Structure

Physi-Chem Properties

Molecular Weight:  743.08
Volume:  593.791
LogP:  -3.708
LogD:  -2.208
LogS:  -0.291
# Rotatable Bonds:  13
TPSA:  362.03
# H-Bond Aceptor:  24
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  27

MedChem Properties

QED Drug-Likeness Score:  0.066
Synthetic Accessibility Score:  6.481
Fsp3:  0.476
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:  -6.713
MDCK Permeability:  1.320317642239388e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.962
Human Intestinal Absorption (HIA):  0.896
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.645
Plasma Protein Binding (PPB):  11.782499313354492%
Volume Distribution (VD):  0.526
Pgp-substrate:  78.62529754638672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.065
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.023
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.04
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.455
Half-life (T1/2):  0.938

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.315
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.071
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.954
Skin Sensitization:  0.479
Carcinogencity:  0.367
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.818

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC10716

Natural Product ID:  NPC10716
Common Name*:   Enniatin J1
IUPAC Name:   (3S,6R,9S,12R,15S,18R)-3,4,10,16-tetramethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:   Enniatin J1
Standard InCHIKey:  IEUFDXNGDNWAKU-MAKNZWJESA-N
Standard InCHI:  InChI=1S/C31H53N3O9/c1-15(2)21-30(39)42-23(17(5)6)26(35)32(12)20(11)29(38)41-24(18(7)8)27(36)33(13)22(16(3)4)31(40)43-25(19(9)10)28(37)34(21)14/h15-25H,1-14H3/t20-,21-,22-,23+,24+,25+/m0/s1
SMILES:  CC([C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H](OC(=O)[C@@H](N(C(=O)[C@H](OC(=O)[C@@H](N(C1=O)C)C(C)C)C(C)C)C)C)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL455737
PubChem CID:   11814110
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO40136 Fusarium sp. F31 Strain Nectriaceae Eukaryota n.a. n.a. n.a. PMID[15165149]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae 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
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC > 100.0 ug.mL-1 PMID[511093]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana Activity > 100.0 ug ml-1 PMID[511093]

☑ 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 NPC10716 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
0.9841 High Similarity NPC29598
0.9841 High Similarity NPC212866
0.9254 High Similarity NPC178919
0.9254 High Similarity NPC263281
0.8732 High Similarity NPC477145
0.8732 High Similarity NPC473741
0.8267 Intermediate Similarity NPC246005
0.7176 Intermediate Similarity NPC474576
0.7093 Intermediate Similarity NPC62263
0.7093 Intermediate Similarity NPC471098
0.7093 Intermediate Similarity NPC173763
0.7059 Intermediate Similarity NPC474593
0.7059 Intermediate Similarity NPC475801
0.6977 Remote Similarity NPC476019
0.6813 Remote Similarity NPC220234
0.6813 Remote Similarity NPC475440
0.6596 Remote Similarity NPC301148
0.6596 Remote Similarity NPC124554
0.6596 Remote Similarity NPC5864
0.6559 Remote Similarity NPC475791
0.6559 Remote Similarity NPC13175
0.6526 Remote Similarity NPC198344
0.6458 Remote Similarity NPC323720
0.6458 Remote Similarity NPC124549
0.6452 Remote Similarity NPC475758
0.6421 Remote Similarity NPC471097
0.6421 Remote Similarity NPC475149
0.6418 Remote Similarity NPC35816
0.6418 Remote Similarity NPC325180
0.6392 Remote Similarity NPC475637
0.6364 Remote Similarity NPC322966
0.6263 Remote Similarity NPC171734
0.6263 Remote Similarity NPC67009
0.6234 Remote Similarity NPC314273
0.6234 Remote Similarity NPC193280
0.6154 Remote Similarity NPC478256
0.6118 Remote Similarity NPC84128
0.6118 Remote Similarity NPC53858
0.6044 Remote Similarity NPC477538
0.6 Remote Similarity NPC141325
0.5978 Remote Similarity NPC315237
0.5949 Remote Similarity NPC476285
0.5949 Remote Similarity NPC476291
0.5926 Remote Similarity NPC138435
0.5895 Remote Similarity NPC473597
0.5854 Remote Similarity NPC327272
0.5844 Remote Similarity NPC325117
0.5844 Remote Similarity NPC322319
0.5844 Remote Similarity NPC326651
0.5816 Remote Similarity NPC188785
0.5783 Remote Similarity NPC476324
0.5783 Remote Similarity NPC476130
0.5765 Remote Similarity NPC31756
0.5732 Remote Similarity NPC476248
0.5732 Remote Similarity NPC43219
0.5714 Remote Similarity NPC128559
0.5698 Remote Similarity NPC476117
0.5698 Remote Similarity NPC476243
0.5698 Remote Similarity NPC476137
0.5698 Remote Similarity NPC476156
0.5696 Remote Similarity NPC306696
0.5663 Remote Similarity NPC86064
0.5632 Remote Similarity NPC477523
0.5632 Remote Similarity NPC476302

  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 NPC10716 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
0.9841 High Similarity NPD7840 Approved
0.6418 Remote Similarity NPD9660 Approved
0.6203 Remote Similarity NPD6704 Discontinued
0.6176 Remote Similarity NPD9202 Approved
0.6154 Remote Similarity NPD1459 Approved
0.6154 Remote Similarity NPD1458 Approved
0.6143 Remote Similarity NPD4281 Clinical (unspecified phase)
0.6143 Remote Similarity NPD9659 Approved
0.6129 Remote Similarity NPD9457 Approved
0.6129 Remote Similarity NPD9456 Approved
0.6029 Remote Similarity NPD9203 Approved
0.6029 Remote Similarity NPD2693 Approved
0.6029 Remote Similarity NPD2692 Approved
0.6024 Remote Similarity NPD8143 Approved
0.6024 Remote Similarity NPD8144 Approved
0.5949 Remote Similarity NPD2696 Approved
0.5949 Remote Similarity NPD2697 Approved
0.5949 Remote Similarity NPD2694 Approved
0.5949 Remote Similarity NPD2695 Approved
0.5946 Remote Similarity NPD3192 Approved
0.5946 Remote Similarity NPD3193 Approved
0.5833 Remote Similarity NPD3714 Approved
0.5833 Remote Similarity NPD3713 Approved
0.5833 Remote Similarity NPD3715 Approved
0.5775 Remote Similarity NPD4277 Approved
0.5775 Remote Similarity NPD4276 Approved
0.575 Remote Similarity NPD2220 Clinical (unspecified phase)
0.5735 Remote Similarity NPD9138 Approved
0.5714 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9648 Approved
0.5667 Remote Similarity NPD7759 Phase 2
0.5667 Remote Similarity NPD7760 Phase 2
0.5625 Remote Similarity NPD3724 Clinical (unspecified phase)
0.56 Remote Similarity NPD902 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