Structure

Physi-Chem Properties

Molecular Weight:  625.39
Volume:  649.755
LogP:  3.485
LogD:  1.86
LogS:  -3.46
# Rotatable Bonds:  6
TPSA:  139.83
# H-Bond Aceptor:  12
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.322
Synthetic Accessibility Score:  5.113
Fsp3:  0.812
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.174
MDCK Permeability:  4.862948480877094e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.044
Human Intestinal Absorption (HIA):  0.88
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.323

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.041
Plasma Protein Binding (PPB):  85.22411346435547%
Volume Distribution (VD):  1.231
Pgp-substrate:  5.993672847747803%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.053
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.915
CYP2C9-inhibitor:  0.051
CYP2C9-substrate:  0.066
CYP2D6-inhibitor:  0.058
CYP2D6-substrate:  0.087
CYP3A4-inhibitor:  0.383
CYP3A4-substrate:  0.91

ADMET: Excretion

Clearance (CL):  5.513
Half-life (T1/2):  0.059

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.986
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.007
Maximum Recommended Daily Dose:  0.013
Skin Sensitization:  0.023
Carcinogencity:  0.002
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.01

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

  Natural Product: NPC29598

Natural Product ID:  NPC29598
Common Name*:   Enniatin K1
IUPAC Name:   (3S,6R,9S,12R,15S,18R)-3-ethyl-4,10,16-trimethyl-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 K1
Standard InCHIKey:  WOLNKVVWOKWVJB-LZNKSJHBSA-N
Standard InCHI:  InChI=1S/C32H55N3O9/c1-15-21-30(39)42-25(19(8)9)28(37)34(13)23(17(4)5)32(41)44-26(20(10)11)29(38)35(14)22(16(2)3)31(40)43-24(18(6)7)27(36)33(21)12/h16-26H,15H2,1-14H3/t21-,22-,23-,24+,25+,26+/m0/s1
SMILES:  CC[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@H](C(C)C)C(=O)N1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505058
PubChem CID:   11006677
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]
NPO24089 Alcea rosea Species Malvaceae 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]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae 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]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae 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]
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]

☑ 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[501355]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana Activity = 100.0 ug ml-1 PMID[501355]

☑ 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 NPC29598 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 NPC212866
0.9841 High Similarity NPC10716
0.9403 High Similarity NPC263281
0.9403 High Similarity NPC178919
0.8873 High Similarity NPC477145
0.8873 High Similarity NPC473741
0.84 Intermediate Similarity NPC246005
0.7093 Intermediate Similarity NPC474576
0.7011 Intermediate Similarity NPC173763
0.7011 Intermediate Similarity NPC471098
0.7011 Intermediate Similarity NPC62263
0.6977 Remote Similarity NPC474593
0.6977 Remote Similarity NPC475801
0.6923 Remote Similarity NPC220234
0.6897 Remote Similarity NPC476019
0.6739 Remote Similarity NPC475440
0.6702 Remote Similarity NPC124554
0.6702 Remote Similarity NPC5864
0.6702 Remote Similarity NPC301148
0.6632 Remote Similarity NPC198344
0.6562 Remote Similarity NPC323720
0.6562 Remote Similarity NPC124549
0.6489 Remote Similarity NPC13175
0.6489 Remote Similarity NPC475791
0.6383 Remote Similarity NPC475758
0.6364 Remote Similarity NPC171734
0.6364 Remote Similarity NPC193280
0.6364 Remote Similarity NPC67009
0.6364 Remote Similarity NPC314273
0.6354 Remote Similarity NPC475149
0.6354 Remote Similarity NPC471097
0.6327 Remote Similarity NPC475637
0.6324 Remote Similarity NPC325180
0.6324 Remote Similarity NPC35816
0.6292 Remote Similarity NPC322966
0.6235 Remote Similarity NPC84128
0.6235 Remote Similarity NPC53858
0.6154 Remote Similarity NPC477538
0.6125 Remote Similarity NPC141325
0.6076 Remote Similarity NPC478256
0.6049 Remote Similarity NPC138435
0.5914 Remote Similarity NPC315237
0.5904 Remote Similarity NPC476324
0.5904 Remote Similarity NPC476130
0.5882 Remote Similarity NPC31756
0.5875 Remote Similarity NPC476291
0.5875 Remote Similarity NPC476285
0.5833 Remote Similarity NPC473597
0.5814 Remote Similarity NPC476243
0.5814 Remote Similarity NPC476156
0.5814 Remote Similarity NPC476117
0.5814 Remote Similarity NPC476137
0.5783 Remote Similarity NPC86064
0.5783 Remote Similarity NPC327272
0.5769 Remote Similarity NPC322319
0.5769 Remote Similarity NPC326651
0.5769 Remote Similarity NPC325117
0.5758 Remote Similarity NPC188785
0.5747 Remote Similarity NPC476302
0.5663 Remote Similarity NPC43219
0.5663 Remote Similarity NPC476248
0.5641 Remote Similarity NPC128559
0.5625 Remote Similarity NPC306696
0.5618 Remote Similarity NPC235078

  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 NPC29598 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
1.0 High Similarity NPD7840 Approved
0.6324 Remote Similarity NPD9660 Approved
0.6145 Remote Similarity NPD8143 Approved
0.6145 Remote Similarity NPD8144 Approved
0.6125 Remote Similarity NPD6704 Discontinued
0.6087 Remote Similarity NPD9202 Approved
0.6061 Remote Similarity NPD1458 Approved
0.6061 Remote Similarity NPD1459 Approved
0.6056 Remote Similarity NPD4281 Clinical (unspecified phase)
0.6056 Remote Similarity NPD9659 Approved
0.6032 Remote Similarity NPD9456 Approved
0.6032 Remote Similarity NPD9457 Approved
0.5942 Remote Similarity NPD2692 Approved
0.5942 Remote Similarity NPD9203 Approved
0.5942 Remote Similarity NPD2693 Approved
0.5875 Remote Similarity NPD2697 Approved
0.5875 Remote Similarity NPD2694 Approved
0.5875 Remote Similarity NPD2695 Approved
0.5875 Remote Similarity NPD2696 Approved
0.5867 Remote Similarity NPD3193 Approved
0.5867 Remote Similarity NPD3192 Approved
0.5778 Remote Similarity NPD7760 Phase 2
0.5778 Remote Similarity NPD7759 Phase 2
0.5773 Remote Similarity NPD3714 Approved
0.5773 Remote Similarity NPD3715 Approved
0.5773 Remote Similarity NPD3713 Approved
0.5694 Remote Similarity NPD4276 Approved
0.5694 Remote Similarity NPD4277 Approved
0.5679 Remote Similarity NPD2220 Clinical (unspecified phase)
0.5652 Remote Similarity NPD9138 Approved
0.5647 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5641 Remote Similarity NPD9648 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