Structure

Physi-Chem Properties

Molecular Weight:  409.21
Volume:  408.085
LogP:  1.095
LogD:  0.524
LogS:  -2.307
# Rotatable Bonds:  11
TPSA:  136.46
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.229
Synthetic Accessibility Score:  5.471
Fsp3:  0.762
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.907
MDCK Permeability:  3.595157613744959e-05
Pgp-inhibitor:  0.435
Pgp-substrate:  0.979
Human Intestinal Absorption (HIA):  0.773
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.314
Plasma Protein Binding (PPB):  46.63639831542969%
Volume Distribution (VD):  0.396
Pgp-substrate:  48.607704162597656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.201
CYP2C19-inhibitor:  0.026
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.542
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.108
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.052

ADMET: Excretion

Clearance (CL):  5.898
Half-life (T1/2):  0.741

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.074
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.267
Maximum Recommended Daily Dose:  0.204
Skin Sensitization:  0.053
Carcinogencity:  0.448
Eye Corrosion:  0.005
Eye Irritation:  0.021
Respiratory Toxicity:  0.803

Download Data

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

  Natural Product: NPC164476

Natural Product ID:  NPC164476
Common Name*:   Isariotin C
IUPAC Name:   n.a.
Synonyms:   Isariotin C
Standard InCHIKey:  BDPGWFYYYPWIAE-YPPQQAOGSA-N
Standard InCHI:  InChI=1S/C21H31NO7/c1-2-3-5-8-12(23)9-6-4-7-10-14(24)22-13-11-21(28)19(27)15(16(13)25)17(26)18-20(21)29-18/h7,10,13,15-18,20,25-26,28H,2-6,8-9,11H2,1H3,(H,22,24)/b10-7+/t13-,15-,16-,17-,18-,20-,21+/m0/s1
SMILES:  CCCCCC(=O)CCC/C=C/C(=N[C@H]1C[C@]2(C(=O)[C@@H]([C@H]1O)[C@@H]([C@H]1[C@@H]2O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL253125
PubChem CID:   44445762
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO32790 isaria tenuipes bcc 7831 Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[17822299]

☑ 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
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 488000.0 nM PMID[512747]

☑ 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 NPC164476 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
1.0 High Similarity NPC471471
0.9832 High Similarity NPC121601
0.8676 High Similarity NPC475837
0.8195 Intermediate Similarity NPC472430
0.7985 Intermediate Similarity NPC472428
0.7801 Intermediate Similarity NPC77481
0.7801 Intermediate Similarity NPC233770
0.7634 Intermediate Similarity NPC280498
0.7462 Intermediate Similarity NPC323532
0.7122 Intermediate Similarity NPC96425
0.7023 Intermediate Similarity NPC80650
0.6917 Remote Similarity NPC147707
0.6842 Remote Similarity NPC179626
0.6835 Remote Similarity NPC204556
0.6822 Remote Similarity NPC70235
0.6818 Remote Similarity NPC477266
0.6812 Remote Similarity NPC469494
0.6806 Remote Similarity NPC145899
0.6786 Remote Similarity NPC477793
0.6786 Remote Similarity NPC329919
0.6783 Remote Similarity NPC76999
0.6769 Remote Similarity NPC474725
0.6763 Remote Similarity NPC225049
0.6741 Remote Similarity NPC251310
0.6736 Remote Similarity NPC75318
0.6715 Remote Similarity NPC469515
0.6712 Remote Similarity NPC200788
0.6712 Remote Similarity NPC243680
0.6711 Remote Similarity NPC298005
0.6711 Remote Similarity NPC36463
0.6691 Remote Similarity NPC204639
0.6667 Remote Similarity NPC176513
0.6667 Remote Similarity NPC27999
0.6667 Remote Similarity NPC470775
0.6667 Remote Similarity NPC298067
0.6667 Remote Similarity NPC477116
0.6667 Remote Similarity NPC214821
0.6645 Remote Similarity NPC113620
0.6645 Remote Similarity NPC475599
0.6645 Remote Similarity NPC100612
0.6645 Remote Similarity NPC174336
0.6645 Remote Similarity NPC187497
0.6643 Remote Similarity NPC475472
0.6641 Remote Similarity NPC87335
0.6641 Remote Similarity NPC215988
0.664 Remote Similarity NPC236176
0.6622 Remote Similarity NPC172365
0.6622 Remote Similarity NPC82931
0.6622 Remote Similarity NPC210729
0.6615 Remote Similarity NPC475800
0.66 Remote Similarity NPC475892
0.6597 Remote Similarity NPC73829
0.6597 Remote Similarity NPC119794
0.6581 Remote Similarity NPC265699
0.6581 Remote Similarity NPC475527
0.6579 Remote Similarity NPC244380
0.6579 Remote Similarity NPC61717
0.6571 Remote Similarity NPC473709
0.6571 Remote Similarity NPC473919
0.6565 Remote Similarity NPC208461
0.6565 Remote Similarity NPC289702
0.6549 Remote Similarity NPC477352
0.6541 Remote Similarity NPC476023
0.6533 Remote Similarity NPC475584
0.6533 Remote Similarity NPC475394
0.6533 Remote Similarity NPC475152
0.6528 Remote Similarity NPC139585
0.6519 Remote Similarity NPC117712
0.6507 Remote Similarity NPC99864
0.6507 Remote Similarity NPC280941
0.6507 Remote Similarity NPC235772
0.65 Remote Similarity NPC262026
0.65 Remote Similarity NPC473802
0.65 Remote Similarity NPC16709
0.6496 Remote Similarity NPC470776
0.649 Remote Similarity NPC141669
0.649 Remote Similarity NPC160222
0.649 Remote Similarity NPC193753
0.6486 Remote Similarity NPC476558
0.6483 Remote Similarity NPC314361
0.648 Remote Similarity NPC272617
0.6479 Remote Similarity NPC471940
0.6475 Remote Similarity NPC477046
0.6475 Remote Similarity NPC102822
0.6471 Remote Similarity NPC30196
0.6463 Remote Similarity NPC243902
0.6454 Remote Similarity NPC314512
0.6454 Remote Similarity NPC314451
0.6454 Remote Similarity NPC313333
0.6454 Remote Similarity NPC313342
0.6444 Remote Similarity NPC208998
0.6444 Remote Similarity NPC7921
0.6444 Remote Similarity NPC317210
0.6439 Remote Similarity NPC475150
0.6438 Remote Similarity NPC78189
0.6438 Remote Similarity NPC120420
0.6434 Remote Similarity NPC476091
0.6434 Remote Similarity NPC39996
0.6434 Remote Similarity NPC476078
0.6429 Remote Similarity NPC279722
0.6423 Remote Similarity NPC97908
0.6423 Remote Similarity NPC6531
0.6423 Remote Similarity NPC470854
0.6423 Remote Similarity NPC469684
0.6423 Remote Similarity NPC287343
0.6423 Remote Similarity NPC122033
0.6423 Remote Similarity NPC474654
0.6418 Remote Similarity NPC474229
0.6418 Remote Similarity NPC146945
0.6418 Remote Similarity NPC171888
0.6418 Remote Similarity NPC29501
0.6414 Remote Similarity NPC189393
0.6414 Remote Similarity NPC316401
0.6414 Remote Similarity NPC90814
0.6408 Remote Similarity NPC293112
0.6408 Remote Similarity NPC471939
0.6403 Remote Similarity NPC112038
0.6403 Remote Similarity NPC475003
0.6397 Remote Similarity NPC476814
0.6397 Remote Similarity NPC476813
0.6391 Remote Similarity NPC133729
0.6391 Remote Similarity NPC141350
0.6389 Remote Similarity NPC162495
0.6383 Remote Similarity NPC318445
0.6383 Remote Similarity NPC316133
0.6377 Remote Similarity NPC120599
0.6377 Remote Similarity NPC240509
0.6377 Remote Similarity NPC200412
0.6377 Remote Similarity NPC156336
0.637 Remote Similarity NPC469865
0.637 Remote Similarity NPC472002
0.6364 Remote Similarity NPC473253
0.6364 Remote Similarity NPC474716
0.6357 Remote Similarity NPC23963
0.6357 Remote Similarity NPC472401
0.635 Remote Similarity NPC474734
0.635 Remote Similarity NPC207217
0.6345 Remote Similarity NPC475606
0.6345 Remote Similarity NPC475314
0.6345 Remote Similarity NPC475389
0.6345 Remote Similarity NPC477189
0.6345 Remote Similarity NPC473838
0.6345 Remote Similarity NPC251564
0.6338 Remote Similarity NPC81736
0.6338 Remote Similarity NPC476729
0.6338 Remote Similarity NPC172154
0.6336 Remote Similarity NPC74035
0.6336 Remote Similarity NPC160843
0.6333 Remote Similarity NPC265908
0.6333 Remote Similarity NPC180770
0.6333 Remote Similarity NPC302276
0.6331 Remote Similarity NPC470186
0.6331 Remote Similarity NPC268958
0.6331 Remote Similarity NPC469488
0.6329 Remote Similarity NPC4108
0.6328 Remote Similarity NPC306908
0.6324 Remote Similarity NPC198539
0.6316 Remote Similarity NPC102843
0.6312 Remote Similarity NPC19464
0.6312 Remote Similarity NPC312833
0.6309 Remote Similarity NPC230889
0.6308 Remote Similarity NPC128501
0.6304 Remote Similarity NPC156252
0.6304 Remote Similarity NPC476712
0.6304 Remote Similarity NPC58662
0.6304 Remote Similarity NPC296822
0.6304 Remote Similarity NPC476713
0.6301 Remote Similarity NPC475139
0.6301 Remote Similarity NPC180902
0.6301 Remote Similarity NPC474508
0.6301 Remote Similarity NPC473485
0.6296 Remote Similarity NPC317107
0.6296 Remote Similarity NPC157476
0.6294 Remote Similarity NPC217901
0.6288 Remote Similarity NPC166607
0.6288 Remote Similarity NPC472615
0.6276 Remote Similarity NPC470880
0.6268 Remote Similarity NPC67251
0.6268 Remote Similarity NPC91693
0.6268 Remote Similarity NPC105926
0.6268 Remote Similarity NPC265557
0.6268 Remote Similarity NPC11895
0.6268 Remote Similarity NPC469789
0.6268 Remote Similarity NPC18945
0.6268 Remote Similarity NPC472399
0.626 Remote Similarity NPC118902
0.626 Remote Similarity NPC469980
0.626 Remote Similarity NPC104161
0.6259 Remote Similarity NPC478205
0.6259 Remote Similarity NPC478206
0.6259 Remote Similarity NPC17772
0.6259 Remote Similarity NPC204552
0.6259 Remote Similarity NPC284707
0.6259 Remote Similarity NPC188667
0.6259 Remote Similarity NPC9714
0.6259 Remote Similarity NPC108581
0.625 Remote Similarity NPC470882
0.625 Remote Similarity NPC168849
0.625 Remote Similarity NPC261750
0.625 Remote Similarity NPC475273

  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 NPC164476 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
0.6838 Remote Similarity NPD6921 Approved
0.6591 Remote Similarity NPD6421 Discontinued
0.6575 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6565 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6507 Remote Similarity NPD8415 Approved
0.6486 Remote Similarity NPD6333 Approved
0.6486 Remote Similarity NPD6334 Approved
0.6454 Remote Similarity NPD8341 Approved
0.6454 Remote Similarity NPD8299 Approved
0.6454 Remote Similarity NPD8340 Approved
0.6454 Remote Similarity NPD8342 Approved
0.6383 Remote Similarity NPD7642 Approved
0.6294 Remote Similarity NPD8451 Approved
0.6288 Remote Similarity NPD5357 Phase 1
0.625 Remote Similarity NPD8448 Approved
0.6233 Remote Similarity NPD8391 Approved
0.6233 Remote Similarity NPD8390 Approved
0.6233 Remote Similarity NPD8392 Approved
0.6154 Remote Similarity NPD7829 Approved
0.6154 Remote Similarity NPD7830 Approved
0.6138 Remote Similarity NPD8074 Phase 3
0.6069 Remote Similarity NPD8273 Phase 1
0.6058 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6014 Remote Similarity NPD8444 Approved
0.6014 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6014 Remote Similarity NPD6914 Discontinued
0.5972 Remote Similarity NPD8080 Discontinued
0.5944 Remote Similarity NPD6319 Approved
0.5915 Remote Similarity NPD7641 Discontinued
0.5912 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5912 Remote Similarity NPD7274 Clinical (unspecified phase)
0.5906 Remote Similarity NPD3168 Discontinued
0.5899 Remote Similarity NPD5036 Approved
0.5889 Remote Similarity NPD8361 Approved
0.5889 Remote Similarity NPD8360 Approved
0.5887 Remote Similarity NPD619 Phase 3
0.587 Remote Similarity NPD8485 Approved
0.587 Remote Similarity NPD4634 Approved
0.587 Remote Similarity NPD6420 Discontinued
0.5866 Remote Similarity NPD5038 Approved
0.5866 Remote Similarity NPD5037 Approved
0.5865 Remote Similarity NPD5344 Discontinued
0.5859 Remote Similarity NPD7983 Approved
0.5852 Remote Similarity NPD8368 Discontinued
0.5845 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5845 Remote Similarity NPD7500 Approved
0.5845 Remote Similarity NPD7115 Discovery
0.5843 Remote Similarity NPD8407 Phase 2
0.5833 Remote Similarity NPD8384 Approved
0.5833 Remote Similarity NPD6054 Approved
0.5828 Remote Similarity NPD8338 Approved
0.5822 Remote Similarity NPD7604 Phase 2
0.5821 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5802 Remote Similarity NPD4228 Discovery
0.5801 Remote Similarity NPD8435 Approved
0.5793 Remote Similarity NPD6015 Approved
0.5793 Remote Similarity NPD6016 Approved
0.5787 Remote Similarity NPD5035 Approved
0.5775 Remote Similarity NPD8486 Clinical (unspecified phase)
0.5766 Remote Similarity NPD8307 Discontinued
0.5763 Remote Similarity NPD5030 Phase 2
0.5755 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5753 Remote Similarity NPD5988 Approved
0.5753 Remote Similarity NPD6370 Approved
0.575 Remote Similarity NPD2575 Approved
0.5745 Remote Similarity NPD4632 Approved
0.573 Remote Similarity NPD5034 Approved
0.573 Remote Similarity NPD36 Approved
0.573 Remote Similarity NPD5028 Approved
0.573 Remote Similarity NPD5026 Approved
0.573 Remote Similarity NPD4954 Approved
0.573 Remote Similarity NPD4955 Approved
0.5724 Remote Similarity NPD6059 Approved
0.5714 Remote Similarity NPD8328 Phase 3
0.5714 Remote Similarity NPD2204 Approved
0.5714 Remote Similarity NPD1719 Phase 1
0.5704 Remote Similarity NPD8086 Approved
0.5704 Remote Similarity NPD8085 Approved
0.5704 Remote Similarity NPD8082 Approved
0.5704 Remote Similarity NPD5211 Phase 2
0.5704 Remote Similarity NPD8139 Approved
0.5704 Remote Similarity NPD8084 Approved
0.5704 Remote Similarity NPD8083 Approved
0.5704 Remote Similarity NPD8138 Approved
0.5692 Remote Similarity NPD5779 Approved
0.5692 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5692 Remote Similarity NPD5778 Approved
0.5685 Remote Similarity NPD6909 Approved
0.5685 Remote Similarity NPD6908 Approved
0.5683 Remote Similarity NPD6413 Approved
0.5676 Remote Similarity NPD7492 Approved
0.5662 Remote Similarity NPD8276 Approved
0.5662 Remote Similarity NPD8275 Approved
0.5652 Remote Similarity NPD8140 Approved
0.5643 Remote Similarity NPD8087 Discontinued
0.5642 Remote Similarity NPD5032 Approved
0.5638 Remote Similarity NPD6616 Approved
0.562 Remote Similarity NPD5141 Approved
0.562 Remote Similarity NPD8081 Approved
0.5604 Remote Similarity NPD8424 Clinical (unspecified phase)
0.56 Remote Similarity NPD7078 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