Structure

Physi-Chem Properties

Molecular Weight:  232.15
Volume:  269.758
LogP:  3.147
LogD:  3.456
LogS:  -3.765
# Rotatable Bonds:  7
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.416
Synthetic Accessibility Score:  3.711
Fsp3:  0.533
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.192
MDCK Permeability:  2.826876334438566e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.061
20% Bioavailability (F20%):  0.41
30% Bioavailability (F30%):  0.759

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.12
Plasma Protein Binding (PPB):  99.79899597167969%
Volume Distribution (VD):  0.982
Pgp-substrate:  1.4239940643310547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.576
CYP1A2-substrate:  0.746
CYP2C19-inhibitor:  0.916
CYP2C19-substrate:  0.746
CYP2C9-inhibitor:  0.908
CYP2C9-substrate:  0.978
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.698
CYP3A4-inhibitor:  0.858
CYP3A4-substrate:  0.183

ADMET: Excretion

Clearance (CL):  8.481
Half-life (T1/2):  0.445

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.579
Drug-inuced Liver Injury (DILI):  0.916
AMES Toxicity:  0.537
Rat Oral Acute Toxicity:  0.965
Maximum Recommended Daily Dose:  0.966
Skin Sensitization:  0.94
Carcinogencity:  0.636
Eye Corrosion:  0.95
Eye Irritation:  0.982
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC473487

Natural Product ID:  NPC473487
Common Name*:   (+/-)-Montiporyne J
IUPAC Name:   4-hydroxypentadec-14-en-5,7-diyn-2-one
Synonyms:   (+/-)-Montiporyne J
Standard InCHIKey:  HSZSIOCCFYEOGS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H20O2/c1-3-4-5-6-7-8-9-10-11-12-15(17)13-14(2)16/h3,15,17H,1,4-8,13H2,2H3
SMILES:  CC(=O)CC(C#CC#CCCCCCC=C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443341
PubChem CID:   9991550
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
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 3.42 ug ml-1 PMID[473985]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 3.74 ug ml-1 PMID[473985]
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 = 3.85 ug ml-1 PMID[473985]
NPT574 Cell Line XF498 Homo sapiens ED50 = 3.87 ug ml-1 PMID[473985]
NPT81 Cell Line A549 Homo sapiens ED50 = 4.97 ug ml-1 PMID[473985]

☑ 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 NPC473487 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
0.9583 High Similarity NPC473705
0.8269 Intermediate Similarity NPC284224
0.8 Intermediate Similarity NPC193975
0.7872 Intermediate Similarity NPC474361
0.7547 Intermediate Similarity NPC470411
0.75 Intermediate Similarity NPC302310
0.7455 Intermediate Similarity NPC300121
0.7273 Intermediate Similarity NPC217188
0.7273 Intermediate Similarity NPC61177
0.7222 Intermediate Similarity NPC151782
0.7174 Intermediate Similarity NPC213767
0.717 Intermediate Similarity NPC153538
0.7059 Intermediate Similarity NPC108195
0.7037 Intermediate Similarity NPC20934
0.7037 Intermediate Similarity NPC225974
0.7037 Intermediate Similarity NPC72699
0.7037 Intermediate Similarity NPC288381
0.7021 Intermediate Similarity NPC216416
0.7 Intermediate Similarity NPC46248
0.7 Intermediate Similarity NPC249801
0.6923 Remote Similarity NPC474202
0.6923 Remote Similarity NPC276825
0.6923 Remote Similarity NPC474362
0.6909 Remote Similarity NPC93639
0.6909 Remote Similarity NPC59408
0.6909 Remote Similarity NPC71053
0.6852 Remote Similarity NPC85079
0.6852 Remote Similarity NPC248884
0.6852 Remote Similarity NPC475153
0.6852 Remote Similarity NPC31194
0.6842 Remote Similarity NPC256209
0.6842 Remote Similarity NPC110732
0.6842 Remote Similarity NPC48058
0.6842 Remote Similarity NPC137538
0.6842 Remote Similarity NPC49059
0.6833 Remote Similarity NPC318306
0.6833 Remote Similarity NPC473652
0.6792 Remote Similarity NPC124183
0.6792 Remote Similarity NPC19834
0.6792 Remote Similarity NPC157096
0.6792 Remote Similarity NPC55063
0.6792 Remote Similarity NPC35141
0.6735 Remote Similarity NPC306850
0.6731 Remote Similarity NPC101616
0.6727 Remote Similarity NPC328784
0.6727 Remote Similarity NPC291437
0.6724 Remote Similarity NPC52264
0.6724 Remote Similarity NPC471239
0.6667 Remote Similarity NPC187361
0.6667 Remote Similarity NPC174396
0.6667 Remote Similarity NPC477724
0.6667 Remote Similarity NPC470320
0.6667 Remote Similarity NPC226592
0.6667 Remote Similarity NPC26102
0.6667 Remote Similarity NPC31121
0.6613 Remote Similarity NPC168407
0.6607 Remote Similarity NPC28205
0.6607 Remote Similarity NPC29234
0.6557 Remote Similarity NPC278202
0.6557 Remote Similarity NPC222852
0.6552 Remote Similarity NPC189677
0.6552 Remote Similarity NPC473532
0.6545 Remote Similarity NPC267110
0.6545 Remote Similarity NPC471275
0.6545 Remote Similarity NPC125122
0.6545 Remote Similarity NPC471276
0.6545 Remote Similarity NPC471280
0.6508 Remote Similarity NPC29697
0.65 Remote Similarity NPC323436
0.65 Remote Similarity NPC265551
0.65 Remote Similarity NPC44542
0.65 Remote Similarity NPC472445
0.65 Remote Similarity NPC212730
0.6491 Remote Similarity NPC18357
0.6491 Remote Similarity NPC142092
0.6481 Remote Similarity NPC42304
0.6458 Remote Similarity NPC79544
0.6452 Remote Similarity NPC327112
0.6452 Remote Similarity NPC243532
0.6441 Remote Similarity NPC146551
0.6441 Remote Similarity NPC474513
0.6441 Remote Similarity NPC473896
0.6441 Remote Similarity NPC317899
0.6441 Remote Similarity NPC473910
0.6441 Remote Similarity NPC477725
0.6441 Remote Similarity NPC274290
0.6441 Remote Similarity NPC473725
0.6441 Remote Similarity NPC470963
0.6441 Remote Similarity NPC473735
0.6441 Remote Similarity NPC473863
0.6441 Remote Similarity NPC477726
0.6441 Remote Similarity NPC475353
0.6441 Remote Similarity NPC473721
0.6441 Remote Similarity NPC152668
0.6429 Remote Similarity NPC477727
0.6429 Remote Similarity NPC199286
0.6429 Remote Similarity NPC474642
0.6429 Remote Similarity NPC473768
0.6429 Remote Similarity NPC473913
0.6429 Remote Similarity NPC249670
0.6429 Remote Similarity NPC471281
0.6406 Remote Similarity NPC475221
0.6349 Remote Similarity NPC325929
0.6349 Remote Similarity NPC201939
0.6349 Remote Similarity NPC321838
0.6349 Remote Similarity NPC66460
0.6349 Remote Similarity NPC271282
0.6349 Remote Similarity NPC260573
0.6349 Remote Similarity NPC113293
0.6349 Remote Similarity NPC64971
0.6349 Remote Similarity NPC477829
0.6349 Remote Similarity NPC475984
0.6346 Remote Similarity NPC304151
0.6346 Remote Similarity NPC149668
0.6333 Remote Similarity NPC187777
0.6333 Remote Similarity NPC470969
0.6333 Remote Similarity NPC473847
0.6333 Remote Similarity NPC470964
0.6333 Remote Similarity NPC477661
0.6333 Remote Similarity NPC311648
0.6333 Remote Similarity NPC471960
0.6333 Remote Similarity NPC470968
0.6333 Remote Similarity NPC470967
0.6333 Remote Similarity NPC179764
0.6333 Remote Similarity NPC470966
0.6333 Remote Similarity NPC475384
0.6333 Remote Similarity NPC161838
0.6333 Remote Similarity NPC327388
0.6324 Remote Similarity NPC42526
0.6316 Remote Similarity NPC284212
0.6316 Remote Similarity NPC129263
0.6316 Remote Similarity NPC477723
0.6316 Remote Similarity NPC470412
0.6316 Remote Similarity NPC329608
0.6316 Remote Similarity NPC256656
0.6316 Remote Similarity NPC89824
0.6316 Remote Similarity NPC294278
0.6316 Remote Similarity NPC197272
0.6316 Remote Similarity NPC471959
0.6316 Remote Similarity NPC475477
0.6316 Remote Similarity NPC470410
0.6316 Remote Similarity NPC165447
0.6316 Remote Similarity NPC224148
0.6316 Remote Similarity NPC170776
0.6316 Remote Similarity NPC55383
0.6316 Remote Similarity NPC76198
0.6316 Remote Similarity NPC9273
0.6308 Remote Similarity NPC296436
0.6308 Remote Similarity NPC176215
0.6296 Remote Similarity NPC201948
0.6296 Remote Similarity NPC269074
0.6275 Remote Similarity NPC103236
0.6275 Remote Similarity NPC27444
0.6275 Remote Similarity NPC329762
0.6269 Remote Similarity NPC477980
0.625 Remote Similarity NPC470965
0.623 Remote Similarity NPC470970
0.623 Remote Similarity NPC594
0.623 Remote Similarity NPC71755
0.623 Remote Similarity NPC323597
0.623 Remote Similarity NPC211752
0.623 Remote Similarity NPC323498
0.623 Remote Similarity NPC474577
0.623 Remote Similarity NPC48968
0.6226 Remote Similarity NPC252978
0.6226 Remote Similarity NPC76051
0.6212 Remote Similarity NPC83965
0.6207 Remote Similarity NPC129458
0.6207 Remote Similarity NPC161366
0.62 Remote Similarity NPC155880
0.62 Remote Similarity NPC34873
0.62 Remote Similarity NPC92863
0.62 Remote Similarity NPC40434
0.619 Remote Similarity NPC471278
0.619 Remote Similarity NPC321919
0.619 Remote Similarity NPC235242
0.619 Remote Similarity NPC81896
0.619 Remote Similarity NPC328311
0.6182 Remote Similarity NPC180575
0.6176 Remote Similarity NPC470436
0.6167 Remote Similarity NPC54766
0.6167 Remote Similarity NPC45626
0.6154 Remote Similarity NPC476658
0.614 Remote Similarity NPC59051
0.614 Remote Similarity NPC474391
0.6129 Remote Similarity NPC329819
0.6129 Remote Similarity NPC469373
0.6111 Remote Similarity NPC145755
0.6111 Remote Similarity NPC473539
0.6111 Remote Similarity NPC267514
0.6111 Remote Similarity NPC474413
0.6102 Remote Similarity NPC225066
0.6102 Remote Similarity NPC475723
0.6102 Remote Similarity NPC34577
0.6102 Remote Similarity NPC10081
0.6094 Remote Similarity NPC328776
0.6094 Remote Similarity NPC320305
0.6087 Remote Similarity NPC477455
0.6071 Remote Similarity NPC180534
0.6071 Remote Similarity NPC324812

  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 NPC473487 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
0.6452 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6296 Remote Similarity NPD39 Approved
0.6167 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6154 Remote Similarity NPD3197 Phase 1
0.6071 Remote Similarity NPD622 Approved
0.6 Remote Similarity NPD4222 Approved
0.5965 Remote Similarity NPD3173 Approved
0.5926 Remote Similarity NPD5326 Phase 3
0.5873 Remote Similarity NPD6109 Phase 1
0.5833 Remote Similarity NPD3172 Approved
0.5738 Remote Similarity NPD4266 Approved
0.5738 Remote Similarity NPD3196 Approved
0.5738 Remote Similarity NPD3194 Approved
0.5738 Remote Similarity NPD3195 Phase 2
0.5676 Remote Similarity NPD818 Approved
0.5676 Remote Similarity NPD819 Approved
0.5652 Remote Similarity NPD4247 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