Structure

Physi-Chem Properties

Molecular Weight:  256.09
Volume:  243.827
LogP:  0.513
LogD:  0.591
LogS:  -1.538
# Rotatable Bonds:  2
TPSA:  85.36
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.402
Synthetic Accessibility Score:  4.81
Fsp3:  0.667
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:  -5.064
MDCK Permeability:  0.00010604525596136227
Pgp-inhibitor:  0.018
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.6
20% Bioavailability (F20%):  0.019
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.91
Plasma Protein Binding (PPB):  71.96375274658203%
Volume Distribution (VD):  0.834
Pgp-substrate:  32.890621185302734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.042
CYP1A2-substrate:  0.058
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.288
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.091
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.197
CYP3A4-inhibitor:  0.042
CYP3A4-substrate:  0.245

ADMET: Excretion

Clearance (CL):  2.704
Half-life (T1/2):  0.68

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.677
Drug-inuced Liver Injury (DILI):  0.957
AMES Toxicity:  0.3
Rat Oral Acute Toxicity:  0.436
Maximum Recommended Daily Dose:  0.876
Skin Sensitization:  0.32
Carcinogencity:  0.176
Eye Corrosion:  0.054
Eye Irritation:  0.095
Respiratory Toxicity:  0.238

Download Data

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

  Natural Product: NPC473582

Natural Product ID:  NPC473582
Common Name*:   8Alpha-Acetoxymultiplolide A
IUPAC Name:   [(1S,2E,4S,5R,7R,10S)-4-hydroxy-7-methyl-9-oxo-8,11-dioxabicyclo[8.1.0]undec-2-en-5-yl] acetate
Synonyms:  
Standard InCHIKey:  GITGKBOJRJGOIP-GGFJVNIXSA-N
Standard InCHI:  InChI=1S/C12H16O6/c1-6-5-10(17-7(2)13)8(14)3-4-9-11(18-9)12(15)16-6/h3-4,6,8-11,14H,5H2,1-2H3/b4-3+/t6-,8+,9+,10-,11+/m1/s1
SMILES:  CC1CC(C(C=CC2C(O2)C(=O)O1)O)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL446482
PubChem CID:   24862056
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*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
NPO32626 Phomopsis sp. Species Valsaceae Eukaryota n.a. n.a. n.a. PMID[18336005]
NPO32626 Phomopsis sp. Species Valsaceae Eukaryota n.a. n.a. n.a. PMID[22233864]
NPO32626 Phomopsis sp. Species Valsaceae Eukaryota n.a. n.a. n.a. PMID[32686414]

☑ 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
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum MIC > 500.0 ug.mL-1 PMID[480729]
NPT6148 Organism Helminthosporium maydis Helminthosporium maydis MIC = 500.0 ug.mL-1 PMID[480729]
NPT6149 Organism Penicillium islandicum Penicillium islandicum MIC = 250.0 ug.mL-1 PMID[480729]
NPT6150 Organism Ophiostoma minus Ophiostoma minus MIC = 31.25 ug.mL-1 PMID[480729]
NPT2781 Organism Fusarium moniliforme Gibberella moniliformis MIC = 500.0 ug.mL-1 PMID[480729]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 125.0 ug.mL-1 PMID[480729]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC = 62.5 ug.mL-1 PMID[480729]

☑ 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 NPC473582 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
0.9855 High Similarity NPC473489
0.9855 High Similarity NPC326504
0.9583 High Similarity NPC318481
0.8472 Intermediate Similarity NPC130618
0.8194 Intermediate Similarity NPC25298
0.8133 Intermediate Similarity NPC470435
0.8028 Intermediate Similarity NPC475221
0.7945 Intermediate Similarity NPC122627
0.7922 Intermediate Similarity NPC473948
0.7917 Intermediate Similarity NPC19769
0.7838 Intermediate Similarity NPC63873
0.7778 Intermediate Similarity NPC470808
0.7765 Intermediate Similarity NPC287089
0.7733 Intermediate Similarity NPC470436
0.7733 Intermediate Similarity NPC475982
0.7703 Intermediate Similarity NPC478097
0.7703 Intermediate Similarity NPC478100
0.7671 Intermediate Similarity NPC478099
0.7671 Intermediate Similarity NPC478098
0.7595 Intermediate Similarity NPC49392
0.7595 Intermediate Similarity NPC190400
0.7568 Intermediate Similarity NPC201356
0.7568 Intermediate Similarity NPC478101
0.7568 Intermediate Similarity NPC276299
0.75 Intermediate Similarity NPC113293
0.7465 Intermediate Similarity NPC318306
0.7432 Intermediate Similarity NPC96414
0.7361 Intermediate Similarity NPC81896
0.7361 Intermediate Similarity NPC321919
0.7308 Intermediate Similarity NPC293114
0.7284 Intermediate Similarity NPC474278
0.7262 Intermediate Similarity NPC11383
0.7262 Intermediate Similarity NPC474959
0.7262 Intermediate Similarity NPC475046
0.7262 Intermediate Similarity NPC310450
0.726 Intermediate Similarity NPC26810
0.725 Intermediate Similarity NPC161038
0.7222 Intermediate Similarity NPC97570
0.7215 Intermediate Similarity NPC284006
0.72 Intermediate Similarity NPC470123
0.7195 Intermediate Similarity NPC473471
0.7179 Intermediate Similarity NPC202011
0.7176 Intermediate Similarity NPC286770
0.7176 Intermediate Similarity NPC229799
0.7176 Intermediate Similarity NPC284472
0.716 Intermediate Similarity NPC301207
0.716 Intermediate Similarity NPC127118
0.716 Intermediate Similarity NPC209113
0.7143 Intermediate Similarity NPC297440
0.7123 Intermediate Similarity NPC258788
0.7108 Intermediate Similarity NPC475210
0.7108 Intermediate Similarity NPC99651
0.7105 Intermediate Similarity NPC146811
0.7105 Intermediate Similarity NPC124586
0.7073 Intermediate Similarity NPC474818
0.7073 Intermediate Similarity NPC49302
0.7073 Intermediate Similarity NPC51809
0.7073 Intermediate Similarity NPC275530
0.7073 Intermediate Similarity NPC125365
0.7073 Intermediate Similarity NPC176329
0.7067 Intermediate Similarity NPC308457
0.7042 Intermediate Similarity NPC327388
0.7037 Intermediate Similarity NPC260396
0.7011 Intermediate Similarity NPC471156
0.6988 Remote Similarity NPC248775
0.6988 Remote Similarity NPC279214
0.6988 Remote Similarity NPC279532
0.6988 Remote Similarity NPC221095
0.6986 Remote Similarity NPC322186
0.6986 Remote Similarity NPC478095
0.6974 Remote Similarity NPC476654
0.6974 Remote Similarity NPC476657
0.6974 Remote Similarity NPC476655
0.6974 Remote Similarity NPC273600
0.6951 Remote Similarity NPC470705
0.6951 Remote Similarity NPC205615
0.6951 Remote Similarity NPC203277
0.6951 Remote Similarity NPC16279
0.6951 Remote Similarity NPC68819
0.6951 Remote Similarity NPC256640
0.6947 Remote Similarity NPC475949
0.6944 Remote Similarity NPC323597
0.6944 Remote Similarity NPC323498
0.6944 Remote Similarity NPC323436
0.6944 Remote Similarity NPC211752
0.6941 Remote Similarity NPC150502
0.6933 Remote Similarity NPC474774
0.6932 Remote Similarity NPC469910
0.6932 Remote Similarity NPC478112
0.6914 Remote Similarity NPC474545
0.6914 Remote Similarity NPC107654
0.6914 Remote Similarity NPC315843
0.6914 Remote Similarity NPC474280
0.6905 Remote Similarity NPC470148
0.6905 Remote Similarity NPC470149
0.6905 Remote Similarity NPC180725
0.6905 Remote Similarity NPC1180
0.6897 Remote Similarity NPC469809
0.6883 Remote Similarity NPC476659
0.6883 Remote Similarity NPC475555
0.6883 Remote Similarity NPC475675
0.6883 Remote Similarity NPC476656
0.6867 Remote Similarity NPC272267
0.6867 Remote Similarity NPC233071
0.6867 Remote Similarity NPC474026
0.6867 Remote Similarity NPC475711
0.686 Remote Similarity NPC474252
0.6857 Remote Similarity NPC477780
0.6857 Remote Similarity NPC477781
0.6854 Remote Similarity NPC266957
0.6849 Remote Similarity NPC478096
0.6842 Remote Similarity NPC25747
0.6842 Remote Similarity NPC148233
0.6842 Remote Similarity NPC476658
0.6829 Remote Similarity NPC478191
0.6829 Remote Similarity NPC478194
0.6829 Remote Similarity NPC478193
0.6829 Remote Similarity NPC478196
0.6829 Remote Similarity NPC478195
0.6829 Remote Similarity NPC478192
0.6824 Remote Similarity NPC470147
0.6824 Remote Similarity NPC133226
0.6824 Remote Similarity NPC121374
0.6818 Remote Similarity NPC475034
0.6813 Remote Similarity NPC474232
0.6804 Remote Similarity NPC471148
0.68 Remote Similarity NPC14862
0.68 Remote Similarity NPC233379
0.68 Remote Similarity NPC55376
0.68 Remote Similarity NPC474664
0.6795 Remote Similarity NPC99619
0.6795 Remote Similarity NPC22101
0.6795 Remote Similarity NPC127091
0.6795 Remote Similarity NPC26500
0.6795 Remote Similarity NPC271921
0.6795 Remote Similarity NPC104537
0.6795 Remote Similarity NPC148192
0.6795 Remote Similarity NPC330426
0.6786 Remote Similarity NPC182292
0.6786 Remote Similarity NPC127526
0.6782 Remote Similarity NPC161045
0.6778 Remote Similarity NPC476803
0.6774 Remote Similarity NPC121825
0.6771 Remote Similarity NPC324667
0.6757 Remote Similarity NPC302564
0.6753 Remote Similarity NPC282760
0.675 Remote Similarity NPC476037
0.675 Remote Similarity NPC42526
0.675 Remote Similarity NPC473361
0.675 Remote Similarity NPC329904
0.6747 Remote Similarity NPC188860
0.6747 Remote Similarity NPC470899
0.6744 Remote Similarity NPC221510
0.6744 Remote Similarity NPC474894
0.6744 Remote Similarity NPC159714
0.6742 Remote Similarity NPC278283
0.6733 Remote Similarity NPC15218
0.6709 Remote Similarity NPC141481
0.6709 Remote Similarity NPC273508
0.6709 Remote Similarity NPC209327
0.6709 Remote Similarity NPC324981
0.6709 Remote Similarity NPC48218
0.6709 Remote Similarity NPC473559
0.6707 Remote Similarity NPC476590
0.6707 Remote Similarity NPC114727
0.6706 Remote Similarity NPC471537
0.6705 Remote Similarity NPC158756
0.6705 Remote Similarity NPC32676
0.6701 Remote Similarity NPC474339
0.6701 Remote Similarity NPC164598
0.67 Remote Similarity NPC72813
0.67 Remote Similarity NPC474421
0.67 Remote Similarity NPC194620
0.67 Remote Similarity NPC326994
0.67 Remote Similarity NPC324327
0.67 Remote Similarity NPC266514
0.6667 Remote Similarity NPC253364
0.6667 Remote Similarity NPC316185
0.6667 Remote Similarity NPC45409
0.6667 Remote Similarity NPC26223
0.6667 Remote Similarity NPC161855
0.6667 Remote Similarity NPC475037
0.6667 Remote Similarity NPC469645
0.6667 Remote Similarity NPC471738
0.6667 Remote Similarity NPC469692
0.6634 Remote Similarity NPC169888
0.6634 Remote Similarity NPC55972
0.6634 Remote Similarity NPC327286
0.6632 Remote Similarity NPC473291
0.663 Remote Similarity NPC473311
0.663 Remote Similarity NPC274075
0.663 Remote Similarity NPC475879
0.6629 Remote Similarity NPC470755
0.6629 Remote Similarity NPC11804
0.6629 Remote Similarity NPC470124
0.6622 Remote Similarity NPC187770
0.66 Remote Similarity NPC475802
0.66 Remote Similarity NPC16313
0.66 Remote Similarity NPC9303
0.6593 Remote Similarity NPC119740

  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 NPC473582 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
0.7324 Intermediate Similarity NPD585 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6109 Phase 1
0.6622 Remote Similarity NPD69 Approved
0.6622 Remote Similarity NPD9119 Approved
0.6548 Remote Similarity NPD819 Approved
0.6548 Remote Similarity NPD818 Approved
0.6486 Remote Similarity NPD9118 Approved
0.6452 Remote Similarity NPD7838 Discovery
0.6452 Remote Similarity NPD6698 Approved
0.6452 Remote Similarity NPD46 Approved
0.6447 Remote Similarity NPD4246 Clinical (unspecified phase)
0.641 Remote Similarity NPD3197 Phase 1
0.6383 Remote Similarity NPD7983 Approved
0.6375 Remote Similarity NPD4247 Clinical (unspecified phase)
0.625 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6023 Remote Similarity NPD4271 Approved
0.6023 Remote Similarity NPD4268 Approved
0.6 Remote Similarity NPD4225 Approved
0.596 Remote Similarity NPD4792 Clinical (unspecified phase)
0.589 Remote Similarity NPD6927 Phase 3
0.5889 Remote Similarity NPD4821 Approved
0.5889 Remote Similarity NPD4819 Approved
0.5889 Remote Similarity NPD4820 Approved
0.5889 Remote Similarity NPD4252 Approved
0.5889 Remote Similarity NPD4822 Approved
0.5882 Remote Similarity NPD5344 Discontinued
0.587 Remote Similarity NPD7154 Phase 3
0.5851 Remote Similarity NPD4249 Approved
0.5823 Remote Similarity NPD9120 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4250 Approved
0.5789 Remote Similarity NPD4251 Approved
0.5773 Remote Similarity NPD5785 Approved
0.5761 Remote Similarity NPD4269 Approved
0.5761 Remote Similarity NPD4270 Approved
0.5755 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5741 Remote Similarity NPD6371 Approved
0.5732 Remote Similarity NPD2685 Clinical (unspecified phase)
0.573 Remote Similarity NPD4756 Discovery
0.5714 Remote Similarity NPD7637 Suspended
0.57 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5699 Remote Similarity NPD6110 Phase 1
0.5694 Remote Similarity NPD5343 Approved
0.5688 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5686 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5684 Remote Similarity NPD5786 Approved
0.5657 Remote Similarity NPD5779 Approved
0.5657 Remote Similarity NPD5778 Approved
0.5638 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5634 Remote Similarity NPD4222 Approved
0.5634 Remote Similarity NPD39 Approved
0.5616 Remote Similarity NPD3173 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