Structure

Physi-Chem Properties

Molecular Weight:  380.4
Volume:  458.486
LogP:  10.706
LogD:  4.502
LogS:  -7.28
# Rotatable Bonds:  20
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.209
Synthetic Accessibility Score:  1.867
Fsp3:  1.0
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:  -5.181
MDCK Permeability:  6.098820904298918e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  97.4817886352539%
Volume Distribution (VD):  4.0
Pgp-substrate:  0.7543195486068726%

ADMET: Metabolism

CYP1A2-inhibitor:  0.054
CYP1A2-substrate:  0.144
CYP2C19-inhibitor:  0.127
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.97
CYP2D6-inhibitor:  0.067
CYP2D6-substrate:  0.026
CYP3A4-inhibitor:  0.165
CYP3A4-substrate:  0.018

ADMET: Excretion

Clearance (CL):  5.002
Half-life (T1/2):  0.019

ADMET: Toxicity

hERG Blockers:  0.531
Human Hepatotoxicity (H-HT):  0.021
Drug-inuced Liver Injury (DILI):  0.235
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.977
Carcinogencity:  0.022
Eye Corrosion:  0.993
Eye Irritation:  0.916
Respiratory Toxicity:  0.243

Download Data

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

  Natural Product: NPC469759

Natural Product ID:  NPC469759
Common Name*:   20-Cyclohexylicosan-1-Ol
IUPAC Name:   20-cyclohexylicosan-1-ol
Synonyms:   1'-Hydroxydocasanyl Cyclohexane
Standard InCHIKey:  RDWUOKKSOYENMQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C26H52O/c27-25-21-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-18-22-26-23-19-17-20-24-26/h26-27H,1-25H2
SMILES:  OCCCCCCCCCCCCCCCCCCCCC1CCCCC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1170105
PubChem CID:   49797776
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota whole plant Cholistan desert near district Bahawalpur (Punjab), Pakistan 2003-Oct PMID[20542692]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae 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
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 100.0 ug.mL-1 PMID[489184]

☑ 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 NPC469759 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 NPC160261
0.9211 High Similarity NPC221022
0.8684 High Similarity NPC177022
0.7955 Intermediate Similarity NPC473914
0.7907 Intermediate Similarity NPC144891
0.7895 Intermediate Similarity NPC283682
0.7778 Intermediate Similarity NPC287550
0.7778 Intermediate Similarity NPC147343
0.7778 Intermediate Similarity NPC176309
0.7778 Intermediate Similarity NPC223468
0.7778 Intermediate Similarity NPC84030
0.7778 Intermediate Similarity NPC198540
0.7727 Intermediate Similarity NPC215358
0.7632 Intermediate Similarity NPC12231
0.7632 Intermediate Similarity NPC185538
0.7632 Intermediate Similarity NPC181516
0.7632 Intermediate Similarity NPC205141
0.7632 Intermediate Similarity NPC291158
0.7632 Intermediate Similarity NPC272998
0.7632 Intermediate Similarity NPC152759
0.7632 Intermediate Similarity NPC139131
0.7609 Intermediate Similarity NPC314087
0.7368 Intermediate Similarity NPC126915
0.7333 Intermediate Similarity NPC240994
0.725 Intermediate Similarity NPC97967
0.7174 Intermediate Similarity NPC87439
0.7143 Intermediate Similarity NPC307022
0.7105 Intermediate Similarity NPC163556
0.7105 Intermediate Similarity NPC236797
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
0.7073 Intermediate Similarity NPC474914
0.7073 Intermediate Similarity NPC328441
0.7073 Intermediate Similarity NPC474392
0.7073 Intermediate Similarity NPC61665
0.6981 Remote Similarity NPC135438
0.6957 Remote Similarity NPC313795
0.6923 Remote Similarity NPC267243
0.6905 Remote Similarity NPC74352
0.6889 Remote Similarity NPC474125
0.6889 Remote Similarity NPC474126
0.6852 Remote Similarity NPC476735
0.6809 Remote Similarity NPC77550
0.6809 Remote Similarity NPC108441
0.675 Remote Similarity NPC319034
0.675 Remote Similarity NPC193062
0.675 Remote Similarity NPC66124
0.675 Remote Similarity NPC72324
0.675 Remote Similarity NPC1748
0.6731 Remote Similarity NPC53209
0.6667 Remote Similarity NPC236588
0.6667 Remote Similarity NPC14552
0.6604 Remote Similarity NPC84824
0.6604 Remote Similarity NPC67508
0.6604 Remote Similarity NPC471269
0.6591 Remote Similarity NPC471282
0.6579 Remote Similarity NPC279895
0.6531 Remote Similarity NPC324793
0.6531 Remote Similarity NPC477878
0.65 Remote Similarity NPC122962
0.6491 Remote Similarity NPC148174
0.6491 Remote Similarity NPC218585
0.6491 Remote Similarity NPC71460
0.64 Remote Similarity NPC294858
0.64 Remote Similarity NPC316035
0.6379 Remote Similarity NPC114891
0.6379 Remote Similarity NPC292419
0.6379 Remote Similarity NPC290791
0.6364 Remote Similarity NPC322148
0.6364 Remote Similarity NPC469712
0.6364 Remote Similarity NPC197039
0.6364 Remote Similarity NPC473568
0.6364 Remote Similarity NPC469714
0.6327 Remote Similarity NPC21844
0.6316 Remote Similarity NPC39869
0.6316 Remote Similarity NPC276332
0.6275 Remote Similarity NPC131623
0.6271 Remote Similarity NPC69149
0.6271 Remote Similarity NPC118937
0.6271 Remote Similarity NPC281540
0.6271 Remote Similarity NPC225415
0.6271 Remote Similarity NPC159654
0.6271 Remote Similarity NPC167995
0.625 Remote Similarity NPC475515
0.625 Remote Similarity NPC87296
0.625 Remote Similarity NPC215671
0.625 Remote Similarity NPC47663
0.6226 Remote Similarity NPC161473
0.62 Remote Similarity NPC100445
0.6167 Remote Similarity NPC476737
0.6167 Remote Similarity NPC472946
0.6167 Remote Similarity NPC260116
0.6167 Remote Similarity NPC475943
0.6167 Remote Similarity NPC190827
0.6167 Remote Similarity NPC473276
0.6167 Remote Similarity NPC27243
0.6167 Remote Similarity NPC80463
0.6167 Remote Similarity NPC474380
0.6167 Remote Similarity NPC163678
0.6167 Remote Similarity NPC243469
0.6167 Remote Similarity NPC41577
0.6154 Remote Similarity NPC325345
0.614 Remote Similarity NPC185116
0.614 Remote Similarity NPC122239
0.6122 Remote Similarity NPC314679
0.6111 Remote Similarity NPC286752
0.6087 Remote Similarity NPC152008
0.6066 Remote Similarity NPC44122
0.6066 Remote Similarity NPC142712
0.6066 Remote Similarity NPC149680
0.6066 Remote Similarity NPC286669
0.6066 Remote Similarity NPC222366
0.6066 Remote Similarity NPC476406
0.6066 Remote Similarity NPC476039
0.6034 Remote Similarity NPC240506
0.6 Remote Similarity NPC178223
0.6 Remote Similarity NPC166894
0.6 Remote Similarity NPC110884
0.6 Remote Similarity NPC290367
0.6 Remote Similarity NPC283655
0.6 Remote Similarity NPC277917
0.6 Remote Similarity NPC89069
0.5968 Remote Similarity NPC472984
0.5968 Remote Similarity NPC48079
0.5968 Remote Similarity NPC68703
0.5968 Remote Similarity NPC63190
0.5968 Remote Similarity NPC204233
0.5968 Remote Similarity NPC69649
0.5968 Remote Similarity NPC476928
0.5968 Remote Similarity NPC475884
0.5968 Remote Similarity NPC197805
0.5968 Remote Similarity NPC473230
0.5965 Remote Similarity NPC162685
0.5932 Remote Similarity NPC185547
0.5932 Remote Similarity NPC475251
0.5932 Remote Similarity NPC147524
0.5932 Remote Similarity NPC95804
0.5926 Remote Similarity NPC36002
0.5926 Remote Similarity NPC72722
0.5926 Remote Similarity NPC102336
0.5918 Remote Similarity NPC55023
0.5918 Remote Similarity NPC469781
0.5893 Remote Similarity NPC24443
0.5873 Remote Similarity NPC208999
0.5873 Remote Similarity NPC475893
0.5873 Remote Similarity NPC472741
0.5873 Remote Similarity NPC478228
0.5873 Remote Similarity NPC180777
0.5873 Remote Similarity NPC469987
0.5873 Remote Similarity NPC160209
0.5873 Remote Similarity NPC260319
0.5873 Remote Similarity NPC2648
0.5873 Remote Similarity NPC216460
0.5873 Remote Similarity NPC103647
0.5873 Remote Similarity NPC474954
0.5873 Remote Similarity NPC32055
0.5873 Remote Similarity NPC2568
0.5862 Remote Similarity NPC470363
0.5862 Remote Similarity NPC95958
0.5849 Remote Similarity NPC291724
0.5849 Remote Similarity NPC274261
0.5849 Remote Similarity NPC251335
0.5833 Remote Similarity NPC236099
0.5833 Remote Similarity NPC474552
0.5833 Remote Similarity NPC235788
0.5833 Remote Similarity NPC249078
0.5833 Remote Similarity NPC209686
0.5833 Remote Similarity NPC279200
0.5818 Remote Similarity NPC202146
0.5818 Remote Similarity NPC32222
0.5814 Remote Similarity NPC474120
0.5814 Remote Similarity NPC474089
0.5814 Remote Similarity NPC139569
0.58 Remote Similarity NPC210560
0.58 Remote Similarity NPC165651
0.58 Remote Similarity NPC30195
0.58 Remote Similarity NPC12438
0.58 Remote Similarity NPC76976
0.58 Remote Similarity NPC24824
0.5789 Remote Similarity NPC29976
0.5789 Remote Similarity NPC150713
0.5789 Remote Similarity NPC291147
0.5789 Remote Similarity NPC275462
0.5789 Remote Similarity NPC119425
0.5789 Remote Similarity NPC172053
0.5789 Remote Similarity NPC213764
0.5781 Remote Similarity NPC299948
0.5781 Remote Similarity NPC241085
0.5781 Remote Similarity NPC476734
0.5781 Remote Similarity NPC252032
0.5781 Remote Similarity NPC477820
0.5781 Remote Similarity NPC319671
0.5781 Remote Similarity NPC210323
0.5781 Remote Similarity NPC9942
0.5781 Remote Similarity NPC66407
0.5781 Remote Similarity NPC470833
0.5781 Remote Similarity NPC107919

  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 NPC469759 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
0.7778 Intermediate Similarity NPD384 Approved
0.7778 Intermediate Similarity NPD385 Approved
0.7632 Intermediate Similarity NPD5383 Approved
0.7632 Intermediate Similarity NPD2272 Approved
0.6809 Remote Similarity NPD388 Approved
0.6809 Remote Similarity NPD386 Approved
0.6522 Remote Similarity NPD1462 Approved
0.6444 Remote Similarity NPD1460 Approved
0.6154 Remote Similarity NPD8988 Clinical (unspecified phase)
0.614 Remote Similarity NPD3198 Approved
0.6122 Remote Similarity NPD634 Phase 3
0.6111 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6087 Remote Similarity NPD7536 Approved
0.6038 Remote Similarity NPD3186 Phase 1
0.5957 Remote Similarity NPD9426 Discontinued
0.5902 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5873 Remote Similarity NPD6705 Phase 1
0.5849 Remote Similarity NPD7348 Clinical (unspecified phase)
0.5818 Remote Similarity NPD615 Clinical (unspecified phase)
0.5781 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5738 Remote Similarity NPD7909 Approved
0.5738 Remote Similarity NPD371 Approved
0.5714 Remote Similarity NPD367 Approved
0.5714 Remote Similarity NPD342 Phase 1
0.5692 Remote Similarity NPD4787 Phase 1
0.5692 Remote Similarity NPD4244 Approved
0.5692 Remote Similarity NPD4245 Approved
0.5692 Remote Similarity NPD4789 Approved
0.5686 Remote Similarity NPD3211 Approved
0.5606 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5606 Remote Similarity NPD4809 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