Structure

Physi-Chem Properties

Molecular Weight:  296.13
Volume:  281.239
LogP:  1.028
LogD:  0.714
LogS:  -3.903
# Rotatable Bonds:  0
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.618
Synthetic Accessibility Score:  5.697
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.678
MDCK Permeability:  0.00010501733049750328
Pgp-inhibitor:  0.005
Pgp-substrate:  0.121
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.588
30% Bioavailability (F30%):  0.617

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.77
Plasma Protein Binding (PPB):  20.43229103088379%
Volume Distribution (VD):  0.328
Pgp-substrate:  71.37754821777344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.975
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.593
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.021
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.038
CYP3A4-inhibitor:  0.561
CYP3A4-substrate:  0.839

ADMET: Excretion

Clearance (CL):  3.017
Half-life (T1/2):  0.14

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.524
Drug-inuced Liver Injury (DILI):  0.282
AMES Toxicity:  0.301
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.819
Carcinogencity:  0.998
Eye Corrosion:  0.188
Eye Irritation:  0.072
Respiratory Toxicity:  0.991

Download Data

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

  Natural Product: NPC157328

Natural Product ID:  NPC157328
Common Name*:   Anislactone B
IUPAC Name:   n.a.
Synonyms:   Anislactone B
Standard InCHIKey:  QMZMARJPDZSGFF-VSCRVHDNSA-N
Standard InCHI:  InChI=1S/C15H20O6/c1-11-7-20-10(18)13(11,3)9(17)14-6-8(16)21-12(14,2)4-5-15(11,14)19/h9,17,19H,4-7H2,1-3H3/t9-,11-,12+,13+,14-,15+/m1/s1
SMILES:  C[C@@]12COC(=O)[C@]1(C)[C@H]([C@]13CC(=O)O[C@@]1(C)CC[C@]23O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL561908
PubChem CID:   45267954
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO20732 Illicium merrillianum Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[11325221]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota pericarps n.a. n.a. PMID[19159273]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[19496609]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[20411974]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. stem n.a. PMID[21524101]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. root n.a. PMID[25966312]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20732 Illicium merrillianum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20825 Illicium anisatum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20825 Illicium anisatum Species Schisandraceae 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
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 12.55 % PMID[529731]

☑ 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 NPC157328 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
0.8352 Intermediate Similarity NPC278028
0.8352 Intermediate Similarity NPC328180
0.8202 Intermediate Similarity NPC474065
0.8125 Intermediate Similarity NPC477867
0.8025 Intermediate Similarity NPC179922
0.8021 Intermediate Similarity NPC114365
0.8021 Intermediate Similarity NPC132304
0.8021 Intermediate Similarity NPC18044
0.8021 Intermediate Similarity NPC169089
0.8021 Intermediate Similarity NPC18433
0.8021 Intermediate Similarity NPC123070
0.8021 Intermediate Similarity NPC154962
0.8021 Intermediate Similarity NPC177518
0.8021 Intermediate Similarity NPC88890
0.7912 Intermediate Similarity NPC472237
0.7912 Intermediate Similarity NPC472238
0.7901 Intermediate Similarity NPC125164
0.7901 Intermediate Similarity NPC215030
0.7835 Intermediate Similarity NPC473701
0.7835 Intermediate Similarity NPC473526
0.7831 Intermediate Similarity NPC214030
0.7831 Intermediate Similarity NPC83108
0.7812 Intermediate Similarity NPC292803
0.7802 Intermediate Similarity NPC474699
0.7791 Intermediate Similarity NPC212340
0.7625 Intermediate Similarity NPC475062
0.7625 Intermediate Similarity NPC98711
0.7576 Intermediate Similarity NPC168890
0.7527 Intermediate Similarity NPC476189
0.75 Intermediate Similarity NPC211087
0.75 Intermediate Similarity NPC253995
0.75 Intermediate Similarity NPC176756
0.7449 Intermediate Similarity NPC213528
0.7449 Intermediate Similarity NPC244969
0.7439 Intermediate Similarity NPC470243
0.7426 Intermediate Similarity NPC220773
0.7426 Intermediate Similarity NPC167044
0.7426 Intermediate Similarity NPC278693
0.7416 Intermediate Similarity NPC291310
0.7412 Intermediate Similarity NPC70996
0.7391 Intermediate Similarity NPC200580
0.7368 Intermediate Similarity NPC470191
0.7353 Intermediate Similarity NPC217041
0.7333 Intermediate Similarity NPC470115
0.7333 Intermediate Similarity NPC473350
0.7333 Intermediate Similarity NPC470116
0.7303 Intermediate Similarity NPC111409
0.73 Intermediate Similarity NPC100078
0.7292 Intermediate Similarity NPC142529
0.7292 Intermediate Similarity NPC116683
0.7292 Intermediate Similarity NPC126156
0.7292 Intermediate Similarity NPC91771
0.7284 Intermediate Similarity NPC319007
0.7282 Intermediate Similarity NPC182185
0.7263 Intermediate Similarity NPC470424
0.7228 Intermediate Similarity NPC306776
0.7228 Intermediate Similarity NPC469441
0.7228 Intermediate Similarity NPC166079
0.7228 Intermediate Similarity NPC228311
0.7228 Intermediate Similarity NPC41674
0.7188 Intermediate Similarity NPC37408
0.7176 Intermediate Similarity NPC228411
0.7176 Intermediate Similarity NPC155441
0.7158 Intermediate Similarity NPC153590
0.7158 Intermediate Similarity NPC475488
0.7158 Intermediate Similarity NPC200237
0.7157 Intermediate Similarity NPC469788
0.7157 Intermediate Similarity NPC290247
0.7157 Intermediate Similarity NPC469787
0.7143 Intermediate Similarity NPC98870
0.7143 Intermediate Similarity NPC478111
0.7143 Intermediate Similarity NPC274695
0.7129 Intermediate Similarity NPC88469
0.7128 Intermediate Similarity NPC216284
0.7128 Intermediate Similarity NPC246173
0.7128 Intermediate Similarity NPC35809
0.7126 Intermediate Similarity NPC470014
0.7113 Intermediate Similarity NPC193785
0.7103 Intermediate Similarity NPC277583
0.7097 Intermediate Similarity NPC470009
0.7097 Intermediate Similarity NPC471221
0.7097 Intermediate Similarity NPC191221
0.7087 Intermediate Similarity NPC329876
0.7073 Intermediate Similarity NPC119838
0.7065 Intermediate Similarity NPC470657
0.7053 Intermediate Similarity NPC29821
0.7053 Intermediate Similarity NPC35959
0.7053 Intermediate Similarity NPC171360
0.7053 Intermediate Similarity NPC63193
0.7053 Intermediate Similarity NPC133888
0.7053 Intermediate Similarity NPC293001
0.7053 Intermediate Similarity NPC57304
0.7041 Intermediate Similarity NPC311904
0.7033 Intermediate Similarity NPC477434
0.7021 Intermediate Similarity NPC215556
0.7021 Intermediate Similarity NPC155935
0.7021 Intermediate Similarity NPC61688
0.7011 Intermediate Similarity NPC474003
0.7011 Intermediate Similarity NPC169389
0.7 Intermediate Similarity NPC298266
0.7 Intermediate Similarity NPC314103
0.7 Intermediate Similarity NPC171759
0.7 Intermediate Similarity NPC39683
0.7 Intermediate Similarity NPC259654
0.6989 Remote Similarity NPC31349
0.6989 Remote Similarity NPC314364
0.6979 Remote Similarity NPC473263
0.6979 Remote Similarity NPC60386
0.6979 Remote Similarity NPC473234
0.6979 Remote Similarity NPC308656
0.6979 Remote Similarity NPC473273
0.6977 Remote Similarity NPC35871
0.6977 Remote Similarity NPC132064
0.6977 Remote Similarity NPC68565
0.6966 Remote Similarity NPC156658
0.6966 Remote Similarity NPC258965
0.6962 Remote Similarity NPC469923
0.6951 Remote Similarity NPC469925
0.6947 Remote Similarity NPC54065
0.6947 Remote Similarity NPC297474
0.6932 Remote Similarity NPC475616
0.6923 Remote Similarity NPC29342
0.6923 Remote Similarity NPC2572
0.6923 Remote Similarity NPC472847
0.6923 Remote Similarity NPC15091
0.6923 Remote Similarity NPC69953
0.6923 Remote Similarity NPC128246
0.6916 Remote Similarity NPC285086
0.6916 Remote Similarity NPC312017
0.6916 Remote Similarity NPC9848
0.6915 Remote Similarity NPC226491
0.6915 Remote Similarity NPC33398
0.6915 Remote Similarity NPC79549
0.6915 Remote Similarity NPC477614
0.6914 Remote Similarity NPC476330
0.6914 Remote Similarity NPC157518
0.6907 Remote Similarity NPC470423
0.6907 Remote Similarity NPC206878
0.6907 Remote Similarity NPC473331
0.69 Remote Similarity NPC108371
0.69 Remote Similarity NPC471381
0.6889 Remote Similarity NPC254123
0.6875 Remote Similarity NPC286341
0.6875 Remote Similarity NPC191339
0.6875 Remote Similarity NPC184063
0.6875 Remote Similarity NPC155215
0.6869 Remote Similarity NPC471241
0.6869 Remote Similarity NPC471150
0.6863 Remote Similarity NPC471253
0.6852 Remote Similarity NPC471382
0.6852 Remote Similarity NPC79193
0.6842 Remote Similarity NPC97032
0.6842 Remote Similarity NPC168679
0.6842 Remote Similarity NPC12872
0.6842 Remote Similarity NPC477443
0.6842 Remote Similarity NPC477440
0.6837 Remote Similarity NPC62407
0.6837 Remote Similarity NPC287354
0.6837 Remote Similarity NPC472873
0.6837 Remote Similarity NPC469873
0.6837 Remote Similarity NPC163228
0.6837 Remote Similarity NPC476053
0.6835 Remote Similarity NPC469921
0.6832 Remote Similarity NPC477950
0.6832 Remote Similarity NPC474053
0.6832 Remote Similarity NPC304624
0.6832 Remote Similarity NPC162024
0.6832 Remote Similarity NPC178853
0.6818 Remote Similarity NPC161060
0.6813 Remote Similarity NPC311642
0.6813 Remote Similarity NPC100366
0.6813 Remote Similarity NPC242771
0.6813 Remote Similarity NPC164289
0.6813 Remote Similarity NPC477935
0.6809 Remote Similarity NPC475773
0.6809 Remote Similarity NPC239938
0.6804 Remote Similarity NPC161035
0.6804 Remote Similarity NPC258216
0.6804 Remote Similarity NPC472232
0.6804 Remote Similarity NPC475788
0.6804 Remote Similarity NPC472231
0.6796 Remote Similarity NPC327093
0.6792 Remote Similarity NPC98633
0.6792 Remote Similarity NPC475463
0.6789 Remote Similarity NPC475490
0.6778 Remote Similarity NPC1882
0.6778 Remote Similarity NPC51507
0.6778 Remote Similarity NPC134227
0.6771 Remote Similarity NPC477433
0.6771 Remote Similarity NPC19087
0.6771 Remote Similarity NPC477444
0.6771 Remote Similarity NPC77756
0.6771 Remote Similarity NPC477442
0.6768 Remote Similarity NPC24956
0.6768 Remote Similarity NPC18019
0.6765 Remote Similarity NPC470172
0.675 Remote Similarity NPC469922
0.6744 Remote Similarity NPC473775
0.6744 Remote Similarity NPC473699
0.6744 Remote Similarity NPC475232

  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 NPC157328 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
0.8021 Intermediate Similarity NPD4056 Clinical (unspecified phase)
0.8021 Intermediate Similarity NPD4057 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD1700 Approved
0.7073 Intermediate Similarity NPD229 Approved
0.6742 Remote Similarity NPD4802 Phase 2
0.6742 Remote Similarity NPD4238 Approved
0.6591 Remote Similarity NPD3702 Approved
0.6506 Remote Similarity NPD9496 Clinical (unspecified phase)
0.65 Remote Similarity NPD3198 Approved
0.6452 Remote Similarity NPD6435 Approved
0.6237 Remote Similarity NPD5368 Approved
0.6196 Remote Similarity NPD6697 Approved
0.6196 Remote Similarity NPD6115 Approved
0.6196 Remote Similarity NPD6114 Approved
0.6196 Remote Similarity NPD6118 Approved
0.6186 Remote Similarity NPD4249 Approved
0.6176 Remote Similarity NPD1698 Clinical (unspecified phase)
0.617 Remote Similarity NPD5369 Approved
0.6168 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6122 Remote Similarity NPD4251 Approved
0.6122 Remote Similarity NPD4250 Approved
0.6087 Remote Similarity NPD6116 Phase 1
0.6083 Remote Similarity NPD7078 Approved
0.6076 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6053 Discontinued
0.602 Remote Similarity NPD5786 Approved
0.6 Remote Similarity NPD7320 Approved
0.5978 Remote Similarity NPD6117 Approved
0.5963 Remote Similarity NPD6008 Approved
0.5934 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5922 Remote Similarity NPD5282 Discontinued
0.5917 Remote Similarity NPD7492 Approved
0.5909 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5893 Remote Similarity NPD6371 Approved
0.5889 Remote Similarity NPD5777 Approved
0.587 Remote Similarity NPD3703 Phase 2
0.5868 Remote Similarity NPD6616 Approved
0.5847 Remote Similarity NPD6319 Approved
0.5847 Remote Similarity NPD6054 Approved
0.5847 Remote Similarity NPD6059 Approved
0.5843 Remote Similarity NPD3698 Phase 2
0.5842 Remote Similarity NPD1695 Approved
0.582 Remote Similarity NPD8293 Discontinued
0.5818 Remote Similarity NPD6675 Approved
0.5818 Remote Similarity NPD7128 Approved
0.5818 Remote Similarity NPD5739 Approved
0.5818 Remote Similarity NPD6402 Approved
0.5814 Remote Similarity NPD7909 Approved
0.5804 Remote Similarity NPD6373 Approved
0.5804 Remote Similarity NPD6372 Approved
0.5798 Remote Similarity NPD6015 Approved
0.5798 Remote Similarity NPD6016 Approved
0.5784 Remote Similarity NPD5785 Approved
0.5778 Remote Similarity NPD4245 Approved
0.5778 Remote Similarity NPD4244 Approved
0.5773 Remote Similarity NPD7345 Approved
0.5773 Remote Similarity NPD4270 Approved
0.5773 Remote Similarity NPD4269 Approved
0.5772 Remote Similarity NPD7736 Approved
0.5766 Remote Similarity NPD5697 Approved
0.5766 Remote Similarity NPD5701 Approved
0.5758 Remote Similarity NPD6082 Clinical (unspecified phase)
0.575 Remote Similarity NPD6370 Approved
0.575 Remote Similarity NPD5988 Approved
0.5747 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5732 Remote Similarity NPD73 Approved
0.5729 Remote Similarity NPD4820 Approved
0.5729 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4822 Approved
0.5729 Remote Similarity NPD4819 Approved
0.5729 Remote Similarity NPD6928 Phase 2
0.5729 Remote Similarity NPD4821 Approved
0.5714 Remote Similarity NPD5362 Discontinued
0.5714 Remote Similarity NPD6899 Approved
0.5714 Remote Similarity NPD6881 Approved
0.5714 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6649 Approved
0.5702 Remote Similarity NPD6650 Approved
0.5664 Remote Similarity NPD6012 Approved
0.5664 Remote Similarity NPD6013 Approved
0.5664 Remote Similarity NPD6014 Approved
0.5614 Remote Similarity NPD7102 Approved
0.5614 Remote Similarity NPD7290 Approved
0.5614 Remote Similarity NPD6883 Approved
0.5607 Remote Similarity NPD6083 Phase 2
0.5607 Remote Similarity NPD6084 Phase 2
0.5603 Remote Similarity NPD4632 Approved
0.56 Remote Similarity NPD7319 Approved
0.56 Remote Similarity NPD5363 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