Structure

Physi-Chem Properties

Molecular Weight:  180.09
Volume:  175.826
LogP:  0.987
LogD:  1.152
LogS:  -1.28
# Rotatable Bonds:  4
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.624
Synthetic Accessibility Score:  3.125
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.212
MDCK Permeability:  3.6951267247786745e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.554
Plasma Protein Binding (PPB):  6.627126216888428%
Volume Distribution (VD):  0.887
Pgp-substrate:  79.77688598632812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.612
CYP1A2-substrate:  0.867
CYP2C19-inhibitor:  0.864
CYP2C19-substrate:  0.923
CYP2C9-inhibitor:  0.445
CYP2C9-substrate:  0.671
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.714
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.265

ADMET: Excretion

Clearance (CL):  4.468
Half-life (T1/2):  0.866

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.065
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.062
Carcinogencity:  0.439
Eye Corrosion:  0.61
Eye Irritation:  0.911
Respiratory Toxicity:  0.188

Download Data

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

  Natural Product: NPC68114

Natural Product ID:  NPC68114
Common Name*:   Methylphosphonic Acid Diisopropyl Ester
IUPAC Name:   2-[methyl(propan-2-yloxy)phosphoryl]oxypropane
Synonyms:  
Standard InCHIKey:  WOAFDHWYKSOANX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3
SMILES:  CC(C)OP(=O)(C)OC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1232236
PubChem CID:   3073
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000419] Organic phosphonic acids and derivatives
        • [CHEMONTID:0003893] Phosphonic acid diesters
          • [CHEMONTID:0004482] Dialkyl alkylphosphonates

*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
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11473446]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruits n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22234 Ficus carica Species Moraceae 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
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43277.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34376.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12310.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 17228.9 nM PubChem BioAssay data set

☑ 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 NPC68114 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
0.7857 Intermediate Similarity NPC120097
0.6774 Remote Similarity NPC306022
0.6667 Remote Similarity NPC327597
0.6364 Remote Similarity NPC266566
0.6364 Remote Similarity NPC31433
0.6364 Remote Similarity NPC321170
0.5758 Remote Similarity NPC290971
0.5676 Remote Similarity NPC314319
0.5667 Remote Similarity NPC314978

  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 NPC68114 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
0.8519 High Similarity NPD9038 Approved
0.7407 Intermediate Similarity NPD8559 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD9679 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8219 Approved
0.6897 Remote Similarity NPD8220 Approved
0.6774 Remote Similarity NPD8218 Approved
0.6364 Remote Similarity NPD8237 Approved
0.6061 Remote Similarity NPD8234 Approved
0.6061 Remote Similarity NPD8235 Approved
0.6061 Remote Similarity NPD8236 Phase 1
0.5862 Remote Similarity NPD7385 Approved
0.5833 Remote Similarity NPD9208 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8612 Approved
0.5641 Remote Similarity NPD5799 Discontinued

  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