686 Remote Similarity NPC252918
0.5686 Remote Similarity NPC249754
0.5686 Remote Similarity NPC321087
0.5682 Remote Similarity NPC325034
0.5682 Remote Similarity NPC66052
0.5682 Remote Similarity NPC192065
0.5682 Remote Similarity NPC293908
0.5682 Remote Similarity NPC86412
0.5667 Remote Similarity NPC172622
0.566 Remote Similarity NPC90904
0.5652 Remote Similarity NPC469714
0.5652 Remote Similarity NPC473568
0.5652 Remote Similarity NPC469712
0.5645 Remote Similarity NPC474402
0.5636 Remote Similarity NPC269166
0.5636 Remote Similarity NPC58629
0.5636 Remote Similarity NPC145112
0.5636 Remote Similarity NPC130683
0.5636 Remote Similarity NPC157514
0.5636 Remote Similarity NPC246558
0.5636 Remote Similarity NPC242073
0.5636 Remote Similarity NPC67660
0.5636 Remote Similarity NPC323361
0.5636 Remote Similarity NPC165198
0.5636 Remote Similarity NPC107914
0.5636 Remote Similarity NPC89145
0.5625 Remote Similarity NPC196924
0.5625 Remote Similarity NPC141481
0.5625 Remote Similarity NPC307783
0.5625 Remote Similarity NPC82315

  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 NPC152008 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
1.0 High Similarity NPD7536 Approved
0.7632 Intermediate Similarity NPD5383 Approved
0.7632 Intermediate Similarity NPD2272 Approved
0.7059 Intermediate Similarity NPD3730 Approved
0.7059 Intermediate Similarity NPD3728 Approved
0.65 Remote Similarity NPD907 Approved
0.65 Remote Similarity NPD1461 Approved
0.65 Remote Similarity NPD908 Approved
0.6346 Remote Similarity NPD2269 Approved
0.6222 Remote Similarity NPD5799 Discontinued
0.62 Remote Similarity NPD6125 Clinical (unspecified phase)
0.6182 Remote Similarity NPD2267 Suspended
0.6 Remote Similarity NPD3211 Approved
0.5918 Remote Similarity NPD2699 Approved
0.5849 Remote Similarity NPD905 Approved
0.5849 Remote Similarity NPD904 Phase 3
0.5833 Remote Similarity NPD8957 Approved
0.5714 Remote Similarity NPD9006 Approved
0.5714 Remote Similarity NPD6950 Discontinued
0.5692 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5682 Remote Similarity NPD9053 Approved
0.5682 Remote Similarity NPD9051 Approved
0.5682 Remote Similarity NPD9052 Approved
0.5636 Remote Similarity NPD893 Approved
0.5636 Remote Similarity NPD890 Clinical (unspecified phase)
0.5636 Remote Similarity NPD889 Approved
0.5636 Remote Similarity NPD888 Phase 3
0.5636 Remote Similarity NPD895 Approved
0.5636 Remote Similarity NPD887 Approved
0.5636 Remote Similarity NPD891 Phase 3
0.5636 Remote Similarity NPD892 Phase 3
0.5636 Remote Similarity NPD894 Approved
0.5625 Remote Similarity NPD2270 Approved
0.56 Remote Similarity NPD9218 Clinical (unspecified phase)
0.56 Remote Similarity NPD9219 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