Structure

Physi-Chem Properties

Molecular Weight:  256.09
Volume:  243.827
LogP:  0.526
LogD:  0.43
LogS:  -2.005
# 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:  4.87
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:  -5.12
MDCK Permeability:  0.00010161348473047838
Pgp-inhibitor:  0.034
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.562
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.925
Plasma Protein Binding (PPB):  73.53751373291016%
Volume Distribution (VD):  0.929
Pgp-substrate:  27.4620361328125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.054
CYP1A2-substrate:  0.062
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.338
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.099
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.261
CYP3A4-inhibitor:  0.042
CYP3A4-substrate:  0.244

ADMET: Excretion

Clearance (CL):  2.349
Half-life (T1/2):  0.513

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.73
Drug-inuced Liver Injury (DILI):  0.945
AMES Toxicity:  0.323
Rat Oral Acute Toxicity:  0.352
Maximum Recommended Daily Dose:  0.692
Skin Sensitization:  0.213
Carcinogencity:  0.125
Eye Corrosion:  0.04
Eye Irritation:  0.035
Respiratory Toxicity:  0.579

Download Data

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

  Natural Product: NPC473489

Natural Product ID:  NPC473489
Common Name*:   7Alpha-Acetoxymultiplolide A
IUPAC Name:   [(1S,2E,4S,5R,7R,10S)-5-hydroxy-7-methyl-9-oxo-8,11-dioxabicyclo[8.1.0]undec-2-en-4-yl] acetate
Synonyms:  
Standard InCHIKey:  FGKZKXGAWZPSOJ-LQZLSNOLSA-N
Standard InCHI:  InChI=1S/C12H16O6/c1-6-5-8(14)9(17-7(2)13)3-4-10-11(18-10)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)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443368
PubChem CID:   24850147
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
NPT6148 Organism Helminthosporium maydis Helminthosporium maydis MIC > 500.0 ug.mL-1 PMID[551977]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum MIC > 500.0 ug.mL-1 PMID[551977]
NPT6149 Organism Penicillium islandicum Penicillium islandicum MIC > 500.0 ug.mL-1 PMID[551977]
NPT6150 Organism Ophiostoma minus Ophiostoma minus MIC > 500.0 ug.mL-1 PMID[551977]
NPT2781 Organism Fusarium moniliforme Gibberella moniliformis MIC > 500.0 ug.mL-1 PMID[551977]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 125.0 ug.mL-1 PMID[551977]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC > 500.0 ug.mL-1 PMID[551977]

☑ 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 NPC473489 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 NPC473582
0.971 High Similarity NPC326504
0.9444 High Similarity NPC318481
0.8333 Intermediate Similarity NPC130618
0.8056 Intermediate Similarity NPC25298
0.8026 Intermediate Similarity NPC473948
0.8 Intermediate Similarity NPC470435
0.7887 Intermediate Similarity NPC475221
0.7808 Intermediate Similarity NPC478100
0.7808 Intermediate Similarity NPC122627
0.7778 Intermediate Similarity NPC19769
0.7703 Intermediate Similarity NPC63873
0.7692 Intermediate Similarity NPC49392
0.7692 Intermediate Similarity NPC190400
0.7671 Intermediate Similarity NPC478101
0.7671 Intermediate Similarity NPC276299
0.7647 Intermediate Similarity NPC287089
0.7639 Intermediate Similarity NPC470808
0.76 Intermediate Similarity NPC470436
0.76 Intermediate Similarity NPC475982
0.7568 Intermediate Similarity NPC478097
0.7534 Intermediate Similarity NPC478098
0.7534 Intermediate Similarity NPC478099
0.7465 Intermediate Similarity NPC81896
0.7465 Intermediate Similarity NPC321919
0.7432 Intermediate Similarity NPC201356
0.7361 Intermediate Similarity NPC113293
0.7324 Intermediate Similarity NPC318306
0.7297 Intermediate Similarity NPC96414
0.7229 Intermediate Similarity NPC297440
0.72 Intermediate Similarity NPC124586
0.7195 Intermediate Similarity NPC99651
0.7179 Intermediate Similarity NPC293114
0.7162 Intermediate Similarity NPC308457
0.716 Intermediate Similarity NPC474278
0.7143 Intermediate Similarity NPC310450
0.7143 Intermediate Similarity NPC327388
0.7143 Intermediate Similarity NPC11383
0.7143 Intermediate Similarity NPC474959
0.7143 Intermediate Similarity NPC475046
0.7125 Intermediate Similarity NPC161038
0.7123 Intermediate Similarity NPC26810
0.7089 Intermediate Similarity NPC284006
0.7083 Intermediate Similarity NPC478095
0.7083 Intermediate Similarity NPC97570
0.7073 Intermediate Similarity NPC473471
0.7067 Intermediate Similarity NPC470123
0.7067 Intermediate Similarity NPC476655
0.7067 Intermediate Similarity NPC476657
0.7067 Intermediate Similarity NPC476654
0.7059 Intermediate Similarity NPC284472
0.7059 Intermediate Similarity NPC286770
0.7059 Intermediate Similarity NPC229799
0.7051 Intermediate Similarity NPC202011
0.7042 Intermediate Similarity NPC323436
0.7042 Intermediate Similarity NPC211752
0.7042 Intermediate Similarity NPC323597
0.7042 Intermediate Similarity NPC323498
0.7037 Intermediate Similarity NPC127118
0.7037 Intermediate Similarity NPC301207
0.7037 Intermediate Similarity NPC209113
0.7027 Intermediate Similarity NPC474774
0.7021 Intermediate Similarity NPC475949
0.7011 Intermediate Similarity NPC478112
0.7 Intermediate Similarity NPC107654
0.6988 Remote Similarity NPC475210
0.6986 Remote Similarity NPC258788
0.6974 Remote Similarity NPC476656
0.6974 Remote Similarity NPC475555
0.6974 Remote Similarity NPC475675
0.6974 Remote Similarity NPC476659
0.6974 Remote Similarity NPC146811
0.6957 Remote Similarity NPC477780
0.6957 Remote Similarity NPC477781
0.6951 Remote Similarity NPC275530
0.6951 Remote Similarity NPC474818
0.6951 Remote Similarity NPC125365
0.6951 Remote Similarity NPC51809
0.6951 Remote Similarity NPC176329
0.6951 Remote Similarity NPC475711
0.6951 Remote Similarity NPC474026
0.6951 Remote Similarity NPC49302
0.6944 Remote Similarity NPC478096
0.6933 Remote Similarity NPC148233
0.6933 Remote Similarity NPC476658
0.6933 Remote Similarity NPC25747
0.6932 Remote Similarity NPC266957
0.6914 Remote Similarity NPC260396
0.6897 Remote Similarity NPC471156
0.6883 Remote Similarity NPC330426
0.6883 Remote Similarity NPC148192
0.6883 Remote Similarity NPC22101
0.6883 Remote Similarity NPC104537
0.6883 Remote Similarity NPC127091
0.6883 Remote Similarity NPC271921
0.6875 Remote Similarity NPC471148
0.6867 Remote Similarity NPC279214
0.6867 Remote Similarity NPC279532
0.6867 Remote Similarity NPC182292
0.6867 Remote Similarity NPC221095
0.6867 Remote Similarity NPC248775
0.6849 Remote Similarity NPC322186
0.6842 Remote Similarity NPC273600
0.6835 Remote Similarity NPC42526
0.6829 Remote Similarity NPC470899
0.6829 Remote Similarity NPC470705
0.6829 Remote Similarity NPC203277
0.6829 Remote Similarity NPC68819
0.6829 Remote Similarity NPC205615
0.6829 Remote Similarity NPC16279
0.6829 Remote Similarity NPC256640
0.6824 Remote Similarity NPC474894
0.6824 Remote Similarity NPC150502
0.6818 Remote Similarity NPC469910
0.6795 Remote Similarity NPC48218
0.6795 Remote Similarity NPC324981
0.6795 Remote Similarity NPC273508
0.6795 Remote Similarity NPC209327
0.6795 Remote Similarity NPC473559
0.6795 Remote Similarity NPC141481
0.679 Remote Similarity NPC315843
0.679 Remote Similarity NPC474280
0.679 Remote Similarity NPC474545
0.6786 Remote Similarity NPC470148
0.6786 Remote Similarity NPC470149
0.6786 Remote Similarity NPC1180
0.6786 Remote Similarity NPC180725
0.6782 Remote Similarity NPC469809
0.6771 Remote Similarity NPC474339
0.6771 Remote Similarity NPC164598
0.6768 Remote Similarity NPC326994
0.6768 Remote Similarity NPC72813
0.6768 Remote Similarity NPC194620
0.6768 Remote Similarity NPC324327
0.6768 Remote Similarity NPC474421
0.6757 Remote Similarity NPC26223
0.6747 Remote Similarity NPC233071
0.6747 Remote Similarity NPC272267
0.6744 Remote Similarity NPC474252
0.6737 Remote Similarity NPC161855
0.6712 Remote Similarity NPC187770
0.6707 Remote Similarity NPC478194
0.6707 Remote Similarity NPC478193
0.6707 Remote Similarity NPC478192
0.6707 Remote Similarity NPC478191
0.6707 Remote Similarity NPC478195
0.6707 Remote Similarity NPC478196
0.6706 Remote Similarity NPC133226
0.6706 Remote Similarity NPC121374
0.6706 Remote Similarity NPC470147
0.6705 Remote Similarity NPC470124
0.6705 Remote Similarity NPC475034
0.6703 Remote Similarity NPC274075
0.6703 Remote Similarity NPC474232
0.6703 Remote Similarity NPC473311
0.6702 Remote Similarity NPC473291
0.67 Remote Similarity NPC233379
0.67 Remote Similarity NPC14862
0.67 Remote Similarity NPC169888
0.67 Remote Similarity NPC55972
0.67 Remote Similarity NPC327286
0.67 Remote Similarity NPC474664
0.6667 Remote Similarity NPC161045
0.6667 Remote Similarity NPC328776
0.6667 Remote Similarity NPC473829
0.6667 Remote Similarity NPC127526
0.6667 Remote Similarity NPC231601
0.6667 Remote Similarity NPC55376
0.6667 Remote Similarity NPC475443
0.6667 Remote Similarity NPC320305
0.6667 Remote Similarity NPC99619
0.6667 Remote Similarity NPC324667
0.6667 Remote Similarity NPC476803
0.6667 Remote Similarity NPC321838
0.6667 Remote Similarity NPC16313
0.6667 Remote Similarity NPC121825
0.6667 Remote Similarity NPC9303
0.6667 Remote Similarity NPC26500
0.6634 Remote Similarity NPC15218
0.6629 Remote Similarity NPC278283
0.6628 Remote Similarity NPC159714
0.6628 Remote Similarity NPC221510
0.6627 Remote Similarity NPC188860
0.6625 Remote Similarity NPC476660
0.6625 Remote Similarity NPC473361
0.6625 Remote Similarity NPC476037
0.6625 Remote Similarity NPC476012
0.6625 Remote Similarity NPC329904
0.6623 Remote Similarity NPC282760
0.6622 Remote Similarity NPC222852
0.6622 Remote Similarity NPC329249
0.6622 Remote Similarity NPC302564
0.662 Remote Similarity NPC137538
0.66 Remote Similarity NPC477513
0.66 Remote Similarity NPC266514
0.6598 Remote Similarity NPC472753
0.6591 Remote Similarity NPC32676
0.6591 Remote Similarity NPC474251
0.6591 Remote Similarity NPC158756
0.6588 Remote Similarity NPC471537

  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 NPC473489 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
0.7429 Intermediate Similarity NPD6109 Phase 1
0.7183 Intermediate Similarity NPD585 Clinical (unspecified phase)
0.6712 Remote Similarity NPD9119 Approved
0.6712 Remote Similarity NPD69 Approved
0.6627 Remote Similarity NPD819 Approved
0.6627 Remote Similarity NPD818 Approved
0.6575 Remote Similarity NPD9118 Approved
0.6522 Remote Similarity NPD46 Approved
0.6522 Remote Similarity NPD6698 Approved
0.6522 Remote Similarity NPD7838 Discovery
0.6494 Remote Similarity NPD3197 Phase 1
0.6316 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6277 Remote Similarity NPD7983 Approved
0.625 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6136 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5972 Remote Similarity NPD6927 Phase 3
0.5909 Remote Similarity NPD4268 Approved
0.5909 Remote Similarity NPD4271 Approved
0.59 Remote Similarity NPD4225 Approved
0.5897 Remote Similarity NPD9120 Clinical (unspecified phase)
0.5859 Remote Similarity NPD4792 Clinical (unspecified phase)
0.581 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5802 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5784 Remote Similarity NPD5344 Discontinued
0.5778 Remote Similarity NPD4822 Approved
0.5778 Remote Similarity NPD4252 Approved
0.5778 Remote Similarity NPD4819 Approved
0.5778 Remote Similarity NPD4820 Approved
0.5778 Remote Similarity NPD4821 Approved
0.5775 Remote Similarity NPD5343 Approved
0.5761 Remote Similarity NPD7154 Phase 3
0.5758 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5745 Remote Similarity NPD4249 Approved
0.5714 Remote Similarity NPD39 Approved
0.5714 Remote Similarity NPD4222 Approved
0.5694 Remote Similarity NPD3173 Approved
0.5684 Remote Similarity NPD4250 Approved
0.5684 Remote Similarity NPD4251 Approved
0.567 Remote Similarity NPD5785 Approved
0.5652 Remote Similarity NPD4269 Approved
0.5652 Remote Similarity NPD5209 Approved
0.5652 Remote Similarity NPD4270 Approved
0.5648 Remote Similarity NPD6371 Approved
0.5638 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5638 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5618 Remote Similarity NPD4756 Discovery
0.5612 Remote Similarity NPD7637 Suspended

  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