Structure

Physi-Chem Properties

Molecular Weight:  250.12
Volume:  258.202
LogP:  1.867
LogD:  1.268
LogS:  -2.29
# Rotatable Bonds:  3
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.74
Synthetic Accessibility Score:  4.581
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.449
MDCK Permeability:  2.0407538613653742e-05
Pgp-inhibitor:  0.305
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.904
Plasma Protein Binding (PPB):  77.21138000488281%
Volume Distribution (VD):  0.972
Pgp-substrate:  9.939859390258789%

ADMET: Metabolism

CYP1A2-inhibitor:  0.072
CYP1A2-substrate:  0.395
CYP2C19-inhibitor:  0.168
CYP2C19-substrate:  0.668
CYP2C9-inhibitor:  0.182
CYP2C9-substrate:  0.467
CYP2D6-inhibitor:  0.131
CYP2D6-substrate:  0.166
CYP3A4-inhibitor:  0.197
CYP3A4-substrate:  0.531

ADMET: Excretion

Clearance (CL):  5.496
Half-life (T1/2):  0.764

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.746
Drug-inuced Liver Injury (DILI):  0.072
AMES Toxicity:  0.766
Rat Oral Acute Toxicity:  0.745
Maximum Recommended Daily Dose:  0.916
Skin Sensitization:  0.929
Carcinogencity:  0.894
Eye Corrosion:  0.02
Eye Irritation:  0.773
Respiratory Toxicity:  0.829

Download Data

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

  Natural Product: NPC291260

Natural Product ID:  NPC291260
Common Name*:   2,3-Dehydroillifunone
IUPAC Name:   (2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:   2,3-Dehydroillifunone
Standard InCHIKey:  WCLMJRDKWOPYPI-OCCSQVGLSA-N
Standard InCHI:  InChI=1S/C14H18O4/c1-4-5-9-7-14(17)8-12(13(2,3)16)18-11(14)6-10(9)15/h4,6-7,12,16-17H,1,5,8H2,2-3H3/t12-,14+/m1/s1
SMILES:  C=CCC1=C[C@@]2(C[C@H](C(C)(C)O)OC2=CC1=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL565015
PubChem CID:   45267410
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans

*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
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota pericarps n.a. n.a. PMID[19159273]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[19496609]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. stem n.a. PMID[21524101]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. root n.a. PMID[25966312]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 4.8 % PMID[519930]

☑ 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 NPC291260 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
0.8391 Intermediate Similarity NPC14322
0.8235 Intermediate Similarity NPC228415
0.8235 Intermediate Similarity NPC87189
0.7654 Intermediate Similarity NPC474197
0.7625 Intermediate Similarity NPC474545
0.7561 Intermediate Similarity NPC474278
0.75 Intermediate Similarity NPC101670
0.75 Intermediate Similarity NPC23622
0.75 Intermediate Similarity NPC300779
0.7474 Intermediate Similarity NPC9878
0.7468 Intermediate Similarity NPC107848
0.7386 Intermediate Similarity NPC472009
0.7386 Intermediate Similarity NPC278283
0.7381 Intermediate Similarity NPC475210
0.7363 Intermediate Similarity NPC476705
0.7356 Intermediate Similarity NPC32676
0.7356 Intermediate Similarity NPC475035
0.7303 Intermediate Similarity NPC472007
0.7294 Intermediate Similarity NPC91332
0.7294 Intermediate Similarity NPC162741
0.7273 Intermediate Similarity NPC473722
0.7273 Intermediate Similarity NPC475034
0.7263 Intermediate Similarity NPC300584
0.7253 Intermediate Similarity NPC144133
0.7253 Intermediate Similarity NPC179394
0.7253 Intermediate Similarity NPC166554
0.7241 Intermediate Similarity NPC44261
0.7234 Intermediate Similarity NPC93271
0.7234 Intermediate Similarity NPC135576
0.7222 Intermediate Similarity NPC150063
0.7222 Intermediate Similarity NPC119740
0.7222 Intermediate Similarity NPC472008
0.7195 Intermediate Similarity NPC474280
0.7195 Intermediate Similarity NPC160540
0.7179 Intermediate Similarity NPC137163
0.7159 Intermediate Similarity NPC469809
0.7158 Intermediate Similarity NPC20066
0.7143 Intermediate Similarity NPC475711
0.7143 Intermediate Similarity NPC475221
0.7143 Intermediate Similarity NPC133450
0.7126 Intermediate Similarity NPC474252
0.7125 Intermediate Similarity NPC472947
0.7111 Intermediate Similarity NPC475037
0.7097 Intermediate Similarity NPC288240
0.7097 Intermediate Similarity NPC162205
0.7097 Intermediate Similarity NPC295204
0.7097 Intermediate Similarity NPC475912
0.7097 Intermediate Similarity NPC320552
0.7097 Intermediate Similarity NPC61275
0.7097 Intermediate Similarity NPC273579
0.7093 Intermediate Similarity NPC472948
0.7065 Intermediate Similarity NPC177668
0.7065 Intermediate Similarity NPC265856
0.7065 Intermediate Similarity NPC327253
0.7065 Intermediate Similarity NPC475855
0.7065 Intermediate Similarity NPC473448
0.7059 Intermediate Similarity NPC68119
0.7059 Intermediate Similarity NPC13823
0.7041 Intermediate Similarity NPC195510
0.7041 Intermediate Similarity NPC13171
0.7033 Intermediate Similarity NPC476706
0.7033 Intermediate Similarity NPC476707
0.7033 Intermediate Similarity NPC153570
0.7011 Intermediate Similarity NPC159714
0.7011 Intermediate Similarity NPC221510
0.7011 Intermediate Similarity NPC297440
0.7011 Intermediate Similarity NPC280367
0.7 Intermediate Similarity NPC311163
0.7 Intermediate Similarity NPC478112
0.6989 Remote Similarity NPC473321
0.6989 Remote Similarity NPC146852
0.6989 Remote Similarity NPC475441
0.6988 Remote Similarity NPC114727
0.6988 Remote Similarity NPC227814
0.6988 Remote Similarity NPC144995
0.6988 Remote Similarity NPC476590
0.6979 Remote Similarity NPC474194
0.6979 Remote Similarity NPC471490
0.6979 Remote Similarity NPC266842
0.6977 Remote Similarity NPC473981
0.6977 Remote Similarity NPC473980
0.6974 Remote Similarity NPC258788
0.697 Remote Similarity NPC104161
0.697 Remote Similarity NPC118902
0.697 Remote Similarity NPC469980
0.6957 Remote Similarity NPC87306
0.6947 Remote Similarity NPC36954
0.6947 Remote Similarity NPC270013
0.6947 Remote Similarity NPC14961
0.6941 Remote Similarity NPC476703
0.6941 Remote Similarity NPC473536
0.6939 Remote Similarity NPC471401
0.6923 Remote Similarity NPC160138
0.6923 Remote Similarity NPC473248
0.6915 Remote Similarity NPC475098
0.6915 Remote Similarity NPC282644
0.6915 Remote Similarity NPC189651
0.6915 Remote Similarity NPC476300
0.6915 Remote Similarity NPC29798
0.6914 Remote Similarity NPC475982
0.6907 Remote Similarity NPC187268
0.6907 Remote Similarity NPC475284
0.6907 Remote Similarity NPC281608
0.6905 Remote Similarity NPC478196
0.6905 Remote Similarity NPC478193
0.6905 Remote Similarity NPC478195
0.6905 Remote Similarity NPC478192
0.6905 Remote Similarity NPC478194
0.6905 Remote Similarity NPC478191
0.6897 Remote Similarity NPC470947
0.6897 Remote Similarity NPC470945
0.6897 Remote Similarity NPC470946
0.6889 Remote Similarity NPC11804
0.6889 Remote Similarity NPC21469
0.6889 Remote Similarity NPC242233
0.6889 Remote Similarity NPC471223
0.6889 Remote Similarity NPC67081
0.6882 Remote Similarity NPC473455
0.6882 Remote Similarity NPC3952
0.6882 Remote Similarity NPC478003
0.6882 Remote Similarity NPC474761
0.6882 Remote Similarity NPC474232
0.6882 Remote Similarity NPC476004
0.6882 Remote Similarity NPC51004
0.6882 Remote Similarity NPC473619
0.6882 Remote Similarity NPC478004
0.6882 Remote Similarity NPC158388
0.6875 Remote Similarity NPC106613
0.6875 Remote Similarity NPC279621
0.6875 Remote Similarity NPC473333
0.6875 Remote Similarity NPC251429
0.6875 Remote Similarity NPC8803
0.6869 Remote Similarity NPC70369
0.6869 Remote Similarity NPC149371
0.6869 Remote Similarity NPC39996
0.686 Remote Similarity NPC326753
0.686 Remote Similarity NPC248775
0.686 Remote Similarity NPC473471
0.686 Remote Similarity NPC475699
0.686 Remote Similarity NPC279532
0.6854 Remote Similarity NPC116543
0.6854 Remote Similarity NPC471987
0.6854 Remote Similarity NPC477784
0.6854 Remote Similarity NPC27314
0.6854 Remote Similarity NPC263087
0.6854 Remote Similarity NPC477786
0.6854 Remote Similarity NPC161045
0.6854 Remote Similarity NPC31019
0.6854 Remote Similarity NPC2379
0.6854 Remote Similarity NPC106912
0.6854 Remote Similarity NPC250315
0.6854 Remote Similarity NPC477785
0.6854 Remote Similarity NPC52923
0.6848 Remote Similarity NPC476704
0.6848 Remote Similarity NPC309656
0.6848 Remote Similarity NPC473715
0.6848 Remote Similarity NPC476708
0.6842 Remote Similarity NPC114162
0.6842 Remote Similarity NPC469819
0.6842 Remote Similarity NPC81386
0.6842 Remote Similarity NPC256368
0.6842 Remote Similarity NPC474035
0.6842 Remote Similarity NPC477241
0.6835 Remote Similarity NPC19769
0.6832 Remote Similarity NPC472751
0.6832 Remote Similarity NPC472749
0.6829 Remote Similarity NPC202011
0.6824 Remote Similarity NPC229655
0.6824 Remote Similarity NPC127118
0.6824 Remote Similarity NPC470705
0.6824 Remote Similarity NPC326661
0.6824 Remote Similarity NPC170148
0.6824 Remote Similarity NPC209113
0.6824 Remote Similarity NPC301207
0.6818 Remote Similarity NPC474980
0.6813 Remote Similarity NPC308412
0.6813 Remote Similarity NPC134885
0.6813 Remote Similarity NPC473687
0.6813 Remote Similarity NPC210218
0.6813 Remote Similarity NPC204686
0.6813 Remote Similarity NPC134807
0.6813 Remote Similarity NPC69082
0.6813 Remote Similarity NPC279267
0.6813 Remote Similarity NPC477015
0.6813 Remote Similarity NPC219498
0.6809 Remote Similarity NPC30515
0.6809 Remote Similarity NPC184463
0.6809 Remote Similarity NPC142838
0.6809 Remote Similarity NPC208839
0.6804 Remote Similarity NPC205143
0.6804 Remote Similarity NPC2666
0.6804 Remote Similarity NPC120446
0.68 Remote Similarity NPC472747
0.68 Remote Similarity NPC472750
0.68 Remote Similarity NPC472755
0.68 Remote Similarity NPC475945
0.68 Remote Similarity NPC475871
0.6796 Remote Similarity NPC471400
0.6786 Remote Similarity NPC315843
0.6786 Remote Similarity NPC107654

  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 NPC291260 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
0.7241 Intermediate Similarity NPD6110 Phase 1
0.6842 Remote Similarity NPD5282 Discontinued
0.6702 Remote Similarity NPD7838 Discovery
0.663 Remote Similarity NPD4249 Approved
0.6559 Remote Similarity NPD4251 Approved
0.6559 Remote Similarity NPD4250 Approved
0.6526 Remote Similarity NPD46 Approved
0.6526 Remote Similarity NPD6698 Approved
0.6436 Remote Similarity NPD5344 Discontinued
0.64 Remote Similarity NPD4225 Approved
0.64 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4756 Discovery
0.6304 Remote Similarity NPD7154 Phase 3
0.6289 Remote Similarity NPD7983 Approved
0.6286 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6371 Approved
0.6176 Remote Similarity NPD6648 Approved
0.6154 Remote Similarity NPD5790 Clinical (unspecified phase)
0.61 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6061 Remote Similarity NPD5778 Approved
0.6061 Remote Similarity NPD5779 Approved
0.6055 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6055 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6049 Remote Similarity NPD368 Approved
0.6042 Remote Similarity NPD7524 Approved
0.6 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5978 Remote Similarity NPD4822 Approved
0.5978 Remote Similarity NPD4821 Approved
0.5978 Remote Similarity NPD4819 Approved
0.5978 Remote Similarity NPD4820 Approved
0.5976 Remote Similarity NPD2664 Clinical (unspecified phase)
0.596 Remote Similarity NPD7637 Suspended
0.5952 Remote Similarity NPD3704 Approved
0.5952 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5949 Remote Similarity NPD8779 Phase 3
0.5934 Remote Similarity NPD4271 Approved
0.5934 Remote Similarity NPD4268 Approved
0.5929 Remote Similarity NPD7115 Discovery
0.5926 Remote Similarity NPD6686 Approved
0.5909 Remote Similarity NPD4732 Discontinued
0.5895 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5875 Remote Similarity NPD585 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6053 Discontinued
0.5833 Remote Similarity NPD1696 Phase 3
0.5833 Remote Similarity NPD5363 Approved
0.5833 Remote Similarity NPD6412 Phase 2
0.5833 Remote Similarity NPD1694 Approved
0.5789 Remote Similarity NPD6695 Phase 3
0.5765 Remote Similarity NPD7331 Phase 2
0.5758 Remote Similarity NPD1695 Approved
0.5755 Remote Similarity NPD5211 Phase 2
0.5726 Remote Similarity NPD7503 Approved
0.57 Remote Similarity NPD5785 Approved
0.5696 Remote Similarity NPD342 Phase 1
0.5684 Remote Similarity NPD5209 Approved
0.5679 Remote Similarity NPD6109 Phase 1
0.5676 Remote Similarity NPD4634 Approved
0.5664 Remote Similarity NPD4632 Approved
0.5648 Remote Similarity NPD5141 Approved
0.5647 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5641 Remote Similarity NPD6319 Approved
0.5641 Remote Similarity NPD6054 Approved
0.5638 Remote Similarity NPD7514 Phase 3
0.5638 Remote Similarity NPD4252 Approved
0.5638 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5638 Remote Similarity NPD4695 Discontinued
0.5638 Remote Similarity NPD7332 Phase 2
0.5625 Remote Similarity NPD5362 Discontinued
0.5612 Remote Similarity NPD4519 Discontinued
0.5612 Remote Similarity NPD4623 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