Structure

Physi-Chem Properties

Molecular Weight:  262.16
Volume:  295.844
LogP:  4.232
LogD:  2.156
LogS:  -3.906
# Rotatable Bonds:  10
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.374
Synthetic Accessibility Score:  2.953
Fsp3:  0.562
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.906
MDCK Permeability:  5.340061034075916e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.046
30% Bioavailability (F30%):  0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  100.56573486328125%
Volume Distribution (VD):  0.413
Pgp-substrate:  0.7932050228118896%

ADMET: Metabolism

CYP1A2-inhibitor:  0.064
CYP1A2-substrate:  0.141
CYP2C19-inhibitor:  0.714
CYP2C19-substrate:  0.239
CYP2C9-inhibitor:  0.865
CYP2C9-substrate:  0.963
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.297
CYP3A4-inhibitor:  0.457
CYP3A4-substrate:  0.04

ADMET: Excretion

Clearance (CL):  2.71
Half-life (T1/2):  0.787

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.128
Drug-inuced Liver Injury (DILI):  0.936
AMES Toxicity:  0.442
Rat Oral Acute Toxicity:  0.074
Maximum Recommended Daily Dose:  0.035
Skin Sensitization:  0.955
Carcinogencity:  0.644
Eye Corrosion:  0.992
Eye Irritation:  0.992
Respiratory Toxicity:  0.917

Download Data

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

  Natural Product: NPC236872

Natural Product ID:  NPC236872
Common Name*:   Monotiporic Acid B
IUPAC Name:   2-tetradec-13-en-2,4-diynoxyacetic acid
Synonyms:   monotiporic acid B
Standard InCHIKey:  ODJULCBAODTNBX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H22O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-19-15-16(17)18/h2H,1,3-9,14-15H2,(H,17,18)
SMILES:  C=CCCCCCCCC#CC#CCOCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453153
PubChem CID:   177349
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001205] Carboxylic acids

*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
NPO15905 Montipora digitata Species Acroporidae Eukaryota eggs n.a. n.a. PMID[8792626]
NPO15905 Montipora digitata Species Acroporidae 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
NPT168 Cell Line P388 Mus musculus IC50 = 12.0 ug.mL-1 PMID[488395]

☑ 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 NPC236872 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
0.9375 High Similarity NPC473551
0.9184 High Similarity NPC301482
0.8958 High Similarity NPC474204
0.7755 Intermediate Similarity NPC144829
0.7755 Intermediate Similarity NPC31121
0.7547 Intermediate Similarity NPC477778
0.7344 Intermediate Similarity NPC477980
0.7321 Intermediate Similarity NPC477781
0.7321 Intermediate Similarity NPC477780
0.7143 Intermediate Similarity NPC225963
0.7143 Intermediate Similarity NPC474205
0.7015 Intermediate Similarity NPC477981
0.7015 Intermediate Similarity NPC477983
0.7 Intermediate Similarity NPC469373
0.6897 Remote Similarity NPC269615
0.6885 Remote Similarity NPC329424
0.6857 Remote Similarity NPC470899
0.6833 Remote Similarity NPC212730
0.6833 Remote Similarity NPC265551
0.678 Remote Similarity NPC474513
0.678 Remote Similarity NPC470963
0.678 Remote Similarity NPC146551
0.6774 Remote Similarity NPC471278
0.6769 Remote Similarity NPC477982
0.6735 Remote Similarity NPC216416
0.6667 Remote Similarity NPC470964
0.6667 Remote Similarity NPC66460
0.6667 Remote Similarity NPC271282
0.6667 Remote Similarity NPC311648
0.6667 Remote Similarity NPC325929
0.6607 Remote Similarity NPC475153
0.6607 Remote Similarity NPC207815
0.6562 Remote Similarity NPC29697
0.6557 Remote Similarity NPC44542
0.6557 Remote Similarity NPC471277
0.6557 Remote Similarity NPC594
0.6557 Remote Similarity NPC48968
0.6557 Remote Similarity NPC471279
0.6552 Remote Similarity NPC106531
0.6552 Remote Similarity NPC18357
0.6552 Remote Similarity NPC161366
0.6531 Remote Similarity NPC213767
0.65 Remote Similarity NPC152668
0.6462 Remote Similarity NPC476658
0.6415 Remote Similarity NPC149668
0.6364 Remote Similarity NPC476655
0.6364 Remote Similarity NPC476657
0.6364 Remote Similarity NPC476654
0.6349 Remote Similarity NPC474267
0.6349 Remote Similarity NPC222852
0.629 Remote Similarity NPC472445
0.629 Remote Similarity NPC474577
0.6271 Remote Similarity NPC473705
0.6269 Remote Similarity NPC476659
0.6269 Remote Similarity NPC476656
0.625 Remote Similarity NPC321919
0.625 Remote Similarity NPC81896
0.625 Remote Similarity NPC299730
0.625 Remote Similarity NPC157096
0.625 Remote Similarity NPC81052
0.623 Remote Similarity NPC474672
0.623 Remote Similarity NPC54766
0.623 Remote Similarity NPC45626
0.6182 Remote Similarity NPC108195
0.6176 Remote Similarity NPC330426
0.6176 Remote Similarity NPC22101
0.6176 Remote Similarity NPC104537
0.6176 Remote Similarity NPC271921
0.6176 Remote Similarity NPC148192
0.6176 Remote Similarity NPC127091
0.6176 Remote Similarity NPC473829
0.6176 Remote Similarity NPC475443
0.6167 Remote Similarity NPC475723
0.6167 Remote Similarity NPC71761
0.6154 Remote Similarity NPC475984
0.6129 Remote Similarity NPC179764
0.6129 Remote Similarity NPC187777
0.6102 Remote Similarity NPC29234
0.6102 Remote Similarity NPC93639
0.6102 Remote Similarity NPC470412
0.6102 Remote Similarity NPC470410
0.6087 Remote Similarity NPC209327
0.6087 Remote Similarity NPC324981
0.6087 Remote Similarity NPC473559
0.6087 Remote Similarity NPC48218
0.6087 Remote Similarity NPC273508
0.6087 Remote Similarity NPC141481
0.6071 Remote Similarity NPC269074
0.6071 Remote Similarity NPC201948
0.6066 Remote Similarity NPC48058
0.6066 Remote Similarity NPC137538
0.6061 Remote Similarity NPC470965
0.6038 Remote Similarity NPC27444
0.6038 Remote Similarity NPC103236
0.6038 Remote Similarity NPC329762
0.6034 Remote Similarity NPC471276
0.6034 Remote Similarity NPC471275
0.6034 Remote Similarity NPC31194
0.6034 Remote Similarity NPC248884
0.6034 Remote Similarity NPC471280
0.6034 Remote Similarity NPC125122
0.6034 Remote Similarity NPC85079
0.6032 Remote Similarity NPC193975
0.6 Remote Similarity NPC473772
0.6 Remote Similarity NPC130618
0.6 Remote Similarity NPC142092
0.6 Remote Similarity NPC469495
0.6 Remote Similarity NPC129458
0.5968 Remote Similarity NPC200845
0.5968 Remote Similarity NPC474913
0.5968 Remote Similarity NPC28779
0.5968 Remote Similarity NPC52264
0.5968 Remote Similarity NPC223677
0.5968 Remote Similarity NPC128061
0.5968 Remote Similarity NPC10316
0.5968 Remote Similarity NPC471239
0.5968 Remote Similarity NPC473863
0.5968 Remote Similarity NPC274290
0.5965 Remote Similarity NPC124183
0.5965 Remote Similarity NPC19834
0.5965 Remote Similarity NPC55063
0.5965 Remote Similarity NPC35141
0.5938 Remote Similarity NPC329819
0.5932 Remote Similarity NPC471281
0.5932 Remote Similarity NPC199286
0.5932 Remote Similarity NPC72699
0.5932 Remote Similarity NPC477727
0.5932 Remote Similarity NPC473768
0.5932 Remote Similarity NPC59051
0.5932 Remote Similarity NPC473487
0.5921 Remote Similarity NPC209995
0.5915 Remote Similarity NPC42526
0.5915 Remote Similarity NPC476660
0.5909 Remote Similarity NPC328776
0.5909 Remote Similarity NPC321838
0.5909 Remote Similarity NPC320305
0.5902 Remote Similarity NPC225066
0.5902 Remote Similarity NPC10081
0.5902 Remote Similarity NPC284224
0.5893 Remote Similarity NPC101616
0.5893 Remote Similarity NPC473539
0.5893 Remote Similarity NPC474413
0.5873 Remote Similarity NPC327388
0.5862 Remote Similarity NPC180534
0.5862 Remote Similarity NPC216130
0.5846 Remote Similarity NPC473866
0.5844 Remote Similarity NPC200446
0.5833 Remote Similarity NPC129263
0.5833 Remote Similarity NPC256656
0.5833 Remote Similarity NPC470411
0.5833 Remote Similarity NPC76198
0.5833 Remote Similarity NPC197272
0.5833 Remote Similarity NPC28205
0.5833 Remote Similarity NPC284212
0.5833 Remote Similarity NPC477723
0.5833 Remote Similarity NPC151782
0.5833 Remote Similarity NPC165447
0.5833 Remote Similarity NPC475477
0.5833 Remote Similarity NPC224148
0.5833 Remote Similarity NPC9273
0.5833 Remote Similarity NPC471959
0.5833 Remote Similarity NPC89824
0.5833 Remote Similarity NPC329608
0.5833 Remote Similarity NPC170776
0.5833 Remote Similarity NPC294278
0.5833 Remote Similarity NPC55383
0.5821 Remote Similarity NPC54925
0.5806 Remote Similarity NPC289979
0.5789 Remote Similarity NPC474362
0.5789 Remote Similarity NPC474202
0.5789 Remote Similarity NPC276825
0.5781 Remote Similarity NPC121034
0.5781 Remote Similarity NPC323436
0.5781 Remote Similarity NPC323597
0.5781 Remote Similarity NPC323498
0.5781 Remote Similarity NPC211752
0.5781 Remote Similarity NPC225929
0.5763 Remote Similarity NPC302310
0.5763 Remote Similarity NPC153538
0.5741 Remote Similarity NPC203382
0.5741 Remote Similarity NPC123357
0.5738 Remote Similarity NPC92114
0.5738 Remote Similarity NPC295765
0.5738 Remote Similarity NPC303765
0.5735 Remote Similarity NPC226592
0.5735 Remote Similarity NPC68343
0.5735 Remote Similarity NPC470320
0.5735 Remote Similarity NPC328089
0.5714 Remote Similarity NPC225272
0.5714 Remote Similarity NPC478100
0.5714 Remote Similarity NPC473357
0.5714 Remote Similarity NPC477984
0.5714 Remote Similarity NPC193029
0.5714 Remote Similarity NPC25298
0.5692 Remote Similarity NPC267817
0.569 Remote Similarity NPC180575
0.569 Remote Similarity NPC197467
0.569 Remote Similarity NPC42304
0.5676 Remote Similarity NPC104644
0.5676 Remote Similarity NPC474321

  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 NPC236872 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
0.7 Intermediate Similarity NPD6109 Phase 1
0.6212 Remote Similarity NPD3197 Phase 1
0.5893 Remote Similarity NPD6097 Approved
0.5893 Remote Similarity NPD6096 Approved
0.5862 Remote Similarity NPD5343 Approved
0.5862 Remote Similarity NPD622 Approved
0.5789 Remote Similarity NPD39 Approved
0.5645 Remote Similarity NPD3172 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