Structure

Physi-Chem Properties

Molecular Weight:  102.07
Volume:  104.06
LogP:  -0.287
LogD:  -0.131
LogS:  0.952
# Rotatable Bonds:  1
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.511
Synthetic Accessibility Score:  2.656
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:  -4.242
MDCK Permeability:  0.00022592216555494815
Pgp-inhibitor:  0.001
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.438
Plasma Protein Binding (PPB):  12.406475067138672%
Volume Distribution (VD):  1.164
Pgp-substrate:  80.20655059814453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.064
CYP1A2-substrate:  0.65
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.765
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.177
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.19
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.196

ADMET: Excretion

Clearance (CL):  7.961
Half-life (T1/2):  0.762

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.43
Drug-inuced Liver Injury (DILI):  0.049
AMES Toxicity:  0.118
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.039
Skin Sensitization:  0.671
Carcinogencity:  0.764
Eye Corrosion:  0.164
Eye Irritation:  0.975
Respiratory Toxicity:  0.034

Download Data

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

  Natural Product: NPC227267

Natural Product ID:  NPC227267
Common Name*:   Oxolan-2-Ylmethanol
IUPAC Name:   oxolan-2-ylmethanol
Synonyms:  
Standard InCHIKey:  BSYVTEYKTMYBMK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2
SMILES:  C1CC(CO)OC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2287521
PubChem CID:   7360
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002648] Tetrahydrofurans

*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
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota Flowers Tantempango, Hidalgo, Mexico 2019-May DOI[10.1007/s11130-020-00822-2]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[16297615]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. whole plant n.a. PMID[18543151]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[24358188]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. PMID[8778246]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2837 Aloe spicata Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2997 Aloe africana Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14763 Aloe ferox Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11578 Aloe vera Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2997 Aloe africana Species Xanthorrhoeaceae 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. 54947.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 55957.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 78369.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27539.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24995.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48972.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27806.6 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 NPC227267 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
0.7949 Intermediate Similarity NPC320189
0.775 Intermediate Similarity NPC29721
0.7647 Intermediate Similarity NPC149070
0.7647 Intermediate Similarity NPC127074
0.7647 Intermediate Similarity NPC197207
0.7647 Intermediate Similarity NPC182541
0.7647 Intermediate Similarity NPC187058
0.75 Intermediate Similarity NPC272307
0.7436 Intermediate Similarity NPC266553
0.7297 Intermediate Similarity NPC313405
0.7209 Intermediate Similarity NPC252918
0.7209 Intermediate Similarity NPC230789
0.7188 Intermediate Similarity NPC128335
0.7188 Intermediate Similarity NPC252154
0.7097 Intermediate Similarity NPC199270
0.7073 Intermediate Similarity NPC134252
0.7073 Intermediate Similarity NPC317182
0.7073 Intermediate Similarity NPC291502
0.7073 Intermediate Similarity NPC213159
0.7073 Intermediate Similarity NPC86191
0.7073 Intermediate Similarity NPC298699
0.7045 Intermediate Similarity NPC112363
0.7027 Intermediate Similarity NPC293908
0.7027 Intermediate Similarity NPC192065
0.7027 Intermediate Similarity NPC86412
0.7027 Intermediate Similarity NPC325034
0.7027 Intermediate Similarity NPC66052
0.697 Remote Similarity NPC320326
0.6905 Remote Similarity NPC320240
0.6905 Remote Similarity NPC70756
0.6889 Remote Similarity NPC82512
0.6889 Remote Similarity NPC46254
0.6875 Remote Similarity NPC140389
0.6875 Remote Similarity NPC304786
0.6765 Remote Similarity NPC301586
0.6765 Remote Similarity NPC238135
0.6765 Remote Similarity NPC33415
0.6739 Remote Similarity NPC329128
0.6739 Remote Similarity NPC322158
0.6739 Remote Similarity NPC323574
0.6667 Remote Similarity NPC560
0.6596 Remote Similarity NPC329095
0.6591 Remote Similarity NPC285364
0.6591 Remote Similarity NPC289758
0.6591 Remote Similarity NPC21209
0.6591 Remote Similarity NPC69445
0.6591 Remote Similarity NPC199857
0.6591 Remote Similarity NPC92246
0.6591 Remote Similarity NPC176017
0.6591 Remote Similarity NPC73906
0.6591 Remote Similarity NPC255377
0.6591 Remote Similarity NPC165846
0.6562 Remote Similarity NPC318912
0.6562 Remote Similarity NPC114270
0.6562 Remote Similarity NPC237965
0.6562 Remote Similarity NPC157340
0.6562 Remote Similarity NPC245688
0.6458 Remote Similarity NPC320043
0.6458 Remote Similarity NPC103672
0.6444 Remote Similarity NPC321087
0.6444 Remote Similarity NPC88638
0.6444 Remote Similarity NPC277475
0.6364 Remote Similarity NPC213764
0.6364 Remote Similarity NPC207656
0.6364 Remote Similarity NPC88887
0.6364 Remote Similarity NPC232554
0.6364 Remote Similarity NPC107091
0.6327 Remote Similarity NPC323361
0.6327 Remote Similarity NPC130683
0.6304 Remote Similarity NPC14144
0.6286 Remote Similarity NPC159845
0.6286 Remote Similarity NPC325345
0.625 Remote Similarity NPC52403
0.625 Remote Similarity NPC39977
0.619 Remote Similarity NPC111882
0.619 Remote Similarity NPC102981
0.619 Remote Similarity NPC99573
0.619 Remote Similarity NPC227707
0.619 Remote Similarity NPC88278
0.6176 Remote Similarity NPC317724
0.6176 Remote Similarity NPC329496
0.6176 Remote Similarity NPC230452
0.617 Remote Similarity NPC42503
0.617 Remote Similarity NPC299781
0.617 Remote Similarity NPC157193
0.617 Remote Similarity NPC282143
0.6111 Remote Similarity NPC110884
0.6098 Remote Similarity NPC197039
0.6087 Remote Similarity NPC8597
0.6 Remote Similarity NPC24967
0.6 Remote Similarity NPC103612
0.6 Remote Similarity NPC62014
0.5938 Remote Similarity NPC299484
0.5938 Remote Similarity NPC219266
0.5918 Remote Similarity NPC326533
0.5918 Remote Similarity NPC23134
0.5918 Remote Similarity NPC124963
0.5918 Remote Similarity NPC233726
0.5909 Remote Similarity NPC313565
0.5909 Remote Similarity NPC228782
0.5909 Remote Similarity NPC259982
0.5882 Remote Similarity NPC275462
0.5849 Remote Similarity NPC219040
0.5849 Remote Similarity NPC293692
0.5814 Remote Similarity NPC320331
0.5814 Remote Similarity NPC152008
0.5806 Remote Similarity NPC327092
0.5789 Remote Similarity NPC267243
0.5789 Remote Similarity NPC122962
0.5789 Remote Similarity NPC317060
0.575 Remote Similarity NPC325165
0.5741 Remote Similarity NPC290179
0.5741 Remote Similarity NPC34877
0.5686 Remote Similarity NPC58629
0.5686 Remote Similarity NPC317626
0.5686 Remote Similarity NPC67660
0.5686 Remote Similarity NPC314821
0.5686 Remote Similarity NPC89145
0.5686 Remote Similarity NPC269166
0.5686 Remote Similarity NPC157514
0.5686 Remote Similarity NPC107914
0.5686 Remote Similarity NPC165198
0.5686 Remote Similarity NPC317501
0.5686 Remote Similarity NPC246558
0.5686 Remote Similarity NPC242073
0.5686 Remote Similarity NPC145112
0.566 Remote Similarity NPC293551
0.5652 Remote Similarity NPC242655
0.5652 Remote Similarity NPC85078
0.5652 Remote Similarity NPC38891
0.5641 Remote Similarity NPC319034
0.5641 Remote Similarity NPC66124
0.5641 Remote Similarity NPC72324
0.5641 Remote Similarity NPC193062
0.5641 Remote Similarity NPC1748
0.5625 Remote Similarity NPC294703
0.561 Remote Similarity NPC474392
0.561 Remote Similarity NPC5505
0.561 Remote Similarity NPC474914
0.561 Remote Similarity NPC233231
0.561 Remote Similarity NPC321699

  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 NPC227267 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
0.7949 Intermediate Similarity NPD8957 Approved
0.775 Intermediate Similarity NPD9006 Approved
0.7647 Intermediate Similarity NPD8814 Phase 3
0.7073 Intermediate Similarity NPD8788 Approved
0.7045 Intermediate Similarity NPD9139 Approved
0.7027 Intermediate Similarity NPD9051 Approved
0.7027 Intermediate Similarity NPD9052 Approved
0.7027 Intermediate Similarity NPD9053 Approved
0.6765 Remote Similarity NPD8549 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8958 Phase 2
0.6591 Remote Similarity NPD8999 Phase 3
0.6591 Remote Similarity NPD8998 Phase 2
0.6591 Remote Similarity NPD8994 Approved
0.6591 Remote Similarity NPD8997 Approved
0.6591 Remote Similarity NPD9000 Phase 3
0.6591 Remote Similarity NPD8993 Phase 1
0.6562 Remote Similarity NPD8226 Approved
0.6562 Remote Similarity NPD8225 Phase 3
0.6458 Remote Similarity NPD9049 Discontinued
0.6458 Remote Similarity NPD9050 Approved
0.6429 Remote Similarity NPD8967 Approved
0.6364 Remote Similarity NPD9219 Approved
0.6364 Remote Similarity NPD9218 Clinical (unspecified phase)
0.6327 Remote Similarity NPD895 Approved
0.6327 Remote Similarity NPD887 Approved
0.6327 Remote Similarity NPD894 Approved
0.6327 Remote Similarity NPD889 Approved
0.6304 Remote Similarity NPD8965 Approved
0.6304 Remote Similarity NPD8966 Approved
0.6286 Remote Similarity NPD8988 Clinical (unspecified phase)
0.619 Remote Similarity NPD8996 Phase 3
0.619 Remote Similarity NPD8995 Clinical (unspecified phase)
0.6098 Remote Similarity NPD8977 Phase 3
0.6098 Remote Similarity NPD8976 Approved
0.5962 Remote Similarity NPD2267 Suspended
0.5918 Remote Similarity NPD904 Phase 3
0.5918 Remote Similarity NPD905 Approved
0.5814 Remote Similarity NPD7536 Approved
0.5686 Remote Similarity NPD891 Phase 3
0.5686 Remote Similarity NPD890 Clinical (unspecified phase)
0.5686 Remote Similarity NPD9036 Phase 3
0.5686 Remote Similarity NPD893 Approved
0.5686 Remote Similarity NPD892 Phase 3
0.5686 Remote Similarity NPD9035 Clinical (unspecified phase)
0.5686 Remote Similarity NPD888 Phase 3
0.5652 Remote Similarity NPD9110 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