Structure

Physi-Chem Properties

Molecular Weight:  826.47
Volume:  807.129
LogP:  3.034
LogD:  3.419
LogS:  -4.103
# Rotatable Bonds:  7
TPSA:  215.45
# H-Bond Aceptor:  15
# H-Bond Donor:  7
# Rings:  9
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.182
Synthetic Accessibility Score:  6.636
Fsp3:  1.0
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:  -5.684
MDCK Permeability:  9.319800301454961e-05
Pgp-inhibitor:  0.279
Pgp-substrate:  0.992
Human Intestinal Absorption (HIA):  0.117
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  56.2490234375%
Volume Distribution (VD):  0.109
Pgp-substrate:  10.820629119873047%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.954
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.091
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.004
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.026
CYP3A4-substrate:  0.063

ADMET: Excretion

Clearance (CL):  1.061
Half-life (T1/2):  0.575

ADMET: Toxicity

hERG Blockers:  0.989
Human Hepatotoxicity (H-HT):  0.212
Drug-inuced Liver Injury (DILI):  0.188
AMES Toxicity:  0.552
Rat Oral Acute Toxicity:  0.177
Maximum Recommended Daily Dose:  0.87
Skin Sensitization:  0.965
Carcinogencity:  0.274
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC264101

Natural Product ID:  NPC264101
Common Name*:   Aspafilioside B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LGUTXUSCHKEEJA-BFTDEGHSSA-N
Standard InCHI:  InChI=1S/C43H70O15/c1-20-7-12-43(54-16-20)21(2)33-30(58-43)14-26-24-6-5-22-13-23(8-10-41(22,3)25(24)9-11-42(26,33)4)55-32-15-27(44)38(57-40-37(50)35(48)29(46)18-52-40)31(56-32)19-53-39-36(49)34(47)28(45)17-51-39/h20-40,44-50H,5-19H2,1-4H3/t20-,21-,22+,23-,24+,25-,26-,27+,28-,29+,30-,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+/m0/s1
SMILES:  C[C@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O[C@H]1C[C@@H](O)[C@H]([C@H](O1)CO[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL400900
PubChem CID:   44445744
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
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[11032480]
NPO4755 Asparagus filicinus Species Asparagaceae Eukaryota Roots n.a. n.a. PMID[17629328]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4755 Asparagus filicinus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4755 Asparagus filicinus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4755 Asparagus filicinus Species Asparagaceae 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
NPT81 Cell Line A549 Homo sapiens EC50 = 7.6 ug.mL-1 PMID[549118]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 10.4 ug.mL-1 PMID[549118]

☑ 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 NPC264101 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 NPC471464
0.9886 High Similarity NPC19400
0.9886 High Similarity NPC206003
0.9886 High Similarity NPC107188
0.9886 High Similarity NPC475351
0.9886 High Similarity NPC473610
0.9886 High Similarity NPC211354
0.9886 High Similarity NPC473727
0.9886 High Similarity NPC6295
0.9886 High Similarity NPC107962
0.9885 High Similarity NPC297348
0.9885 High Similarity NPC249204
0.9885 High Similarity NPC325828
0.9885 High Similarity NPC250393
0.9885 High Similarity NPC477547
0.9885 High Similarity NPC177834
0.9885 High Similarity NPC141769
0.9885 High Similarity NPC234352
0.9885 High Similarity NPC477451
0.9885 High Similarity NPC48339
0.9775 High Similarity NPC195297
0.9775 High Similarity NPC97700
0.9775 High Similarity NPC116756
0.9775 High Similarity NPC475643
0.9775 High Similarity NPC232037
0.9775 High Similarity NPC470864
0.9775 High Similarity NPC30856
0.9775 High Similarity NPC103616
0.9775 High Similarity NPC98018
0.9775 High Similarity NPC132080
0.9775 High Similarity NPC470863
0.9775 High Similarity NPC128572
0.9775 High Similarity NPC287483
0.9775 High Similarity NPC84111
0.9775 High Similarity NPC184617
0.9775 High Similarity NPC160426
0.9775 High Similarity NPC284104
0.9775 High Similarity NPC470866
0.9775 High Similarity NPC475625
0.9775 High Similarity NPC473601
0.9775 High Similarity NPC470865
0.9773 High Similarity NPC291547
0.9773 High Similarity NPC174024
0.9773 High Similarity NPC217205
0.9773 High Similarity NPC179859
0.9773 High Similarity NPC291203
0.9773 High Similarity NPC253268
0.9773 High Similarity NPC475436
0.9773 High Similarity NPC294686
0.9773 High Similarity NPC131693
0.9773 High Similarity NPC222731
0.9773 High Similarity NPC312678
0.9773 High Similarity NPC473851
0.9667 High Similarity NPC274200
0.9667 High Similarity NPC83137
0.9667 High Similarity NPC470862
0.9667 High Similarity NPC476112
0.9667 High Similarity NPC307534
0.9667 High Similarity NPC470861
0.9667 High Similarity NPC51520
0.9667 High Similarity NPC232611
0.9667 High Similarity NPC115165
0.9667 High Similarity NPC303069
0.9663 High Similarity NPC474399
0.9659 High Similarity NPC149400
0.9659 High Similarity NPC88962
0.9659 High Similarity NPC144790
0.956 High Similarity NPC473518
0.956 High Similarity NPC291548
0.9556 High Similarity NPC139271
0.9556 High Similarity NPC121453
0.9556 High Similarity NPC304011
0.9551 High Similarity NPC252253
0.9551 High Similarity NPC45959
0.9551 High Similarity NPC473774
0.9551 High Similarity NPC24960
0.9438 High Similarity NPC137004
0.9438 High Similarity NPC172838
0.9432 High Similarity NPC473542
0.9432 High Similarity NPC65550
0.9341 High Similarity NPC142264
0.9341 High Similarity NPC476510
0.9333 High Similarity NPC305418
0.9326 High Similarity NPC307167
0.9326 High Similarity NPC5632
0.9326 High Similarity NPC204881
0.9326 High Similarity NPC210759
0.9326 High Similarity NPC473830
0.9326 High Similarity NPC149966
0.9326 High Similarity NPC229801
0.9239 High Similarity NPC233649
0.9239 High Similarity NPC477223
0.9239 High Similarity NPC475207
0.9239 High Similarity NPC477222
0.9239 High Similarity NPC470028
0.9222 High Similarity NPC473726
0.9222 High Similarity NPC167644
0.9222 High Similarity NPC311246
0.9205 High Similarity NPC281004
0.914 High Similarity NPC473616
0.9121 High Similarity NPC309866
0.9121 High Similarity NPC3538
0.9121 High Similarity NPC113500
0.9121 High Similarity NPC477224
0.9121 High Similarity NPC175
0.9101 High Similarity NPC82955
0.9101 High Similarity NPC473472
0.9101 High Similarity NPC102725
0.9101 High Similarity NPC20822
0.9101 High Similarity NPC131466
0.9032 High Similarity NPC470591
0.9032 High Similarity NPC210157
0.9022 High Similarity NPC473065
0.9022 High Similarity NPC473067
0.9022 High Similarity NPC477494
0.9022 High Similarity NPC473064
0.9022 High Similarity NPC92196
0.9 High Similarity NPC223143
0.9 High Similarity NPC279329
0.8947 High Similarity NPC475574
0.8947 High Similarity NPC472081
0.8947 High Similarity NPC108227
0.8947 High Similarity NPC476512
0.8925 High Similarity NPC296936
0.8925 High Similarity NPC203434
0.8925 High Similarity NPC237071
0.8925 High Similarity NPC238796
0.8901 High Similarity NPC476668
0.8901 High Similarity NPC36372
0.8901 High Similarity NPC293609
0.8901 High Similarity NPC473637
0.8876 High Similarity NPC140446
0.8876 High Similarity NPC43912
0.8854 High Similarity NPC114700
0.8854 High Similarity NPC134967
0.8854 High Similarity NPC310138
0.8854 High Similarity NPC470029
0.8804 High Similarity NPC277774
0.8804 High Similarity NPC476669
0.8788 High Similarity NPC51172
0.8788 High Similarity NPC49032
0.8788 High Similarity NPC92890
0.8788 High Similarity NPC202898
0.8788 High Similarity NPC125324
0.8788 High Similarity NPC475319
0.8776 High Similarity NPC215408
0.8763 High Similarity NPC139181
0.8763 High Similarity NPC476837
0.8763 High Similarity NPC97260
0.875 High Similarity NPC227260
0.875 High Similarity NPC476838
0.875 High Similarity NPC476839
0.8737 High Similarity NPC473638
0.871 High Similarity NPC473503
0.871 High Similarity NPC475325
0.871 High Similarity NPC77717
0.871 High Similarity NPC471373
0.871 High Similarity NPC148593
0.871 High Similarity NPC30687
0.871 High Similarity NPC253611
0.871 High Similarity NPC267238
0.87 High Similarity NPC220836
0.87 High Similarity NPC233433
0.87 High Similarity NPC473817
0.87 High Similarity NPC151134
0.87 High Similarity NPC94086
0.87 High Similarity NPC92297
0.87 High Similarity NPC273002
0.8696 High Similarity NPC59006
0.8687 High Similarity NPC54619
0.866 High Similarity NPC310031
0.866 High Similarity NPC80191
0.8652 High Similarity NPC273290
0.8652 High Similarity NPC232044
0.8652 High Similarity NPC290612
0.8646 High Similarity NPC20028
0.8617 High Similarity NPC469710
0.8617 High Similarity NPC471425
0.8617 High Similarity NPC471424
0.8617 High Similarity NPC57964
0.8617 High Similarity NPC189575
0.8617 High Similarity NPC471429
0.8617 High Similarity NPC205129
0.8617 High Similarity NPC94582
0.8617 High Similarity NPC106701
0.8614 High Similarity NPC470867
0.8602 High Similarity NPC224003
0.8602 High Similarity NPC323231
0.8602 High Similarity NPC470623
0.8602 High Similarity NPC18724
0.8602 High Similarity NPC171741
0.8557 High Similarity NPC477225
0.8526 High Similarity NPC473287
0.8523 High Similarity NPC296734
0.8523 High Similarity NPC470611
0.8506 High Similarity NPC248944
0.8506 High Similarity NPC7479
0.8506 High Similarity NPC257296
0.8478 Intermediate Similarity NPC228059
0.8462 Intermediate Similarity NPC472396

  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 NPC264101 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
0.9885 High Similarity NPD8171 Discontinued
0.8866 High Similarity NPD8170 Clinical (unspecified phase)
0.8506 High Similarity NPD6928 Phase 2
0.7589 Intermediate Similarity NPD8377 Approved
0.7589 Intermediate Similarity NPD8294 Approved
0.7523 Intermediate Similarity NPD8133 Approved
0.7522 Intermediate Similarity NPD8378 Approved
0.7522 Intermediate Similarity NPD8296 Approved
0.7522 Intermediate Similarity NPD8380 Approved
0.7522 Intermediate Similarity NPD8335 Approved
0.7522 Intermediate Similarity NPD8379 Approved
0.75 Intermediate Similarity NPD7991 Discontinued
0.7368 Intermediate Similarity NPD8033 Approved
0.7105 Intermediate Similarity NPD7328 Approved
0.7105 Intermediate Similarity NPD7327 Approved
0.7043 Intermediate Similarity NPD7516 Approved
0.6966 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6911 Remote Similarity NPD8449 Approved
0.6855 Remote Similarity NPD8450 Suspended
0.6848 Remote Similarity NPD1810 Approved
0.6848 Remote Similarity NPD1811 Approved
0.6818 Remote Similarity NPD6412 Phase 2
0.6696 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6694 Remote Similarity NPD7507 Approved
0.6639 Remote Similarity NPD7503 Approved
0.6638 Remote Similarity NPD6940 Discontinued
0.6607 Remote Similarity NPD8174 Phase 2
0.6581 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6532 Remote Similarity NPD7319 Approved
0.6522 Remote Similarity NPD2686 Approved
0.6522 Remote Similarity NPD4787 Phase 1
0.6522 Remote Similarity NPD2687 Approved
0.6522 Remote Similarity NPD2254 Approved
0.6452 Remote Similarity NPD7736 Approved
0.64 Remote Similarity NPD3670 Clinical (unspecified phase)
0.64 Remote Similarity NPD3669 Approved
0.6392 Remote Similarity NPD6115 Approved
0.6392 Remote Similarity NPD6118 Approved
0.6392 Remote Similarity NPD6114 Approved
0.6392 Remote Similarity NPD6697 Approved
0.6344 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6311 Remote Similarity NPD6370 Approved
0.6289 Remote Similarity NPD6116 Phase 1
0.626 Remote Similarity NPD8328 Phase 3
0.625 Remote Similarity NPD6123 Approved
0.624 Remote Similarity NPD8293 Discontinued
0.6186 Remote Similarity NPD6117 Approved
0.6148 Remote Similarity NPD6054 Approved
0.6148 Remote Similarity NPD6059 Approved
0.6146 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6044 Remote Similarity NPD371 Approved
0.6034 Remote Similarity NPD6686 Approved
0.6 Remote Similarity NPD4244 Approved
0.6 Remote Similarity NPD6067 Discontinued
0.6 Remote Similarity NPD4245 Approved
0.5968 Remote Similarity NPD6015 Approved
0.5968 Remote Similarity NPD6016 Approved
0.5952 Remote Similarity NPD7492 Approved
0.5941 Remote Similarity NPD7525 Registered
0.5926 Remote Similarity NPD8035 Phase 2
0.5926 Remote Similarity NPD8034 Phase 2
0.592 Remote Similarity NPD5988 Approved
0.5918 Remote Similarity NPD3702 Approved
0.5918 Remote Similarity NPD3703 Phase 2
0.5913 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5913 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5906 Remote Similarity NPD6616 Approved
0.5899 Remote Similarity NPD7625 Phase 1
0.5895 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5895 Remote Similarity NPD3698 Phase 2
0.5895 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5859 Remote Similarity NPD7078 Approved
0.584 Remote Similarity NPD8516 Approved
0.584 Remote Similarity NPD8515 Approved
0.584 Remote Similarity NPD8517 Approved
0.5795 Remote Similarity NPD2267 Suspended
0.5789 Remote Similarity NPD1700 Approved
0.5773 Remote Similarity NPD5777 Approved
0.5752 Remote Similarity NPD7638 Approved
0.5728 Remote Similarity NPD1780 Approved
0.5728 Remote Similarity NPD1779 Approved
0.5714 Remote Similarity NPD8513 Phase 3
0.5702 Remote Similarity NPD7639 Approved
0.5702 Remote Similarity NPD6882 Approved
0.5702 Remote Similarity NPD7640 Approved
0.5702 Remote Similarity NPD8297 Approved
0.5701 Remote Similarity NPD7524 Approved
0.5692 Remote Similarity NPD6033 Approved
0.5686 Remote Similarity NPD7645 Phase 2
0.5678 Remote Similarity NPD7646 Clinical (unspecified phase)
0.567 Remote Similarity NPD4789 Approved
0.566 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5645 Remote Similarity NPD6009 Approved
0.5635 Remote Similarity NPD6319 Approved
0.5632 Remote Similarity NPD887 Approved
0.5632 Remote Similarity NPD892 Phase 3
0.5632 Remote Similarity NPD890 Clinical (unspecified phase)
0.5632 Remote Similarity NPD888 Phase 3
0.5632 Remote Similarity NPD895 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
0.5625 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5360 Phase 3
0.562 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5607 Remote Similarity NPD8308 Discontinued
0.5603 Remote Similarity NPD7632 Discontinued

  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