Structure

Physi-Chem Properties

Molecular Weight:  767.55
Volume:  829.444
LogP:  7.282
LogD:  4.515
LogS:  -2.89
# Rotatable Bonds:  36
TPSA:  182.85
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  1
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.018
Synthetic Accessibility Score:  4.818
Fsp3:  0.837
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  4
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.477
MDCK Permeability:  1.638205321796704e-05
Pgp-inhibitor:  0.304
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.682
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  91.37748718261719%
Volume Distribution (VD):  0.984
Pgp-substrate:  1.4461448192596436%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.088
CYP2C19-inhibitor:  0.288
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.132
CYP2C9-substrate:  0.973
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.018
CYP3A4-inhibitor:  0.198
CYP3A4-substrate:  0.008

ADMET: Excretion

Clearance (CL):  2.494
Half-life (T1/2):  0.276

ADMET: Toxicity

hERG Blockers:  0.458
Human Hepatotoxicity (H-HT):  0.251
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.528
Rat Oral Acute Toxicity:  0.05
Maximum Recommended Daily Dose:  0.069
Skin Sensitization:  0.958
Carcinogencity:  0.025
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.058

Download Data

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

  Natural Product: NPC201128

Natural Product ID:  NPC201128
Common Name*:   Alternaroside A
IUPAC Name:   (E,2R)-2-hydroxy-N-[(E,2S,3R)-3-hydroxy-9-methylidene-8-oxo-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]octadec-3-enamide
Synonyms:  
Standard InCHIKey:  MFDPZDJWPLVIDT-GOHCNHTRSA-N
Standard InCHI:  InChI=1S/C43H77NO10/c1-4-6-8-10-12-13-14-15-16-17-18-20-22-24-30-37(48)42(52)44-34(32-53-43-41(51)40(50)39(49)38(31-45)54-43)36(47)29-26-25-28-35(46)33(3)27-23-21-19-11-9-7-5-2/h24,26,29-30,34,36-41,43,45,47-51H,3-23,25,27-28,31-32H2,1-2H3,(H,44,52)/b29-26+,30-24+/t34-,36+,37+,38+,39+,40-,41+,43+/m0/s1
SMILES:  CCCCCCCCCCCCCC/C=C/[C@H](C(=N[C@H]([C@@H](/C=C/CCC(=O)C(=C)CCCCCCCCC)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078814
PubChem CID:   44478418
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000257] Sphingolipids
        • [CHEMONTID:0003258] Glycosphingolipids
          • [CHEMONTID:0001419] Neutral glycosphingolipids
            • [CHEMONTID:0001428] Simple glycosylceramides
              • [CHEMONTID:0004305] Glycosyl-N-acylsphingosines

*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
NPO32519 alternaria raphani Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[19685913]

☑ 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
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 100000.0 nM PMID[502285]
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[502285]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 100000.0 nM PMID[502285]
NPT168 Cell Line P388 Mus musculus IC50 > 100000.0 nM PMID[502285]
NPT20 Organism Candida albicans Candida albicans MIC = 260000.0 nM PMID[502285]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 130000.0 nM PMID[502285]
NPT19 Organism Escherichia coli Escherichia coli MIC = 130000.0 nM PMID[502285]
NPT1 Others Radical scavenging activity IC50 > 500000.0 nM PMID[502285]

☑ 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 NPC201128 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
0.8969 High Similarity NPC35269
0.8969 High Similarity NPC23454
0.8969 High Similarity NPC70323
0.8969 High Similarity NPC262312
0.8788 High Similarity NPC45313
0.8776 High Similarity NPC3568
0.8776 High Similarity NPC17290
0.8776 High Similarity NPC192066
0.8776 High Similarity NPC256570
0.8763 High Similarity NPC282705
0.8763 High Similarity NPC182632
0.86 High Similarity NPC8098
0.86 High Similarity NPC197294
0.86 High Similarity NPC183449
0.8571 High Similarity NPC15851
0.8571 High Similarity NPC309898
0.8571 High Similarity NPC111567
0.8571 High Similarity NPC473604
0.8571 High Similarity NPC473581
0.8571 High Similarity NPC475125
0.8571 High Similarity NPC263545
0.8571 High Similarity NPC473950
0.8571 High Similarity NPC186840
0.8469 Intermediate Similarity NPC209047
0.8469 Intermediate Similarity NPC43074
0.8469 Intermediate Similarity NPC74672
0.8469 Intermediate Similarity NPC242503
0.8469 Intermediate Similarity NPC139782
0.84 Intermediate Similarity NPC157353
0.84 Intermediate Similarity NPC156782
0.84 Intermediate Similarity NPC54961
0.84 Intermediate Similarity NPC282088
0.84 Intermediate Similarity NPC158445
0.802 Intermediate Similarity NPC475603
0.802 Intermediate Similarity NPC61894
0.787 Intermediate Similarity NPC74035
0.7685 Intermediate Similarity NPC477198
0.7636 Intermediate Similarity NPC475918
0.7544 Intermediate Similarity NPC469865
0.7476 Intermediate Similarity NPC159369
0.7476 Intermediate Similarity NPC39290
0.7436 Intermediate Similarity NPC6531
0.735 Intermediate Similarity NPC30196
0.7345 Intermediate Similarity NPC475150
0.7281 Intermediate Similarity NPC473578
0.7241 Intermediate Similarity NPC1111
0.7241 Intermediate Similarity NPC261750
0.7222 Intermediate Similarity NPC175614
0.72 Intermediate Similarity NPC21693
0.72 Intermediate Similarity NPC280367
0.72 Intermediate Similarity NPC236649
0.717 Intermediate Similarity NPC472197
0.7109 Intermediate Similarity NPC78189
0.7094 Intermediate Similarity NPC60432
0.7075 Intermediate Similarity NPC473311
0.7073 Intermediate Similarity NPC314629
0.7071 Intermediate Similarity NPC133377
0.7064 Intermediate Similarity NPC475503
0.7059 Intermediate Similarity NPC156089
0.7059 Intermediate Similarity NPC470313
0.7059 Intermediate Similarity NPC473500
0.7059 Intermediate Similarity NPC38295
0.7031 Intermediate Similarity NPC314361
0.7016 Intermediate Similarity NPC313333
0.7016 Intermediate Similarity NPC313342
0.7016 Intermediate Similarity NPC314451
0.7016 Intermediate Similarity NPC314512
0.7016 Intermediate Similarity NPC204639
0.7009 Intermediate Similarity NPC29501
0.7009 Intermediate Similarity NPC472199
0.697 Remote Similarity NPC110813
0.6953 Remote Similarity NPC139585
0.6953 Remote Similarity NPC316401
0.6947 Remote Similarity NPC230889
0.6944 Remote Similarity NPC320089
0.6944 Remote Similarity NPC238090
0.6944 Remote Similarity NPC472196
0.6944 Remote Similarity NPC472195
0.6935 Remote Similarity NPC318445
0.6935 Remote Similarity NPC316133
0.6935 Remote Similarity NPC315783
0.6929 Remote Similarity NPC316205
0.6929 Remote Similarity NPC315387
0.6887 Remote Similarity NPC470137
0.6885 Remote Similarity NPC67917
0.6885 Remote Similarity NPC477515
0.6885 Remote Similarity NPC314268
0.6885 Remote Similarity NPC313802
0.6881 Remote Similarity NPC159698
0.6881 Remote Similarity NPC472198
0.6863 Remote Similarity NPC469469
0.6857 Remote Similarity NPC208473
0.6855 Remote Similarity NPC273185
0.685 Remote Similarity NPC477793
0.685 Remote Similarity NPC329919
0.6847 Remote Similarity NPC476613
0.6847 Remote Similarity NPC475646
0.6847 Remote Similarity NPC474194
0.6847 Remote Similarity NPC476612
0.6837 Remote Similarity NPC288086
0.6827 Remote Similarity NPC473308
0.6792 Remote Similarity NPC475186
0.6792 Remote Similarity NPC118077
0.6789 Remote Similarity NPC320552
0.6772 Remote Similarity NPC314282
0.6759 Remote Similarity NPC473904
0.6757 Remote Similarity NPC306041
0.6754 Remote Similarity NPC223834
0.6746 Remote Similarity NPC469494
0.6731 Remote Similarity NPC142111
0.6731 Remote Similarity NPC228638
0.6731 Remote Similarity NPC473315
0.6724 Remote Similarity NPC154601
0.6715 Remote Similarity NPC298067
0.6715 Remote Similarity NPC214821
0.67 Remote Similarity NPC326661
0.6698 Remote Similarity NPC47937
0.6696 Remote Similarity NPC278506
0.6696 Remote Similarity NPC55336
0.6692 Remote Similarity NPC475472
0.6667 Remote Similarity NPC192025
0.6667 Remote Similarity NPC288471
0.6667 Remote Similarity NPC475035
0.6667 Remote Similarity NPC125253
0.6667 Remote Similarity NPC139418
0.6667 Remote Similarity NPC253975
0.6667 Remote Similarity NPC476523
0.6667 Remote Similarity NPC476611
0.6643 Remote Similarity NPC298005
0.6643 Remote Similarity NPC36463
0.6641 Remote Similarity NPC119794
0.6641 Remote Similarity NPC73829
0.6637 Remote Similarity NPC61630
0.6637 Remote Similarity NPC81483
0.6637 Remote Similarity NPC198422
0.6637 Remote Similarity NPC169468
0.6637 Remote Similarity NPC307517
0.6637 Remote Similarity NPC40182
0.6636 Remote Similarity NPC475037
0.6636 Remote Similarity NPC473561
0.6636 Remote Similarity NPC475173
0.6636 Remote Similarity NPC473663
0.6636 Remote Similarity NPC11456
0.6636 Remote Similarity NPC473723
0.6635 Remote Similarity NPC251026
0.6635 Remote Similarity NPC474312
0.6619 Remote Similarity NPC244380
0.6619 Remote Similarity NPC61717
0.6607 Remote Similarity NPC189629
0.6606 Remote Similarity NPC327253
0.6604 Remote Similarity NPC182383
0.6604 Remote Similarity NPC470124
0.6602 Remote Similarity NPC127295
0.6602 Remote Similarity NPC163362
0.6593 Remote Similarity NPC302276
0.6593 Remote Similarity NPC180770
0.6591 Remote Similarity NPC76999
0.6587 Remote Similarity NPC469943
0.6585 Remote Similarity NPC475642
0.6585 Remote Similarity NPC316325
0.6579 Remote Similarity NPC206711
0.6579 Remote Similarity NPC271207
0.6579 Remote Similarity NPC255175
0.6579 Remote Similarity NPC225978
0.6577 Remote Similarity NPC25701
0.6577 Remote Similarity NPC2003
0.6574 Remote Similarity NPC137368
0.6574 Remote Similarity NPC20339
0.6574 Remote Similarity NPC280621
0.6574 Remote Similarity NPC471756
0.6574 Remote Similarity NPC233551
0.6574 Remote Similarity NPC471755
0.6574 Remote Similarity NPC40376
0.6574 Remote Similarity NPC48338
0.6574 Remote Similarity NPC21208
0.656 Remote Similarity NPC473808
0.6557 Remote Similarity NPC471645
0.6549 Remote Similarity NPC266842
0.6545 Remote Similarity NPC477349
0.6545 Remote Similarity NPC270005
0.6545 Remote Similarity NPC208537
0.6545 Remote Similarity NPC473707
0.6542 Remote Similarity NPC477015
0.6541 Remote Similarity NPC235772
0.6541 Remote Similarity NPC75318
0.6541 Remote Similarity NPC280941
0.6532 Remote Similarity NPC234522
0.6525 Remote Similarity NPC251330
0.6525 Remote Similarity NPC315426
0.6522 Remote Similarity NPC154127
0.6522 Remote Similarity NPC141669
0.6518 Remote Similarity NPC108141
0.6514 Remote Similarity NPC477016
0.6514 Remote Similarity NPC477017
0.6514 Remote Similarity NPC285588
0.6509 Remote Similarity NPC266718
0.6508 Remote Similarity NPC469515
0.6504 Remote Similarity NPC7905
0.6504 Remote Similarity NPC315652
0.6503 Remote Similarity NPC475527

  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 NPC201128 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
0.8469 Intermediate Similarity NPD8522 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD6421 Discontinued
0.7227 Intermediate Similarity NPD7641 Discontinued
0.7016 Intermediate Similarity NPD8340 Approved
0.7016 Intermediate Similarity NPD8342 Approved
0.7016 Intermediate Similarity NPD8341 Approved
0.7016 Intermediate Similarity NPD8299 Approved
0.6991 Remote Similarity NPD1407 Approved
0.6935 Remote Similarity NPD7830 Approved
0.6935 Remote Similarity NPD7642 Approved
0.6935 Remote Similarity NPD7829 Approved
0.6911 Remote Similarity NPD8444 Approved
0.6825 Remote Similarity NPD8451 Approved
0.6772 Remote Similarity NPD8448 Approved
0.6615 Remote Similarity NPD8390 Approved
0.6615 Remote Similarity NPD8392 Approved
0.6615 Remote Similarity NPD8391 Approved
0.6585 Remote Similarity NPD7500 Approved
0.6583 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6512 Remote Similarity NPD8074 Phase 3
0.646 Remote Similarity NPD7839 Suspended
0.6457 Remote Similarity NPD8080 Discontinued
0.6455 Remote Similarity NPD6698 Approved
0.6455 Remote Similarity NPD46 Approved
0.6452 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7983 Approved
0.6393 Remote Similarity NPD6429 Approved
0.6393 Remote Similarity NPD6430 Approved
0.6378 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6914 Discontinued
0.6348 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6686 Approved
0.6328 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6328 Remote Similarity NPD7623 Phase 3
0.626 Remote Similarity NPD7747 Phase 1
0.626 Remote Similarity NPD7746 Phase 1
0.6216 Remote Similarity NPD3716 Discontinued
0.6183 Remote Similarity NPD8273 Phase 1
0.6179 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6174 Remote Similarity NPD6428 Approved
0.6131 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6124 Remote Similarity NPD7739 Clinical (unspecified phase)
0.609 Remote Similarity NPD8336 Approved
0.609 Remote Similarity NPD8337 Approved
0.6058 Remote Similarity NPD8415 Approved
0.6033 Remote Similarity NPD5357 Phase 1
0.6029 Remote Similarity NPD8338 Approved
0.6018 Remote Similarity NPD7838 Discovery
0.6016 Remote Similarity NPD8305 Approved
0.6016 Remote Similarity NPD8306 Approved
0.6 Remote Similarity NPD8516 Approved
0.6 Remote Similarity NPD8515 Approved
0.6 Remote Similarity NPD8517 Approved
0.6 Remote Similarity NPD8275 Approved
0.6 Remote Similarity NPD8276 Approved
0.6 Remote Similarity NPD8513 Phase 3
0.5984 Remote Similarity NPD6412 Phase 2
0.5982 Remote Similarity NPD618 Clinical (unspecified phase)
0.5954 Remote Similarity NPD6436 Phase 3
0.594 Remote Similarity NPD4816 Clinical (unspecified phase)
0.5938 Remote Similarity NPD7505 Discontinued
0.5917 Remote Similarity NPD8085 Approved
0.5917 Remote Similarity NPD8082 Approved
0.5917 Remote Similarity NPD8084 Approved
0.5917 Remote Similarity NPD8138 Approved
0.5917 Remote Similarity NPD8083 Approved
0.5917 Remote Similarity NPD8086 Approved
0.5917 Remote Similarity NPD8139 Approved
0.5913 Remote Similarity NPD1446 Phase 3
0.5913 Remote Similarity NPD1447 Phase 3
0.5902 Remote Similarity NPD8393 Approved
0.5902 Remote Similarity NPD4211 Phase 1
0.5897 Remote Similarity NPD4228 Discovery
0.5887 Remote Similarity NPD6941 Approved
0.5868 Remote Similarity NPD2259 Approved
0.5868 Remote Similarity NPD2258 Approved
0.584 Remote Similarity NPD6420 Discontinued
0.582 Remote Similarity NPD8081 Approved
0.5798 Remote Similarity NPD2255 Approved
0.5785 Remote Similarity NPD7139 Approved
0.5785 Remote Similarity NPD7140 Approved
0.5785 Remote Similarity NPD7141 Clinical (unspecified phase)
0.5772 Remote Similarity NPD8389 Clinical (unspecified phase)
0.576 Remote Similarity NPD6413 Approved
0.5752 Remote Similarity NPD4759 Clinical (unspecified phase)
0.5738 Remote Similarity NPD8045 Clinical (unspecified phase)
0.5692 Remote Similarity NPD6935 Phase 3
0.5692 Remote Similarity NPD6936 Clinical (unspecified phase)
0.5682 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5669 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5645 Remote Similarity NPD6640 Phase 3
0.5639 Remote Similarity NPD8269 Approved
0.5639 Remote Similarity NPD8268 Approved
0.5639 Remote Similarity NPD8267 Approved
0.5639 Remote Similarity NPD8266 Approved
0.5635 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5631 Remote Similarity NPD9445 Approved
0.5603 Remote Similarity NPD6095 Approved
0.5603 Remote Similarity NPD6094 Approved
0.56 Remote Similarity NPD8307 Discontinued
0.56 Remote Similarity NPD8140 Approved
0.56 Remote Similarity NPD7899 Clinical (unspecified phase)

  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