Structure

Physi-Chem Properties

Molecular Weight:  441.25
Volume:  469.075
LogP:  4.047
LogD:  3.413
LogS:  -4.233
# Rotatable Bonds:  9
TPSA:  88.76
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.236
Synthetic Accessibility Score:  5.14
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:  -4.727
MDCK Permeability:  2.1637613826896995e-05
Pgp-inhibitor:  0.03
Pgp-substrate:  0.016
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  98.9465560913086%
Volume Distribution (VD):  0.665
Pgp-substrate:  2.4691967964172363%

ADMET: Metabolism

CYP1A2-inhibitor:  0.576
CYP1A2-substrate:  0.471
CYP2C19-inhibitor:  0.926
CYP2C19-substrate:  0.337
CYP2C9-inhibitor:  0.94
CYP2C9-substrate:  0.99
CYP2D6-inhibitor:  0.853
CYP2D6-substrate:  0.772
CYP3A4-inhibitor:  0.898
CYP3A4-substrate:  0.321

ADMET: Excretion

Clearance (CL):  2.384
Half-life (T1/2):  0.11

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.276
Drug-inuced Liver Injury (DILI):  0.212
AMES Toxicity:  0.569
Rat Oral Acute Toxicity:  0.589
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.55
Carcinogencity:  0.806
Eye Corrosion:  0.003
Eye Irritation:  0.04
Respiratory Toxicity:  0.619

Download Data

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

  Natural Product: NPC470072

Natural Product ID:  NPC470072
Common Name*:   Militarinone F
IUPAC Name:   n.a.
Synonyms:   Militarinone F
Standard InCHIKey:  HJCSSOXITDMEEP-FOBKFMRFSA-N
Standard InCHI:  InChI=1S/C26H35NO5/c1-5-17(2)14-19(4)15-18(3)8-6-7-9-22(28)23-24(29)21(16-27(31)25(23)30)26-12-10-20(32-26)11-13-26/h6-9,15-17,19-20,29,31H,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)n(O)cc(c1O)[C@]12CC[C@@H](O2)CC1)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1669192
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:0001564] Bicyclic 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 > 150000.0 nM PMID[487937]
NPT81 Cell Line A549 Homo sapiens IC50 > 120000.0 nM PMID[487937]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 > 150000.0 nM PMID[487937]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae IC50 > 150000.0 nM PMID[487937]

☑ 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 NPC470072 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
0.875 High Similarity NPC470073
0.8725 High Similarity NPC316730
0.8654 High Similarity NPC318544
0.7131 Intermediate Similarity NPC477143
0.7131 Intermediate Similarity NPC477140
0.675 Remote Similarity NPC21713
0.675 Remote Similarity NPC44733
0.675 Remote Similarity NPC475608
0.6726 Remote Similarity NPC52820
0.6724 Remote Similarity NPC68001
0.6724 Remote Similarity NPC199831
0.6724 Remote Similarity NPC474828
0.6724 Remote Similarity NPC474827
0.6613 Remote Similarity NPC475642
0.6591 Remote Similarity NPC103605
0.6591 Remote Similarity NPC81092
0.6579 Remote Similarity NPC476344
0.6549 Remote Similarity NPC150041
0.6535 Remote Similarity NPC475383
0.6535 Remote Similarity NPC156379
0.6508 Remote Similarity NPC241050
0.65 Remote Similarity NPC474099
0.6496 Remote Similarity NPC474244
0.6486 Remote Similarity NPC473056
0.6435 Remote Similarity NPC265662
0.6393 Remote Similarity NPC469603
0.6387 Remote Similarity NPC469604
0.6372 Remote Similarity NPC247316
0.6355 Remote Similarity NPC473810
0.6333 Remote Similarity NPC154601
0.6311 Remote Similarity NPC21324
0.6306 Remote Similarity NPC60765
0.6271 Remote Similarity NPC469851
0.6271 Remote Similarity NPC175531
0.6262 Remote Similarity NPC277341
0.6262 Remote Similarity NPC226982
0.625 Remote Similarity NPC133420
0.6218 Remote Similarity NPC128501
0.6216 Remote Similarity NPC113370
0.6216 Remote Similarity NPC476079
0.6216 Remote Similarity NPC103743
0.6207 Remote Similarity NPC175614
0.6198 Remote Similarity NPC271269
0.6148 Remote Similarity NPC251330
0.6147 Remote Similarity NPC16488
0.6134 Remote Similarity NPC77703
0.6126 Remote Similarity NPC322672
0.6126 Remote Similarity NPC316426
0.6126 Remote Similarity NPC315395
0.6106 Remote Similarity NPC81195
0.6099 Remote Similarity NPC315210
0.6099 Remote Similarity NPC315848
0.6098 Remote Similarity NPC476276
0.6087 Remote Similarity NPC29798
0.6087 Remote Similarity NPC59646
0.6087 Remote Similarity NPC282644
0.6075 Remote Similarity NPC471768
0.6071 Remote Similarity NPC473525
0.6066 Remote Similarity NPC469852
0.6048 Remote Similarity NPC24389
0.6038 Remote Similarity NPC46268
0.6038 Remote Similarity NPC315394
0.6036 Remote Similarity NPC319913
0.6036 Remote Similarity NPC2640
0.6036 Remote Similarity NPC307112
0.6034 Remote Similarity NPC470521
0.6018 Remote Similarity NPC473658
0.6018 Remote Similarity NPC26078
0.6018 Remote Similarity NPC260343
0.6016 Remote Similarity NPC469853
0.6 Remote Similarity NPC175842
0.6 Remote Similarity NPC32552
0.6 Remote Similarity NPC313234
0.6 Remote Similarity NPC32494
0.6 Remote Similarity NPC475083
0.6 Remote Similarity NPC111114
0.6 Remote Similarity NPC261607
0.6 Remote Similarity NPC300312
0.5985 Remote Similarity NPC120335
0.5984 Remote Similarity NPC75523
0.5982 Remote Similarity NPC234038
0.5981 Remote Similarity NPC108816
0.5981 Remote Similarity NPC93763
0.5981 Remote Similarity NPC267231
0.5968 Remote Similarity NPC220730
0.5966 Remote Similarity NPC203627
0.5966 Remote Similarity NPC475068
0.5965 Remote Similarity NPC212598
0.5965 Remote Similarity NPC471054
0.5965 Remote Similarity NPC51358
0.5965 Remote Similarity NPC307092
0.5963 Remote Similarity NPC112868
0.5963 Remote Similarity NPC315731
0.595 Remote Similarity NPC291500
0.595 Remote Similarity NPC303653
0.595 Remote Similarity NPC473289
0.595 Remote Similarity NPC140591
0.595 Remote Similarity NPC189609
0.595 Remote Similarity NPC197835
0.5948 Remote Similarity NPC475098
0.5948 Remote Similarity NPC189651
0.5935 Remote Similarity NPC476328
0.5932 Remote Similarity NPC16967
0.5929 Remote Similarity NPC160138
0.5929 Remote Similarity NPC72513
0.5926 Remote Similarity NPC139712
0.5926 Remote Similarity NPC471537
0.5917 Remote Similarity NPC26597
0.5913 Remote Similarity NPC3436
0.5913 Remote Similarity NPC144133
0.5913 Remote Similarity NPC179394
0.5906 Remote Similarity NPC314550
0.5897 Remote Similarity NPC477241
0.5897 Remote Similarity NPC167219
0.5897 Remote Similarity NPC14322
0.5897 Remote Similarity NPC474338
0.5882 Remote Similarity NPC472166
0.5882 Remote Similarity NPC472167
0.5882 Remote Similarity NPC239895
0.5882 Remote Similarity NPC241426
0.5873 Remote Similarity NPC477997
0.5873 Remote Similarity NPC122926
0.5873 Remote Similarity NPC113012
0.5872 Remote Similarity NPC209232
0.587 Remote Similarity NPC213969
0.587 Remote Similarity NPC165726
0.5868 Remote Similarity NPC316250
0.5865 Remote Similarity NPC316185
0.5862 Remote Similarity NPC32944
0.5862 Remote Similarity NPC470520
0.5862 Remote Similarity NPC193396
0.5856 Remote Similarity NPC169575
0.5856 Remote Similarity NPC474809
0.5856 Remote Similarity NPC40746
0.5856 Remote Similarity NPC44261
0.5852 Remote Similarity NPC309525
0.5849 Remote Similarity NPC315552
0.5849 Remote Similarity NPC34672
0.5847 Remote Similarity NPC304886
0.5846 Remote Similarity NPC471145
0.5846 Remote Similarity NPC476190
0.5841 Remote Similarity NPC291712
0.5841 Remote Similarity NPC305475
0.5841 Remote Similarity NPC47220
0.5841 Remote Similarity NPC475461
0.5841 Remote Similarity NPC186332
0.584 Remote Similarity NPC220155
0.5833 Remote Similarity NPC326753
0.5833 Remote Similarity NPC270813
0.5827 Remote Similarity NPC58281
0.5826 Remote Similarity NPC225283
0.5826 Remote Similarity NPC115179
0.5826 Remote Similarity NPC106040
0.5826 Remote Similarity NPC133450
0.5818 Remote Similarity NPC184208
0.5818 Remote Similarity NPC8538
0.5818 Remote Similarity NPC325031
0.5812 Remote Similarity NPC162615
0.5812 Remote Similarity NPC109406
0.5812 Remote Similarity NPC159092
0.5812 Remote Similarity NPC248193
0.5812 Remote Similarity NPC152778
0.5812 Remote Similarity NPC205034
0.5812 Remote Similarity NPC476049
0.5809 Remote Similarity NPC262845
0.5809 Remote Similarity NPC68293
0.5806 Remote Similarity NPC266570
0.5804 Remote Similarity NPC96259
0.5804 Remote Similarity NPC196487
0.5804 Remote Similarity NPC141193
0.5804 Remote Similarity NPC14575
0.5804 Remote Similarity NPC475975
0.5798 Remote Similarity NPC135576
0.5798 Remote Similarity NPC93271
0.5794 Remote Similarity NPC137911
0.5794 Remote Similarity NPC271070
0.5794 Remote Similarity NPC228477
0.5789 Remote Similarity NPC313658
0.5789 Remote Similarity NPC241054
0.5789 Remote Similarity NPC23622
0.5789 Remote Similarity NPC316138
0.5789 Remote Similarity NPC199382
0.5785 Remote Similarity NPC227865
0.5785 Remote Similarity NPC290802
0.578 Remote Similarity NPC291260
0.578 Remote Similarity NPC63649
0.578 Remote Similarity NPC264227
0.578 Remote Similarity NPC472965
0.5776 Remote Similarity NPC182136
0.5776 Remote Similarity NPC158388
0.5776 Remote Similarity NPC475855
0.5776 Remote Similarity NPC474098
0.5776 Remote Similarity NPC475995
0.5776 Remote Similarity NPC47230
0.5776 Remote Similarity NPC478003
0.5776 Remote Similarity NPC17143
0.5776 Remote Similarity NPC177668
0.5776 Remote Similarity NPC53240
0.5776 Remote Similarity NPC473448
0.5776 Remote Similarity NPC129419

  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 NPC470072 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
0.6031 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5985 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5985 Remote Similarity NPD7623 Phase 3
0.5954 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5827 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5806 Remote Similarity NPD7333 Discontinued
0.5755 Remote Similarity NPD7260 Phase 2
0.5735 Remote Similarity NPD8273 Phase 1
0.5714 Remote Similarity NPD6845 Suspended
0.5702 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5693 Remote Similarity NPD7746 Phase 1
0.5693 Remote Similarity NPD7747 Phase 1
0.5682 Remote Similarity NPD7641 Discontinued
0.5678 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5641 Remote Similarity NPD7838 Discovery
0.563 Remote Similarity NPD5282 Discontinued
0.5606 Remote Similarity NPD7500 Approved
0.5606 Remote Similarity NPD7505 Discontinued

  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