Structure

Physi-Chem Properties

Molecular Weight:  578.38
Volume:  589.751
LogP:  4.323
LogD:  3.97
LogS:  -4.864
# Rotatable Bonds:  2
TPSA:  117.84
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  7
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.393
Synthetic Accessibility Score:  5.918
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
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:  -5.156
MDCK Permeability:  4.206897574476898e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.981
Human Intestinal Absorption (HIA):  0.115
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  70.3390121459961%
Volume Distribution (VD):  0.755
Pgp-substrate:  9.743070602416992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.759
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.678
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.014
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.111
CYP3A4-inhibitor:  0.16
CYP3A4-substrate:  0.169

ADMET: Excretion

Clearance (CL):  10.53
Half-life (T1/2):  0.351

ADMET: Toxicity

hERG Blockers:  0.966
Human Hepatotoxicity (H-HT):  0.299
Drug-inuced Liver Injury (DILI):  0.409
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.222
Maximum Recommended Daily Dose:  0.576
Skin Sensitization:  0.947
Carcinogencity:  0.396
Eye Corrosion:  0.215
Eye Irritation:  0.032
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC473774

Natural Product ID:  NPC473774
Common Name*:   Brisbagenin Fucoside
IUPAC Name:   n.a.
Synonyms:   brisbagenin fucoside
Standard InCHIKey:  FYUIDFGRAOPZPR-AKHCJCDBSA-N
Standard InCHI:  InChI=1S/C33H54O8/c1-16-8-11-33(38-15-16)17(2)26-24(41-33)14-23-21-7-6-19-12-20(34)13-25(32(19,5)22(21)9-10-31(23,26)4)40-30-29(37)28(36)27(35)18(3)39-30/h16-30,34-37H,6-15H2,1-5H3/t16-,17-,18-,19-,20+,21+,22-,23-,24-,25+,26-,27+,28+,29-,30+,31-,32-,33+/m0/s1
SMILES:  O[C@@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2([C@@H](C1)O[C@H]1O[C@@H](C)[C@H]([C@H]([C@@H]1O)O)O)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@]1(O2)CC[C@@H](CO1)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451455
PubChem CID:   44584499
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides
          • [CHEMONTID:0002364] Steroidal saponins

*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
NPO32671 chamaedorea linearis Species Arecaceae Eukaryota n.a. n.a. n.a. PMID[8254345]

☑ 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
NPT137 Cell Line L1210 Mus musculus IC50 = 5000.0 nM PMID[510936]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 2.6 ug PMID[510936]

☑ 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 NPC473774 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 NPC24960
0.9885 High Similarity NPC149400
0.9885 High Similarity NPC144790
0.9885 High Similarity NPC88962
0.9773 High Similarity NPC291547
0.9773 High Similarity NPC312678
0.9773 High Similarity NPC174024
0.9773 High Similarity NPC45959
0.9773 High Similarity NPC253268
0.9773 High Similarity NPC179859
0.9773 High Similarity NPC475436
0.9773 High Similarity NPC131693
0.9773 High Similarity NPC473851
0.9773 High Similarity NPC252253
0.977 High Similarity NPC204881
0.977 High Similarity NPC473830
0.9667 High Similarity NPC477222
0.9667 High Similarity NPC477223
0.9659 High Similarity NPC311246
0.9659 High Similarity NPC234352
0.9659 High Similarity NPC477451
0.9659 High Similarity NPC177834
0.9659 High Similarity NPC249204
0.9659 High Similarity NPC141769
0.9659 High Similarity NPC167644
0.9659 High Similarity NPC250393
0.9659 High Similarity NPC297348
0.9659 High Similarity NPC325828
0.9659 High Similarity NPC48339
0.9659 High Similarity NPC477547
0.9655 High Similarity NPC65550
0.9655 High Similarity NPC473542
0.956 High Similarity NPC473616
0.9556 High Similarity NPC139271
0.9556 High Similarity NPC476510
0.9556 High Similarity NPC121453
0.9556 High Similarity NPC142264
0.9556 High Similarity NPC304011
0.9551 High Similarity NPC309866
0.9551 High Similarity NPC217205
0.9551 High Similarity NPC113500
0.9551 High Similarity NPC471464
0.9551 High Similarity NPC3538
0.9551 High Similarity NPC477224
0.9551 High Similarity NPC222731
0.9551 High Similarity NPC264101
0.9551 High Similarity NPC294686
0.9551 High Similarity NPC291203
0.9545 High Similarity NPC149966
0.9545 High Similarity NPC5632
0.9545 High Similarity NPC229801
0.9545 High Similarity NPC307167
0.9545 High Similarity NPC210759
0.9451 High Similarity NPC475207
0.9451 High Similarity NPC476112
0.9451 High Similarity NPC470028
0.9451 High Similarity NPC307534
0.9451 High Similarity NPC233649
0.9444 High Similarity NPC19400
0.9444 High Similarity NPC107962
0.9444 High Similarity NPC474399
0.9444 High Similarity NPC206003
0.9444 High Similarity NPC475351
0.9444 High Similarity NPC473727
0.9444 High Similarity NPC6295
0.9444 High Similarity NPC211354
0.9444 High Similarity NPC92196
0.9444 High Similarity NPC107188
0.9444 High Similarity NPC473610
0.9438 High Similarity NPC137004
0.9438 High Similarity NPC172838
0.9438 High Similarity NPC473726
0.9432 High Similarity NPC279329
0.9425 High Similarity NPC281004
0.9355 High Similarity NPC475574
0.9348 High Similarity NPC473518
0.9341 High Similarity NPC470865
0.9341 High Similarity NPC473601
0.9341 High Similarity NPC232037
0.9341 High Similarity NPC128572
0.9341 High Similarity NPC98018
0.9341 High Similarity NPC470863
0.9341 High Similarity NPC475625
0.9341 High Similarity NPC184617
0.9341 High Similarity NPC30856
0.9341 High Similarity NPC470864
0.9341 High Similarity NPC475643
0.9341 High Similarity NPC84111
0.9341 High Similarity NPC132080
0.9341 High Similarity NPC470866
0.9341 High Similarity NPC195297
0.9341 High Similarity NPC296936
0.9341 High Similarity NPC160426
0.9341 High Similarity NPC287483
0.9341 High Similarity NPC97700
0.9341 High Similarity NPC284104
0.9341 High Similarity NPC103616
0.9341 High Similarity NPC116756
0.9333 High Similarity NPC175
0.9333 High Similarity NPC305418
0.9326 High Similarity NPC36372
0.9326 High Similarity NPC293609
0.9318 High Similarity NPC473472
0.9318 High Similarity NPC131466
0.9318 High Similarity NPC20822
0.9318 High Similarity NPC102725
0.9318 High Similarity NPC82955
0.9239 High Similarity NPC274200
0.9239 High Similarity NPC470861
0.9239 High Similarity NPC51520
0.9239 High Similarity NPC303069
0.9239 High Similarity NPC470862
0.9239 High Similarity NPC83137
0.9239 High Similarity NPC115165
0.9239 High Similarity NPC232611
0.9231 High Similarity NPC473067
0.9231 High Similarity NPC473064
0.9231 High Similarity NPC473065
0.9222 High Similarity NPC277774
0.9213 High Similarity NPC223143
0.9149 High Similarity NPC108227
0.9149 High Similarity NPC472081
0.9149 High Similarity NPC476512
0.914 High Similarity NPC291548
0.914 High Similarity NPC473638
0.913 High Similarity NPC237071
0.913 High Similarity NPC203434
0.913 High Similarity NPC238796
0.9121 High Similarity NPC473503
0.9111 High Similarity NPC476668
0.9111 High Similarity NPC473637
0.9091 High Similarity NPC43912
0.9091 High Similarity NPC140446
0.9053 High Similarity NPC134967
0.9053 High Similarity NPC114700
0.9053 High Similarity NPC470029
0.9053 High Similarity NPC310138
0.9032 High Similarity NPC470591
0.9022 High Similarity NPC469710
0.9022 High Similarity NPC477494
0.9011 High Similarity NPC476669
0.8958 High Similarity NPC139181
0.8958 High Similarity NPC476837
0.8958 High Similarity NPC97260
0.8947 High Similarity NPC477225
0.8925 High Similarity NPC473287
0.8913 High Similarity NPC30687
0.8913 High Similarity NPC475325
0.8901 High Similarity NPC59006
0.8876 High Similarity NPC472396
0.8864 High Similarity NPC273290
0.8864 High Similarity NPC232044
0.8864 High Similarity NPC290612
0.883 High Similarity NPC210157
0.8817 High Similarity NPC94582
0.8817 High Similarity NPC57964
0.875 High Similarity NPC227260
0.875 High Similarity NPC476838
0.875 High Similarity NPC476839
0.8736 High Similarity NPC296734
0.8736 High Similarity NPC470611
0.8681 High Similarity NPC228059
0.8673 High Similarity NPC475521
0.8667 High Similarity NPC161928
0.8667 High Similarity NPC210658
0.8646 High Similarity NPC470030
0.8646 High Similarity NPC20028
0.8602 High Similarity NPC224003
0.8602 High Similarity NPC470623
0.8602 High Similarity NPC18724
0.8602 High Similarity NPC323231
0.8602 High Similarity NPC171741
0.8586 High Similarity NPC215408
0.8571 High Similarity NPC128475
0.8557 High Similarity NPC477172
0.8556 High Similarity NPC471240
0.8526 High Similarity NPC156377
0.8511 High Similarity NPC191915
0.8511 High Similarity NPC471373
0.8511 High Similarity NPC267238
0.8511 High Similarity NPC77717
0.8511 High Similarity NPC253611
0.8511 High Similarity NPC148593
0.8511 High Similarity NPC151214
0.8506 High Similarity NPC7479
0.8506 High Similarity NPC248944
0.8506 High Similarity NPC257296
0.85 High Similarity NPC54619
0.85 High Similarity NPC473469
0.8485 Intermediate Similarity NPC475365
0.8469 Intermediate Similarity NPC310031
0.8469 Intermediate Similarity NPC80191
0.8454 Intermediate Similarity NPC41843
0.8438 Intermediate Similarity NPC76486
0.8421 Intermediate Similarity NPC106701
0.8421 Intermediate Similarity NPC205129
0.8421 Intermediate Similarity NPC471425
0.8421 Intermediate Similarity NPC189575
0.8421 Intermediate Similarity NPC471424
0.8421 Intermediate Similarity NPC471429

  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 NPC473774 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
0.9659 High Similarity NPD8171 Discontinued
0.8673 High Similarity NPD8170 Clinical (unspecified phase)
0.8506 High Similarity NPD6928 Phase 2
0.7679 Intermediate Similarity NPD8296 Approved
0.7679 Intermediate Similarity NPD8335 Approved
0.7679 Intermediate Similarity NPD8380 Approved
0.7679 Intermediate Similarity NPD8379 Approved
0.7679 Intermediate Similarity NPD8378 Approved
0.7589 Intermediate Similarity NPD8377 Approved
0.7589 Intermediate Similarity NPD8294 Approved
0.7522 Intermediate Similarity NPD8033 Approved
0.75 Intermediate Similarity NPD7991 Discontinued
0.7411 Intermediate Similarity NPD7327 Approved
0.7411 Intermediate Similarity NPD7328 Approved
0.7364 Intermediate Similarity NPD8133 Approved
0.7345 Intermediate Similarity NPD7516 Approved
0.7159 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD1811 Approved
0.7033 Intermediate Similarity NPD1810 Approved
0.6847 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7507 Approved
0.6818 Remote Similarity NPD6412 Phase 2
0.6803 Remote Similarity NPD7319 Approved
0.678 Remote Similarity NPD7503 Approved
0.6724 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6703 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6703 Remote Similarity NPD2686 Approved
0.6703 Remote Similarity NPD2687 Approved
0.6703 Remote Similarity NPD2254 Approved
0.664 Remote Similarity NPD8449 Approved
0.6638 Remote Similarity NPD6940 Discontinued
0.6607 Remote Similarity NPD8174 Phase 2
0.6587 Remote Similarity NPD8450 Suspended
0.6585 Remote Similarity NPD7736 Approved
0.6566 Remote Similarity NPD3669 Approved
0.6566 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6562 Remote Similarity NPD6118 Approved
0.6562 Remote Similarity NPD6115 Approved
0.6562 Remote Similarity NPD6697 Approved
0.6562 Remote Similarity NPD6114 Approved
0.6522 Remote Similarity NPD4787 Phase 1
0.6458 Remote Similarity NPD6116 Phase 1
0.6446 Remote Similarity NPD6370 Approved
0.6404 Remote Similarity NPD371 Approved
0.6393 Remote Similarity NPD8328 Phase 3
0.6371 Remote Similarity NPD8293 Discontinued
0.6354 Remote Similarity NPD6117 Approved
0.6281 Remote Similarity NPD6054 Approved
0.6281 Remote Similarity NPD6059 Approved
0.6146 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6129 Remote Similarity NPD6067 Discontinued
0.6105 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4809 Clinical (unspecified phase)
0.61 Remote Similarity NPD7525 Registered
0.6098 Remote Similarity NPD6016 Approved
0.6098 Remote Similarity NPD6015 Approved
0.6082 Remote Similarity NPD3703 Phase 2
0.608 Remote Similarity NPD7492 Approved
0.6075 Remote Similarity NPD8034 Phase 2
0.6075 Remote Similarity NPD8035 Phase 2
0.6071 Remote Similarity NPD1700 Approved
0.6048 Remote Similarity NPD5988 Approved
0.6034 Remote Similarity NPD6686 Approved
0.6032 Remote Similarity NPD6616 Approved
0.6014 Remote Similarity NPD7625 Phase 1
0.6 Remote Similarity NPD4244 Approved
0.6 Remote Similarity NPD4245 Approved
0.5984 Remote Similarity NPD7078 Approved
0.5918 Remote Similarity NPD3702 Approved
0.5913 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5913 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5895 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5895 Remote Similarity NPD3698 Phase 2
0.5895 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5893 Remote Similarity NPD7638 Approved
0.5889 Remote Similarity NPD6123 Approved
0.5882 Remote Similarity NPD1780 Approved
0.5882 Remote Similarity NPD1779 Approved
0.5849 Remote Similarity NPD7524 Approved
0.5842 Remote Similarity NPD7645 Phase 2
0.5841 Remote Similarity NPD7639 Approved
0.5841 Remote Similarity NPD7640 Approved
0.5833 Remote Similarity NPD8297 Approved
0.5833 Remote Similarity NPD6882 Approved
0.5814 Remote Similarity NPD6033 Approved
0.581 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5795 Remote Similarity NPD2267 Suspended
0.5773 Remote Similarity NPD5777 Approved
0.5772 Remote Similarity NPD6009 Approved
0.5763 Remote Similarity NPD5345 Clinical (unspecified phase)
0.576 Remote Similarity NPD6319 Approved
0.5755 Remote Similarity NPD8308 Discontinued
0.5739 Remote Similarity NPD7632 Discontinued
0.5714 Remote Similarity NPD8516 Approved
0.5714 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8513 Phase 3
0.5714 Remote Similarity NPD8515 Approved
0.5714 Remote Similarity NPD8517 Approved
0.5688 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5688 Remote Similarity NPD6700 Approved
0.5678 Remote Similarity NPD7646 Clinical (unspecified phase)
0.567 Remote Similarity NPD4789 Approved
0.5656 Remote Similarity NPD4632 Approved
0.5652 Remote Similarity NPD4159 Approved
0.5636 Remote Similarity NPD6703 Approved
0.5636 Remote Similarity NPD6702 Approved
0.5632 Remote Similarity NPD890 Clinical (unspecified phase)
0.5632 Remote Similarity NPD892 Phase 3
0.5632 Remote Similarity NPD888 Phase 3
0.5632 Remote Similarity NPD895 Approved
0.5632 Remote Similarity NPD887 Approved
0.5632 Remote Similarity NPD894 Approved
0.5632 Remote Similarity NPD889 Approved
0.5632 Remote Similarity NPD893 Approved
0.5632 Remote Similarity NPD891 Phase 3
0.563 Remote Similarity NPD7320 Approved
0.5625 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5360 Phase 3
0.5619 Remote Similarity NPD6695 Phase 3

  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