Structure

Physi-Chem Properties

Molecular Weight:  176.12
Volume:  211.716
LogP:  3.617
LogD:  2.883
LogS:  -3.463
# Rotatable Bonds:  5
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.386
Synthetic Accessibility Score:  3.094
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.035
MDCK Permeability:  5.34351565875113e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.616
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  99.43722534179688%
Volume Distribution (VD):  1.365
Pgp-substrate:  1.1092413663864136%

ADMET: Metabolism

CYP1A2-inhibitor:  0.922
CYP1A2-substrate:  0.394
CYP2C19-inhibitor:  0.945
CYP2C19-substrate:  0.513
CYP2C9-inhibitor:  0.898
CYP2C9-substrate:  0.952
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.685
CYP3A4-inhibitor:  0.856
CYP3A4-substrate:  0.139

ADMET: Excretion

Clearance (CL):  9.07
Half-life (T1/2):  0.522

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.036
Drug-inuced Liver Injury (DILI):  0.79
AMES Toxicity:  0.509
Rat Oral Acute Toxicity:  0.084
Maximum Recommended Daily Dose:  0.56
Skin Sensitization:  0.964
Carcinogencity:  0.842
Eye Corrosion:  0.986
Eye Irritation:  0.99
Respiratory Toxicity:  0.936

Download Data

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

  Natural Product: NPC213767

Natural Product ID:  NPC213767
Common Name*:   Montiporyne G
IUPAC Name:   dodec-11-en-2,4-diyn-1-ol
Synonyms:   Montiporyne G
Standard InCHIKey:  LGNSCSQFQCDGPG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H16O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2,13H,1,3-7,12H2
SMILES:  C=CCCCCCC#CC#CCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443245
PubChem CID:   11126805
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] 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
NPO33414 montipora sp. Species Acroporidae Eukaryota n.a. n.a. n.a. PMID[11087594]
NPO33414 montipora sp. Species Acroporidae Eukaryota n.a. n.a. n.a. PMID[11520227]

☑ 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
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 9.56 ug ml-1 PMID[450485]
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 = 9.79 ug ml-1 PMID[450485]
NPT574 Cell Line XF498 Homo sapiens ED50 = 10.78 ug ml-1 PMID[450485]
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 12.93 ug ml-1 PMID[450485]
NPT81 Cell Line A549 Homo sapiens ED50 = 13.78 ug ml-1 PMID[450485]

☑ 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 NPC213767 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
0.9706 High Similarity NPC216416
0.8462 Intermediate Similarity NPC31121
0.8462 Intermediate Similarity NPC149668
0.8421 Intermediate Similarity NPC27444
0.8421 Intermediate Similarity NPC329762
0.8421 Intermediate Similarity NPC103236
0.8049 Intermediate Similarity NPC108195
0.8049 Intermediate Similarity NPC101616
0.8 Intermediate Similarity NPC304151
0.7857 Intermediate Similarity NPC269074
0.7857 Intermediate Similarity NPC276825
0.7674 Intermediate Similarity NPC35141
0.7674 Intermediate Similarity NPC124183
0.7674 Intermediate Similarity NPC55063
0.7674 Intermediate Similarity NPC180575
0.7674 Intermediate Similarity NPC19834
0.7333 Intermediate Similarity NPC31194
0.7333 Intermediate Similarity NPC475153
0.7333 Intermediate Similarity NPC471280
0.7333 Intermediate Similarity NPC471275
0.7333 Intermediate Similarity NPC153538
0.7333 Intermediate Similarity NPC302310
0.7333 Intermediate Similarity NPC248884
0.7333 Intermediate Similarity NPC471276
0.7333 Intermediate Similarity NPC125122
0.7333 Intermediate Similarity NPC85079
0.7273 Intermediate Similarity NPC157096
0.725 Intermediate Similarity NPC15934
0.7174 Intermediate Similarity NPC72699
0.7174 Intermediate Similarity NPC474642
0.7174 Intermediate Similarity NPC473913
0.7174 Intermediate Similarity NPC249670
0.7174 Intermediate Similarity NPC199286
0.7174 Intermediate Similarity NPC471281
0.7174 Intermediate Similarity NPC473487
0.7174 Intermediate Similarity NPC477727
0.7143 Intermediate Similarity NPC46248
0.7143 Intermediate Similarity NPC206906
0.7143 Intermediate Similarity NPC249801
0.7021 Intermediate Similarity NPC477723
0.7021 Intermediate Similarity NPC165447
0.7021 Intermediate Similarity NPC55383
0.7021 Intermediate Similarity NPC89824
0.7021 Intermediate Similarity NPC256656
0.7021 Intermediate Similarity NPC475477
0.7021 Intermediate Similarity NPC93639
0.7021 Intermediate Similarity NPC329608
0.7021 Intermediate Similarity NPC129263
0.7021 Intermediate Similarity NPC197272
0.7021 Intermediate Similarity NPC170776
0.7021 Intermediate Similarity NPC471959
0.7021 Intermediate Similarity NPC9273
0.7021 Intermediate Similarity NPC151782
0.7021 Intermediate Similarity NPC224148
0.7021 Intermediate Similarity NPC294278
0.7021 Intermediate Similarity NPC76198
0.7 Intermediate Similarity NPC34873
0.7 Intermediate Similarity NPC40434
0.6977 Remote Similarity NPC252978
0.6875 Remote Similarity NPC142092
0.6875 Remote Similarity NPC473705
0.6857 Remote Similarity NPC223195
0.6829 Remote Similarity NPC306850
0.6809 Remote Similarity NPC473768
0.6735 Remote Similarity NPC475723
0.6735 Remote Similarity NPC187361
0.6735 Remote Similarity NPC34577
0.6735 Remote Similarity NPC284224
0.6735 Remote Similarity NPC477724
0.6735 Remote Similarity NPC26102
0.6667 Remote Similarity NPC29234
0.6667 Remote Similarity NPC76976
0.6667 Remote Similarity NPC59408
0.6667 Remote Similarity NPC71053
0.6667 Remote Similarity NPC474362
0.6667 Remote Similarity NPC474202
0.66 Remote Similarity NPC49059
0.66 Remote Similarity NPC110732
0.66 Remote Similarity NPC48058
0.66 Remote Similarity NPC256209
0.66 Remote Similarity NPC473532
0.6531 Remote Similarity NPC236872
0.6522 Remote Similarity NPC474204
0.65 Remote Similarity NPC79544
0.6471 Remote Similarity NPC473896
0.6471 Remote Similarity NPC38513
0.6471 Remote Similarity NPC473721
0.6471 Remote Similarity NPC477726
0.6471 Remote Similarity NPC470963
0.6471 Remote Similarity NPC474644
0.6471 Remote Similarity NPC473735
0.6471 Remote Similarity NPC471239
0.6471 Remote Similarity NPC88325
0.6471 Remote Similarity NPC477725
0.6471 Remote Similarity NPC473910
0.6471 Remote Similarity NPC146551
0.6471 Remote Similarity NPC473725
0.6471 Remote Similarity NPC474513
0.6471 Remote Similarity NPC475353
0.6471 Remote Similarity NPC152668
0.6458 Remote Similarity NPC328784
0.6458 Remote Similarity NPC291437
0.6444 Remote Similarity NPC474413
0.6444 Remote Similarity NPC473539
0.6429 Remote Similarity NPC29091
0.6429 Remote Similarity NPC103213
0.6429 Remote Similarity NPC255042
0.6429 Remote Similarity NPC182840
0.641 Remote Similarity NPC62779
0.641 Remote Similarity NPC81989
0.64 Remote Similarity NPC61177
0.6346 Remote Similarity NPC471960
0.6346 Remote Similarity NPC470967
0.6346 Remote Similarity NPC470968
0.6346 Remote Similarity NPC161838
0.6346 Remote Similarity NPC311648
0.6346 Remote Similarity NPC470964
0.6346 Remote Similarity NPC475384
0.6346 Remote Similarity NPC474643
0.6346 Remote Similarity NPC473847
0.6346 Remote Similarity NPC473865
0.6346 Remote Similarity NPC477661
0.6346 Remote Similarity NPC470966
0.6346 Remote Similarity NPC470969
0.6341 Remote Similarity NPC174396
0.6316 Remote Similarity NPC196831
0.6304 Remote Similarity NPC201948
0.6286 Remote Similarity NPC31891
0.6286 Remote Similarity NPC266539
0.6286 Remote Similarity NPC266144
0.6286 Remote Similarity NPC287191
0.6279 Remote Similarity NPC48930
0.625 Remote Similarity NPC473551
0.625 Remote Similarity NPC58957
0.6226 Remote Similarity NPC48968
0.6226 Remote Similarity NPC265551
0.6226 Remote Similarity NPC470970
0.6226 Remote Similarity NPC594
0.6226 Remote Similarity NPC212730
0.6226 Remote Similarity NPC193975
0.6154 Remote Similarity NPC63121
0.6154 Remote Similarity NPC197356
0.6136 Remote Similarity NPC33489
0.6136 Remote Similarity NPC269823
0.6136 Remote Similarity NPC473625
0.6122 Remote Similarity NPC301482
0.6111 Remote Similarity NPC469373
0.6087 Remote Similarity NPC267514
0.6087 Remote Similarity NPC138935
0.6087 Remote Similarity NPC145755
0.6 Remote Similarity NPC298710
0.6 Remote Similarity NPC287397
0.6 Remote Similarity NPC473652
0.6 Remote Similarity NPC213538
0.6 Remote Similarity NPC250734
0.6 Remote Similarity NPC470411
0.6 Remote Similarity NPC67920
0.6 Remote Similarity NPC256766
0.5962 Remote Similarity NPC300121
0.5957 Remote Similarity NPC87439
0.5957 Remote Similarity NPC24824
0.5957 Remote Similarity NPC165651
0.5957 Remote Similarity NPC210560
0.5946 Remote Similarity NPC179103
0.5946 Remote Similarity NPC76765
0.5926 Remote Similarity NPC44542
0.5926 Remote Similarity NPC121034
0.5926 Remote Similarity NPC474577
0.5918 Remote Similarity NPC474445
0.5893 Remote Similarity NPC471278
0.5882 Remote Similarity NPC18357
0.587 Remote Similarity NPC15162
0.587 Remote Similarity NPC116934
0.587 Remote Similarity NPC269862
0.5854 Remote Similarity NPC182392
0.58 Remote Similarity NPC288381
0.58 Remote Similarity NPC475071
0.58 Remote Similarity NPC182102
0.58 Remote Similarity NPC20934
0.58 Remote Similarity NPC26960
0.5789 Remote Similarity NPC271282
0.5789 Remote Similarity NPC168407
0.5789 Remote Similarity NPC325929
0.5789 Remote Similarity NPC475984
0.5789 Remote Similarity NPC66460
0.5778 Remote Similarity NPC7754
0.5778 Remote Similarity NPC469713
0.5778 Remote Similarity NPC270170
0.5714 Remote Similarity NPC471958
0.5714 Remote Similarity NPC306009
0.5714 Remote Similarity NPC473866
0.5714 Remote Similarity NPC222852
0.569 Remote Similarity NPC470965
0.569 Remote Similarity NPC29697
0.5686 Remote Similarity NPC28205
0.5686 Remote Similarity NPC244038
0.5686 Remote Similarity NPC473672
0.5686 Remote Similarity NPC474495
0.5682 Remote Similarity NPC277382
0.5682 Remote Similarity NPC217923

  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 NPC213767 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
0.5625 Remote Similarity NPD4265 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