Structure

Physi-Chem Properties

Molecular Weight:  311.25
Volume:  349.342
LogP:  4.192
LogD:  3.529
LogS:  -3.709
# Rotatable Bonds:  15
TPSA:  55.4
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.316
Synthetic Accessibility Score:  3.184
Fsp3:  0.778
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.641
MDCK Permeability:  2.9178476324887015e-05
Pgp-inhibitor:  0.843
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.024
20% Bioavailability (F20%):  0.908
30% Bioavailability (F30%):  0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.905
Plasma Protein Binding (PPB):  91.79818725585938%
Volume Distribution (VD):  1.29
Pgp-substrate:  12.05477523803711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.172
CYP1A2-substrate:  0.156
CYP2C19-inhibitor:  0.362
CYP2C19-substrate:  0.356
CYP2C9-inhibitor:  0.245
CYP2C9-substrate:  0.493
CYP2D6-inhibitor:  0.193
CYP2D6-substrate:  0.34
CYP3A4-inhibitor:  0.868
CYP3A4-substrate:  0.202

ADMET: Excretion

Clearance (CL):  2.755
Half-life (T1/2):  0.617

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.349
Drug-inuced Liver Injury (DILI):  0.095
AMES Toxicity:  0.134
Rat Oral Acute Toxicity:  0.027
Maximum Recommended Daily Dose:  0.035
Skin Sensitization:  0.795
Carcinogencity:  0.209
Eye Corrosion:  0.008
Eye Irritation:  0.502
Respiratory Toxicity:  0.217

Download Data

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

  Natural Product: NPC474812

Natural Product ID:  NPC474812
Common Name*:   Diacetyl Halaminol A
IUPAC Name:   [(2S,3R)-2-acetamidotetradec-13-en-3-yl] acetate
Synonyms:  
Standard InCHIKey:  HKCVQKQNBZLFNI-MAUKXSAKSA-N
Standard InCHI:  InChI=1S/C18H33NO3/c1-5-6-7-8-9-10-11-12-13-14-18(22-17(4)21)15(2)19-16(3)20/h5,15,18H,1,6-14H2,2-4H3,(H,19,20)/t15-,18+/m0/s1
SMILES:  C=CCCCCCCCCC[C@H]([C@@H](N=C(O)C)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL483809
PubChem CID:   10968962
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001093] Carboxylic acid derivatives
          • [CHEMONTID:0000475] Carboxylic acid amides
            • [CHEMONTID:0003922] Acetamides

*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
NPO32555 haliclona n. sp. Species Chalinidae Eukaryota n.a. n.a. n.a. PMID[11754615]

☑ 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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 7.0 mm PMID[496387]

☑ 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 NPC474812 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 NPC474833
0.7821 Intermediate Similarity NPC474312
0.7536 Intermediate Similarity NPC316674
0.7176 Intermediate Similarity NPC159369
0.7176 Intermediate Similarity NPC39290
0.7162 Intermediate Similarity NPC291196
0.7162 Intermediate Similarity NPC45060
0.7162 Intermediate Similarity NPC103712
0.7162 Intermediate Similarity NPC280065
0.7143 Intermediate Similarity NPC217095
0.7143 Intermediate Similarity NPC264417
0.7101 Intermediate Similarity NPC326524
0.7101 Intermediate Similarity NPC329003
0.7101 Intermediate Similarity NPC325550
0.7027 Intermediate Similarity NPC249713
0.7027 Intermediate Similarity NPC474299
0.7027 Intermediate Similarity NPC475808
0.7027 Intermediate Similarity NPC28348
0.7027 Intermediate Similarity NPC474298
0.7027 Intermediate Similarity NPC473985
0.697 Remote Similarity NPC270041
0.6957 Remote Similarity NPC325734
0.6957 Remote Similarity NPC321030
0.6883 Remote Similarity NPC43219
0.6812 Remote Similarity NPC168308
0.6812 Remote Similarity NPC302569
0.6795 Remote Similarity NPC86064
0.6795 Remote Similarity NPC288086
0.6795 Remote Similarity NPC470994
0.6757 Remote Similarity NPC113224
0.6709 Remote Similarity NPC3094
0.6703 Remote Similarity NPC175614
0.6629 Remote Similarity NPC475603
0.6629 Remote Similarity NPC61894
0.6618 Remote Similarity NPC471917
0.6562 Remote Similarity NPC74035
0.6538 Remote Similarity NPC474403
0.6528 Remote Similarity NPC477644
0.6522 Remote Similarity NPC242930
0.6515 Remote Similarity NPC319110
0.6515 Remote Similarity NPC329181
0.6495 Remote Similarity NPC475918
0.6494 Remote Similarity NPC478256
0.6463 Remote Similarity NPC469492
0.6438 Remote Similarity NPC328776
0.6438 Remote Similarity NPC47333
0.6438 Remote Similarity NPC320305
0.6395 Remote Similarity NPC477199
0.6386 Remote Similarity NPC469517
0.6364 Remote Similarity NPC207815
0.6351 Remote Similarity NPC477106
0.6341 Remote Similarity NPC325936
0.6333 Remote Similarity NPC139782
0.6333 Remote Similarity NPC74672
0.6333 Remote Similarity NPC43074
0.6333 Remote Similarity NPC209047
0.6333 Remote Similarity NPC242503
0.6329 Remote Similarity NPC320865
0.6329 Remote Similarity NPC477643
0.6329 Remote Similarity NPC477641
0.631 Remote Similarity NPC79367
0.6286 Remote Similarity NPC52264
0.6282 Remote Similarity NPC477642
0.6279 Remote Similarity NPC178758
0.6279 Remote Similarity NPC196102
0.6267 Remote Similarity NPC328089
0.6267 Remote Similarity NPC68343
0.6264 Remote Similarity NPC111567
0.6264 Remote Similarity NPC15851
0.6264 Remote Similarity NPC263545
0.6264 Remote Similarity NPC473950
0.6264 Remote Similarity NPC475125
0.6264 Remote Similarity NPC473604
0.6264 Remote Similarity NPC319473
0.6264 Remote Similarity NPC473581
0.6264 Remote Similarity NPC309898
0.6264 Remote Similarity NPC186840
0.6235 Remote Similarity NPC82799
0.6216 Remote Similarity NPC66460
0.6216 Remote Similarity NPC271282
0.6216 Remote Similarity NPC325929
0.6216 Remote Similarity NPC201939
0.6216 Remote Similarity NPC145627
0.62 Remote Similarity NPC171734
0.6176 Remote Similarity NPC29501
0.6146 Remote Similarity NPC233932
0.6143 Remote Similarity NPC137538
0.6133 Remote Similarity NPC29697
0.6133 Remote Similarity NPC182758
0.6129 Remote Similarity NPC282088
0.6129 Remote Similarity NPC158445
0.6129 Remote Similarity NPC256570
0.6129 Remote Similarity NPC54961
0.6129 Remote Similarity NPC192066
0.6129 Remote Similarity NPC157353
0.6129 Remote Similarity NPC3568
0.6129 Remote Similarity NPC17290
0.6129 Remote Similarity NPC156782
0.6122 Remote Similarity NPC469895
0.6105 Remote Similarity NPC4834
0.6092 Remote Similarity NPC155670
0.6092 Remote Similarity NPC145748
0.6092 Remote Similarity NPC95478
0.6087 Remote Similarity NPC182632
0.6087 Remote Similarity NPC282705
0.6082 Remote Similarity NPC474873
0.6081 Remote Similarity NPC243532
0.6061 Remote Similarity NPC319709
0.6061 Remote Similarity NPC289484
0.6061 Remote Similarity NPC119329
0.6056 Remote Similarity NPC223677
0.6056 Remote Similarity NPC128061
0.6056 Remote Similarity NPC200845
0.6056 Remote Similarity NPC28779
0.6056 Remote Similarity NPC10316
0.6049 Remote Similarity NPC305223
0.6042 Remote Similarity NPC475758
0.604 Remote Similarity NPC476034
0.604 Remote Similarity NPC474969
0.6027 Remote Similarity NPC469373
0.6026 Remote Similarity NPC271921
0.6026 Remote Similarity NPC475443
0.6026 Remote Similarity NPC148192
0.6026 Remote Similarity NPC22101
0.6026 Remote Similarity NPC330426
0.6026 Remote Similarity NPC473829
0.6026 Remote Similarity NPC127091
0.6026 Remote Similarity NPC104537
0.6023 Remote Similarity NPC227051
0.602 Remote Similarity NPC477198
0.6019 Remote Similarity NPC476875
0.6 Remote Similarity NPC183449
0.6 Remote Similarity NPC101106
0.6 Remote Similarity NPC197294
0.6 Remote Similarity NPC97614
0.6 Remote Similarity NPC135216
0.6 Remote Similarity NPC29468
0.6 Remote Similarity NPC8098
0.6 Remote Similarity NPC321838
0.598 Remote Similarity NPC474891
0.5979 Remote Similarity NPC475791
0.5979 Remote Similarity NPC13175
0.5974 Remote Similarity NPC477525
0.5962 Remote Similarity NPC80834
0.5962 Remote Similarity NPC469968
0.5957 Remote Similarity NPC70323
0.5957 Remote Similarity NPC23454
0.5957 Remote Similarity NPC262312
0.5957 Remote Similarity NPC35269
0.5949 Remote Similarity NPC473559
0.5949 Remote Similarity NPC48218
0.5949 Remote Similarity NPC141481
0.5949 Remote Similarity NPC324981
0.5946 Remote Similarity NPC474267
0.5946 Remote Similarity NPC312826
0.5941 Remote Similarity NPC250187
0.5921 Remote Similarity NPC55068
0.5921 Remote Similarity NPC54925
0.5921 Remote Similarity NPC145658
0.5909 Remote Similarity NPC228638
0.5904 Remote Similarity NPC51055
0.5904 Remote Similarity NPC140327
0.5904 Remote Similarity NPC62293
0.5904 Remote Similarity NPC212008
0.59 Remote Similarity NPC477001
0.59 Remote Similarity NPC14537
0.59 Remote Similarity NPC205176
0.59 Remote Similarity NPC477000
0.589 Remote Similarity NPC323597
0.589 Remote Similarity NPC211752
0.589 Remote Similarity NPC323498
0.5882 Remote Similarity NPC287572
0.5882 Remote Similarity NPC475363
0.5882 Remote Similarity NPC473971
0.5882 Remote Similarity NPC473972
0.5882 Remote Similarity NPC473984
0.5882 Remote Similarity NPC471636
0.5876 Remote Similarity NPC132931
0.5875 Remote Similarity NPC476291
0.5875 Remote Similarity NPC470436
0.5875 Remote Similarity NPC473772
0.5875 Remote Similarity NPC476285
0.5875 Remote Similarity NPC317583
0.5867 Remote Similarity NPC130807
0.5867 Remote Similarity NPC229252
0.5867 Remote Similarity NPC143857
0.5859 Remote Similarity NPC475149
0.5859 Remote Similarity NPC471097
0.5859 Remote Similarity NPC72401
0.5859 Remote Similarity NPC325339
0.5857 Remote Similarity NPC188341
0.5857 Remote Similarity NPC49494
0.5857 Remote Similarity NPC123814
0.5857 Remote Similarity NPC474322
0.5854 Remote Similarity NPC314678
0.5854 Remote Similarity NPC208657
0.5849 Remote Similarity NPC471645
0.5842 Remote Similarity NPC473252
0.5842 Remote Similarity NPC36497
0.5833 Remote Similarity NPC45313

  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 NPC474812 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
0.6742 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6333 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6329 Remote Similarity NPD2256 Clinical (unspecified phase)
0.6216 Remote Similarity NPD3205 Discontinued
0.6154 Remote Similarity NPD3724 Clinical (unspecified phase)
0.6122 Remote Similarity NPD2259 Approved
0.6122 Remote Similarity NPD2258 Approved
0.6078 Remote Similarity NPD6421 Discontinued
0.6061 Remote Similarity NPD3211 Approved
0.6 Remote Similarity NPD4211 Phase 1
0.6 Remote Similarity NPD4228 Discovery
0.598 Remote Similarity NPD6413 Approved
0.5952 Remote Similarity NPD3160 Suspended
0.5921 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5882 Remote Similarity NPD3732 Approved
0.5857 Remote Similarity NPD3215 Phase 1
0.5844 Remote Similarity NPD3197 Phase 1
0.5806 Remote Similarity NPD6094 Approved
0.5806 Remote Similarity NPD6095 Approved
0.5797 Remote Similarity NPD3214 Discontinued
0.5795 Remote Similarity NPD7345 Approved
0.5789 Remote Similarity NPD6949 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6420 Discontinued
0.5732 Remote Similarity NPD6944 Clinical (unspecified phase)
0.5698 Remote Similarity NPD7918 Clinical (unspecified phase)
0.5698 Remote Similarity NPD7917 Clinical (unspecified phase)
0.5696 Remote Similarity NPD5380 Approved
0.5694 Remote Similarity NPD4266 Approved
0.5694 Remote Similarity NPD3194 Approved
0.5694 Remote Similarity NPD3196 Approved
0.5694 Remote Similarity NPD3195 Phase 2
0.567 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5658 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5625 Remote Similarity NPD8394 Approved
0.56 Remote Similarity NPD6109 Phase 1

  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