Structure

Physi-Chem Properties

Molecular Weight:  186.09
Volume:  185.552
LogP:  0.246
LogD:  -0.21
LogS:  -0.401
# Rotatable Bonds:  2
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.629
Synthetic Accessibility Score:  4.011
Fsp3:  0.778
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:  -4.498
MDCK Permeability:  0.00011637400166364387
Pgp-inhibitor:  0.001
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.42
Plasma Protein Binding (PPB):  22.250591278076172%
Volume Distribution (VD):  1.048
Pgp-substrate:  83.56834411621094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.248
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.625
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.244
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.341
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.265

ADMET: Excretion

Clearance (CL):  7.59
Half-life (T1/2):  0.843

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.2
Drug-inuced Liver Injury (DILI):  0.317
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.357
Skin Sensitization:  0.346
Carcinogencity:  0.29
Eye Corrosion:  0.956
Eye Irritation:  0.892
Respiratory Toxicity:  0.058

Download Data

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

  Natural Product: NPC202011

Natural Product ID:  NPC202011
Common Name*:   Dihydroaspyrone
IUPAC Name:   (2R,3S)-3-hydroxy-5-[(2S)-2-hydroxypropyl]-2-methyl-2,3-dihydropyran-6-one
Synonyms:   Dihydroaspyrone
Standard InCHIKey:  QURYMMSJKKNQFX-BBVRLYRLSA-N
Standard InCHI:  InChI=1S/C9H14O4/c1-5(10)3-7-4-8(11)6(2)13-9(7)12/h4-6,8,10-11H,3H2,1-2H3/t5-,6+,8-/m0/s1
SMILES:  C[C@@H](CC1=C[C@H](O)[C@H](OC1=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL399445
PubChem CID:   16196967
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones and derivatives
          • [CHEMONTID:0001211] Dihydropyranones

*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
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17994702]
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1807834]
NPO4417 Aspergillus ostianus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18078344]
NPO4417 Aspergillus ostianus Species Aspergillaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 8275.3 nM PMID[458776]

☑ 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 NPC202011 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
0.9028 High Similarity NPC28049
0.8696 High Similarity NPC475982
0.8657 High Similarity NPC273600
0.8611 High Similarity NPC478191
0.8611 High Similarity NPC478193
0.8611 High Similarity NPC478192
0.8611 High Similarity NPC478194
0.8611 High Similarity NPC478196
0.8611 High Similarity NPC478195
0.8529 High Similarity NPC201356
0.8382 Intermediate Similarity NPC96414
0.8382 Intermediate Similarity NPC470123
0.8382 Intermediate Similarity NPC19769
0.8356 Intermediate Similarity NPC161038
0.8289 Intermediate Similarity NPC121374
0.8243 Intermediate Similarity NPC470705
0.8219 Intermediate Similarity NPC476590
0.8219 Intermediate Similarity NPC114727
0.8182 Intermediate Similarity NPC302564
0.8133 Intermediate Similarity NPC275530
0.8133 Intermediate Similarity NPC475711
0.8077 Intermediate Similarity NPC11383
0.8077 Intermediate Similarity NPC474959
0.8077 Intermediate Similarity NPC475046
0.8077 Intermediate Similarity NPC310450
0.8 Intermediate Similarity NPC475555
0.8 Intermediate Similarity NPC475675
0.8 Intermediate Similarity NPC276299
0.7975 Intermediate Similarity NPC286770
0.7975 Intermediate Similarity NPC284472
0.7975 Intermediate Similarity NPC229799
0.7857 Intermediate Similarity NPC478099
0.7857 Intermediate Similarity NPC478098
0.7826 Intermediate Similarity NPC68110
0.7778 Intermediate Similarity NPC63873
0.7778 Intermediate Similarity NPC182383
0.7763 Intermediate Similarity NPC301207
0.7763 Intermediate Similarity NPC68819
0.7746 Intermediate Similarity NPC478101
0.7722 Intermediate Similarity NPC297440
0.7722 Intermediate Similarity NPC150502
0.7692 Intermediate Similarity NPC99651
0.7683 Intermediate Similarity NPC47937
0.7681 Intermediate Similarity NPC26810
0.7662 Intermediate Similarity NPC125365
0.7662 Intermediate Similarity NPC474818
0.7662 Intermediate Similarity NPC51809
0.7662 Intermediate Similarity NPC176329
0.7662 Intermediate Similarity NPC49302
0.7654 Intermediate Similarity NPC474251
0.7639 Intermediate Similarity NPC122627
0.7639 Intermediate Similarity NPC478097
0.7639 Intermediate Similarity NPC478100
0.7632 Intermediate Similarity NPC473948
0.7612 Intermediate Similarity NPC135863
0.7606 Intermediate Similarity NPC282760
0.76 Intermediate Similarity NPC284006
0.7571 Intermediate Similarity NPC473737
0.7571 Intermediate Similarity NPC2328
0.7564 Intermediate Similarity NPC248775
0.7564 Intermediate Similarity NPC221095
0.7564 Intermediate Similarity NPC473471
0.7564 Intermediate Similarity NPC318481
0.7564 Intermediate Similarity NPC279214
0.7561 Intermediate Similarity NPC283085
0.7561 Intermediate Similarity NPC231009
0.7561 Intermediate Similarity NPC110710
0.7561 Intermediate Similarity NPC103284
0.7561 Intermediate Similarity NPC132496
0.7561 Intermediate Similarity NPC473651
0.7561 Intermediate Similarity NPC66346
0.7561 Intermediate Similarity NPC223871
0.7561 Intermediate Similarity NPC286338
0.7561 Intermediate Similarity NPC82795
0.7561 Intermediate Similarity NPC473669
0.7561 Intermediate Similarity NPC473478
0.7561 Intermediate Similarity NPC107986
0.7561 Intermediate Similarity NPC1083
0.7536 Intermediate Similarity NPC26223
0.7534 Intermediate Similarity NPC238223
0.7532 Intermediate Similarity NPC203277
0.7532 Intermediate Similarity NPC209113
0.7532 Intermediate Similarity NPC127118
0.7531 Intermediate Similarity NPC44261
0.75 Intermediate Similarity NPC248125
0.75 Intermediate Similarity NPC107654
0.75 Intermediate Similarity NPC315843
0.747 Intermediate Similarity NPC103523
0.747 Intermediate Similarity NPC219498
0.747 Intermediate Similarity NPC107717
0.747 Intermediate Similarity NPC232555
0.747 Intermediate Similarity NPC69082
0.747 Intermediate Similarity NPC171174
0.747 Intermediate Similarity NPC231096
0.747 Intermediate Similarity NPC134865
0.747 Intermediate Similarity NPC112685
0.747 Intermediate Similarity NPC279267
0.747 Intermediate Similarity NPC308412
0.747 Intermediate Similarity NPC134807
0.747 Intermediate Similarity NPC134885
0.747 Intermediate Similarity NPC210218
0.747 Intermediate Similarity NPC475581
0.747 Intermediate Similarity NPC114694
0.747 Intermediate Similarity NPC142117
0.747 Intermediate Similarity NPC473687
0.747 Intermediate Similarity NPC62118
0.747 Intermediate Similarity NPC240695
0.747 Intermediate Similarity NPC204686
0.7468 Intermediate Similarity NPC470148
0.7468 Intermediate Similarity NPC180725
0.7468 Intermediate Similarity NPC470149
0.7465 Intermediate Similarity NPC470808
0.7465 Intermediate Similarity NPC148233
0.7465 Intermediate Similarity NPC25747
0.7436 Intermediate Similarity NPC474026
0.7432 Intermediate Similarity NPC476591
0.7432 Intermediate Similarity NPC88877
0.7432 Intermediate Similarity NPC151481
0.7429 Intermediate Similarity NPC151648
0.7412 Intermediate Similarity NPC139418
0.7397 Intermediate Similarity NPC25298
0.7397 Intermediate Similarity NPC132286
0.7397 Intermediate Similarity NPC203335
0.7391 Intermediate Similarity NPC97570
0.7381 Intermediate Similarity NPC178215
0.7375 Intermediate Similarity NPC470147
0.7375 Intermediate Similarity NPC133226
0.7353 Intermediate Similarity NPC249850
0.7353 Intermediate Similarity NPC293437
0.7349 Intermediate Similarity NPC470124
0.7349 Intermediate Similarity NPC21469
0.7342 Intermediate Similarity NPC477314
0.7342 Intermediate Similarity NPC93763
0.7342 Intermediate Similarity NPC108816
0.7342 Intermediate Similarity NPC279532
0.7333 Intermediate Similarity NPC59558
0.7326 Intermediate Similarity NPC274075
0.7326 Intermediate Similarity NPC473904
0.7324 Intermediate Similarity NPC475073
0.7317 Intermediate Similarity NPC169575
0.7317 Intermediate Similarity NPC315559
0.7317 Intermediate Similarity NPC40746
0.7317 Intermediate Similarity NPC116543
0.7308 Intermediate Similarity NPC16279
0.7308 Intermediate Similarity NPC205615
0.7308 Intermediate Similarity NPC256640
0.7308 Intermediate Similarity NPC190400
0.7308 Intermediate Similarity NPC49392
0.7297 Intermediate Similarity NPC287705
0.7294 Intermediate Similarity NPC61257
0.7294 Intermediate Similarity NPC100454
0.7294 Intermediate Similarity NPC39754
0.7294 Intermediate Similarity NPC169511
0.7294 Intermediate Similarity NPC191929
0.7294 Intermediate Similarity NPC151403
0.7294 Intermediate Similarity NPC20339
0.7294 Intermediate Similarity NPC274446
0.7294 Intermediate Similarity NPC171135
0.7294 Intermediate Similarity NPC172821
0.7294 Intermediate Similarity NPC320569
0.7294 Intermediate Similarity NPC233551
0.7294 Intermediate Similarity NPC40376
0.7294 Intermediate Similarity NPC21208
0.7294 Intermediate Similarity NPC133730
0.7294 Intermediate Similarity NPC287164
0.7294 Intermediate Similarity NPC234077
0.7294 Intermediate Similarity NPC48338
0.7294 Intermediate Similarity NPC242364
0.7294 Intermediate Similarity NPC261952
0.7294 Intermediate Similarity NPC280621
0.7294 Intermediate Similarity NPC81045
0.7286 Intermediate Similarity NPC79756
0.7284 Intermediate Similarity NPC24417
0.7284 Intermediate Similarity NPC474980
0.7273 Intermediate Similarity NPC326504
0.7262 Intermediate Similarity NPC469910
0.726 Intermediate Similarity NPC472072
0.726 Intermediate Similarity NPC37382
0.726 Intermediate Similarity NPC146811
0.726 Intermediate Similarity NPC124586
0.725 Intermediate Similarity NPC475210
0.7246 Intermediate Similarity NPC254095
0.7246 Intermediate Similarity NPC223679
0.7241 Intermediate Similarity NPC473321
0.7241 Intermediate Similarity NPC472010
0.7237 Intermediate Similarity NPC316185
0.7229 Intermediate Similarity NPC475035
0.7229 Intermediate Similarity NPC243618
0.7229 Intermediate Similarity NPC163093
0.7229 Intermediate Similarity NPC156804
0.7229 Intermediate Similarity NPC70424
0.7222 Intermediate Similarity NPC308457
0.7215 Intermediate Similarity NPC141195
0.7215 Intermediate Similarity NPC116177
0.7215 Intermediate Similarity NPC320630
0.7215 Intermediate Similarity NPC474278
0.7215 Intermediate Similarity NPC7563
0.7215 Intermediate Similarity NPC47844
0.7209 Intermediate Similarity NPC130359
0.7209 Intermediate Similarity NPC473504

  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 NPC202011 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
0.6932 Remote Similarity NPD46 Approved
0.6932 Remote Similarity NPD6698 Approved
0.6761 Remote Similarity NPD69 Approved
0.6761 Remote Similarity NPD9119 Approved
0.662 Remote Similarity NPD9118 Approved
0.6596 Remote Similarity NPD4225 Approved
0.6596 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7838 Discovery
0.6528 Remote Similarity NPD6109 Phase 1
0.6528 Remote Similarity NPD585 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6927 Phase 3
0.6437 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6386 Remote Similarity NPD4756 Discovery
0.6351 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6322 Remote Similarity NPD6110 Phase 1
0.6282 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6196 Remote Similarity NPD5785 Approved
0.6163 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6154 Remote Similarity NPD9411 Phase 1
0.6129 Remote Similarity NPD7983 Approved
0.6122 Remote Similarity NPD5344 Discontinued
0.6117 Remote Similarity NPD6371 Approved
0.6105 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6026 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6 Remote Similarity NPD5363 Approved
0.598 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5955 Remote Similarity NPD7154 Phase 3
0.593 Remote Similarity NPD4268 Approved
0.593 Remote Similarity NPD4271 Approved
0.5926 Remote Similarity NPD7115 Discovery
0.5922 Remote Similarity NPD6686 Approved
0.5905 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5897 Remote Similarity NPD3197 Phase 1
0.5843 Remote Similarity NPD5209 Approved
0.5824 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5797 Remote Similarity NPD5343 Approved
0.5795 Remote Similarity NPD4822 Approved
0.5795 Remote Similarity NPD4820 Approved
0.5795 Remote Similarity NPD4819 Approved
0.5795 Remote Similarity NPD4252 Approved
0.5795 Remote Similarity NPD4821 Approved
0.5778 Remote Similarity NPD5362 Discontinued
0.5765 Remote Similarity NPD1452 Discontinued
0.5761 Remote Similarity NPD4249 Approved
0.5735 Remote Similarity NPD4265 Approved
0.5735 Remote Similarity NPD4222 Approved
0.5714 Remote Similarity NPD4220 Pre-registration
0.57 Remote Similarity NPD7639 Approved
0.57 Remote Similarity NPD7640 Approved
0.57 Remote Similarity NPD6648 Approved
0.5699 Remote Similarity NPD4250 Approved
0.5699 Remote Similarity NPD4251 Approved
0.5667 Remote Similarity NPD4270 Approved
0.5667 Remote Similarity NPD4269 Approved
0.5667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5652 Remote Similarity NPD1694 Approved
0.5604 Remote Similarity NPD5332 Approved
0.5604 Remote Similarity NPD5331 Approved
0.56 Remote Similarity NPD7638 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