Structure

Physi-Chem Properties

Molecular Weight:  459.26
Volume:  486.422
LogP:  2.878
LogD:  1.463
LogS:  -3.644
# Rotatable Bonds:  9
TPSA:  119.99
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.19
Synthetic Accessibility Score:  4.28
Fsp3:  0.538
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:  -4.905
MDCK Permeability:  1.3498284715751652e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.939
Human Intestinal Absorption (HIA):  0.198
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.486

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  93.85774993896484%
Volume Distribution (VD):  0.52
Pgp-substrate:  7.419724941253662%

ADMET: Metabolism

CYP1A2-inhibitor:  0.619
CYP1A2-substrate:  0.449
CYP2C19-inhibitor:  0.67
CYP2C19-substrate:  0.1
CYP2C9-inhibitor:  0.913
CYP2C9-substrate:  0.989
CYP2D6-inhibitor:  0.767
CYP2D6-substrate:  0.703
CYP3A4-inhibitor:  0.808
CYP3A4-substrate:  0.194

ADMET: Excretion

Clearance (CL):  5.316
Half-life (T1/2):  0.191

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.172
Drug-inuced Liver Injury (DILI):  0.139
AMES Toxicity:  0.629
Rat Oral Acute Toxicity:  0.185
Maximum Recommended Daily Dose:  0.946
Skin Sensitization:  0.321
Carcinogencity:  0.658
Eye Corrosion:  0.003
Eye Irritation:  0.025
Respiratory Toxicity:  0.547

Download Data

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

  Natural Product: NPC470073

Natural Product ID:  NPC470073
Common Name*:   Militarinone A
IUPAC Name:   n.a.
Synonyms:   Militarinone A
Standard InCHIKey:  TURMFSNDIZERMD-FOBKFMRFSA-N
Standard InCHI:  InChI=1S/C26H37NO6/c1-5-17(2)14-19(4)15-18(3)8-6-7-9-22(29)23-24(30)21(16-27(33)25(23)31)26(32)12-10-20(28)11-13-26/h6-9,15-17,19-20,28,30,32-33H,5,10-14H2,1-4H3/b8-6+,9-7+,18-15+/t17-,19-,20-,26+/m1/s1
SMILES:  CC[C@H](C[C@H](/C=C(/C=C/C=C/C(=O)c1c(O)c(cn(c1=O)O)[C@]1(O)CC[C@H](CC1)O)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1669196
PubChem CID:   n.a.
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 = 1750.0 nM PMID[541986]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 > 150000.0 nM PMID[541986]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae IC50 > 150000.0 nM PMID[541986]
NPT20 Organism Candida albicans Candida albicans IC50 > 150000.0 nM PMID[541986]

☑ 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 NPC470073 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
0.9896 High Similarity NPC318544
0.9381 High Similarity NPC316730
0.875 High Similarity NPC470072
0.7311 Intermediate Similarity NPC477143
0.7311 Intermediate Similarity NPC477140
0.6981 Remote Similarity NPC473056
0.6852 Remote Similarity NPC247316
0.6639 Remote Similarity NPC44733
0.6525 Remote Similarity NPC476276
0.6504 Remote Similarity NPC475642
0.65 Remote Similarity NPC21713
0.65 Remote Similarity NPC475608
0.6489 Remote Similarity NPC81092
0.6489 Remote Similarity NPC103605
0.6429 Remote Similarity NPC156379
0.6429 Remote Similarity NPC475383
0.64 Remote Similarity NPC241050
0.6356 Remote Similarity NPC476328
0.6316 Remote Similarity NPC265662
0.6293 Remote Similarity NPC77703
0.6286 Remote Similarity NPC277341
0.6286 Remote Similarity NPC226982
0.6226 Remote Similarity NPC473810
0.6218 Remote Similarity NPC154601
0.619 Remote Similarity NPC209232
0.6182 Remote Similarity NPC60765
0.6176 Remote Similarity NPC34672
0.6174 Remote Similarity NPC472166
0.6154 Remote Similarity NPC316250
0.6148 Remote Similarity NPC476290
0.614 Remote Similarity NPC180950
0.6083 Remote Similarity NPC472856
0.6071 Remote Similarity NPC19771
0.6055 Remote Similarity NPC2640
0.6055 Remote Similarity NPC32037
0.6053 Remote Similarity NPC299100
0.6053 Remote Similarity NPC474690
0.605 Remote Similarity NPC474827
0.605 Remote Similarity NPC199831
0.605 Remote Similarity NPC474828
0.605 Remote Similarity NPC68001
0.6048 Remote Similarity NPC476269
0.6036 Remote Similarity NPC7280
0.6036 Remote Similarity NPC229612
0.6034 Remote Similarity NPC474938
0.6034 Remote Similarity NPC52820
0.6034 Remote Similarity NPC474785
0.6033 Remote Similarity NPC251330
0.6018 Remote Similarity NPC314500
0.6017 Remote Similarity NPC144714
0.6017 Remote Similarity NPC100810
0.6 Remote Similarity NPC231739
0.6 Remote Similarity NPC322672
0.5984 Remote Similarity NPC220730
0.5984 Remote Similarity NPC235421
0.5982 Remote Similarity NPC257485
0.5982 Remote Similarity NPC471054
0.5982 Remote Similarity NPC472688
0.5982 Remote Similarity NPC472676
0.5981 Remote Similarity NPC6663
0.5963 Remote Similarity NPC302360
0.595 Remote Similarity NPC271269
0.5948 Remote Similarity NPC175614
0.5946 Remote Similarity NPC476079
0.5946 Remote Similarity NPC113370
0.5946 Remote Similarity NPC103743
0.5946 Remote Similarity NPC473525
0.5938 Remote Similarity NPC471673
0.5935 Remote Similarity NPC21324
0.5929 Remote Similarity NPC469464
0.5909 Remote Similarity NPC187529
0.5909 Remote Similarity NPC319913
0.5909 Remote Similarity NPC242233
0.5905 Remote Similarity NPC203403
0.5905 Remote Similarity NPC46268
0.5905 Remote Similarity NPC82666
0.5905 Remote Similarity NPC97173
0.5905 Remote Similarity NPC471061
0.5902 Remote Similarity NPC469853
0.5902 Remote Similarity NPC315531
0.5897 Remote Similarity NPC476344
0.5897 Remote Similarity NPC91036
0.5893 Remote Similarity NPC316186
0.5887 Remote Similarity NPC315848
0.5887 Remote Similarity NPC315210
0.5882 Remote Similarity NPC115862
0.5882 Remote Similarity NPC282524
0.5882 Remote Similarity NPC469851
0.5882 Remote Similarity NPC175531
0.5877 Remote Similarity NPC472978
0.5877 Remote Similarity NPC32552
0.5872 Remote Similarity NPC477786
0.5872 Remote Similarity NPC16488
0.5872 Remote Similarity NPC477785
0.5872 Remote Similarity NPC477784
0.5872 Remote Similarity NPC57370
0.5872 Remote Similarity NPC44261
0.5862 Remote Similarity NPC150041
0.5859 Remote Similarity NPC476190
0.5856 Remote Similarity NPC472974
0.5856 Remote Similarity NPC315395
0.5856 Remote Similarity NPC316426
0.5854 Remote Similarity NPC474099
0.5849 Remote Similarity NPC248624
0.5841 Remote Similarity NPC472983
0.5841 Remote Similarity NPC307092
0.5841 Remote Similarity NPC51358
0.5841 Remote Similarity NPC81195
0.5833 Remote Similarity NPC474244
0.5833 Remote Similarity NPC112868
0.5833 Remote Similarity NPC128501
0.5826 Remote Similarity NPC29798
0.5826 Remote Similarity NPC282644
0.582 Remote Similarity NPC472615
0.582 Remote Similarity NPC32006
0.582 Remote Similarity NPC85529
0.582 Remote Similarity NPC469852
0.5818 Remote Similarity NPC475975
0.5812 Remote Similarity NPC16967
0.5812 Remote Similarity NPC301534
0.5812 Remote Similarity NPC250757
0.581 Remote Similarity NPC477708
0.581 Remote Similarity NPC167873
0.581 Remote Similarity NPC250621
0.581 Remote Similarity NPC1973
0.5806 Remote Similarity NPC137911
0.5806 Remote Similarity NPC133729
0.5806 Remote Similarity NPC228477
0.5804 Remote Similarity NPC241054
0.5798 Remote Similarity NPC477964
0.5794 Remote Similarity NPC471597
0.5789 Remote Similarity NPC134321
0.5789 Remote Similarity NPC47230
0.5789 Remote Similarity NPC17143
0.5785 Remote Similarity NPC475050
0.5785 Remote Similarity NPC320294
0.5784 Remote Similarity NPC318766
0.5781 Remote Similarity NPC30196
0.578 Remote Similarity NPC224455
0.5776 Remote Similarity NPC472977
0.5776 Remote Similarity NPC103527
0.5776 Remote Similarity NPC473162
0.5776 Remote Similarity NPC191521
0.5776 Remote Similarity NPC472976
0.5769 Remote Similarity NPC144995
0.5769 Remote Similarity NPC227814
0.5766 Remote Similarity NPC476426
0.5766 Remote Similarity NPC280203
0.5766 Remote Similarity NPC307112
0.5766 Remote Similarity NPC109528
0.5763 Remote Similarity NPC472167
0.5763 Remote Similarity NPC99726
0.576 Remote Similarity NPC469603
0.576 Remote Similarity NPC477997
0.5755 Remote Similarity NPC315394
0.5755 Remote Similarity NPC476007
0.5755 Remote Similarity NPC85105
0.5755 Remote Similarity NPC149550
0.5752 Remote Similarity NPC26078
0.5752 Remote Similarity NPC472011
0.5752 Remote Similarity NPC292491
0.5752 Remote Similarity NPC104560
0.5752 Remote Similarity NPC473658
0.5752 Remote Similarity NPC310752
0.5752 Remote Similarity NPC106051
0.575 Remote Similarity NPC470184
0.575 Remote Similarity NPC115899
0.5741 Remote Similarity NPC74086
0.5741 Remote Similarity NPC476560
0.5739 Remote Similarity NPC472010
0.5739 Remote Similarity NPC142838
0.5738 Remote Similarity NPC75523
0.5738 Remote Similarity NPC472616
0.5738 Remote Similarity NPC118911
0.5738 Remote Similarity NPC469604
0.5738 Remote Similarity NPC133420
0.5736 Remote Similarity NPC6531
0.5728 Remote Similarity NPC95863
0.5727 Remote Similarity NPC475083
0.5727 Remote Similarity NPC79945
0.5727 Remote Similarity NPC471987
0.5726 Remote Similarity NPC476245
0.5726 Remote Similarity NPC91408
0.5726 Remote Similarity NPC102843
0.5726 Remote Similarity NPC307903
0.5726 Remote Similarity NPC140251
0.5714 Remote Similarity NPC472136
0.5714 Remote Similarity NPC186332
0.5714 Remote Similarity NPC203795
0.5714 Remote Similarity NPC47220
0.5714 Remote Similarity NPC314629
0.5714 Remote Similarity NPC474885
0.5714 Remote Similarity NPC35717
0.5714 Remote Similarity NPC315552
0.5703 Remote Similarity NPC145501
0.5702 Remote Similarity NPC314727
0.5702 Remote Similarity NPC36668
0.5702 Remote Similarity NPC118011
0.5702 Remote Similarity NPC212598
0.5702 Remote Similarity NPC472973

  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 NPC470073 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
0.6218 Remote Similarity NPD7333 Discontinued
0.5882 Remote Similarity NPD815 Approved
0.5882 Remote Similarity NPD816 Approved
0.5878 Remote Similarity NPD7623 Phase 3
0.5878 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5846 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5814 Remote Similarity NPD7641 Discontinued
0.5802 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5741 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4208 Discontinued
0.563 Remote Similarity NPD8273 Phase 1

  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