Structure

Physi-Chem Properties

Molecular Weight:  230.13
Volume:  267.121
LogP:  3.479
LogD:  2.982
LogS:  -3.868
# Rotatable Bonds:  7
TPSA:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.221
Synthetic Accessibility Score:  3.326
Fsp3:  0.467
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.375
MDCK Permeability:  3.4674329072004184e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.747
30% Bioavailability (F30%):  0.533

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  98.36176300048828%
Volume Distribution (VD):  0.626
Pgp-substrate:  1.122778058052063%

ADMET: Metabolism

CYP1A2-inhibitor:  0.78
CYP1A2-substrate:  0.649
CYP2C19-inhibitor:  0.901
CYP2C19-substrate:  0.574
CYP2C9-inhibitor:  0.894
CYP2C9-substrate:  0.972
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.399
CYP3A4-inhibitor:  0.854
CYP3A4-substrate:  0.163

ADMET: Excretion

Clearance (CL):  7.659
Half-life (T1/2):  0.703

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.112
Drug-inuced Liver Injury (DILI):  0.93
AMES Toxicity:  0.545
Rat Oral Acute Toxicity:  0.7
Maximum Recommended Daily Dose:  0.08
Skin Sensitization:  0.971
Carcinogencity:  0.73
Eye Corrosion:  0.991
Eye Irritation:  0.977
Respiratory Toxicity:  0.964

Download Data

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

  Natural Product: NPC474362

Natural Product ID:  NPC474362
Common Name*:   Montipoyrne L
IUPAC Name:   (3E)-4-hydroxypentadeca-3,14-dien-5,7-diyn-2-one
Synonyms:  
Standard InCHIKey:  NJLYIXSKKJGBRZ-FYWRMAATSA-N
Standard InCHI:  InChI=1S/C15H18O2/c1-3-4-5-6-7-8-9-10-11-12-15(17)13-14(2)16/h3,13,17H,1,4-8H2,2H3/b15-13+
SMILES:  CC(=O)C=C(C#CC#CCCCCCC=C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465633
PubChem CID:   44567171
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0003131] Alpha,beta-unsaturated carbonyl compounds
            • [CHEMONTID:0003672] Alpha,beta-unsaturated ketones
              • [CHEMONTID:0001363] Enones

*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
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 = 3.52 ug ml-1 PMID[538430]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 4.21 ug ml-1 PMID[538430]
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 4.56 ug ml-1 PMID[538430]
NPT574 Cell Line XF498 Homo sapiens ED50 = 5.5 ug ml-1 PMID[538430]
NPT81 Cell Line A549 Homo sapiens ED50 = 6.39 ug ml-1 PMID[538430]

☑ 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 NPC474362 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 NPC474202
0.8444 Intermediate Similarity NPC267514
0.8444 Intermediate Similarity NPC145755
0.8182 Intermediate Similarity NPC7754
0.8182 Intermediate Similarity NPC270170
0.814 Intermediate Similarity NPC217923
0.7917 Intermediate Similarity NPC471958
0.78 Intermediate Similarity NPC477458
0.76 Intermediate Similarity NPC474391
0.7547 Intermediate Similarity NPC471239
0.75 Intermediate Similarity NPC284224
0.7358 Intermediate Similarity NPC300121
0.7255 Intermediate Similarity NPC20934
0.7255 Intermediate Similarity NPC288381
0.717 Intermediate Similarity NPC61177
0.7111 Intermediate Similarity NPC155880
0.7111 Intermediate Similarity NPC92863
0.7083 Intermediate Similarity NPC301972
0.7059 Intermediate Similarity NPC31194
0.7059 Intermediate Similarity NPC85079
0.7059 Intermediate Similarity NPC302310
0.7059 Intermediate Similarity NPC153538
0.7059 Intermediate Similarity NPC248884
0.7037 Intermediate Similarity NPC48058
0.7021 Intermediate Similarity NPC33489
0.7 Intermediate Similarity NPC35141
0.7 Intermediate Similarity NPC262558
0.7 Intermediate Similarity NPC100380
0.7 Intermediate Similarity NPC55063
0.7 Intermediate Similarity NPC124183
0.7 Intermediate Similarity NPC8610
0.7 Intermediate Similarity NPC19834
0.6964 Remote Similarity NPC193975
0.6939 Remote Similarity NPC101616
0.6939 Remote Similarity NPC108195
0.6923 Remote Similarity NPC473487
0.6923 Remote Similarity NPC72699
0.6897 Remote Similarity NPC235242
0.6875 Remote Similarity NPC304151
0.6875 Remote Similarity NPC67920
0.6875 Remote Similarity NPC287397
0.6875 Remote Similarity NPC298710
0.6875 Remote Similarity NPC149668
0.6863 Remote Similarity NPC324812
0.6809 Remote Similarity NPC27444
0.6809 Remote Similarity NPC329762
0.6809 Remote Similarity NPC103236
0.68 Remote Similarity NPC191337
0.68 Remote Similarity NPC269074
0.68 Remote Similarity NPC276825
0.6792 Remote Similarity NPC93639
0.6792 Remote Similarity NPC151782
0.6792 Remote Similarity NPC29234
0.6792 Remote Similarity NPC28205
0.6786 Remote Similarity NPC325977
0.678 Remote Similarity NPC168407
0.6735 Remote Similarity NPC216921
0.6731 Remote Similarity NPC471280
0.6731 Remote Similarity NPC471276
0.6731 Remote Similarity NPC471275
0.6731 Remote Similarity NPC125122
0.6727 Remote Similarity NPC322461
0.6727 Remote Similarity NPC189677
0.6667 Remote Similarity NPC212730
0.6667 Remote Similarity NPC192843
0.6667 Remote Similarity NPC157096
0.6667 Remote Similarity NPC180575
0.6667 Remote Similarity NPC213767
0.6667 Remote Similarity NPC142092
0.6667 Remote Similarity NPC42304
0.6667 Remote Similarity NPC281230
0.6667 Remote Similarity NPC265551
0.6667 Remote Similarity NPC473705
0.6607 Remote Similarity NPC297280
0.6607 Remote Similarity NPC470963
0.6607 Remote Similarity NPC474513
0.6607 Remote Similarity NPC473863
0.6607 Remote Similarity NPC146551
0.6607 Remote Similarity NPC317899
0.6607 Remote Similarity NPC152668
0.6607 Remote Similarity NPC274290
0.6604 Remote Similarity NPC15325
0.6604 Remote Similarity NPC473913
0.6604 Remote Similarity NPC471281
0.6604 Remote Similarity NPC477727
0.6604 Remote Similarity NPC474642
0.6604 Remote Similarity NPC249670
0.6604 Remote Similarity NPC199286
0.6604 Remote Similarity NPC225974
0.66 Remote Similarity NPC477686
0.66 Remote Similarity NPC304079
0.66 Remote Similarity NPC25771
0.66 Remote Similarity NPC6963
0.6596 Remote Similarity NPC33761
0.6591 Remote Similarity NPC12889
0.6552 Remote Similarity NPC469373
0.6531 Remote Similarity NPC208936
0.6522 Remote Similarity NPC216416
0.6522 Remote Similarity NPC185839
0.6508 Remote Similarity NPC473752
0.6491 Remote Similarity NPC311648
0.6491 Remote Similarity NPC187777
0.6491 Remote Similarity NPC473733
0.6491 Remote Similarity NPC470964
0.6491 Remote Similarity NPC179764
0.6481 Remote Similarity NPC165447
0.6481 Remote Similarity NPC294278
0.6481 Remote Similarity NPC197272
0.6481 Remote Similarity NPC329608
0.6481 Remote Similarity NPC284212
0.6481 Remote Similarity NPC256656
0.6481 Remote Similarity NPC89824
0.6481 Remote Similarity NPC477723
0.6481 Remote Similarity NPC170776
0.6481 Remote Similarity NPC475477
0.6481 Remote Similarity NPC224148
0.6481 Remote Similarity NPC71053
0.6481 Remote Similarity NPC59408
0.6481 Remote Similarity NPC55383
0.6481 Remote Similarity NPC471959
0.6481 Remote Similarity NPC76198
0.6481 Remote Similarity NPC9273
0.6458 Remote Similarity NPC111474
0.6458 Remote Similarity NPC113082
0.6441 Remote Similarity NPC274927
0.6441 Remote Similarity NPC106851
0.6441 Remote Similarity NPC473652
0.6429 Remote Similarity NPC49059
0.6429 Remote Similarity NPC110732
0.6429 Remote Similarity NPC256209
0.6415 Remote Similarity NPC145311
0.64 Remote Similarity NPC292463
0.6393 Remote Similarity NPC477707
0.6383 Remote Similarity NPC180840
0.6379 Remote Similarity NPC48968
0.6379 Remote Similarity NPC594
0.6379 Remote Similarity NPC44542
0.6364 Remote Similarity NPC229046
0.6364 Remote Similarity NPC129458
0.6364 Remote Similarity NPC266979
0.6364 Remote Similarity NPC46565
0.6346 Remote Similarity NPC308331
0.6346 Remote Similarity NPC471752
0.6333 Remote Similarity NPC471278
0.6333 Remote Similarity NPC251042
0.6333 Remote Similarity NPC174447
0.6333 Remote Similarity NPC122521
0.6327 Remote Similarity NPC221250
0.6316 Remote Similarity NPC45626
0.6316 Remote Similarity NPC54766
0.6304 Remote Similarity NPC38497
0.6296 Remote Similarity NPC473768
0.6296 Remote Similarity NPC32351
0.6296 Remote Similarity NPC118788
0.6296 Remote Similarity NPC291437
0.6296 Remote Similarity NPC228776
0.6296 Remote Similarity NPC328784
0.6296 Remote Similarity NPC59051
0.6275 Remote Similarity NPC471753
0.6271 Remote Similarity NPC329819
0.625 Remote Similarity NPC14002
0.625 Remote Similarity NPC187361
0.625 Remote Similarity NPC477724
0.625 Remote Similarity NPC296311
0.625 Remote Similarity NPC15934
0.625 Remote Similarity NPC45283
0.625 Remote Similarity NPC217188
0.625 Remote Similarity NPC10081
0.625 Remote Similarity NPC26102
0.625 Remote Similarity NPC225066
0.623 Remote Similarity NPC325929
0.623 Remote Similarity NPC40082
0.623 Remote Similarity NPC271282
0.623 Remote Similarity NPC66460
0.6226 Remote Similarity NPC91495
0.6222 Remote Similarity NPC62779
0.6207 Remote Similarity NPC477201
0.6207 Remote Similarity NPC324224
0.6207 Remote Similarity NPC472808
0.62 Remote Similarity NPC31121
0.62 Remote Similarity NPC206906
0.6182 Remote Similarity NPC129263
0.617 Remote Similarity NPC220061
0.617 Remote Similarity NPC279300
0.617 Remote Similarity NPC24833
0.6167 Remote Similarity NPC329550
0.6167 Remote Similarity NPC222852
0.6167 Remote Similarity NPC329424
0.6154 Remote Similarity NPC166788
0.6154 Remote Similarity NPC117572
0.614 Remote Similarity NPC473532
0.614 Remote Similarity NPC269615
0.614 Remote Similarity NPC5626
0.614 Remote Similarity NPC137538
0.614 Remote Similarity NPC474127
0.6136 Remote Similarity NPC196831
0.6129 Remote Similarity NPC29697
0.6129 Remote Similarity NPC477830
0.6122 Remote Similarity NPC12319
0.6122 Remote Similarity NPC18205

  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 NPC474362 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
0.6607 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6471 Remote Similarity NPD39 Approved
0.6415 Remote Similarity NPD4220 Pre-registration
0.625 Remote Similarity NPD5783 Phase 3
0.6154 Remote Similarity NPD4222 Approved
0.614 Remote Similarity NPD539 Approved
0.6111 Remote Similarity NPD3173 Approved
0.6078 Remote Similarity NPD5326 Phase 3
0.5965 Remote Similarity NPD3172 Approved
0.5873 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5862 Remote Similarity NPD3194 Approved
0.5862 Remote Similarity NPD3195 Phase 2
0.5862 Remote Similarity NPD3196 Approved
0.5862 Remote Similarity NPD4266 Approved
0.5849 Remote Similarity NPD9090 Phase 3
0.5849 Remote Similarity NPD3174 Discontinued
0.5714 Remote Similarity NPD4194 Approved
0.5714 Remote Similarity NPD4191 Approved
0.5714 Remote Similarity NPD4192 Approved
0.5714 Remote Similarity NPD4193 Approved
0.5614 Remote Similarity NPD29 Approved
0.5614 Remote Similarity NPD28 Approved
0.5606 Remote Similarity NPD7331 Phase 2
0.5606 Remote Similarity NPD6108 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