Structure

Physi-Chem Properties

Molecular Weight:  441.25
Volume:  474.995
LogP:  4.053
LogD:  2.663
LogS:  -3.737
# Rotatable Bonds:  9
TPSA:  99.76
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.216
Synthetic Accessibility Score:  4.463
Fsp3:  0.462
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.846
MDCK Permeability:  1.740666266414337e-05
Pgp-inhibitor:  0.317
Pgp-substrate:  0.146
Human Intestinal Absorption (HIA):  0.026
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.155

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  97.44268035888672%
Volume Distribution (VD):  0.671
Pgp-substrate:  4.286322593688965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.938
CYP1A2-substrate:  0.314
CYP2C19-inhibitor:  0.896
CYP2C19-substrate:  0.076
CYP2C9-inhibitor:  0.947
CYP2C9-substrate:  0.988
CYP2D6-inhibitor:  0.8
CYP2D6-substrate:  0.819
CYP3A4-inhibitor:  0.864
CYP3A4-substrate:  0.223

ADMET: Excretion

Clearance (CL):  5.417
Half-life (T1/2):  0.247

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.294
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.345
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.971
Skin Sensitization:  0.925
Carcinogencity:  0.759
Eye Corrosion:  0.003
Eye Irritation:  0.053
Respiratory Toxicity:  0.874

Download Data

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

  Natural Product: NPC316730

Natural Product ID:  NPC316730
Common Name*:   Militarinone E
IUPAC Name:   1,4-dihydroxy-5-[(4S)-4-hydroxycyclohexen-1-yl]-3-[(2E,4E,6E,8R,10R)-6,8,10-trimethyldodeca-2,4,6-trienoyl]pyridin-2-one
Synonyms:   Militarinone E
Standard InCHIKey:  BFJKFLDLQKCOHR-BFIBXSCBSA-N
Standard InCHI:  InChI=1S/C26H35NO5/c1-5-17(2)14-19(4)15-18(3)8-6-7-9-23(29)24-25(30)22(16-27(32)26(24)31)20-10-12-21(28)13-11-20/h6-10,15-17,19,21,28,30,32H,5,11-14H2,1-4H3/b8-6+,9-7+,18-15+/t17-,19-,21-/m1/s1
SMILES:  CC[C@H](C[C@H](/C=C(/C=C/C=C/C(=O)c1c(O)c(cn(c1=O)O)C1=CC[C@H](CC1)O)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1669191
PubChem CID:   54732917
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO10809 Isaria farinosa Species Cordycipitaceae Eukaryota Cordyceps-colonizing isolate of Isaria farinosa n.a. n.a. PMID[19572613]
NPO10809 Isaria farinosa Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21158423]
NPO10809 Isaria farinosa Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21495659]
NPO10809 Isaria farinosa Species Cordycipitaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 1590.0 nM PMID[523200]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 > 150000.0 nM PMID[523200]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae IC50 > 150000.0 nM PMID[523200]
NPT20 Organism Candida albicans Candida albicans IC50 > 150000.0 nM PMID[523200]

☑ 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 NPC316730 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
0.9381 High Similarity NPC470073
0.9278 High Similarity NPC318544
0.8725 High Similarity NPC470072
0.7087 Intermediate Similarity NPC473056
0.6975 Remote Similarity NPC477140
0.6975 Remote Similarity NPC477143
0.6952 Remote Similarity NPC247316
0.6724 Remote Similarity NPC44733
0.6667 Remote Similarity NPC77703
0.6609 Remote Similarity NPC476276
0.6581 Remote Similarity NPC21713
0.6581 Remote Similarity NPC475608
0.6562 Remote Similarity NPC81092
0.6562 Remote Similarity NPC103605
0.6545 Remote Similarity NPC472166
0.6535 Remote Similarity NPC226982
0.6535 Remote Similarity NPC277341
0.6471 Remote Similarity NPC473810
0.6446 Remote Similarity NPC475642
0.6442 Remote Similarity NPC2640
0.6436 Remote Similarity NPC209232
0.6435 Remote Similarity NPC476328
0.6429 Remote Similarity NPC34672
0.6396 Remote Similarity NPC265662
0.6356 Remote Similarity NPC476290
0.63 Remote Similarity NPC471061
0.6293 Remote Similarity NPC472856
0.6286 Remote Similarity NPC32037
0.6262 Remote Similarity NPC316186
0.6262 Remote Similarity NPC7280
0.6262 Remote Similarity NPC229612
0.6261 Remote Similarity NPC68001
0.6261 Remote Similarity NPC199831
0.6261 Remote Similarity NPC474827
0.6261 Remote Similarity NPC474828
0.625 Remote Similarity NPC52820
0.625 Remote Similarity NPC476269
0.624 Remote Similarity NPC475383
0.624 Remote Similarity NPC156379
0.6239 Remote Similarity NPC314500
0.6239 Remote Similarity NPC251330
0.6228 Remote Similarity NPC144714
0.6228 Remote Similarity NPC100810
0.6228 Remote Similarity NPC316250
0.6226 Remote Similarity NPC322672
0.6214 Remote Similarity NPC6663
0.621 Remote Similarity NPC241050
0.619 Remote Similarity NPC302360
0.6186 Remote Similarity NPC220730
0.6168 Remote Similarity NPC113370
0.6168 Remote Similarity NPC103743
0.6168 Remote Similarity NPC476079
0.6168 Remote Similarity NPC473525
0.6161 Remote Similarity NPC175614
0.6154 Remote Similarity NPC271269
0.6154 Remote Similarity NPC154601
0.6139 Remote Similarity NPC46268
0.6139 Remote Similarity NPC203403
0.6134 Remote Similarity NPC21324
0.6132 Remote Similarity NPC319913
0.6122 Remote Similarity NPC95863
0.6117 Remote Similarity NPC74086
0.6111 Remote Similarity NPC60765
0.6106 Remote Similarity NPC476344
0.6106 Remote Similarity NPC91036
0.6106 Remote Similarity NPC472167
0.6095 Remote Similarity NPC16488
0.6095 Remote Similarity NPC57370
0.6078 Remote Similarity NPC231739
0.6078 Remote Similarity NPC475994
0.6075 Remote Similarity NPC316426
0.6075 Remote Similarity NPC315395
0.6075 Remote Similarity NPC472136
0.6071 Remote Similarity NPC150041
0.6068 Remote Similarity NPC133420
0.6055 Remote Similarity NPC81195
0.6055 Remote Similarity NPC471054
0.605 Remote Similarity NPC307903
0.605 Remote Similarity NPC140251
0.605 Remote Similarity NPC474099
0.6048 Remote Similarity NPC476190
0.604 Remote Similarity NPC250621
0.6038 Remote Similarity NPC475975
0.6036 Remote Similarity NPC282644
0.6036 Remote Similarity NPC29798
0.6034 Remote Similarity NPC474244
0.6034 Remote Similarity NPC128501
0.602 Remote Similarity NPC318766
0.602 Remote Similarity NPC203819
0.6019 Remote Similarity NPC287079
0.6019 Remote Similarity NPC241054
0.6019 Remote Similarity NPC19900
0.6017 Remote Similarity NPC472615
0.6 Remote Similarity NPC47230
0.6 Remote Similarity NPC19771
0.6 Remote Similarity NPC158411
0.6 Remote Similarity NPC477964
0.6 Remote Similarity NPC224455
0.6 Remote Similarity NPC38796
0.6 Remote Similarity NPC17143
0.5984 Remote Similarity NPC314550
0.5983 Remote Similarity NPC474563
0.5982 Remote Similarity NPC473162
0.5982 Remote Similarity NPC474690
0.5982 Remote Similarity NPC299100
0.5981 Remote Similarity NPC187529
0.5981 Remote Similarity NPC475614
0.5981 Remote Similarity NPC15807
0.5981 Remote Similarity NPC307112
0.5981 Remote Similarity NPC242233
0.5981 Remote Similarity NPC109528
0.5981 Remote Similarity NPC76283
0.598 Remote Similarity NPC315394
0.598 Remote Similarity NPC82666
0.598 Remote Similarity NPC97173
0.5966 Remote Similarity NPC315531
0.5963 Remote Similarity NPC472011
0.5963 Remote Similarity NPC106051
0.5962 Remote Similarity NPC476560
0.5948 Remote Similarity NPC175531
0.5948 Remote Similarity NPC469851
0.5946 Remote Similarity NPC142838
0.5946 Remote Similarity NPC32552
0.5946 Remote Similarity NPC472010
0.5943 Remote Similarity NPC477786
0.5943 Remote Similarity NPC475083
0.5943 Remote Similarity NPC477784
0.5943 Remote Similarity NPC477785
0.5941 Remote Similarity NPC474885
0.5941 Remote Similarity NPC315552
0.5938 Remote Similarity NPC137163
0.5932 Remote Similarity NPC472616
0.5929 Remote Similarity NPC180950
0.5926 Remote Similarity NPC472974
0.5926 Remote Similarity NPC203795
0.5922 Remote Similarity NPC192006
0.5922 Remote Similarity NPC478122
0.592 Remote Similarity NPC271621
0.592 Remote Similarity NPC59751
0.592 Remote Similarity NPC27413
0.592 Remote Similarity NPC235421
0.5909 Remote Similarity NPC472983
0.5909 Remote Similarity NPC472688
0.5909 Remote Similarity NPC472676
0.5905 Remote Similarity NPC275766
0.59 Remote Similarity NPC186042
0.5888 Remote Similarity NPC33913
0.5888 Remote Similarity NPC472265
0.5882 Remote Similarity NPC477708
0.5882 Remote Similarity NPC469852
0.5878 Remote Similarity NPC473249
0.5877 Remote Similarity NPC250757
0.5877 Remote Similarity NPC301534
0.5876 Remote Similarity NPC96962
0.5876 Remote Similarity NPC106613
0.5873 Remote Similarity NPC471673
0.5872 Remote Similarity NPC313658
0.5872 Remote Similarity NPC324506
0.5872 Remote Similarity NPC316138
0.5868 Remote Similarity NPC133729
0.5865 Remote Similarity NPC471597
0.5862 Remote Similarity NPC185253
0.5862 Remote Similarity NPC215253
0.5856 Remote Similarity NPC265856
0.5856 Remote Similarity NPC53240
0.5847 Remote Similarity NPC320294
0.5842 Remote Similarity NPC227396
0.5841 Remote Similarity NPC78159
0.5841 Remote Similarity NPC472977
0.5841 Remote Similarity NPC474882
0.5841 Remote Similarity NPC472976
0.5833 Remote Similarity NPC470177
0.5833 Remote Similarity NPC469853
0.5833 Remote Similarity NPC176773
0.5833 Remote Similarity NPC476426
0.5826 Remote Similarity NPC99726
0.5826 Remote Similarity NPC474938
0.5826 Remote Similarity NPC474785
0.5826 Remote Similarity NPC471694
0.5826 Remote Similarity NPC241426
0.5826 Remote Similarity NPC161147
0.5825 Remote Similarity NPC476007
0.582 Remote Similarity NPC469603
0.582 Remote Similarity NPC328052
0.582 Remote Similarity NPC477997
0.5816 Remote Similarity NPC117804
0.581 Remote Similarity NPC471514
0.5804 Remote Similarity NPC472978
0.58 Remote Similarity NPC67076
0.58 Remote Similarity NPC319163
0.5798 Remote Similarity NPC9436
0.5798 Remote Similarity NPC469604
0.5794 Remote Similarity NPC297398
0.5784 Remote Similarity NPC171148
0.5784 Remote Similarity NPC313179
0.5784 Remote Similarity NPC69383
0.578 Remote Similarity NPC186332
0.578 Remote Similarity NPC118648
0.578 Remote Similarity NPC183736
0.578 Remote Similarity NPC194417

  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 NPC316730 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
0.619 Remote Similarity NPD7624 Clinical (unspecified phase)
0.619 Remote Similarity NPD7623 Phase 3
0.616 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7333 Discontinued
0.6117 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6033 Remote Similarity NPD7116 Clinical (unspecified phase)
0.596 Remote Similarity NPD815 Approved
0.596 Remote Similarity NPD816 Approved
0.5878 Remote Similarity NPD7746 Phase 1
0.5878 Remote Similarity NPD7747 Phase 1
0.5784 Remote Similarity NPD8264 Approved
0.5748 Remote Similarity NPD7641 Discontinued
0.5704 Remote Similarity NPD7260 Phase 2
0.5704 Remote Similarity NPD4208 Discontinued
0.5688 Remote Similarity NPD5363 Approved
0.5673 Remote Similarity NPD4756 Discovery
0.5669 Remote Similarity NPD7500 Approved
0.5641 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5614 Remote Similarity NPD5779 Approved
0.5614 Remote Similarity NPD5778 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