Structure

Physi-Chem Properties

Molecular Weight:  282.11
Volume:  275.783
LogP:  1.046
LogD:  0.324
LogS:  -2.039
# Rotatable Bonds:  3
TPSA:  85.36
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.343
Synthetic Accessibility Score:  4.994
Fsp3:  0.571
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:  -5.067
MDCK Permeability:  7.717437256360427e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.518
20% Bioavailability (F20%):  0.11
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.972
Plasma Protein Binding (PPB):  77.88411712646484%
Volume Distribution (VD):  1.185
Pgp-substrate:  16.01880645751953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.069
CYP1A2-substrate:  0.075
CYP2C19-inhibitor:  0.078
CYP2C19-substrate:  0.666
CYP2C9-inhibitor:  0.038
CYP2C9-substrate:  0.164
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.359
CYP3A4-inhibitor:  0.102
CYP3A4-substrate:  0.261

ADMET: Excretion

Clearance (CL):  2.58
Half-life (T1/2):  0.689

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.434
Drug-inuced Liver Injury (DILI):  0.818
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.386
Maximum Recommended Daily Dose:  0.955
Skin Sensitization:  0.744
Carcinogencity:  0.145
Eye Corrosion:  0.015
Eye Irritation:  0.034
Respiratory Toxicity:  0.363

Download Data

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

  Natural Product: NPC318481

Natural Product ID:  NPC318481
Common Name*:   Multiplolide B
IUPAC Name:   [(2E,4S,5R,7R)-4-hydroxy-7-methyl-9-oxo-8,11-dioxabicyclo[8.1.0]undec-2-en-5-yl] (E)-but-2-enoate
Synonyms:  
Standard InCHIKey:  MKNCRDRXKFGNDG-BGEOUFIESA-N
Standard InCHI:  InChI=1S/C14H18O6/c1-3-4-12(16)19-11-7-8(2)18-14(17)13-10(20-13)6-5-9(11)15/h3-6,8-11,13,15H,7H2,1-2H3/b4-3+,6-5+/t8-,9+,10?,11-,13?/m1/s1
SMILES:  CC=CC(=O)OC1CC(OC(=O)C2C(O2)C=CC1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL459619
PubChem CID:   11778517
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty acid esters

*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
NPO13735 Xylaria multiplex Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[11473437]
NPO13735 Xylaria multiplex Species Xylariaceae 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
NPT20 Organism Candida albicans Candida albicans IC50 = 2.0 ug.mL-1 PMID[507687]

☑ 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 NPC318481 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
0.9583 High Similarity NPC473582
0.9444 High Similarity NPC326504
0.9444 High Similarity NPC473489
0.8356 Intermediate Similarity NPC122627
0.8333 Intermediate Similarity NPC19769
0.8243 Intermediate Similarity NPC63873
0.8194 Intermediate Similarity NPC470808
0.8133 Intermediate Similarity NPC130618
0.8133 Intermediate Similarity NPC475982
0.7973 Intermediate Similarity NPC276299
0.7973 Intermediate Similarity NPC201356
0.7907 Intermediate Similarity NPC287089
0.7867 Intermediate Similarity NPC25298
0.7838 Intermediate Similarity NPC96414
0.7821 Intermediate Similarity NPC470435
0.7703 Intermediate Similarity NPC475221
0.7692 Intermediate Similarity NPC293114
0.7671 Intermediate Similarity NPC26810
0.7639 Intermediate Similarity NPC97570
0.7625 Intermediate Similarity NPC161038
0.7625 Intermediate Similarity NPC473948
0.7619 Intermediate Similarity NPC11383
0.7619 Intermediate Similarity NPC474959
0.7619 Intermediate Similarity NPC310450
0.7619 Intermediate Similarity NPC475046
0.7595 Intermediate Similarity NPC284006
0.7564 Intermediate Similarity NPC202011
0.7561 Intermediate Similarity NPC473471
0.7531 Intermediate Similarity NPC301207
0.7531 Intermediate Similarity NPC209113
0.7531 Intermediate Similarity NPC127118
0.7529 Intermediate Similarity NPC284472
0.7529 Intermediate Similarity NPC229799
0.7529 Intermediate Similarity NPC286770
0.75 Intermediate Similarity NPC297440
0.75 Intermediate Similarity NPC146811
0.75 Intermediate Similarity NPC124586
0.7467 Intermediate Similarity NPC308457
0.7439 Intermediate Similarity NPC275530
0.7439 Intermediate Similarity NPC125365
0.7439 Intermediate Similarity NPC474818
0.7439 Intermediate Similarity NPC49302
0.7439 Intermediate Similarity NPC51809
0.7439 Intermediate Similarity NPC176329
0.7436 Intermediate Similarity NPC470436
0.7407 Intermediate Similarity NPC260396
0.7403 Intermediate Similarity NPC478100
0.7403 Intermediate Similarity NPC478097
0.7368 Intermediate Similarity NPC273600
0.7368 Intermediate Similarity NPC478099
0.7368 Intermediate Similarity NPC470123
0.7368 Intermediate Similarity NPC478098
0.7349 Intermediate Similarity NPC248775
0.7349 Intermediate Similarity NPC279214
0.7349 Intermediate Similarity NPC279532
0.7349 Intermediate Similarity NPC221095
0.7333 Intermediate Similarity NPC474774
0.7317 Intermediate Similarity NPC16279
0.7317 Intermediate Similarity NPC256640
0.7317 Intermediate Similarity NPC203277
0.7317 Intermediate Similarity NPC190400
0.7317 Intermediate Similarity NPC205615
0.7317 Intermediate Similarity NPC49392
0.7317 Intermediate Similarity NPC470705
0.7294 Intermediate Similarity NPC150502
0.7284 Intermediate Similarity NPC474545
0.7284 Intermediate Similarity NPC107654
0.7284 Intermediate Similarity NPC315843
0.7273 Intermediate Similarity NPC475675
0.7273 Intermediate Similarity NPC478101
0.7273 Intermediate Similarity NPC475555
0.7262 Intermediate Similarity NPC1180
0.7262 Intermediate Similarity NPC470149
0.7262 Intermediate Similarity NPC470148
0.7262 Intermediate Similarity NPC99651
0.7262 Intermediate Similarity NPC180725
0.7241 Intermediate Similarity NPC469809
0.7237 Intermediate Similarity NPC25747
0.7237 Intermediate Similarity NPC148233
0.7229 Intermediate Similarity NPC272267
0.7229 Intermediate Similarity NPC233071
0.7229 Intermediate Similarity NPC475711
0.7229 Intermediate Similarity NPC474026
0.72 Intermediate Similarity NPC113293
0.7195 Intermediate Similarity NPC478194
0.7195 Intermediate Similarity NPC478193
0.7195 Intermediate Similarity NPC478195
0.7195 Intermediate Similarity NPC478196
0.7195 Intermediate Similarity NPC478192
0.7195 Intermediate Similarity NPC478191
0.7176 Intermediate Similarity NPC121374
0.7176 Intermediate Similarity NPC470147
0.7176 Intermediate Similarity NPC133226
0.7162 Intermediate Similarity NPC302564
0.7162 Intermediate Similarity NPC318306
0.7159 Intermediate Similarity NPC475034
0.7143 Intermediate Similarity NPC182292
0.7126 Intermediate Similarity NPC161045
0.7125 Intermediate Similarity NPC476037
0.7108 Intermediate Similarity NPC68819
0.7108 Intermediate Similarity NPC188860
0.7097 Intermediate Similarity NPC121825
0.7093 Intermediate Similarity NPC221510
0.7093 Intermediate Similarity NPC159714
0.7083 Intermediate Similarity NPC475949
0.7079 Intermediate Similarity NPC469910
0.7073 Intermediate Similarity NPC476590
0.7073 Intermediate Similarity NPC114727
0.7067 Intermediate Similarity NPC81896
0.7067 Intermediate Similarity NPC26223
0.7067 Intermediate Similarity NPC321919
0.7037 Intermediate Similarity NPC316185
0.7024 Intermediate Similarity NPC474278
0.701 Intermediate Similarity NPC474339
0.701 Intermediate Similarity NPC164598
0.7 Intermediate Similarity NPC266514
0.7 Intermediate Similarity NPC475037
0.7 Intermediate Similarity NPC266957
0.6989 Remote Similarity NPC469692
0.6989 Remote Similarity NPC469645
0.6979 Remote Similarity NPC161855
0.6966 Remote Similarity NPC11804
0.6966 Remote Similarity NPC470124
0.6966 Remote Similarity NPC470755
0.6957 Remote Similarity NPC473311
0.6957 Remote Similarity NPC474232
0.6951 Remote Similarity NPC329890
0.6947 Remote Similarity NPC473291
0.6941 Remote Similarity NPC28049
0.6939 Remote Similarity NPC471148
0.6932 Remote Similarity NPC142111
0.6932 Remote Similarity NPC473315
0.6932 Remote Similarity NPC315559
0.6932 Remote Similarity NPC44261
0.6923 Remote Similarity NPC282760
0.6923 Remote Similarity NPC150063
0.6923 Remote Similarity NPC470137
0.6923 Remote Similarity NPC119740
0.6923 Remote Similarity NPC476803
0.6914 Remote Similarity NPC476012
0.6905 Remote Similarity NPC326661
0.6882 Remote Similarity NPC158061
0.6875 Remote Similarity NPC475760
0.6869 Remote Similarity NPC469980
0.6869 Remote Similarity NPC118902
0.6869 Remote Similarity NPC104161
0.686 Remote Similarity NPC475210
0.6854 Remote Similarity NPC158756
0.6854 Remote Similarity NPC475035
0.6854 Remote Similarity NPC474251
0.6854 Remote Similarity NPC473308
0.6842 Remote Similarity NPC258788
0.6837 Remote Similarity NPC110443
0.6837 Remote Similarity NPC133907
0.6837 Remote Similarity NPC128733
0.6837 Remote Similarity NPC185141
0.6837 Remote Similarity NPC46998
0.6832 Remote Similarity NPC477513
0.6818 Remote Similarity NPC313677
0.6818 Remote Similarity NPC253364
0.6818 Remote Similarity NPC251026
0.6818 Remote Similarity NPC26624
0.6813 Remote Similarity NPC45409
0.6813 Remote Similarity NPC471738
0.6809 Remote Similarity NPC165383
0.6804 Remote Similarity NPC471144
0.68 Remote Similarity NPC187770
0.6778 Remote Similarity NPC471156
0.6778 Remote Similarity NPC77971
0.6774 Remote Similarity NPC3952
0.6774 Remote Similarity NPC475879
0.6774 Remote Similarity NPC274075
0.6771 Remote Similarity NPC477921
0.6768 Remote Similarity NPC39996
0.6757 Remote Similarity NPC324224
0.6757 Remote Similarity NPC472808
0.6757 Remote Similarity NPC327388
0.6747 Remote Similarity NPC329914
0.6747 Remote Similarity NPC327383
0.6747 Remote Similarity NPC185186
0.6744 Remote Similarity NPC477314
0.6742 Remote Similarity NPC40746
0.6742 Remote Similarity NPC116543
0.6742 Remote Similarity NPC169575
0.6739 Remote Similarity NPC476805
0.6739 Remote Similarity NPC475819
0.6735 Remote Similarity NPC288876
0.6711 Remote Similarity NPC478095
0.6711 Remote Similarity NPC322186
0.6709 Remote Similarity NPC476654
0.6709 Remote Similarity NPC476655
0.6709 Remote Similarity NPC476657
0.6705 Remote Similarity NPC24417
0.6705 Remote Similarity NPC469469
0.6705 Remote Similarity NPC474980
0.6705 Remote Similarity NPC112868
0.6703 Remote Similarity NPC69082
0.6703 Remote Similarity NPC478112
0.6703 Remote Similarity NPC196381
0.6703 Remote Similarity NPC279267

  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 NPC318481 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
0.7027 Intermediate Similarity NPD6109 Phase 1
0.7027 Intermediate Similarity NPD585 Clinical (unspecified phase)
0.68 Remote Similarity NPD69 Approved
0.68 Remote Similarity NPD9119 Approved
0.6774 Remote Similarity NPD7838 Discovery
0.6667 Remote Similarity NPD9118 Approved
0.6596 Remote Similarity NPD46 Approved
0.6596 Remote Similarity NPD6698 Approved
0.6322 Remote Similarity NPD818 Approved
0.6322 Remote Similarity NPD819 Approved
0.63 Remote Similarity NPD4225 Approved
0.6203 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7983 Approved
0.6176 Remote Similarity NPD5344 Discontinued
0.6173 Remote Similarity NPD3197 Phase 1
0.6145 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6082 Remote Similarity NPD5785 Approved
0.6067 Remote Similarity NPD4756 Discovery
0.6044 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6038 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6371 Approved
0.6 Remote Similarity NPD1698 Clinical (unspecified phase)
0.598 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5914 Remote Similarity NPD5209 Approved
0.5904 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5895 Remote Similarity NPD5363 Approved
0.5851 Remote Similarity NPD6110 Phase 1
0.5841 Remote Similarity NPD7115 Discovery
0.5824 Remote Similarity NPD4268 Approved
0.5824 Remote Similarity NPD4271 Approved
0.5802 Remote Similarity NPD9120 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5784 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6648 Approved
0.5729 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5699 Remote Similarity NPD4821 Approved
0.5699 Remote Similarity NPD4819 Approved
0.5699 Remote Similarity NPD4822 Approved
0.5699 Remote Similarity NPD4252 Approved
0.5699 Remote Similarity NPD4820 Approved
0.5684 Remote Similarity NPD7154 Phase 3
0.5676 Remote Similarity NPD7601 Clinical (unspecified phase)
0.567 Remote Similarity NPD4249 Approved
0.5658 Remote Similarity NPD6927 Phase 3
0.5612 Remote Similarity NPD4250 Approved
0.5612 Remote Similarity NPD4251 Approved
0.5607 Remote Similarity NPD1407 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