Structure

Physi-Chem Properties

Molecular Weight:  844.6
Volume:  878.59
LogP:  5.873
LogD:  4.198
LogS:  -4.859
# Rotatable Bonds:  24
TPSA:  194.43
# H-Bond Aceptor:  14
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.047
Synthetic Accessibility Score:  6.78
Fsp3:  0.891
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.587
MDCK Permeability:  3.147369352518581e-05
Pgp-inhibitor:  0.559
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.869
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  94.9056625366211%
Volume Distribution (VD):  0.501
Pgp-substrate:  3.8032374382019043%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.096
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.235
CYP2C9-inhibitor:  0.082
CYP2C9-substrate:  0.076
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.2
CYP3A4-inhibitor:  0.915
CYP3A4-substrate:  0.847

ADMET: Excretion

Clearance (CL):  7.106
Half-life (T1/2):  0.019

ADMET: Toxicity

hERG Blockers:  0.684
Human Hepatotoxicity (H-HT):  0.982
Drug-inuced Liver Injury (DILI):  0.371
AMES Toxicity:  0.065
Rat Oral Acute Toxicity:  0.203
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.953
Carcinogencity:  0.086
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.932

Download Data

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

  Natural Product: NPC319334

Natural Product ID:  NPC319334
Common Name*:   Monanchocidin E
IUPAC Name:   n.a.
Synonyms:   Monanchocidin E
Standard InCHIKey:  CGSPIRSDEUJHCF-OBPUHCEQSA-N
Standard InCHI:  InChI=1S/C46H80N6O8.C2HF3O2/c1-4-6-20-36-25-27-44(59-36)32-34-23-24-37-39(45(26-17-19-33(3)58-45)50-43(49-44)52(34)37)41(54)57-35(5-2)21-15-13-11-9-7-8-10-12-14-16-22-38-40(53)51(31-18-29-47)42(55)46(56,60-38)28-30-48;3-2(4,5)1(6)7/h6,20,33-39,42,55-56H,4-5,7-19,21-32,47-48H2,1-3H3,(H,49,50);(H,6,7)/b20-6+;/t33-,34+,35?,36+,37-,38-,39-,42-,44+,45-,46+;/m0./s1
SMILES:  OC(=O)C(F)(F)F.NCCCN1C(=O)[C@H](CCCCCCCCCCCCC(OC(=O)[C@@H]2[C@@H]3CC[C@H]4N3C(=N[C@]3(C4)CC[C@H](O3)/C=C/CC)N[C@@]32CCC[C@@H](O3)C)CC)O[C@]([C@@H]1O)(O)CCN
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1822165
PubChem CID:   54671473
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000107] Oxazinanes
        • [CHEMONTID:0000392] Morpholines

*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
NPO7622 Monanchora pulchra Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[21848268]
NPO7622 Monanchora pulchra Species Crambeidae Eukaryota n.a. Urup Island (4557,9 N; 15044,9 E; depth 66 m) 2008-AUG PMID[21848268]
NPO7622 Monanchora pulchra Species Crambeidae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 650.0 nM PMID[480950]

☑ 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 NPC319334 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 NPC327517
1.0 High Similarity NPC322372
0.9726 High Similarity NPC317377
0.9726 High Similarity NPC321485
0.8456 Intermediate Similarity NPC142761
0.8224 Intermediate Similarity NPC477519
0.8082 Intermediate Similarity NPC261730
0.7671 Intermediate Similarity NPC477518
0.6899 Remote Similarity NPC99864
0.6835 Remote Similarity NPC120420
0.6795 Remote Similarity NPC324722
0.6795 Remote Similarity NPC198644
0.6795 Remote Similarity NPC311244
0.6784 Remote Similarity NPC316244
0.6687 Remote Similarity NPC471256
0.6603 Remote Similarity NPC471263
0.6599 Remote Similarity NPC472737
0.6599 Remote Similarity NPC469389
0.6599 Remote Similarity NPC469388
0.6516 Remote Similarity NPC471262
0.6398 Remote Similarity NPC120335
0.6369 Remote Similarity NPC471255
0.6346 Remote Similarity NPC315188
0.6325 Remote Similarity NPC473955
0.6323 Remote Similarity NPC471261
0.6289 Remote Similarity NPC309525
0.6287 Remote Similarity NPC315210
0.6287 Remote Similarity NPC315848
0.6282 Remote Similarity NPC314482
0.6242 Remote Similarity NPC245534
0.6138 Remote Similarity NPC472736
0.6115 Remote Similarity NPC313802
0.6115 Remote Similarity NPC314268
0.6115 Remote Similarity NPC67917
0.6115 Remote Similarity NPC477515
0.608 Remote Similarity NPC162104
0.6078 Remote Similarity NPC476875
0.6067 Remote Similarity NPC477398
0.6067 Remote Similarity NPC471259
0.6056 Remote Similarity NPC1390
0.6056 Remote Similarity NPC62104
0.6049 Remote Similarity NPC314282
0.6048 Remote Similarity NPC477400
0.6048 Remote Similarity NPC82129
0.6039 Remote Similarity NPC478024
0.6024 Remote Similarity NPC475987
0.6024 Remote Similarity NPC318142
0.6024 Remote Similarity NPC313348
0.6023 Remote Similarity NPC475278
0.6023 Remote Similarity NPC247776
0.6023 Remote Similarity NPC309450
0.6023 Remote Similarity NPC304299
0.6023 Remote Similarity NPC475266
0.6 Remote Similarity NPC197743
0.6 Remote Similarity NPC297145
0.5987 Remote Similarity NPC171734
0.5976 Remote Similarity NPC469387
0.5973 Remote Similarity NPC471258
0.5965 Remote Similarity NPC477399
0.5965 Remote Similarity NPC477401
0.5963 Remote Similarity NPC315783
0.595 Remote Similarity NPC477550
0.595 Remote Similarity NPC477552
0.5949 Remote Similarity NPC235625
0.5938 Remote Similarity NPC23963
0.5926 Remote Similarity NPC313342
0.5926 Remote Similarity NPC314512
0.5926 Remote Similarity NPC470653
0.5926 Remote Similarity NPC314451
0.5926 Remote Similarity NPC470654
0.5926 Remote Similarity NPC313333
0.5926 Remote Similarity NPC470650
0.5924 Remote Similarity NPC210377
0.5924 Remote Similarity NPC222481
0.5924 Remote Similarity NPC5719
0.5924 Remote Similarity NPC217804
0.5924 Remote Similarity NPC470621
0.5924 Remote Similarity NPC22883
0.5922 Remote Similarity NPC475342
0.5921 Remote Similarity NPC271562
0.5906 Remote Similarity NPC188785
0.5904 Remote Similarity NPC316401
0.5902 Remote Similarity NPC73655
0.5901 Remote Similarity NPC273185
0.5899 Remote Similarity NPC265699
0.5899 Remote Similarity NPC475527
0.5891 Remote Similarity NPC477551
0.589 Remote Similarity NPC119225
0.589 Remote Similarity NPC25033
0.589 Remote Similarity NPC476261
0.589 Remote Similarity NPC471635
0.589 Remote Similarity NPC470382
0.5871 Remote Similarity NPC147238
0.5866 Remote Similarity NPC174336
0.5866 Remote Similarity NPC187497
0.5866 Remote Similarity NPC100612
0.5866 Remote Similarity NPC113620
0.5866 Remote Similarity NPC475599
0.586 Remote Similarity NPC472536
0.586 Remote Similarity NPC103391
0.586 Remote Similarity NPC63040
0.586 Remote Similarity NPC259586
0.5848 Remote Similarity NPC25025
0.5838 Remote Similarity NPC71866
0.5828 Remote Similarity NPC476877
0.5828 Remote Similarity NPC471260
0.5819 Remote Similarity NPC471821
0.5819 Remote Similarity NPC471820
0.5818 Remote Similarity NPC477793
0.5818 Remote Similarity NPC329919
0.5816 Remote Similarity NPC94862
0.5814 Remote Similarity NPC82931
0.5814 Remote Similarity NPC210729
0.5814 Remote Similarity NPC172365
0.581 Remote Similarity NPC315809
0.581 Remote Similarity NPC314050
0.5806 Remote Similarity NPC15068
0.5793 Remote Similarity NPC474371
0.5789 Remote Similarity NPC477000
0.5789 Remote Similarity NPC64168
0.5789 Remote Similarity NPC477001
0.5789 Remote Similarity NPC477462
0.5783 Remote Similarity NPC316205
0.5783 Remote Similarity NPC315387
0.5779 Remote Similarity NPC475150
0.5776 Remote Similarity NPC470652
0.5776 Remote Similarity NPC11379
0.5771 Remote Similarity NPC276822
0.5767 Remote Similarity NPC325750
0.5765 Remote Similarity NPC297058
0.5759 Remote Similarity NPC469423
0.5758 Remote Similarity NPC61332
0.5758 Remote Similarity NPC96010
0.5758 Remote Similarity NPC317654
0.5758 Remote Similarity NPC240130
0.5758 Remote Similarity NPC473249
0.5752 Remote Similarity NPC10897
0.5752 Remote Similarity NPC325900
0.5752 Remote Similarity NPC476876
0.5749 Remote Similarity NPC313657
0.5747 Remote Similarity NPC475584
0.5747 Remote Similarity NPC475394
0.5747 Remote Similarity NPC475152
0.5741 Remote Similarity NPC477238
0.5741 Remote Similarity NPC160688
0.5732 Remote Similarity NPC314550
0.5732 Remote Similarity NPC469865
0.5724 Remote Similarity NPC279833
0.5724 Remote Similarity NPC6271
0.5724 Remote Similarity NPC80439
0.5724 Remote Similarity NPC173690
0.5723 Remote Similarity NPC471086
0.5714 Remote Similarity NPC475892
0.5706 Remote Similarity NPC75318
0.5706 Remote Similarity NPC473703
0.5706 Remote Similarity NPC239252
0.5698 Remote Similarity NPC2501
0.5698 Remote Similarity NPC200788
0.5698 Remote Similarity NPC243680
0.5698 Remote Similarity NPC287885
0.5695 Remote Similarity NPC144714
0.5695 Remote Similarity NPC100810
0.5694 Remote Similarity NPC478007
0.5694 Remote Similarity NPC478005
0.5691 Remote Similarity NPC473341
0.5691 Remote Similarity NPC122590
0.5689 Remote Similarity NPC313962
0.5687 Remote Similarity NPC6531
0.5686 Remote Similarity NPC62845
0.5686 Remote Similarity NPC166242
0.5686 Remote Similarity NPC189854
0.5686 Remote Similarity NPC92874
0.5686 Remote Similarity NPC322449
0.5682 Remote Similarity NPC476978
0.5677 Remote Similarity NPC207820
0.5673 Remote Similarity NPC145899
0.5672 Remote Similarity NPC302715
0.5671 Remote Similarity NPC316133
0.5671 Remote Similarity NPC314629
0.5671 Remote Similarity NPC318445
0.5671 Remote Similarity NPC473477
0.5669 Remote Similarity NPC58281
0.5669 Remote Similarity NPC30911
0.5669 Remote Similarity NPC316984
0.5663 Remote Similarity NPC262880
0.5663 Remote Similarity NPC247902
0.566 Remote Similarity NPC474984
0.5658 Remote Similarity NPC471097
0.5658 Remote Similarity NPC475149
0.5652 Remote Similarity NPC106791
0.5652 Remote Similarity NPC324850
0.5652 Remote Similarity NPC174463
0.5652 Remote Similarity NPC201889
0.565 Remote Similarity NPC209509
0.565 Remote Similarity NPC5620
0.5649 Remote Similarity NPC271269
0.5647 Remote Similarity NPC76999
0.5644 Remote Similarity NPC314293
0.5642 Remote Similarity NPC240848
0.5642 Remote Similarity NPC478008

  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 NPC319334 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
0.6899 Remote Similarity NPD8415 Approved
0.675 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6725 Remote Similarity NPD8414 Discontinued
0.6497 Remote Similarity NPD4816 Clinical (unspecified phase)
0.6446 Remote Similarity NPD8384 Approved
0.6387 Remote Similarity NPD8345 Approved
0.6387 Remote Similarity NPD8346 Approved
0.6387 Remote Similarity NPD8347 Approved
0.6335 Remote Similarity NPD8390 Approved
0.6335 Remote Similarity NPD8391 Approved
0.6335 Remote Similarity NPD8392 Approved
0.6124 Remote Similarity NPD8417 Discontinued
0.609 Remote Similarity NPD6935 Phase 3
0.609 Remote Similarity NPD6936 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8451 Approved
0.6087 Remote Similarity NPD8273 Phase 1
0.6049 Remote Similarity NPD8448 Approved
0.5963 Remote Similarity NPD7830 Approved
0.5963 Remote Similarity NPD7829 Approved
0.5949 Remote Similarity NPD7756 Clinical (unspecified phase)
0.5926 Remote Similarity NPD8342 Approved
0.5926 Remote Similarity NPD8299 Approved
0.5926 Remote Similarity NPD8340 Approved
0.5926 Remote Similarity NPD8341 Approved
0.5924 Remote Similarity NPD869 Approved
0.5849 Remote Similarity NPD6918 Phase 1
0.5839 Remote Similarity NPD8444 Approved
0.5839 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5824 Remote Similarity NPD7749 Clinical (unspecified phase)
0.5806 Remote Similarity NPD8087 Discontinued
0.5758 Remote Similarity NPD7746 Phase 1
0.5758 Remote Similarity NPD7747 Phase 1
0.5741 Remote Similarity NPD8268 Approved
0.5741 Remote Similarity NPD8266 Approved
0.5741 Remote Similarity NPD8269 Approved
0.5741 Remote Similarity NPD8267 Approved
0.5722 Remote Similarity NPD7613 Discontinued
0.5706 Remote Similarity NPD8080 Discontinued
0.5687 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5679 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5671 Remote Similarity NPD7642 Approved
0.5669 Remote Similarity NPD2204 Approved
0.5613 Remote Similarity NPD8307 Discontinued
0.5613 Remote Similarity NPD8140 Approved
0.561 Remote Similarity NPD7623 Phase 3
0.561 Remote Similarity NPD4828 Approved
0.561 Remote Similarity NPD4827 Approved
0.561 Remote Similarity NPD4826 Approved
0.561 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5607 Remote Similarity NPD5767 Discontinued
0.5605 Remote Similarity NPD1804 Phase 2
0.5605 Remote Similarity NPD1805 Phase 2

  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