Structure

Physi-Chem Properties

Molecular Weight:  146.06
Volume:  142.22
LogP:  0.376
LogD:  0.494
LogS:  -0.881
# Rotatable Bonds:  4
TPSA:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.419
Synthetic Accessibility Score:  2.267
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.521
MDCK Permeability:  6.567570380866528e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.98
Plasma Protein Binding (PPB):  16.870269775390625%
Volume Distribution (VD):  0.913
Pgp-substrate:  79.95174407958984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.499
CYP1A2-substrate:  0.074
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.143
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.071
CYP2D6-inhibitor:  0.322
CYP2D6-substrate:  0.128
CYP3A4-inhibitor:  0.025
CYP3A4-substrate:  0.247

ADMET: Excretion

Clearance (CL):  4.526
Half-life (T1/2):  0.877

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.141
Drug-inuced Liver Injury (DILI):  0.781
AMES Toxicity:  0.325
Rat Oral Acute Toxicity:  0.144
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.422
Carcinogencity:  0.428
Eye Corrosion:  0.945
Eye Irritation:  0.978
Respiratory Toxicity:  0.017

Download Data

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

  Natural Product: NPC312003

Natural Product ID:  NPC312003
Common Name*:   1-Acetyloxyethyl Acetate
IUPAC Name:   1-acetyloxyethyl acetate
Synonyms:  
Standard InCHIKey:  ACKALUBLCWJVNB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3
SMILES:  CC(=O)OC(C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3187663
PubChem CID:   222536
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001093] Carboxylic acid derivatives
          • [CHEMONTID:0001238] Carboxylic acid esters
            • [CHEMONTID:0003989] Acylals

*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
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae 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. 70687.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2814.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2009.6 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 NPC312003 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
0.8148 Intermediate Similarity NPC184593
0.7778 Intermediate Similarity NPC2419
0.7778 Intermediate Similarity NPC23508
0.75 Intermediate Similarity NPC110107
0.7407 Intermediate Similarity NPC308490
0.7241 Intermediate Similarity NPC32280
0.7241 Intermediate Similarity NPC41485
0.7241 Intermediate Similarity NPC3693
0.7143 Intermediate Similarity NPC30787
0.7 Intermediate Similarity NPC166804
0.7 Intermediate Similarity NPC201132
0.7 Intermediate Similarity NPC127134
0.6875 Remote Similarity NPC232172
0.6774 Remote Similarity NPC143211
0.6774 Remote Similarity NPC248233
0.6667 Remote Similarity NPC37493
0.6667 Remote Similarity NPC265882
0.6562 Remote Similarity NPC281943
0.6562 Remote Similarity NPC88135
0.6562 Remote Similarity NPC317739
0.6552 Remote Similarity NPC208021
0.6552 Remote Similarity NPC203105
0.6552 Remote Similarity NPC8187
0.6471 Remote Similarity NPC281883
0.6364 Remote Similarity NPC127696
0.6333 Remote Similarity NPC8368
0.6296 Remote Similarity NPC137050
0.6286 Remote Similarity NPC108238
0.6176 Remote Similarity NPC21374
0.6176 Remote Similarity NPC5934
0.6129 Remote Similarity NPC35155
0.6129 Remote Similarity NPC28246
0.6111 Remote Similarity NPC140229
0.6071 Remote Similarity NPC173862
0.6061 Remote Similarity NPC55956
0.6061 Remote Similarity NPC231957
0.6 Remote Similarity NPC40965
0.6 Remote Similarity NPC12904
0.5938 Remote Similarity NPC211250
0.5882 Remote Similarity NPC180423
0.5862 Remote Similarity NPC260610
0.5833 Remote Similarity NPC35371
0.5833 Remote Similarity NPC41007
0.5833 Remote Similarity NPC286695
0.5833 Remote Similarity NPC168714
0.5833 Remote Similarity NPC178643
0.5833 Remote Similarity NPC322892
0.5676 Remote Similarity NPC154396
0.5676 Remote Similarity NPC63354
0.5676 Remote Similarity NPC286498

  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 NPC312003 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
0.7586 Intermediate Similarity NPD8992 Approved
0.7 Intermediate Similarity NPD8989 Approved
0.6471 Remote Similarity NPD9636 Phase 2
0.6176 Remote Similarity NPD8856 Phase 2
0.6111 Remote Similarity NPD900 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